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$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
$625,000
3 Beds ⋅ 3 Baths ⋅ MDFR2086228 MLS
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
$369,000
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
$369,000
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
$475,000
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
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
$839,999
4 Beds ⋅ 5 Baths ⋅ MDFR2084684 MLS
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 home also enjoys a beautiful view of the neighborhood’s open common area directly across the street, creating a spacious and inviting setting . Also 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
$575,000
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, and even hunt on your own property. 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
$709,900
3 Beds ⋅ 4 Baths ⋅ VAFV2042918 MLS
Stunning Cape Cod home is perfectly situated on 2.79 acres within the Belle Grove and Cedar Creek National Historical Park, offering a rare opportunity to enjoy the beauty and privacy of protected parkland with no future development surrounding the property. The current owners have completed numerous upgrades, including added insulation, a new pressure tank, and a new roof installed in 2024 featuring 30-year architectural shingles, along with many other improvements throughout the home. Outdoor living is exceptional, with breathtaking mountain views, a covered wraparound porch, and a spacious rear deck that creates the perfect setting for relaxing or entertaining guests. Inside, you'll find a large open kitchen with breakfast bar, generous living spaces, and numerous updates that enhance both comfort and functionality. The upper level offers three spacious bedrooms and two full bathrooms. The finished walk-out lower level provides additional living and entertaining space and opens to a patio, making it ideal for gatherings or enjoying the peaceful surroundings. A truly special property that combines modern updates, scenic beauty, and a one-of-a-kind location.

461 Veterans Rd, Middletown
$150,000
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
$2,500,000
MDFR2082478 MLS
Experience the flow of space and harmony a private 5-acre sanctuary where mid-century soul meets meticulous architectural restoration. Set among park-like grounds and hundreds of flowering trees, this retreat-like residence is wrapped by protected conservation land on two sides, delivering incomparable privacy and a serene stage for entertaining, work, and retreat. From the views of Middletown Valley and South Mountain to 1960s design roots, to modern comfort, the home embodies seclusion without sacrificing accessibility. At the heart of the living spaces, a grand fireplace anchors the flow, guiding the eye and gathering rooms into a seamless continuum. The layout invites conversations to drift from indoor to outdoor and back again, with spaces merging around this warm, sculptural anchor. From Kentucky pink sandstone and cedar exteriors to warm interior touches—wood floors, custom concrete sinks, maple doors and trim, and a well-organized mudroom and laundry area—every surface speaks to craft and longevity. On the main level the Center Room is designed for living and entertaining. It is enriched by commissioned art, beautiful Kentucky sandstone fireplace and huge windows that look out over the Middletown Valley. A wrap around deck allows transition from the indoors to out, with just a few footsteps. A dedicated library with custom maple shelving creates a quiet, sunlit mezzanine of ideas—is a perfect retreat for reading, group study, or inspiration. The stunning kitchen was designed in collaboration with local architect, Clyde Burger. The two 12’ long walnut islands and all the kitchen cabinetry is hand-built Mennonite woodwork. The work surfaces are polished concrete, and the built-in appliances are professional grade. A kitchen lounge houses built-in cabinetry and encourages family and social time as meals are prepared and enjoyed. An 18-foot NanaWall opens to dissolve the boundary between inside and outdoor. The main level laundry has clean lines, beautiful carpentry, wonderful hand built floating shelves, custom concrete surfaces and sink as well as a wet floor and direct access to the decks and yard. The mudroom and powder room also feature custom cabinetry and specially designed features, such as the concrete sink and the floating concrete benches. The primary suite is un-filled, architectural artistry with an imported floor, two walk-in closets (one cedar-lined), and a bath featuring terrazzo floors and a standout view. Two en-suite bedrooms, renovated December 2025, have wood floors with custom Navajo-inspired wood inlays. Commissioned furnishings fill of the rooms and both enjoy nature views. The lower-level spaces are also remarkable. The second grand room has a vibrant MCM fireplace and is ideal for family activities, mediation or intimate gatherings. The windows showcase the valley view, and the doors open directly to the saltwater pool. Two private rooms are ready to use as bedrooms or office spaces. The full bathroom also has a custom concrete vanity and floor and warm cork tiling. This wing of the lower-level embraces angles and has built floating shelves in the lower library. Additionally, this level offers a bright, versatile studio providing space for creativity of all types—art, writing, design, or restorative projects— to inspire and nurture imagination. The exterior grounds are a living landscape. The 5-acre parcel unfolds as a natural paradise with park-like landscaping and hundreds of flowering trees seen from every window. The long drive lined with light poles and the parking area edged by planters sets a welcoming tone as you approach the home. A multi-level Brazilian hardwood deck overlooks a heated saltwater pool; a detached barn houses a traditional Scandinavian sauna and a lounge for year-round wellness. The homes systems are wellness-oriented including geothermal HVAC, a brand-new roof with a 50-year warranty, a multi-stage water softening system.

9237 Frostown Rd, Middletown
$2,500,000
4 Beds ⋅ 5 Baths ⋅ MDFR2082166 MLS
Experience the flow of space and harmony a private 5-acre sanctuary where mid-century soul meets meticulous architectural restoration. Set among park-like grounds and hundreds of flowering trees, this retreat-like residence is wrapped by protected conservation land on two sides, delivering incomparable privacy and a serene stage for entertaining, work, and retreat. From the views of Middletown Valley and South Mountain to 1960s design roots, to modern comfort, the home embodies seclusion without sacrificing accessibility. At the heart of the living spaces, a grand fireplace anchors the flow, guiding the eye and gathering rooms into a seamless continuum. The layout invites conversations to drift from indoor to outdoor and back again, with spaces merging around this warm, sculptural anchor. From Kentucky pink sandstone and cedar exteriors to warm interior touches—wood floors, custom concrete sinks, maple doors and trim, and a well-organized mudroom and laundry area—every surface speaks to craft and longevity. On the main level the Center Room is designed for living and entertaining. It is enriched by commissioned art, beautiful Kentucky sandstone fireplace and huge windows that look out over the Middletown Valley. A wrap around deck allows transition from the indoors to out, with just a few footsteps. A dedicated library with custom maple shelving creates a quiet, sunlit mezzanine of ideas—is a perfect retreat for reading, group study, or inspiration. The stunning kitchen was designed in collaboration with local architect, Clyde Burger. The two 12’ long walnut islands and all the kitchen cabinetry is hand-built Mennonite woodwork. The work surfaces are polished concrete, and the built-in appliances are professional grade. A kitchen lounge houses built-in cabinetry and encourages family and social time as meals are prepared and enjoyed. An 18-foot NanaWall opens to dissolve the boundary between inside and outdoor. The main level laundry has clean lines, beautiful carpentry, wonderful hand built floating shelves, custom concrete surfaces and sink as well as a wet floor and direct access to the decks and yard. The mudroom and powder room also feature custom cabinetry and specially designed features, such as the concrete sink and the floating concrete benches. The primary suite is un-filled, architectural artistry with an imported floor, two walk-in closets (one cedar-lined), and a bath featuring terrazzo floors and a standout view. Two en-suite bedrooms, renovated December 2025, have wood floors with custom Navajo-inspired wood inlays. Commissioned furnishings fill of the rooms and both enjoy nature views. The lower-level spaces are also remarkable. The second grand room has a vibrant MCM fireplace and is ideal for family activities, mediation or intimate gatherings. The windows showcase the valley view, and the doors open directly to the saltwater pool. Two private rooms are ready to use as bedrooms or office spaces. The full bathroom also has a custom concrete vanity and floor and warm cork tiling. This wing of the lower-level embraces angles and has built floating shelves in the lower library. Additionally, this level offers a bright, versatile studio providing space for creativity of all types—art, writing, design, or restorative projects— to inspire and nurture imagination. The exterior grounds are a living landscape. The 5-acre parcel unfolds as a natural paradise with park-like landscaping and hundreds of flowering trees seen from every window. The long drive lined with light poles and the parking area edged by planters sets a welcoming tone as you approach the home. A multi-level Brazilian hardwood deck overlooks a heated saltwater pool; a detached barn houses a traditional Scandinavian sauna and a lounge for year-round wellness. The homes systems are wellness-oriented including geothermal HVAC, a brand-new roof with a 50-year warranty, a multi-stage water softening system.

9237 Frostown Rd, Middletown
$1,185,000
4 Beds ⋅ 4 Baths ⋅ MDFR2082170 MLS
HOME TO BE BUILT - Don't miss the final opportunity to build your custom home! Experience the breathtaking mountain views and modern luxury in this stunning new construction home to be built by Grossnickle Construction, nestled in the heart of Middletown Valley. This thoughtfully designed 4-bedroom, 3.5 bath home offers the perfect blend of elegance, comfort and functionality. Step inside to discover an open concept floor plan featuring spacious living areas, abundant natural light and high-end finishes throughout. The gourmet kitchen will impress with premium cabinetry, quartz countertops, oversized island and seamless flow into the dining and family rooms - perfect for entertaining or everyday living. Conveniently located near charming downtown Middletown, parks and commuter route, this exceptional to be built home offers the rare opportunity to personalize your dream home.

5901 Cloudberry Ct, Middletown
$464,999
4 Beds ⋅ 3 Baths ⋅ VAFV2041068 MLS
​Welcome to this move-in ready Cedar model in the Villages at Middletown—where modern design meets everyday convenience. Offering 4 bedrooms, 2.5 bathrooms, and approximately 1,900 square feet, this home delivers stylish living with an open-concept layout ideal for today’s lifestyle. The main level impresses with a sleek kitchen featuring upgraded mocha cabinetry, stainless steel appliances, and a seamless flow into the living and dining areas—perfect for both relaxing and entertaining. A versatile flex space provides options for a home office, study, or creative use. Upstairs, the spacious primary suite serves as a private retreat, complete with an oversized walk-in closet and a well-appointed ensuite bath with double vanity and a large shower. Three additional bedrooms, including two with walk-in closets, offer flexibility for a variety of needs. The conveniently located upper-level laundry room adds everyday ease. Enjoy the outdoor setting with a backyard that backs to scenic green space, providing a peaceful backdrop. The walk-out basement offers endless potential for customization—ideal for expanding your living space. A perfect blend of style, space, and opportunity—schedule your tour today.

145 Dursley Cir, Middletown
$924,500
3 Beds ⋅ 3 Baths ⋅ MDFR2080886 MLS
HOME TO BE BUILT. Nestled on a beautiful, wooded 2.25-acre lot, this to-be-built home by Grossnickle Construction offers the perfect blend of luxury and comfort. The home features 3 spacious bedrooms, including a private primary suite, 2 full bathrooms, and a convenient powder room. This plan also includes 400 sqft rec room in the basement and the option for an upstairs bonus room. Enjoy the peaceful, natural setting with mature trees and scenic surroundings while still having the opportunity to personalize your new home. This featured plan can be built as-is, tweaked to your preferences, or you can choose a completely different custom plan to fit this homesite. Don’t miss this chance to build your dream home in a truly serene location.

Mountain Church Rd, Middletown
$1,900,000
VAFV2040920 MLS
An exceptional opportunity in Middletown Virginia! This rare offering includes two parcels totaling nearly 20 acres: 7.97 +- zoned R1 with its adjoining 12.36+- zoned RA . Bring your creativity and fresh ideas, R1 zoning offers an immediate canvas, while the RA parcel invites future potential *subject to proper municipal approval* Conveniently located within town limits, coupled with mountain views and historic charm this unique offering is ready for discerning developers looking for a prime location across the Shenandoah Valley. See documents section for more information!

Tbd Veterans Rd., Middletown
$2,100,000
MDFR2078354 MLS
LOCATION! LOCATION! LOCATION!!! Prime Commercial Property Zoned GC with endless possiblilities, easy access to highways & walkability to downtown/residential development is waiting for your business! Property coonsist of TWO substantial buildings with two entrances! Enormous three story brick containing a plethora of warehouse/storage space, high ceilings, loading doc on first and second level, two restrooms, newly remodeled kitchenette, office area with seperate entence as well as access to entire building. Giant two story block builing also contains a loading doc for each level. Bring your imaginations to life, Call today to schedule a private showing!

106 N Church Street, Middletown
$989,000
3 Beds ⋅ 3 Baths ⋅ MDFR2074476 MLS
Escape the subdivision life for a residence defined by scale, privacy, and rugged utility. Set on 32.39+/- acres, this cabin-style estate is built for those who want their permanent home to feel like a fortress of solitude without sacrificing modern comforts. The interior features a recently updated kitchen equipped with new appliances and granite countertops. While there is a propane furnace, there is also a classic woodstove that provides a high-efficiency heating source and a focal point for the entertainment area in the basement. The home’s footprint is anchored by an expansive rear deck designed for four-season use; whether you’re hosting or decompressing, the integrated hot tub offers total privacy, screened by a dense canopy of mature timber to create an outdoor living room that feels completely removed from the outside world. This isn't just a woodlot; it's a gateway. The property borders Gambrill State Park, providing exploration and recreational opportunities right out your back door. For the serious outdoorsman or the family seeking an active lifestyle, the land offers endless utility for hiking, scouting, and wildlife management. The long, wooded approach ensures a level of seclusion and security that is increasingly rare, making this an ideal primary residence for those seeking a quiet, secure environment. Practicality meets potential inside and out, with a walkout basement that provides the ideal entertainment area or can be converted into a home office, gym, or additional bedrooms to grow with your needs. An existing shed provides organized storage for ATVs and maintenance equipment, keeping your primary living spaces clutter-free. Shown by appointment only, this is more than a getaway—it is a rare opportunity to own a significant piece of acreage with your ideal mountain retreat on your own recreational land in the Catocin Mountains.

8939 Hawbottom Rd, Middletown
$549,000
VAFV2039608 MLS
Rare opportunity in the heart of Middletown! Discover the perfect blend of small-town charm, open space, and future potential on this beautiful 8-acre property surrounded by scenic pastureland and mountain views. Currently used for cattle and hay production, the land is partially fenced and includes a shed, making it ready for agricultural use or the ideal setting for your own private farmette—bring your animals and start living the country lifestyle. Imagine building your dream home while enjoying the peace and wide-open space this property provides. With town water and sewer hookups available or you could do well & septic - depending on costs . you’ll have the convenience of municipal services while still enjoying the feel of rural living. Zoned RA, the parcel may offer up to three homesites (buyer to verify)—perfect for a family compound, custom home sites, or a long-term investment opportunity. Located just a short walk to historic Main Street, you can easily enjoy local restaurants, shops, and community events. Plus, I-81 is only minutes away, making commuting simple while you return home each day to your peaceful countryside retreat. Opportunities like this are hard to find in Middletown. Schedule your showing today and explore the possibilities this special property offers. Property sold as-is. Buyer to verify subdivision potential, utilities, and zoning. Property is currently in land use; rollback taxes may apply if removed. Livestock on property—showings by appointment with agent accompaniment only. The purchaser could choose to do well & septic instead of hooking up to the public utilities Q: Where is Middletown, Virginia located? A: Middletown is located in the scenic Shenandoah Valley of Virginia, just south of Winchester and minutes from Interstate 81. Q: What makes Middletown a desirable place to live? A: Middletown offers small-town charm, historic character, and beautiful mountain views while still being close to shopping, dining, and commuter routes. Q: What outdoor activities are nearby? A: Residents enjoy easy access to hiking, fishing, and exploring the Shenandoah Valley, as well as nearby parks, rivers, and scenic mountain drives. Q: Is Middletown convenient for commuters? A: Yes. With quick access to I-81 and nearby Route 11, Middletown provides a convenient commute to Winchester and surrounding Shenandoah Valley communities. Q: What is the lifestyle like in Middletown? A: The town is known for its welcoming community, historic Main Street, seasonal events, and peaceful rural surroundings that make it a great place to enjoy the Shenandoah Valley lifestyle.

Veterans - Lot 12 Rd, Middletown
$3,100,000
3 Beds ⋅ 3 Baths ⋅ VAFV2038158 MLS
Introducing FOXLEA FARM, A Stately Plantation Style Estate, where Southern Charm Meets Mountain Majesty – 58+/- Acres of Endless Potential! Welcome to your dream property—58+/- acres of scenic, cross-fenced pastureland nestled among breathtaking mountain views. This Southern gem is tailor-made for equestrian lovers, hobby farmers, or anyone seeking wide-open spaces with the comforts of modern living. A few of the Key Features Include: Panoramic Mountain Views in every direction, Automatic Waterers in each pasture—low maintenance, year-round convenience, Horse-Ready Barn with two stalls, Signature Magnolia Tree adding timeless Southern elegance, Home with Dual-Level Balconies—ideal for sunrise coffee or sunset unwinding, Cross-Fenced and ready for livestock or rotational grazing, Just Minutes from the Interstate—secluded but accessible, Possible Subdivide Opportunity—invest or expand! Whether you're looking to build your legacy homestead or develop for future value, this property offers rare versatility and classic Southern beauty. A place where refined elegance meets rustic beauty. Nestled amid rolling pastures and panoramic mountain views, this property boasts a classic English boxwood garden—a tranquil, evergreen sanctuary that adds both prestige and peace to the landscape. Whether you're strolling through boxwood-lined paths, sipping sweet tea on the balcony, or watching your horses graze at sunset, this property captures the romance of the South with timeless sophistication.

1115 Chapel Rd, Middletown
$3,100,000
3 Beds ⋅ 3 Baths ⋅ VAFV2035852 MLS
Introducing FOXLEA FARM, A Stately Plantation Style Estate, where Southern Charm Meets Mountain Majesty – 58+/- Acres of Endless Potential! Welcome to your dream property—58+/- acres of scenic, cross-fenced pastureland nestled among breathtaking mountain views. This Southern gem is tailor-made for equestrian lovers, hobby farmers, or anyone seeking wide-open spaces with the comforts of modern living. A few of the Key Features Include: Panoramic Mountain Views in every direction, Automatic Waterers in each pasture—low maintenance, year-round convenience, Horse-Ready Barn with two stalls, Signature Magnolia Tree adding timeless Southern elegance, Home with Dual-Level Balconies—ideal for sunrise coffee or sunset unwinding, Cross-Fenced and ready for livestock or rotational grazing, Just Minutes from the Interstate—secluded but accessible, Possible Subdivide Opportunity—invest or expand! Whether you're looking to build your legacy homestead or develop for future value, this property offers rare versatility and classic Southern beauty. A place where refined elegance meets rustic beauty. Nestled amid rolling pastures and panoramic mountain views, this property boasts a classic English boxwood garden—a tranquil, evergreen sanctuary that adds both prestige and peace to the landscape. Whether you're strolling through boxwood-lined paths, sipping sweet tea on the balcony, or watching your horses graze at sunset, this property captures the romance of the South with timeless sophistication.

1115 Chapel Rd, Middletown
$1,300,000
VAFV2019018 MLS
Unlock the potential of a timeless landmark with the Wayside Inn, a historic gem nestled in the heart of Middletown, Virginia. This unique property not only boasts a rich history dating back to the 18th century but also offers 22 suites all with bathrooms, 3 bars (tavern, bourbon & Speakeasy, The RED HAT), huge entertaining space for events. This is a prime commercial opportunity with an expansive land for expansion. Just under 4 acres zoned B1. With 4 acres of commercially-zoned land at your disposal, envision the expansion possibilities that could elevate this historic landmark into a thriving hub of activity. Take advantage of the ample space to create a vibrant commercial district that complements the historic character of the Wayside Inn, making it a destination for locals and tourists alike. Situated in the picturesque Shenandoah Valley, the Wayside Inn offers a scenic backdrop that enhances the allure of any commercial venture. The expansive grounds provide ample room for outdoor amenities, gardens, or additional structures to further enhance the property's appeal. Benefit from the strategic location of Middletown, with easy access to major transportation routes. The Wayside Inn's proximity to popular attractions, historic sites, and a supportive local community makes it an ideal location for a successful and sustainable business venture. Don't miss the chance to own a piece of history with a promising future. The Wayside Inn presents a rare investment opportunity where historic charm meets commercial potential. Whether you're an entrepreneur seeking a unique venture or a developer with a vision, this property is your canvas to create something extraordinary. Seize the moment and transform the future of the Wayside Inn. Embrace the legacy, write the next chapter, and make this historic landmark a cornerstone of Middletown's thriving community. Fully running and doing great, we have changed management and its now positive cash flow. its prime for an owner occupant. call for details and appointments. Open to lease option and owner financing available. Kitchen and tavern are leased. Have grants applied for in the millions to renovate it. Have insurance claim coming for a new roof as well.

7783 Main St, Middletown
$645,000
VAFV2013246 MLS
Prime commercial site. This 1.54-acre property boasts a coveted B-2 zoning, making it an ideal location for business ventures. Conveniently positioned just off Interstate 81 and a short drive from Interstate 66, this site offers excellent visibility, ensuring maximum exposure for any enterprise. Situated between two well-known establishments, McDonald's and Econo Lodge, it benefits from high traffic and customer flow. With public utilities readily available, the infrastructure is in place to support a wide range of commercial activities. Moreover, the surrounding area is experiencing substantial residential growth, indicating a thriving market and potential customer base. This commercial site's strategic location, zoning, excellent visibility, proximity to major highways, and supportive infrastructure make it an enticing prospect for entrepreneurs looking to establish or expand their businesses in a rapidly developing area.

Reliance Rd, Middletown
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