Middletown Homes with Frederick County Public Schools School district

Welcome to Middletown, Maryland—a charming town nestled in the heart of Frederick County. Known for its picturesque landscapes and rich history, Middletown offers a delightful blend of small-town charm and modern conveniences. With its tree-lined streets, historic buildings, and vibrant community spirit, this town is the perfect place to call home.

Middletown is ideally situated just a short drive from the bustling city of Frederick, providing residents with easy access to a variety of shopping, dining, and entertainment options. Nature enthusiasts will appreciate the town’s proximity to beautiful parks and outdoor recreational areas, including the stunning Catoctin Mountain Park and the serene Middletown Community Park, which features walking trails, playgrounds, and picnic areas.

Families will find a welcoming environment in Middletown, thanks in part to its strong commitment to education. The town falls within the Frederick County Public Schools district, known for its high-quality educational programs and dedicated staff. Children in Middletown have access to excellent schools that prioritize academic achievement and community involvement, ensuring a bright future for the next generation.

When it comes to real estate, Middletown offers a diverse range of homes to suit various lifestyles and budgets. From charming historic houses to modern family homes, there’s something for everyone. With its friendly atmosphere, exceptional schools, and beautiful surroundings, Middletown is not just a place to live; it’s a community where you can truly thrive. Discover your dream home in this enchanting town and experience the warmth and charm of Middletown for yourself!

Newest Middletown Homes with Frederick County Public Schools School district

$540,000

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

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

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

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

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

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

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

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

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

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

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

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

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