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$235,000

Don’t miss this opportunity to own a home in the heart of Middletown! This livable fixer-upper is the perfect canvas for an investor, first-time buyer, or anyone looking to create their dream home while building valuable sweat equity. Enjoy a charming front porch, a fully fenced backyard, and LVP flooring already installed throughout much of the home. Whether you’re planning light cosmetic updates or a full renovation over time, this property offers incredible potential in a convenient location close to local shops, restaurants, and everyday amenities.

3 Beds ⋅ 2 Baths ⋅ MDFR2086498 MLS

Don’t miss this opportunity to own a home in the heart of Middletown! This livable fixer-upper is the perfect canvas for an investor, first-time buyer, or anyone looking to create their dream home while building valuable sweat equity. Enjoy a charming front porch, a fully fenced backyard, and LVP flooring already installed throughout much of the home. Whether you’re planning light cosmetic updates or a full renovation over time, this property offers incredible potential in a convenient location close to local shops, restaurants, and everyday amenities.

108 S Jefferson St, Middletown

$649,000

Rare commercial opportunity in the heart of Middletown, ideally located directly across the street from the famous Wayside Theater and just minutes from I-81 with excellent accessibility and visibility. Zoned B-1 Commercial, this versatile property offers endless possibilities for business owners, investors, or developers seeking a unique space with flexible use options. Take advantage of the opportunity to live in or rent the attached apartment while running your business from the main portion of the home. See the attached document that outlines potential uses. The property features a beautifully maintained 1920s building full of character, including an inviting front porch, welcoming foyer, grand staircase, hardwood floors, exposed brick, and multiple decorative fireplaces that create a distinctive setting for a variety of commercial uses. The updated kitchen, numerous private rooms, and multiple bathrooms provide a functional layout well suited for professional offices, boutique retail, medical or wellness practices, hospitality, event space, or other approved commercial ventures. A significant advantage is the attached second unit, complete with its own kitchen, living area, two bedrooms, and two-and-a-half baths, offering exceptional flexibility for additional office space, employee accommodations where permitted, rental income, or complementary business operations. The configuration also allows the spaces to function independently or be integrated into one larger commercial operation. Situated on an expansive lot, the property includes a detached two-car garage with additional storage, a storage shed, abundant off-street parking, and ample outdoor space to accommodate a variety of business needs. Combining historic charm, modern updates, and valuable commercial zoning, this is a rare opportunity to establish or expand your business in a prime Middletown location with outstanding long-term investment potential.

VAFV2043814 MLS

Rare commercial opportunity in the heart of Middletown, ideally located directly across the street from the famous Wayside Theater and just minutes from I-81 with excellent accessibility and visibility. Zoned B-1 Commercial, this versatile property offers endless possibilities for business owners, investors, or developers seeking a unique space with flexible use options. Take advantage of the opportunity to live in or rent the attached apartment while running your business from the main portion of the home. See the attached document that outlines potential uses. The property features a beautifully maintained 1920s building full of character, including an inviting front porch, welcoming foyer, grand staircase, hardwood floors, exposed brick, and multiple decorative fireplaces that create a distinctive setting for a variety of commercial uses. The updated kitchen, numerous private rooms, and multiple bathrooms provide a functional layout well suited for professional offices, boutique retail, medical or wellness practices, hospitality, event space, or other approved commercial ventures. A significant advantage is the attached second unit, complete with its own kitchen, living area, two bedrooms, and two-and-a-half baths, offering exceptional flexibility for additional office space, employee accommodations where permitted, rental income, or complementary business operations. The configuration also allows the spaces to function independently or be integrated into one larger commercial operation. Situated on an expansive lot, the property includes a detached two-car garage with additional storage, a storage shed, abundant off-street parking, and ample outdoor space to accommodate a variety of business needs. Combining historic charm, modern updates, and valuable commercial zoning, this is a rare opportunity to establish or expand your business in a prime Middletown location with outstanding long-term investment potential.

7760 Main St, Middletown

$649,000

Exceptional investment opportunity in the heart of Middletown, directly across from the famous Wayside Theater, and conveniently located just minutes from I-81. This unique property features two attached living units, offering outstanding income potential, multigenerational living, or the flexibility to occupy one unit while generating rental income from the other. The main residence showcases the timeless charm of a 1920s home with an inviting front porch, welcoming foyer, beautiful staircase, wood floors, exposed brick, and multiple decorative fireplaces. The updated kitchen features modern cabinetry and a center island. The main unit includes two main-level bedrooms with private en-suite baths, while the upper level offers a spacious primary suite with a walk-in closet and attached bath, plus two additional bedrooms that share a hall bath. The attached second unit is fully equipped with its own kitchen, living room, two bedrooms, and two-and-a-half baths, making it ideal for long-term tenants, short-term rental opportunities (subject to local regulations), or extended family. The property's layout also provides the option to combine both units into one expansive residence if desired. Situated on a generous lot, the property includes a detached two-car garage with additional storage, a storage shed, ample off-street parking, and plenty of outdoor space. Whether you're an investor seeking strong rental potential or a buyer looking for a property with flexible living and income opportunities, this one-of-a-kind multifamily property offers exceptional value in a prime location.

VAFV2043812 MLS

Exceptional investment opportunity in the heart of Middletown, directly across from the famous Wayside Theater, and conveniently located just minutes from I-81. This unique property features two attached living units, offering outstanding income potential, multigenerational living, or the flexibility to occupy one unit while generating rental income from the other. The main residence showcases the timeless charm of a 1920s home with an inviting front porch, welcoming foyer, beautiful staircase, wood floors, exposed brick, and multiple decorative fireplaces. The updated kitchen features modern cabinetry and a center island. The main unit includes two main-level bedrooms with private en-suite baths, while the upper level offers a spacious primary suite with a walk-in closet and attached bath, plus two additional bedrooms that share a hall bath. The attached second unit is fully equipped with its own kitchen, living room, two bedrooms, and two-and-a-half baths, making it ideal for long-term tenants, short-term rental opportunities (subject to local regulations), or extended family. The property's layout also provides the option to combine both units into one expansive residence if desired. Situated on a generous lot, the property includes a detached two-car garage with additional storage, a storage shed, ample off-street parking, and plenty of outdoor space. Whether you're an investor seeking strong rental potential or a buyer looking for a property with flexible living and income opportunities, this one-of-a-kind multifamily property offers exceptional value in a prime location.

7760 Main St, Middletown

$1,349,900

To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is Middletown’s premier 12 lot luxury home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking mountain views, and a strong sense of community, Middletown combines small-town charm with modern convenience. Nestled on 3.78 beautiful acres, 7452 Heritage Oak Terr (Lot 4W) is a gorgeous build-ready homesite with perc approval and well installed. Advertised is the ACL4 plan which features over 4,400 finished sqft, 4 bedrooms and 3.5 baths. A spacious open concept layout is highlighted by 10' main level ceilings, a spacious kitchen with large center island and high end cabinetry, an additional prep kitchen, private office, formal dining room, morning room, private office, a stately Owner's suite w/260 sqft walk-in closet, Hardie Plank siding and full stone water table are just a few standard options in this model. Photos are of a previously built home. Builder has several different plans and many options to choose from. Contact listing agent for available plans, site details, and to explore available homesite options for your future dream home at Heritage Oak Estates!

4 Beds ⋅ 4 Baths ⋅ MDFR2086162 MLS

To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is Middletown’s premier 12 lot luxury home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking mountain views, and a strong sense of community, Middletown combines small-town charm with modern convenience. Nestled on 3.78 beautiful acres, 7452 Heritage Oak Terr (Lot 4W) is a gorgeous build-ready homesite with perc approval and well installed. Advertised is the ACL4 plan which features over 4,400 finished sqft, 4 bedrooms and 3.5 baths. A spacious open concept layout is highlighted by 10' main level ceilings, a spacious kitchen with large center island and high end cabinetry, an additional prep kitchen, private office, formal dining room, morning room, private office, a stately Owner's suite w/260 sqft walk-in closet, Hardie Plank siding and full stone water table are just a few standard options in this model. Photos are of a previously built home. Builder has several different plans and many options to choose from. Contact listing agent for available plans, site details, and to explore available homesite options for your future dream home at Heritage Oak Estates!

7453 Heritage Oak Ter, Middletown

$649,000

Single family or multi-family with an approved, attached apartment - directly across from the famous Wayside Theater! This is a rare opportunity to own prime real estate in Middletown on a beautiful, large lot. Nestled in the heart of Middletown and just minutes from I-81, this exceptional 1920s home blends timeless character with modern updates. From the inviting front porch to the welcoming foyer with its stunning staircase, you'll immediately appreciate the home's classic charm. Beautiful wood floors, exposed brick, and multiple decorative fireplaces add warmth and character throughout. The updated kitchen features modern cabinetry, a center island, and ample space for gathering. Two main-level bedrooms each offer private en-suite baths, providing flexible living arrangements. Upstairs, the spacious primary suite includes a walk-in closet and attached bath, along with two additional bedrooms that share a hall bath. A unique highlight of this property is the attached second living unit located at the rear of the home. Complete with two bedrooms, two-and-a-half baths, a full kitchen, and living room, this space offers endless possibilities. It can serve as an in-law suite, guest quarters, or be seamlessly incorporated into the main residence to significantly expand the home's living space. The property also includes a detached two-car garage with additional storage, a storage shed, abundant parking, and plenty of outdoor space to enjoy. This one-of-a-kind property offers historic charm, flexible living options, and an unbeatable location.

7 Beds ⋅ 7 Baths ⋅ VAFV2043696 MLS

Single family or multi-family with an approved, attached apartment - directly across from the famous Wayside Theater! This is a rare opportunity to own prime real estate in Middletown on a beautiful, large lot. Nestled in the heart of Middletown and just minutes from I-81, this exceptional 1920s home blends timeless character with modern updates. From the inviting front porch to the welcoming foyer with its stunning staircase, you'll immediately appreciate the home's classic charm. Beautiful wood floors, exposed brick, and multiple decorative fireplaces add warmth and character throughout. The updated kitchen features modern cabinetry, a center island, and ample space for gathering. Two main-level bedrooms each offer private en-suite baths, providing flexible living arrangements. Upstairs, the spacious primary suite includes a walk-in closet and attached bath, along with two additional bedrooms that share a hall bath. A unique highlight of this property is the attached second living unit located at the rear of the home. Complete with two bedrooms, two-and-a-half baths, a full kitchen, and living room, this space offers endless possibilities. It can serve as an in-law suite, guest quarters, or be seamlessly incorporated into the main residence to significantly expand the home's living space. The property also includes a detached two-car garage with additional storage, a storage shed, abundant parking, and plenty of outdoor space to enjoy. This one-of-a-kind property offers historic charm, flexible living options, and an unbeatable location.

7760 Main St, Middletown

$1,719,900

To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is a premier 12 lot luxury estate home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking mountain views, and a strong sense of community, Middletown combines small-town charm with modern convenience. Nestled on 7 beautiful acres, 3150 Bidle Rd (Lot 3E) is a gorgeous build-ready homesite with a 5BR septic approval and high yield 10gpm well already installed. Advertised is the ACL5 plan which features over 6,000 finished sqft, 5 bedrooms (including dual owner's suites), 4 full baths and 3 half baths. A spacious open concept layout is highlighted by 10' main level ceilings, a spacious kitchen with large center island and high end cabinetry, an additional prep kitchen, private office, parlor/enterainment room, formal dining room, morning room, upper level bonus room, primary suites on both main and upper levels, Hardie Plank siding and full stone water table are just a few standard options in this model. Photos are of a previously built home. Builder has several different plans and options to choose from. Contact listing agent for available plans, site details, and to explore available homesite options for your future dream home at Heritage Oak Estates!

5 Beds ⋅ 8 Baths ⋅ MDFR2086198 MLS

To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is a premier 12 lot luxury estate home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking mountain views, and a strong sense of community, Middletown combines small-town charm with modern convenience. Nestled on 7 beautiful acres, 3150 Bidle Rd (Lot 3E) is a gorgeous build-ready homesite with a 5BR septic approval and high yield 10gpm well already installed. Advertised is the ACL5 plan which features over 6,000 finished sqft, 5 bedrooms (including dual owner's suites), 4 full baths and 3 half baths. A spacious open concept layout is highlighted by 10' main level ceilings, a spacious kitchen with large center island and high end cabinetry, an additional prep kitchen, private office, parlor/enterainment room, formal dining room, morning room, upper level bonus room, primary suites on both main and upper levels, Hardie Plank siding and full stone water table are just a few standard options in this model. Photos are of a previously built home. Builder has several different plans and options to choose from. Contact listing agent for available plans, site details, and to explore available homesite options for your future dream home at Heritage Oak Estates!

3150 Bidle Rd, Middletown

$1,249,900

To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is Middletown’s premier 12 lot luxury home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking mountain views, and a strong sense of community, Middletown combines small-town charm with modern convenience. Nestled on 4.65 beautiful acres, 3130 Bidle Rd (Lot 1E) is a gorgeous build-ready homesite that offers a perfect combination of protected woodlands and rolling pastoral landscape. Advertised is the ACL3 plan which features over 3,000 finished sqft, 4 bedrooms, 3.5 baths including a main level owner's suite. Additional standard features include a spacious open concept kitchen with large center island and high end cabinetry, beautiful 2 story foyer, morning room, private office, luxurious Owner's suite, Hardie Plank siding and full stone water table. Photos are of a home that builder recently finished in Frederick County. Builder has several different plans and many options to choose from. Contact listing agent for available plans, site details, and to explore available homesite options for your future dream home at Heritage Oak Estates!

4 Beds ⋅ 4 Baths ⋅ MDFR2086098 MLS

To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is Middletown’s premier 12 lot luxury home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking mountain views, and a strong sense of community, Middletown combines small-town charm with modern convenience. Nestled on 4.65 beautiful acres, 3130 Bidle Rd (Lot 1E) is a gorgeous build-ready homesite that offers a perfect combination of protected woodlands and rolling pastoral landscape. Advertised is the ACL3 plan which features over 3,000 finished sqft, 4 bedrooms, 3.5 baths including a main level owner's suite. Additional standard features include a spacious open concept kitchen with large center island and high end cabinetry, beautiful 2 story foyer, morning room, private office, luxurious Owner's suite, Hardie Plank siding and full stone water table. Photos are of a home that builder recently finished in Frederick County. Builder has several different plans and many options to choose from. Contact listing agent for available plans, site details, and to explore available homesite options for your future dream home at Heritage Oak Estates!

3130 Bidle Rd, Middletown

$585,000

Exceptional commercially zoned property in the heart of Middletown, offering outstanding visibility and accessibility on a quiet one-way street just off Main Street and only minutes from I-81. Situated on a beautiful 1-acre lot, this unique property presents endless possibilities for a variety of professional, retail, office, or mixed-use applications. The flexible floor plan provides ample space to customize for your business needs, with multiple large rooms that can easily accommodate private offices, conference areas, client meeting spaces, or collaborative work environments. A convenient half bath on the main level serves customers and staff, while the upper level features additional rooms and two full bathrooms, making the property well-suited for expanded office space, live/work potential or other commercial uses. Inside, the property showcases timeless architectural details that create a distinctive and welcoming atmosphere. Beautiful hardwood floors, impressive thick moldings, custom built-ins, decorative fireplaces, and a grand entrance foyer with a stunning spiral staircase combine historic charm with professional appeal, helping your business make a lasting impression. With abundant space, flexible configuration, exceptional character, and a highly desirable location close to major transportation routes, this is a rare opportunity to establish or expand your business in one of Middletown's most convenient and recognizable locations.

VAFV2043810 MLS

Exceptional commercially zoned property in the heart of Middletown, offering outstanding visibility and accessibility on a quiet one-way street just off Main Street and only minutes from I-81. Situated on a beautiful 1-acre lot, this unique property presents endless possibilities for a variety of professional, retail, office, or mixed-use applications. The flexible floor plan provides ample space to customize for your business needs, with multiple large rooms that can easily accommodate private offices, conference areas, client meeting spaces, or collaborative work environments. A convenient half bath on the main level serves customers and staff, while the upper level features additional rooms and two full bathrooms, making the property well-suited for expanded office space, live/work potential or other commercial uses. Inside, the property showcases timeless architectural details that create a distinctive and welcoming atmosphere. Beautiful hardwood floors, impressive thick moldings, custom built-ins, decorative fireplaces, and a grand entrance foyer with a stunning spiral staircase combine historic charm with professional appeal, helping your business make a lasting impression. With abundant space, flexible configuration, exceptional character, and a highly desirable location close to major transportation routes, this is a rare opportunity to establish or expand your business in one of Middletown's most convenient and recognizable locations.

2239 6th St, Middletown

$585,000

Welcome to this stunning Circa 1872 farmhouse nestled in the heart of Middletown with a stunning view! Situated on a gorgeous 1-acre lot on a quiet one-way street just off Main Street, this spacious property offers the perfect blend of peaceful living and everyday convenience, with easy access to I-81. Zoned B1, it offers many possibilities for either residential or commercial use, including a Bed and Breakfast! (see attached document). Step inside to discover timeless character and charm, featuring gorgeous period details including thick moldings, custom built-ins, decorative fireplaces, and beautiful hardwood floors. The impressive entrance foyer, featuring a grand spiral staircase, welcomes you and creates a memorable first impression. This home is absolutely perfect for entertaining, also featuring a grand dining room and details throughout that only a home of this era can offer. The thoughtfully designed second level offers four spacious bedrooms and two full bathrooms, providing privacy for family and guests. A convenient half bath on the main level is ideal for entertaining. Complete your journey to the third story overlook and enjoy the most beautiful sunsets you can imagine in the Shenandoah Valley - read, paint, meditate, or just relax and enjoy this very unique space. This exceptional home is ready to welcome its next owner.

4 Beds ⋅ 3 Baths ⋅ VAFV2043690 MLS

Welcome to this stunning Circa 1872 farmhouse nestled in the heart of Middletown with a stunning view! Situated on a gorgeous 1-acre lot on a quiet one-way street just off Main Street, this spacious property offers the perfect blend of peaceful living and everyday convenience, with easy access to I-81. Zoned B1, it offers many possibilities for either residential or commercial use, including a Bed and Breakfast! (see attached document). Step inside to discover timeless character and charm, featuring gorgeous period details including thick moldings, custom built-ins, decorative fireplaces, and beautiful hardwood floors. The impressive entrance foyer, featuring a grand spiral staircase, welcomes you and creates a memorable first impression. This home is absolutely perfect for entertaining, also featuring a grand dining room and details throughout that only a home of this era can offer. The thoughtfully designed second level offers four spacious bedrooms and two full bathrooms, providing privacy for family and guests. A convenient half bath on the main level is ideal for entertaining. Complete your journey to the third story overlook and enjoy the most beautiful sunsets you can imagine in the Shenandoah Valley - read, paint, meditate, or just relax and enjoy this very unique space. This exceptional home is ready to welcome its next owner.

2239 Sixth St, Middletown

$540,000

Experience the best of Shenandoah Valley living in this beautifully located home, where breathtaking sunset mountain views create the perfect backdrop to everyday life. Nestled in a quiet, dog-friendly community, you'll enjoy peaceful surroundings without sacrificing convenience. Ideally situated just minutes from I-81 and Route 66, this home offers an easy commute while keeping you close to everything you need. Spend weekends exploring local wineries, hiking trails, parks, and the natural beauty of the Shenandoah Valley, or enjoy the nearby restaurants, shopping, and everyday conveniences just moments away. Built in 2023, this residence boasts a spacious open. layout, perfect for modern living. The kitchen features quartz countertops, a central island, and stainless steel appliances, including a gas stove. With four generous bedrooms, including a main level bedroom, and additional loft this home offers ample space for everyone. The primary suite is a true retreat, complete with a walk-in closet and a luxurious bath. Enjoy the convenience of upper-floor laundry and thoughtful touches like recessed lighting throughout. Outside, the property is equally appealing. The lot backs onto an open common area, providing a sense of privacy, all highlighted by a stunning mountain view. Enjoy leisurely strolls along the nearby jog/walk path or relax in the beautifully landscaped rear yard. The attached two-car garage and concrete driveway offer plenty of parking and storage options. Additional features include school bus pick up within the neighborhood, a playground and sidewalks that enhance the neighborhood's charm. With common area maintenance and management included in the association fee, you can enjoy a low-maintenance lifestyle. This home is not just a place to live; it’s a place to thrive.

4 Beds ⋅ 3 Baths ⋅ VAFV2043622 MLS

Experience the best of Shenandoah Valley living in this beautifully located home, where breathtaking sunset mountain views create the perfect backdrop to everyday life. Nestled in a quiet, dog-friendly community, you'll enjoy peaceful surroundings without sacrificing convenience. Ideally situated just minutes from I-81 and Route 66, this home offers an easy commute while keeping you close to everything you need. Spend weekends exploring local wineries, hiking trails, parks, and the natural beauty of the Shenandoah Valley, or enjoy the nearby restaurants, shopping, and everyday conveniences just moments away. Built in 2023, this residence boasts a spacious open. layout, perfect for modern living. The kitchen features quartz countertops, a central island, and stainless steel appliances, including a gas stove. With four generous bedrooms, including a main level bedroom, and additional loft this home offers ample space for everyone. The primary suite is a true retreat, complete with a walk-in closet and a luxurious bath. Enjoy the convenience of upper-floor laundry and thoughtful touches like recessed lighting throughout. Outside, the property is equally appealing. The lot backs onto an open common area, providing a sense of privacy, all highlighted by a stunning mountain view. Enjoy leisurely strolls along the nearby jog/walk path or relax in the beautifully landscaped rear yard. The attached two-car garage and concrete driveway offer plenty of parking and storage options. Additional features include school bus pick up within the neighborhood, a playground and sidewalks that enhance the neighborhood's charm. With common area maintenance and management included in the association fee, you can enjoy a low-maintenance lifestyle. This home is not just a place to live; it’s a place to thrive.

102 Curtain Fall Dr, Middletown

$369,000

This 3/4 Bedroom home has 2 Full Baths and sits in a country setting. It has been completely remodeled inside and out. New siding, new roof, new windows and landscaping on the outside. The inside has been freshly painted, all new flooring, kitchen has new stainless steel appliances and new cabinets. The eat-in kitchen also has new counter tops, beautiful backsplash and top of the line kitchen sink. The basement family room has built in book shelves and a full bath off of it. The office/ 4th bedroom has built in book shelves as well. There is plenty of storage and the laundry room in the basement too. Large rear yard! Convenient to shopping, schools, travel and historic sites.

3 Beds ⋅ 2 Baths ⋅ MDFR2085892 MLS

This 3/4 Bedroom home has 2 Full Baths and sits in a country setting. It has been completely remodeled inside and out. New siding, new roof, new windows and landscaping on the outside. The inside has been freshly painted, all new flooring, kitchen has new stainless steel appliances and new cabinets. The eat-in kitchen also has new counter tops, beautiful backsplash and top of the line kitchen sink. The basement family room has built in book shelves and a full bath off of it. The office/ 4th bedroom has built in book shelves as well. There is plenty of storage and the laundry room in the basement too. Large rear yard! Convenient to shopping, schools, travel and historic sites.

323 S Jefferson St S, Middletown

$449,900

Welcome to 114 Curtain Fall Drive, an exceptional, practically brand-new ranch home where modern design meets total convenience! Perfectly situated in a vibrant Middletown community with quick access to major commuter routes, local dining, shopping, parks, and schools, this move-in-ready gem delivers effortless one-level living at its absolute finest. From the moment you step inside, sleek LVP floors set a stylish, durable tone that runs seamlessly through the main living spaces. The open-concept layout was custom-made for entertaining, buzzing with natural light and easy flow. You'll instantly fall in love with the beautifully appointed kitchen, which features a spacious eat-in area, upgraded countertops, crisp white cabinetry, stainless steel appliances, and a huge center island that serves as the ultimate gathering spot. The living room offers an inviting anchor for day-to-day relaxation, featuring a breezy ceiling fan and an abundance of natural light. Glass doors open onto the private rear deck, creating a seamless transition to outdoor living. Equipped with a shade awning, the deck is ready for sun-soaked afternoons or cool evening lounge sessions. Beyond the deck, the fully fenced backyard offers a secure spot for pets or play, all framed by mature trees that add rich greenery and a peaceful sense of privacy. Adjacent to the living space, a cozy, tucked-away alcove stands ready to become a home office, reading nook, or play zone. When privacy calls, the clever split-bedroom layout delivers. Two bright bedrooms and a full bath sit tucked away near the front, while your primary retreat claims its own private wing. This space boasts a massive walk-in closet and a stylish sliding door that reveals a spa-like ensuite with double sinks and a huge walk-in shower. Main-level laundry makes chores a breeze, while a huge, unfinished basement offers endless potential for a future recreation room, home gym, or workshop. Topped off with a 2-car attached garage and low-maintenance curb appeal, this home truly has it all!

3 Beds ⋅ 2 Baths ⋅ VAFV2043586 MLS

Welcome to 114 Curtain Fall Drive, an exceptional, practically brand-new ranch home where modern design meets total convenience! Perfectly situated in a vibrant Middletown community with quick access to major commuter routes, local dining, shopping, parks, and schools, this move-in-ready gem delivers effortless one-level living at its absolute finest. From the moment you step inside, sleek LVP floors set a stylish, durable tone that runs seamlessly through the main living spaces. The open-concept layout was custom-made for entertaining, buzzing with natural light and easy flow. You'll instantly fall in love with the beautifully appointed kitchen, which features a spacious eat-in area, upgraded countertops, crisp white cabinetry, stainless steel appliances, and a huge center island that serves as the ultimate gathering spot. The living room offers an inviting anchor for day-to-day relaxation, featuring a breezy ceiling fan and an abundance of natural light. Glass doors open onto the private rear deck, creating a seamless transition to outdoor living. Equipped with a shade awning, the deck is ready for sun-soaked afternoons or cool evening lounge sessions. Beyond the deck, the fully fenced backyard offers a secure spot for pets or play, all framed by mature trees that add rich greenery and a peaceful sense of privacy. Adjacent to the living space, a cozy, tucked-away alcove stands ready to become a home office, reading nook, or play zone. When privacy calls, the clever split-bedroom layout delivers. Two bright bedrooms and a full bath sit tucked away near the front, while your primary retreat claims its own private wing. This space boasts a massive walk-in closet and a stylish sliding door that reveals a spa-like ensuite with double sinks and a huge walk-in shower. Main-level laundry makes chores a breeze, while a huge, unfinished basement offers endless potential for a future recreation room, home gym, or workshop. Topped off with a 2-car attached garage and low-maintenance curb appeal, this home truly has it all!

114 Curtain Fall Dr, Middletown

$475,000

Welcome home to 4 Lamar Lane, a beautifully updated Admar-built rancher tucked away at the peaceful back of the highly sought-after Foxfield 55+ community in Middletown. Thoughtfully designed for easy living and filled with warmth and charm, this move-in ready home offers the perfect blend of comfort, convenience, and low-maintenance living. A covered front porch welcomes you home, while the level-access ramp from the two-car garage provides added ease and accessibility. Inside, you’ll find 1,359 finished square feet on the main level featuring two spacious bedrooms, each with its own private ensuite bath, plus main-level laundry for true one-level living. The heart of the home is the beautifully remodeled kitchen, complete with new cabinetry, countertops, and propane-fueled gas cooking. The inviting living room offers a cozy propane-fueled gas fireplace, creating the perfect space to relax or gather with friends and family. Recent updates throughout include a new roof, new HVAC system, refinished hardwood floors, updated bathrooms, fresh paint, and a low-maintenance exterior, allowing you to simply move in and enjoy. Step outside to discover a fenced backyard with two rear decks, providing wonderful spaces for morning coffee, outdoor dining, gardening, or enjoying the peaceful surroundings. An unfinished basement with windows offers abundant storage and endless possibilities for future expansion. Rarely does a home in Foxfield combine this level of updating, accessibility, outdoor living space, and prime location. This is the kind of home that allows you to spend less time maintaining and more time enjoying everything the Middletown Valley has to offer.

2 Beds ⋅ 2 Baths ⋅ MDFR2086214 MLS

Welcome home to 4 Lamar Lane, a beautifully updated Admar-built rancher tucked away at the peaceful back of the highly sought-after Foxfield 55+ community in Middletown. Thoughtfully designed for easy living and filled with warmth and charm, this move-in ready home offers the perfect blend of comfort, convenience, and low-maintenance living. A covered front porch welcomes you home, while the level-access ramp from the two-car garage provides added ease and accessibility. Inside, you’ll find 1,359 finished square feet on the main level featuring two spacious bedrooms, each with its own private ensuite bath, plus main-level laundry for true one-level living. The heart of the home is the beautifully remodeled kitchen, complete with new cabinetry, countertops, and propane-fueled gas cooking. The inviting living room offers a cozy propane-fueled gas fireplace, creating the perfect space to relax or gather with friends and family. Recent updates throughout include a new roof, new HVAC system, refinished hardwood floors, updated bathrooms, fresh paint, and a low-maintenance exterior, allowing you to simply move in and enjoy. Step outside to discover a fenced backyard with two rear decks, providing wonderful spaces for morning coffee, outdoor dining, gardening, or enjoying the peaceful surroundings. An unfinished basement with windows offers abundant storage and endless possibilities for future expansion. Rarely does a home in Foxfield combine this level of updating, accessibility, outdoor living space, and prime location. This is the kind of home that allows you to spend less time maintaining and more time enjoying everything the Middletown Valley has to offer.

4 Lamar Ln, Middletown

$625,000

***OPEN HOUSE SATURDAY 8/1 - 11:00-1:00!***Welcome to 7 Derr Lane in the sought-after Villages at Foxfield—Middletown’s premier 55+ community—where Original Owners have meticulously maintained and thoughtfully upgraded this beautiful home, showcasing true pride of ownership everywhere you look. Perfectly positioned within walking distance to Middletown Park and its many amenities, this home also backs to serene woods, walking/jogging paths, and open green space—offering both convenience and some privacy. Enjoy peaceful mornings on the covered front porch or unwind in the backyard retreat featuring a walkout patio, koi pond, and a hidden “secret garden” be sure not to miss. Inside, the home blends comfort and modern updates. The kitchen is a standout with a Corian island, mosaic tile backsplash, stainless steel appliances (replaced 2019), induction downdraft cooktop, double oven, and ceramic flooring—ideal for both everyday living and entertaining. The main level boasts hardwood flooring (2018) and a warm, inviting family room with a propane fireplace and direct access to the newer, enlarged Trex deck (2022, with updated door in 2025). The spacious layout includes vaulted ceilings, a tray ceiling in the primary suite, and a dramatic two-story overlook with loft above. The primary bath was beautifully renovated in 2017, and the upper level features new carpet (2019). Additional updates include leased solar panels for energy efficiency (2018), washer and dryer (2021), vinyl fencing (2022), new roof and ventilation (2024), HVAC (2015), and water heater (2018). The unfinished lower level offers a walkout to the backyard, rough-in for a full bath, and a wide-open layout ready to be customized to your needs. Garage is equipped with a 200 amp 240 volt EV charging circuit and a newer garage door opener (2021). This is a rare opportunity to own a truly move-in-ready home in Middletown’s most desirable active adult communities—combining thoughtful upgrades, natural beauty, and a vibrant lifestyle.

3 Beds ⋅ 3 Baths ⋅ MDFR2086228 MLS

***OPEN HOUSE SATURDAY 8/1 - 11:00-1:00!***Welcome to 7 Derr Lane in the sought-after Villages at Foxfield—Middletown’s premier 55+ community—where Original Owners have meticulously maintained and thoughtfully upgraded this beautiful home, showcasing true pride of ownership everywhere you look. Perfectly positioned within walking distance to Middletown Park and its many amenities, this home also backs to serene woods, walking/jogging paths, and open green space—offering both convenience and some privacy. Enjoy peaceful mornings on the covered front porch or unwind in the backyard retreat featuring a walkout patio, koi pond, and a hidden “secret garden” be sure not to miss. Inside, the home blends comfort and modern updates. The kitchen is a standout with a Corian island, mosaic tile backsplash, stainless steel appliances (replaced 2019), induction downdraft cooktop, double oven, and ceramic flooring—ideal for both everyday living and entertaining. The main level boasts hardwood flooring (2018) and a warm, inviting family room with a propane fireplace and direct access to the newer, enlarged Trex deck (2022, with updated door in 2025). The spacious layout includes vaulted ceilings, a tray ceiling in the primary suite, and a dramatic two-story overlook with loft above. The primary bath was beautifully renovated in 2017, and the upper level features new carpet (2019). Additional updates include leased solar panels for energy efficiency (2018), washer and dryer (2021), vinyl fencing (2022), new roof and ventilation (2024), HVAC (2015), and water heater (2018). The unfinished lower level offers a walkout to the backyard, rough-in for a full bath, and a wide-open layout ready to be customized to your needs. Garage is equipped with a 200 amp 240 volt EV charging circuit and a newer garage door opener (2021). This is a rare opportunity to own a truly move-in-ready home in Middletown’s most desirable active adult communities—combining thoughtful upgrades, natural beauty, and a vibrant lifestyle.

7 Derr Ln, Middletown

$699,000

This home is an absolute MUST SEE. This home has been immaculately maintained and features all of it's original charm. You will fall in love with the beautiful hardwood floors throughout this spacious 5 bedroom, 3 full bath colonial that features 3,200 square feet of living space along with a large 832 square foot basement, with outside entrance. This classic beauty is situated on a large, beautifully landscaped and manicured, corner lot of .64 acres in Middletown's Historic District. You will fall in love with all of the historic charm and craftsmanship that blends seamlessly with modern upgrades such as vinyl siding and replacement windows. There are several bonus areas that provide added charm to this already captivating home. There is a family room that was crafted from a former garage, a second floor sunroom area for relaxing, a bonus room that could be a home office and a sitting area off of the formal dining room. This is a true gem and you will be amazed at the incredible condition.

5 Beds ⋅ 3 Baths ⋅ MDFR2085770 MLS

This home is an absolute MUST SEE. This home has been immaculately maintained and features all of it's original charm. You will fall in love with the beautiful hardwood floors throughout this spacious 5 bedroom, 3 full bath colonial that features 3,200 square feet of living space along with a large 832 square foot basement, with outside entrance. This classic beauty is situated on a large, beautifully landscaped and manicured, corner lot of .64 acres in Middletown's Historic District. You will fall in love with all of the historic charm and craftsmanship that blends seamlessly with modern upgrades such as vinyl siding and replacement windows. There are several bonus areas that provide added charm to this already captivating home. There is a family room that was crafted from a former garage, a second floor sunroom area for relaxing, a bonus room that could be a home office and a sitting area off of the formal dining room. This is a true gem and you will be amazed at the incredible condition.

200 Prospect St, Middletown

$499,900

Welcome to this beautiful colonial in the heart of Middletown, MD, where small-town charm, community character, and a prime Main Street address come together on a generous half acre lot! There is SO MUCH potential to revitalize this home to your most creative imagination. Bathed in natural light throughout, this spacious 4-bedroom, 2-bath home features gleaming hardwood floors and a comfortable, flowing layout. The main level offers a primary bedroom with a private ensuite bath, ideal for single-level living convenience, while the upper-level hosts three additional generously sized bedrooms and a full bath. The expansive lot provides plenty of outdoor space to enjoy, entertain, and make your own. A roof updated in 2025 offers genuine peace of mind, and the home is connected to the public sewer system via a Sanitary Sewer Lift Pump, offering the reliability of public utilities. Middletown offers everything you come here for, a small-town feel with walkability to parks, restaurants, the library, and shopping, including beloved local spots like The Main Cup, Fratelli's Italian & Seafood, and Aleko's Village Cafe just down the road. The 79-acre Middletown Community Park is just minutes away, offering basketball courts, soccer fields, disc golf, fishing, picnic shelters, and walking trails. Commuters will appreciate the easy access to I-70 and Rt. 340, with Downtown Frederick just a short drive away. Don't miss this one!

4 Beds ⋅ 2 Baths ⋅ MDFR2085644 MLS

Welcome to this beautiful colonial in the heart of Middletown, MD, where small-town charm, community character, and a prime Main Street address come together on a generous half acre lot! There is SO MUCH potential to revitalize this home to your most creative imagination. Bathed in natural light throughout, this spacious 4-bedroom, 2-bath home features gleaming hardwood floors and a comfortable, flowing layout. The main level offers a primary bedroom with a private ensuite bath, ideal for single-level living convenience, while the upper-level hosts three additional generously sized bedrooms and a full bath. The expansive lot provides plenty of outdoor space to enjoy, entertain, and make your own. A roof updated in 2025 offers genuine peace of mind, and the home is connected to the public sewer system via a Sanitary Sewer Lift Pump, offering the reliability of public utilities. Middletown offers everything you come here for, a small-town feel with walkability to parks, restaurants, the library, and shopping, including beloved local spots like The Main Cup, Fratelli's Italian & Seafood, and Aleko's Village Cafe just down the road. The 79-acre Middletown Community Park is just minutes away, offering basketball courts, soccer fields, disc golf, fishing, picnic shelters, and walking trails. Commuters will appreciate the easy access to I-70 and Rt. 340, with Downtown Frederick just a short drive away. Don't miss this one!

718 E Main St, Middletown

$725,000

Welcome to your dream home in highly sought-after Middletown! Nestled on 2.6 private acres, this stunning colonial offers the perfect blend of space, comfort, and modern upgrades, with 5 bedrooms, 3.5 bathrooms, and over 3,500 finished square feet. From the moment you arrive, the charming full front porch invites you to relax and take in the peaceful surroundings. Step inside to a welcoming foyer that flows effortlessly into a spacious and functional layout, ideal for both everyday living and entertaining. The heart of the home is a beautifully designed country kitchen featuring modern appliances, abundant cabinetry, and generous counter space, perfect for cooking, gathering, and hosting. Just off the kitchen, the cozy family room with fireplace creates a warm and inviting space to unwind. The main level also features a dedicated home office, plus a versatile bonus room that can easily serve as a second office, gym, playroom, craft space, or guest area. Upstairs, the expansive primary suite offers a private retreat with an en-suite bath and ample closet space. Four additional oversized bedrooms, including one with its own en-suite, provide flexibility and comfort for family and guests, along with an additional full bathroom. The unfinished lower level (1,656 sq ft) offers endless potential—create your dream home theater, gym, workshop, or additional living space. Step outside to enjoy your brand new deck, perfect for entertaining, relaxing, or taking in the scenic surroundings. With no HOA and plenty of room to roam, this property offers true freedom for outdoor living. ✨ Major upgrades already done for you: * New HVAC (January 2026) * Brand new deck * New 80-gallon hot water heater * New dog wash station * Newer water treatment system Located just minutes from schools, parks, and commuter routes, this home combines the peace of country living with everyday convenience. This is the one you’ve been waiting for, schedule your private showing today!

5 Beds ⋅ 4 Baths ⋅ VAFV2043584 MLS

Welcome to your dream home in highly sought-after Middletown! Nestled on 2.6 private acres, this stunning colonial offers the perfect blend of space, comfort, and modern upgrades, with 5 bedrooms, 3.5 bathrooms, and over 3,500 finished square feet. From the moment you arrive, the charming full front porch invites you to relax and take in the peaceful surroundings. Step inside to a welcoming foyer that flows effortlessly into a spacious and functional layout, ideal for both everyday living and entertaining. The heart of the home is a beautifully designed country kitchen featuring modern appliances, abundant cabinetry, and generous counter space, perfect for cooking, gathering, and hosting. Just off the kitchen, the cozy family room with fireplace creates a warm and inviting space to unwind. The main level also features a dedicated home office, plus a versatile bonus room that can easily serve as a second office, gym, playroom, craft space, or guest area. Upstairs, the expansive primary suite offers a private retreat with an en-suite bath and ample closet space. Four additional oversized bedrooms, including one with its own en-suite, provide flexibility and comfort for family and guests, along with an additional full bathroom. The unfinished lower level (1,656 sq ft) offers endless potential—create your dream home theater, gym, workshop, or additional living space. Step outside to enjoy your brand new deck, perfect for entertaining, relaxing, or taking in the scenic surroundings. With no HOA and plenty of room to roam, this property offers true freedom for outdoor living. ✨ Major upgrades already done for you: * New HVAC (January 2026) * Brand new deck * New 80-gallon hot water heater * New dog wash station * Newer water treatment system Located just minutes from schools, parks, and commuter routes, this home combines the peace of country living with everyday convenience. This is the one you’ve been waiting for, schedule your private showing today!

258 Chimney Cir, Middletown

$495,000

Some homes simply have a soul—and this beautifully preserved 1920's Craftsman bungalow is one of them. Situated on a rare lot and a half in the heart of historic Middletown, this contributing home to both the National and Frederick Historic Registers has been lovingly cared for by just two families throughout its history. From the moment you arrive, you’ll notice the timeless character that sets this home apart. Tall original windows frame mature trees, gardens, and changing seasonal views from nearly every room, filling the home with natural light and creating a peaceful connection to the outdoors. Original wood floors, handcrafted trim work, pocket doors, custom storm windows, and historic architectural details blend seamlessly with thoughtful modern updates. The sellers have always appreciated the home’s solid clay block construction, which provides a remarkably quiet, comfortable feel and exceptional insulation rarely found in homes of this era. At the heart of the home is a beautifully renovated kitchen that has served as the gathering place for everything from weeknight dinners to holiday celebrations. A spacious island welcomes family and friends, while the thoughtful layout offers the perfect balance of openness and functionality. Upstairs, generously sized bedrooms, second-floor laundry, and an updated bath provide modern convenience while honoring the home’s historic roots. Outside, the property unfolds into a collection of extraordinary outdoor living spaces. Enjoy sunrise views from the backyard, summer sunsets from the welcoming front porch, abundant gardens, mature trees, a kitchen garden, and a private backyard retreat complete with a pergola and gas firepit. Every outdoor space offers its own unique experience, creating a rare sense of privacy and connection to nature in the heart of town. Major improvements include a renovated kitchen and baths, NTI combi-boiler, roof, insulation, updated electrical, propane installation, custom storm windows, and asbestos remediation. Perhaps most special of all are the home’s original handcrafted windows and custom-built storm windows—an increasingly rare treasure that has been lovingly maintained and thoughtfully restored. Throughout their stewardship, the sellers viewed themselves less as owners and more as caretakers of something truly special, dedicated to preserving the integrity and craftsmanship the original builders intended. The result is a home that honors its past while offering the comfort, beauty, and functionality today’s buyers desire. A rare opportunity to own a piece of Middletown history—where historic craftsmanship, thoughtful updates, beautiful gardens, and small-town charm come together to create something truly exceptional. Showings to begin August 1st, not before.

3 Beds ⋅ 2 Baths ⋅ MDFR2084304 MLS

Some homes simply have a soul—and this beautifully preserved 1920's Craftsman bungalow is one of them. Situated on a rare lot and a half in the heart of historic Middletown, this contributing home to both the National and Frederick Historic Registers has been lovingly cared for by just two families throughout its history. From the moment you arrive, you’ll notice the timeless character that sets this home apart. Tall original windows frame mature trees, gardens, and changing seasonal views from nearly every room, filling the home with natural light and creating a peaceful connection to the outdoors. Original wood floors, handcrafted trim work, pocket doors, custom storm windows, and historic architectural details blend seamlessly with thoughtful modern updates. The sellers have always appreciated the home’s solid clay block construction, which provides a remarkably quiet, comfortable feel and exceptional insulation rarely found in homes of this era. At the heart of the home is a beautifully renovated kitchen that has served as the gathering place for everything from weeknight dinners to holiday celebrations. A spacious island welcomes family and friends, while the thoughtful layout offers the perfect balance of openness and functionality. Upstairs, generously sized bedrooms, second-floor laundry, and an updated bath provide modern convenience while honoring the home’s historic roots. Outside, the property unfolds into a collection of extraordinary outdoor living spaces. Enjoy sunrise views from the backyard, summer sunsets from the welcoming front porch, abundant gardens, mature trees, a kitchen garden, and a private backyard retreat complete with a pergola and gas firepit. Every outdoor space offers its own unique experience, creating a rare sense of privacy and connection to nature in the heart of town. Major improvements include a renovated kitchen and baths, NTI combi-boiler, roof, insulation, updated electrical, propane installation, custom storm windows, and asbestos remediation. Perhaps most special of all are the home’s original handcrafted windows and custom-built storm windows—an increasingly rare treasure that has been lovingly maintained and thoughtfully restored. Throughout their stewardship, the sellers viewed themselves less as owners and more as caretakers of something truly special, dedicated to preserving the integrity and craftsmanship the original builders intended. The result is a home that honors its past while offering the comfort, beauty, and functionality today’s buyers desire. A rare opportunity to own a piece of Middletown history—where historic craftsmanship, thoughtful updates, beautiful gardens, and small-town charm come together to create something truly exceptional. Showings to begin August 1st, not before.

106 Prospect St, Middletown

$379,000

An exceptional opportunity to restore and reimagine a historic Main Street property in the heart of Middletown. Prominently located along one of the towns most recognized corridors, this four bedroom, two bath home offers timeless character, outstanding potential, and a location that is difficult to duplicate. Believed to date to the early 1800s, the home has been part of Middletown history for generations and is ready for its next chapter. Just a short walk to local shops, restaurants, cafes, and community gathering spaces, this property offers the charm and convenience of small town living. Situated on a generous in town parcel with desirable B1 zoning, the property provides exceptional flexibility for residential living, professional office, business use, or a mixed use concept subject to local approvals. The additional side land offers potential subdivision opportunities subject to application and approval. Rear alley access further enhances the versatility of this unique property while the prominent Main Street location provides outstanding visibility for a variety of future uses. Inside, the home features four bedrooms, two full baths, and the character expected of a historic residence. The property is ready for restoration and thoughtful updating, presenting an exceptional opportunity to preserve its historic charm while incorporating modern improvements. Whether your vision is a distinctive residence, professional office, investment property, or live and work opportunity, the possibilities are substantial. Historic Main Street properties offering this combination of character, location, flexible B1 zoning, additional land, rear alley access, and future potential rarely become available. Property is being sold as is.

VAFV2043474 MLS

An exceptional opportunity to restore and reimagine a historic Main Street property in the heart of Middletown. Prominently located along one of the towns most recognized corridors, this four bedroom, two bath home offers timeless character, outstanding potential, and a location that is difficult to duplicate. Believed to date to the early 1800s, the home has been part of Middletown history for generations and is ready for its next chapter. Just a short walk to local shops, restaurants, cafes, and community gathering spaces, this property offers the charm and convenience of small town living. Situated on a generous in town parcel with desirable B1 zoning, the property provides exceptional flexibility for residential living, professional office, business use, or a mixed use concept subject to local approvals. The additional side land offers potential subdivision opportunities subject to application and approval. Rear alley access further enhances the versatility of this unique property while the prominent Main Street location provides outstanding visibility for a variety of future uses. Inside, the home features four bedrooms, two full baths, and the character expected of a historic residence. The property is ready for restoration and thoughtful updating, presenting an exceptional opportunity to preserve its historic charm while incorporating modern improvements. Whether your vision is a distinctive residence, professional office, investment property, or live and work opportunity, the possibilities are substantial. Historic Main Street properties offering this combination of character, location, flexible B1 zoning, additional land, rear alley access, and future potential rarely become available. Property is being sold as is.

7927 Main St, Middletown

$439,900

Welcome home to this beautifully updated end-unit townhome in the highly sought-after Glenbrook community, where modern updates, generous living space, and an unbeatable Middletown location come together to create a home you’ll love from the moment you arrive. This spacious three-level home features luxury vinyl plank flooring on all levels, with brand-new carpeting on the staircases (hardwood stairs remain beneath the carpeting, offering future flexibility), fresh paint, and custom blinds. A full three-level bump-out enhances every level, creating an open, airy feel with room to spread out, relax, and entertain. At the heart of the home is the completely renovated kitchen, thoughtfully designed with shaker-style cabinetry, quartz countertops, a spacious center island, gas cooking, and a full suite of Frigidaire Gallery stainless steel appliances. Whether you’re preparing weeknight dinners or hosting holiday gatherings, you’ll love how the kitchen flows seamlessly into the generous dining area and the expanded family room, making it the true gathering place of the home. The main level also offers a welcoming living room and a convenient powder room for guests. Upstairs, you’ll find three spacious bedrooms and two full bathrooms, including an expanded primary suite designed as your own private retreat. The en-suite bath offers a double vanity, soaking tub, separate walk-in shower, and generous space, while a large walk-in closet provides exceptional storage. The finished lower level offers incredible flexibility with a fourth bedroom, an updated full bathroom, a den, a spacious recreation room, and a dedicated laundry and mechanical room—perfect for overnight guests, multigenerational living, a home office, fitness space, or movie nights. Step outside and enjoy one of the many advantages of this end-unit location—a large side and rear yard offering outdoor space that’s hard to find in a townhome community. Two designated parking spaces and additional windows that fill the home with natural light add even more everyday convenience. For added peace of mind, the seller is offering a home warranty. Located in the sought-after Middletown school district, this home is just minutes from charming downtown Middletown, local restaurants, boutique shopping, parks, walking trails, wineries, golf, community events, and convenient commuter routes. With four bedrooms, multiple living areas, and flexible spaces for working from home, entertaining, or hosting guests, this home offers the space and versatility today’s buyers are looking for. Come experience all that Middletown has to offer and discover why this vibrant community is one of Maryland’s most desirable places to call home.

4 Beds ⋅ 4 Baths ⋅ MDFR2085682 MLS

Welcome home to this beautifully updated end-unit townhome in the highly sought-after Glenbrook community, where modern updates, generous living space, and an unbeatable Middletown location come together to create a home you’ll love from the moment you arrive. This spacious three-level home features luxury vinyl plank flooring on all levels, with brand-new carpeting on the staircases (hardwood stairs remain beneath the carpeting, offering future flexibility), fresh paint, and custom blinds. A full three-level bump-out enhances every level, creating an open, airy feel with room to spread out, relax, and entertain. At the heart of the home is the completely renovated kitchen, thoughtfully designed with shaker-style cabinetry, quartz countertops, a spacious center island, gas cooking, and a full suite of Frigidaire Gallery stainless steel appliances. Whether you’re preparing weeknight dinners or hosting holiday gatherings, you’ll love how the kitchen flows seamlessly into the generous dining area and the expanded family room, making it the true gathering place of the home. The main level also offers a welcoming living room and a convenient powder room for guests. Upstairs, you’ll find three spacious bedrooms and two full bathrooms, including an expanded primary suite designed as your own private retreat. The en-suite bath offers a double vanity, soaking tub, separate walk-in shower, and generous space, while a large walk-in closet provides exceptional storage. The finished lower level offers incredible flexibility with a fourth bedroom, an updated full bathroom, a den, a spacious recreation room, and a dedicated laundry and mechanical room—perfect for overnight guests, multigenerational living, a home office, fitness space, or movie nights. Step outside and enjoy one of the many advantages of this end-unit location—a large side and rear yard offering outdoor space that’s hard to find in a townhome community. Two designated parking spaces and additional windows that fill the home with natural light add even more everyday convenience. For added peace of mind, the seller is offering a home warranty. Located in the sought-after Middletown school district, this home is just minutes from charming downtown Middletown, local restaurants, boutique shopping, parks, walking trails, wineries, golf, community events, and convenient commuter routes. With four bedrooms, multiple living areas, and flexible spaces for working from home, entertaining, or hosting guests, this home offers the space and versatility today’s buyers are looking for. Come experience all that Middletown has to offer and discover why this vibrant community is one of Maryland’s most desirable places to call home.

400 Stone Springs Ln, Middletown

$420,000

Welcome to this beautifully maintained brick Cape Cod, tucked away on a private 0.70-acre cul-de-sac lot in Middletown! Thoughtfully updated and meticulously cared for, this home offers the perfect blend of charm, comfort, and outdoor living. Step inside to find fresh interior paint, hardwood floors, updated bathrooms, and a spacious living room featuring a new gas fireplace with thermostat and remote, creating a warm and inviting gathering space. The 20' x 10' sunroom is the perfect place to relax while enjoying peaceful views of the beautifully landscaped backyard. The main-level primary bedroom provides convenient one-level living. Outside is where this property truly shines. The professionally landscaped front yard features a beautiful picket fence with decorative arch, weeping cherry tree, Japanese maple, azaleas, and a raised stone flower bed connected by a charming brick walkway. Garden enthusiasts will appreciate the established butterfly garden, raised garden beds, and mature asparagus. The fully equipped chicken coop is ready for your flock, while the yard attracts abundant wildlife, creating a peaceful country setting. Additional highlights include an oversized one-car garage with floored storage above, an outbuilding/workshop with wood stove (plus a cord of seasoned split firewood), Andersen windows, a new insulated garage door, and owned solar panels that convey free and clear, helping reduce utility costs. For added peace of mind, the sellers have completed a pre-sale home inspection, addressed the noted items, and recently installed a new chimney cap. A new Samsung washer and the sauna also convey with the home. Located at the end of a quiet cul-de-sac, this move-in-ready home offers exceptional privacy, beautiful landscaping, and countless thoughtful updates—making it a rare opportunity in the Middletown area.

3 Beds ⋅ 2 Baths ⋅ VAFV2043396 MLS

Welcome to this beautifully maintained brick Cape Cod, tucked away on a private 0.70-acre cul-de-sac lot in Middletown! Thoughtfully updated and meticulously cared for, this home offers the perfect blend of charm, comfort, and outdoor living. Step inside to find fresh interior paint, hardwood floors, updated bathrooms, and a spacious living room featuring a new gas fireplace with thermostat and remote, creating a warm and inviting gathering space. The 20' x 10' sunroom is the perfect place to relax while enjoying peaceful views of the beautifully landscaped backyard. The main-level primary bedroom provides convenient one-level living. Outside is where this property truly shines. The professionally landscaped front yard features a beautiful picket fence with decorative arch, weeping cherry tree, Japanese maple, azaleas, and a raised stone flower bed connected by a charming brick walkway. Garden enthusiasts will appreciate the established butterfly garden, raised garden beds, and mature asparagus. The fully equipped chicken coop is ready for your flock, while the yard attracts abundant wildlife, creating a peaceful country setting. Additional highlights include an oversized one-car garage with floored storage above, an outbuilding/workshop with wood stove (plus a cord of seasoned split firewood), Andersen windows, a new insulated garage door, and owned solar panels that convey free and clear, helping reduce utility costs. For added peace of mind, the sellers have completed a pre-sale home inspection, addressed the noted items, and recently installed a new chimney cap. A new Samsung washer and the sauna also convey with the home. Located at the end of a quiet cul-de-sac, this move-in-ready home offers exceptional privacy, beautiful landscaping, and countless thoughtful updates—making it a rare opportunity in the Middletown area.

2105 Shawn Dr, Middletown

$379,000

An exceptional opportunity to restore and reimagine a historic Main Street property in the heart of Middletown. Prominently located along one of the towns most recognized corridors, this four bedroom, two bath home offers timeless character, outstanding potential, and a location that is difficult to duplicate. Believed to date to the early 1800s, the home has been part of Middletown history for generations and is ready for its next chapter. Just a short walk to local shops, restaurants, cafes, and community gathering spaces, this property offers the charm and convenience of small town living. Situated on a generous in town parcel with desirable B1 zoning, the property provides exceptional flexibility for residential living, professional office, business use, or a mixed use concept subject to local approvals. The additional side land offers potential subdivision opportunities subject to application and approval. Rear alley access further enhances the versatility of this unique property while the prominent Main Street location provides outstanding visibility for a variety of future uses. Inside, the home features four bedrooms, two full baths, and the character expected of a historic residence. The property is ready for restoration and thoughtful updating, presenting an exceptional opportunity to preserve its historic charm while incorporating modern improvements. Whether your vision is a distinctive residence, professional office, investment property, or live and work opportunity, the possibilities are substantial. Historic Main Street properties offering this combination of character, location, flexible B1 zoning, additional land, rear alley access, and future potential rarely become available. Property is being sold as is.

4 Beds ⋅ 2 Baths ⋅ VAFV2043316 MLS

An exceptional opportunity to restore and reimagine a historic Main Street property in the heart of Middletown. Prominently located along one of the towns most recognized corridors, this four bedroom, two bath home offers timeless character, outstanding potential, and a location that is difficult to duplicate. Believed to date to the early 1800s, the home has been part of Middletown history for generations and is ready for its next chapter. Just a short walk to local shops, restaurants, cafes, and community gathering spaces, this property offers the charm and convenience of small town living. Situated on a generous in town parcel with desirable B1 zoning, the property provides exceptional flexibility for residential living, professional office, business use, or a mixed use concept subject to local approvals. The additional side land offers potential subdivision opportunities subject to application and approval. Rear alley access further enhances the versatility of this unique property while the prominent Main Street location provides outstanding visibility for a variety of future uses. Inside, the home features four bedrooms, two full baths, and the character expected of a historic residence. The property is ready for restoration and thoughtful updating, presenting an exceptional opportunity to preserve its historic charm while incorporating modern improvements. Whether your vision is a distinctive residence, professional office, investment property, or live and work opportunity, the possibilities are substantial. Historic Main Street properties offering this combination of character, location, flexible B1 zoning, additional land, rear alley access, and future potential rarely become available. Property is being sold as is.

7927 Main St, Middletown

$499,000

Welcome to this charming 4-bedroom, 2-bathroom home ideally situated on Main Street in the heart of Middletown, offering the perfect blend of character, comfort, and convenience. Step inside to beautiful hardwood floors that flow throughout the main level, creating a warm and inviting atmosphere. The formal living room features a cozy wood-burning fireplace, making it the perfect place to gather on chilly winter evenings. Just beyond, the formal dining room provides an elegant setting for holiday celebrations, dinner parties, and everyday meals. The updated kitchen is designed with both style and functionality in mind, featuring a spacious island perfect for entertaining, ample cabinet storage, and a bright breakfast area where you can enjoy your morning coffee while overlooking the expansive backyard. The main level offers two comfortable bedrooms and a full bathroom, providing flexible living options for guests, family, or a home office. The finished lower level includes two additional generously sized bedrooms, a second full bathroom, and a spacious laundry room with abundant storage. Outdoor living is just as inviting, with a large deck that's perfect for summer barbecues, outdoor dining, and relaxing evenings. The one-car garage offers additional storage, while the oversized backyard provides endless possibilities with plenty of room for play, gardening, pets, or future outdoor entertaining spaces. Located just moments from Middletown's charming shops, restaurants, parks, and top-rated schools, this home offers small-town living with all the conveniences you need. Don't miss your opportunity to make this beautiful Main Street home your own.

4 Beds ⋅ 2 Baths ⋅ MDFR2084834 MLS

Welcome to this charming 4-bedroom, 2-bathroom home ideally situated on Main Street in the heart of Middletown, offering the perfect blend of character, comfort, and convenience. Step inside to beautiful hardwood floors that flow throughout the main level, creating a warm and inviting atmosphere. The formal living room features a cozy wood-burning fireplace, making it the perfect place to gather on chilly winter evenings. Just beyond, the formal dining room provides an elegant setting for holiday celebrations, dinner parties, and everyday meals. The updated kitchen is designed with both style and functionality in mind, featuring a spacious island perfect for entertaining, ample cabinet storage, and a bright breakfast area where you can enjoy your morning coffee while overlooking the expansive backyard. The main level offers two comfortable bedrooms and a full bathroom, providing flexible living options for guests, family, or a home office. The finished lower level includes two additional generously sized bedrooms, a second full bathroom, and a spacious laundry room with abundant storage. Outdoor living is just as inviting, with a large deck that's perfect for summer barbecues, outdoor dining, and relaxing evenings. The one-car garage offers additional storage, while the oversized backyard provides endless possibilities with plenty of room for play, gardening, pets, or future outdoor entertaining spaces. Located just moments from Middletown's charming shops, restaurants, parks, and top-rated schools, this home offers small-town living with all the conveniences you need. Don't miss your opportunity to make this beautiful Main Street home your own.

708 E Main St, Middletown

$499,900

*One or more photos in this listing have been virtually staged using AI* Completely Renovated & Move-In Ready! Welcome to this beautifully updated ranch-style home situated on a picturesque 2-acre lot in the heart of Middletown Valley. Every detail has been thoughtfully renovated, offering a bright, modern interior with quality finishes throughout. The open and inviting floor plan is perfect for everyday living and entertaining. Step outside to enjoy the spacious backyard, offering endless possibilities for outdoor gatherings, recreation, gardening, or simply relaxing while taking in the peaceful surroundings. Enjoy the tranquility of country living while remaining just minutes from downtown Middletown, Frederick, shopping, dining, schools, parks, and major commuter routes. Whether you're looking for your forever home or a quiet retreat with modern comforts, this exceptional property is ready for its new owner. Don't miss this rare opportunity!

4 Beds ⋅ 3 Baths ⋅ MDFR2084712 MLS

*One or more photos in this listing have been virtually staged using AI* Completely Renovated & Move-In Ready! Welcome to this beautifully updated ranch-style home situated on a picturesque 2-acre lot in the heart of Middletown Valley. Every detail has been thoughtfully renovated, offering a bright, modern interior with quality finishes throughout. The open and inviting floor plan is perfect for everyday living and entertaining. Step outside to enjoy the spacious backyard, offering endless possibilities for outdoor gatherings, recreation, gardening, or simply relaxing while taking in the peaceful surroundings. Enjoy the tranquility of country living while remaining just minutes from downtown Middletown, Frederick, shopping, dining, schools, parks, and major commuter routes. Whether you're looking for your forever home or a quiet retreat with modern comforts, this exceptional property is ready for its new owner. Don't miss this rare opportunity!

9001 Hollow Rd, Middletown

$110,000

Rare opportunity to own a 1.96-acre wooded lot in the historic Town of Middletown! This unique property offers approximately 1.5 acres of buildable land located outside the floodplain, with an additional 0.5-acre parcel across the railroad tracks within the floodplain and bordered by Meadow Creek. An expired PERC approval for a 2-bedroom home is on file. Sellers have also obtained a CSX easement for construction of a barndominium, providing a valuable head start for future development. Enjoy the freedom of no HOA while creating your custom home in a picturesque, historic setting. Conveniently located just minutes from I-81 and I-66 for an easy commute to the Shenandoah Valley, Northern Virginia, and surrounding areas. Middletown is rich in history and surrounded by Civil War landmarks, making this a truly special location. The property has been discussed as a potential future addition to the nearby battlefield park. Buyers are encouraged to perform their own due diligence regarding any future municipal, historical, or conservation plans. Bring your builder and your vision to this exceptional Frederick County property!

VAFV2043052 MLS

Rare opportunity to own a 1.96-acre wooded lot in the historic Town of Middletown! This unique property offers approximately 1.5 acres of buildable land located outside the floodplain, with an additional 0.5-acre parcel across the railroad tracks within the floodplain and bordered by Meadow Creek. An expired PERC approval for a 2-bedroom home is on file. Sellers have also obtained a CSX easement for construction of a barndominium, providing a valuable head start for future development. Enjoy the freedom of no HOA while creating your custom home in a picturesque, historic setting. Conveniently located just minutes from I-81 and I-66 for an easy commute to the Shenandoah Valley, Northern Virginia, and surrounding areas. Middletown is rich in history and surrounded by Civil War landmarks, making this a truly special location. The property has been discussed as a potential future addition to the nearby battlefield park. Buyers are encouraged to perform their own due diligence regarding any future municipal, historical, or conservation plans. Bring your builder and your vision to this exceptional Frederick County property!

209 Mineral St, Middletown

$849,000

Coming soon ! Welcome to 5 Dean Lane, a stunning 4-bedroom, 4.5-bath home in the sought-after Middletown Glen community. Ideally located within walking distance of schools, parks, and the library, this exceptional home is also just minutes from the nature center, local restaurants, golf courses, and major commuter routes. Step inside to a welcoming foyer featuring a private home office, then continue past the elegant formal dining room into the spacious living room that seamlessly opens to the bright, eat-in kitchen—perfect for everyday living and entertaining. Entering through the attached 2-car garage, you'll appreciate the thoughtfully designed mudroom with built-in storage, along with an oversized pantry and convenient powder room on the main level. Upstairs offers an ideal layout with an additional loft-style lounge that provides flexible living space. The luxurious primary suite occupies its own private wing and features a sitting area, two walk-in closets, and a spa-like ensuite bath. Two additional bedrooms share a full hall bath, while the opposite wing includes a fourth bedroom with its own ensuite bath and a conveniently located laundry room. The finished walkout basement is an entertainer's dream, featuring a large recreation area, wet bar, full bathroom, and ample storage space. Outside, the beautifully hardscaped backyard offers a low-maintenance setting that's perfect for relaxing or hosting gatherings. Meticulously maintained and truly move-in ready, this thoughtfully upgraded home combines generous living spaces, quality finishes, and an unbeatable location. 5 Dean Lane has everything you've been looking for.

4 Beds ⋅ 5 Baths ⋅ MDFR2084684 MLS

Coming soon ! Welcome to 5 Dean Lane, a stunning 4-bedroom, 4.5-bath home in the sought-after Middletown Glen community. Ideally located within walking distance of schools, parks, and the library, this exceptional home is also just minutes from the nature center, local restaurants, golf courses, and major commuter routes. Step inside to a welcoming foyer featuring a private home office, then continue past the elegant formal dining room into the spacious living room that seamlessly opens to the bright, eat-in kitchen—perfect for everyday living and entertaining. Entering through the attached 2-car garage, you'll appreciate the thoughtfully designed mudroom with built-in storage, along with an oversized pantry and convenient powder room on the main level. Upstairs offers an ideal layout with an additional loft-style lounge that provides flexible living space. The luxurious primary suite occupies its own private wing and features a sitting area, two walk-in closets, and a spa-like ensuite bath. Two additional bedrooms share a full hall bath, while the opposite wing includes a fourth bedroom with its own ensuite bath and a conveniently located laundry room. The finished walkout basement is an entertainer's dream, featuring a large recreation area, wet bar, full bathroom, and ample storage space. Outside, the beautifully hardscaped backyard offers a low-maintenance setting that's perfect for relaxing or hosting gatherings. Meticulously maintained and truly move-in ready, this thoughtfully upgraded home combines generous living spaces, quality finishes, and an unbeatable location. 5 Dean Lane has everything you've been looking for.

5 Dean Ln, Middletown

$599,000

Welcome to your own private retreat! This 3-bedroom, 3 full bath home offers nearly 2,500 square feet of finished living space and comes with not one, but two parcels totaling approximately 7.63 acres. The home is situated on 5.90 acres and includes an additional 1.73-acre wooded lot located directly behind the property, providing even more privacy and future possibilities. Inside, you'll find beautiful wood flooring throughout the main level and a spacious layout designed for comfortable living. The primary suite features its own private full bath and direct access to a deck overlooking the peaceful surroundings. Two additional bedrooms and a full bath complete the main level. Enjoy the outdoors from the wraparound rear porch or entertain guests on the expansive two-tier deck. During the colder months, cozy up beside one of the home's two wood-burning fireplaces. The lower level offers additional living space along with a third full bath, making it ideal for a recreation room, guest area, or home office. With plenty of driveway parking and a 2-car attached garage, there is ample room for vehicles, equipment, and guests. Conveniently located just minutes from downtown Middletown and within the highly sought-after Middletown School District, this property offers the perfect combination of privacy, acreage, and accessibility.

3 Beds ⋅ 3 Baths ⋅ MDFR2084524 MLS

Welcome to your own private retreat! This 3-bedroom, 3 full bath home offers nearly 2,500 square feet of finished living space and comes with not one, but two parcels totaling approximately 7.63 acres. The home is situated on 5.90 acres and includes an additional 1.73-acre wooded lot located directly behind the property, providing even more privacy and future possibilities. Inside, you'll find beautiful wood flooring throughout the main level and a spacious layout designed for comfortable living. The primary suite features its own private full bath and direct access to a deck overlooking the peaceful surroundings. Two additional bedrooms and a full bath complete the main level. Enjoy the outdoors from the wraparound rear porch or entertain guests on the expansive two-tier deck. During the colder months, cozy up beside one of the home's two wood-burning fireplaces. The lower level offers additional living space along with a third full bath, making it ideal for a recreation room, guest area, or home office. With plenty of driveway parking and a 2-car attached garage, there is ample room for vehicles, equipment, and guests. Conveniently located just minutes from downtown Middletown and within the highly sought-after Middletown School District, this property offers the perfect combination of privacy, acreage, and accessibility.

2748 Bennies Hill Rd, Middletown

$1,475,000

Looking for new construction, but don't want to wait? This gorgeous 2025 built Craftsman is the perfect option! Like new, only better thanks to an investment of all the things that are a hassle to add to a new home - rear yard fence, plantation shutters and luxury shades, water softener/treatment system, an Amish garden shed and more! Move in now and do nothing but pack your personal belongings! Amazing opportunity in quiet Middletown but just minutes to all of the area's conveniences. Relax and escape to your own private retreat, enjoy sunsets on your covered back porch and find plenty of room to stretch out and play - over 5000 square feet of perfectly curated living space. Dedicated home office, formal dining and gourmet open kitchen with oversized island and eat-in breakfast area. Family room with soaring ceilings and a cozy fireplace - truly the perfect setting with floor to ceiling windows that floods the space with natural light. Smart open layout with primary bedroom suite on main level, complete with massive double-sided walk-in closet, dual vanity spaces, a soaking tub and oversized walk-in shower. Upstairs there are three generously sized secondary bedrooms, one with a private en suite bath and walk-in closet and a second hall bath. Gorgeous cat walk hallway overlooks the family room. On the lower level you have a secondary living level with yet another full bedroom and en suite bath, perfect for a guest suite. Tons of conditioned storage space finishes off the walk-out lower level. Enjoy the outdoors from your covered patio off the eat-in breakfast area/morning room and play down below in the spacious split-rail fenced rear yard. New Amish storage shed has space for all of the lawn equipment. Plenty of room for the furry family members or even a chicken run! Attached two car garage and expanded driveway has plenty of space for guest parking as well. While the peaceful setting can make you feel like you're a world away, this home is just two miles to the heart of downtown Middletown and less than 30 minutes to Downtown Frederick. Tons of great area shopping and dining, but the small town feel you've been yearning for. Don't miss out on this incredible opportunity!

5 Beds ⋅ 5 Baths ⋅ MDFR2084352 MLS

Looking for new construction, but don't want to wait? This gorgeous 2025 built Craftsman is the perfect option! Like new, only better thanks to an investment of all the things that are a hassle to add to a new home - rear yard fence, plantation shutters and luxury shades, water softener/treatment system, an Amish garden shed and more! Move in now and do nothing but pack your personal belongings! Amazing opportunity in quiet Middletown but just minutes to all of the area's conveniences. Relax and escape to your own private retreat, enjoy sunsets on your covered back porch and find plenty of room to stretch out and play - over 5000 square feet of perfectly curated living space. Dedicated home office, formal dining and gourmet open kitchen with oversized island and eat-in breakfast area. Family room with soaring ceilings and a cozy fireplace - truly the perfect setting with floor to ceiling windows that floods the space with natural light. Smart open layout with primary bedroom suite on main level, complete with massive double-sided walk-in closet, dual vanity spaces, a soaking tub and oversized walk-in shower. Upstairs there are three generously sized secondary bedrooms, one with a private en suite bath and walk-in closet and a second hall bath. Gorgeous cat walk hallway overlooks the family room. On the lower level you have a secondary living level with yet another full bedroom and en suite bath, perfect for a guest suite. Tons of conditioned storage space finishes off the walk-out lower level. Enjoy the outdoors from your covered patio off the eat-in breakfast area/morning room and play down below in the spacious split-rail fenced rear yard. New Amish storage shed has space for all of the lawn equipment. Plenty of room for the furry family members or even a chicken run! Attached two car garage and expanded driveway has plenty of space for guest parking as well. While the peaceful setting can make you feel like you're a world away, this home is just two miles to the heart of downtown Middletown and less than 30 minutes to Downtown Frederick. Tons of great area shopping and dining, but the small town feel you've been yearning for. Don't miss out on this incredible opportunity!

2802 Bidle Rd, Middletown

$150,000

Charming 1/4 acre buildable on E. Green Street. The buyer of 19 E. Main Street will have the right of first refusal on the sale. Additional photos available on the 19 E. Main Street listing MDFR2082574.

MDFR2082686 MLS

Charming 1/4 acre buildable on E. Green Street. The buyer of 19 E. Main Street will have the right of first refusal on the sale. Additional photos available on the 19 E. Main Street listing MDFR2082574.

Lot 1 E Green St, Middletown

$1,150,000

Carefully reimagined between 2018 and 2021, this historic Main Street home now lives like a luxury boutique retreat hidden in the heart of Middletown — complete with a secret speakeasy concealed behind a swinging bookshelf, a breathtaking custom kitchen addition, and a covered courtyard entertaining area anchored by a stunning stone fireplace. Rich in history yet thoughtfully transformed for modern luxury living, this extraordinary four-bedroom residence with dedicated office space blends timeless craftsmanship with sophisticated design rarely found in historic homes. Perched above historic Main Street with sunset views toward South Mountain, the home showcases soaring ceilings, original architectural details, custom Mennonite-crafted millwork, designer Circa lighting, and extensive infrastructure updates throughout. At the heart of the home is the stunning kitchen addition featuring exposed historic brick, dramatic steel scissor-beam trusses, handcrafted cabinetry, quartz perimeter counters, granite center island, GE Monogram appliances, farmhouse sink, induction cooktop, and a dramatic picture window overlooking the beautifully landscaped courtyard and covered side porch. The original kitchen was transformed into a spacious dining room, creating exceptional flow for entertaining while preserving the home’s historic character. Outdoor living spaces feel like an extension of the home itself with stamped concrete, custom stone fireplace, a covered entertaining area, integrated storage, and beautifully landscaped gathering spaces designed for both intimate evenings and large-scale entertaining. The front parlor was transformed into a stunning library with built-in shelving, restored historic shutters, statement lighting, and the hidden swinging bookshelf leading to the speakeasy featuring a solid wood bar, wet bar, beverage refrigerator, custom ceiling paneling, and dramatic finishes. The family room was created by opening two original parlors and is crowned by a dramatic bay window that floods the space with natural light. Upstairs, the home offers two primary suites along with spacious secondary bedrooms featuring exceptional flexibility, including a custom Murphy bed/work table system and built-in bay window seating. A dedicated office conceals a hidden opening into an untouched portion of the original home, creating a fascinating preserved time capsule rarely found in homes of this era. A covered upper porch overlooks the courtyard below, while the redesigned laundry room introduces marble countertops, statement lighting, and additional storage. The finished attic was transformed into a truly unique owner’s retreat featuring reclaimed oak flooring, exposed brick chimneys, preserved historic wall surfaces, dressing room, laundry chute, separate staircase access, and a spa-inspired bath with a hidden Japanese-inspired Ofuro soaking tub room. Infrastructure improvements include dedicated high-end Carrier HVAC systems with hospital-grade filtration and smart thermostats, radiant heated floors, replaced electrical systems in 2020, updated copper plumbing, Japanese toilets, hand-tooled standing seam metal roof, replacement gutters, energy-efficient wooden sash windows, composite porch decking, central vacuum, Sonos integration, and extensive custom woodworking throughout. Stretching from Main Street to West Green Street, the property also includes a subdivided, buildable rear lot. The purchaser of 19 E Main Street will have first right of refusal on the lot, which is also available separately, creating a rare opportunity for future expansion or investment in the heart of Middletown. Located on one of Maryland’s historic designated Main Streets, just steps from Middletown’s restaurants, library, shops, parks, & sought-after schools, this extraordinary residence offers a lifestyle as rare as the home itself. Owned by only three families in 100+ years, this one-of-a-kind home blends history, luxury, & craftsmanship.

4 Beds ⋅ 4 Baths ⋅ MDFR2082574 MLS

Carefully reimagined between 2018 and 2021, this historic Main Street home now lives like a luxury boutique retreat hidden in the heart of Middletown — complete with a secret speakeasy concealed behind a swinging bookshelf, a breathtaking custom kitchen addition, and a covered courtyard entertaining area anchored by a stunning stone fireplace. Rich in history yet thoughtfully transformed for modern luxury living, this extraordinary four-bedroom residence with dedicated office space blends timeless craftsmanship with sophisticated design rarely found in historic homes. Perched above historic Main Street with sunset views toward South Mountain, the home showcases soaring ceilings, original architectural details, custom Mennonite-crafted millwork, designer Circa lighting, and extensive infrastructure updates throughout. At the heart of the home is the stunning kitchen addition featuring exposed historic brick, dramatic steel scissor-beam trusses, handcrafted cabinetry, quartz perimeter counters, granite center island, GE Monogram appliances, farmhouse sink, induction cooktop, and a dramatic picture window overlooking the beautifully landscaped courtyard and covered side porch. The original kitchen was transformed into a spacious dining room, creating exceptional flow for entertaining while preserving the home’s historic character. Outdoor living spaces feel like an extension of the home itself with stamped concrete, custom stone fireplace, a covered entertaining area, integrated storage, and beautifully landscaped gathering spaces designed for both intimate evenings and large-scale entertaining. The front parlor was transformed into a stunning library with built-in shelving, restored historic shutters, statement lighting, and the hidden swinging bookshelf leading to the speakeasy featuring a solid wood bar, wet bar, beverage refrigerator, custom ceiling paneling, and dramatic finishes. The family room was created by opening two original parlors and is crowned by a dramatic bay window that floods the space with natural light. Upstairs, the home offers two primary suites along with spacious secondary bedrooms featuring exceptional flexibility, including a custom Murphy bed/work table system and built-in bay window seating. A dedicated office conceals a hidden opening into an untouched portion of the original home, creating a fascinating preserved time capsule rarely found in homes of this era. A covered upper porch overlooks the courtyard below, while the redesigned laundry room introduces marble countertops, statement lighting, and additional storage. The finished attic was transformed into a truly unique owner’s retreat featuring reclaimed oak flooring, exposed brick chimneys, preserved historic wall surfaces, dressing room, laundry chute, separate staircase access, and a spa-inspired bath with a hidden Japanese-inspired Ofuro soaking tub room. Infrastructure improvements include dedicated high-end Carrier HVAC systems with hospital-grade filtration and smart thermostats, radiant heated floors, replaced electrical systems in 2020, updated copper plumbing, Japanese toilets, hand-tooled standing seam metal roof, replacement gutters, energy-efficient wooden sash windows, composite porch decking, central vacuum, Sonos integration, and extensive custom woodworking throughout. Stretching from Main Street to West Green Street, the property also includes a subdivided, buildable rear lot. The purchaser of 19 E Main Street will have first right of refusal on the lot, which is also available separately, creating a rare opportunity for future expansion or investment in the heart of Middletown. Located on one of Maryland’s historic designated Main Streets, just steps from Middletown’s restaurants, library, shops, parks, & sought-after schools, this extraordinary residence offers a lifestyle as rare as the home itself. Owned by only three families in 100+ years, this one-of-a-kind home blends history, luxury, & craftsmanship.

19 E Main St, Middletown