Middletown VA Homes For Sale

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

Listing courtesy of Colony Realty. Contact:

$725,000

5 Beds ⋅ 4 Baths

Professional Pictures Coming Soon!! 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

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475

$1,350,000

4 Beds ⋅ 4 Baths

Luxury Farmhouse **To Be Built **on 8.75 Private Acres Experience the perfect blend of refined craftsmanship and modern farmhouse elegance in this exceptional to-be-built custom residence, gracefully positioned on 8.75 picturesque acres. Designed with sophisticated living in mind, this stunning home offers 4 bedrooms, 3 full baths, and 1 half bath. where timeless architecture meets thoughtfully curated finishes. Step inside to soaring 10-foot ceilings, an expansive open-concept design, and a breathtaking great room anchored by a dramatic stone surrounded fireplace. Rich architectural details, including an exposed timber beam spanning the kitchen and dining area, create warmth, character, and effortless style. The gourmet kitchen is designed to impress, featuring elegant granite countertops premium, Energy Star® stainless steel appliances, custom-quality cabinetry, and generous workspace for both everyday living and entertaining. Retreat to the luxurious owner's suite, where a spa-inspired bath offers a beautifully tiled walk-in shower, a deep, soaking tub, and a tranquil atmosphere designed for relaxation. Premium luxury vinyl plank flooring throughout the main living areas provides both beauty and durability while complementing the home's sophisticated aesthetic. The striking exterior showcases crisp white smart siding, dramatic black windows, and timeless farmhouse architecture that creates unforgettable curb appeal. A spacious three-car garage and a full unfinished basement offer abundant storage and endless opportunities to customize additional living space. For those seeking an even more personalized luxury experience, a selection of premium upgrades is available, including a metal roof, an impressive double front entry door, a bonus room above the garage, and upgraded hardwood or tile flooring. Surrounded by the beauty and privacy of nearly nine acres, this extraordinary property offers the rare opportunity to create a custom home that reflects your vision while enjoying the serenity of country living with convenient access to modern amenities. Every detail has been thoughtfully designed to deliver exceptional comfort, enduring quality, and timeless appeal. *Renderings and photographs are for illustrative purposes only. Final specifications, finishes, and pricing are subject to change. Optional upgrades available at additional cost.*

Gruver Grade Dr, Middletown

Listing courtesy of Key Move Properties, LLC.. Contact: (540) 692-8186

$825,000

4 Beds ⋅ 3 Baths

Custom builder's home on 20 flat, private acres in Middletown offering the perfect blend of quality craftsmanship, comfort, and functionality. Thoughtfully designed with an open floor plan filled with abundant natural light, this home features an oversized kitchen island, stainless steel appliances, and a convenient hot water pot filler. A main-level bedroom with an adjoining full bath, currently used as an office, offers exceptional flexibility for guests, multigenerational living, or a dedicated workspace. Several bedrooms feature private ensuite baths, providing added comfort and privacy. Enjoy year-round comfort with a dual HVAC system, main-level laundry, and the potential for an upstairs laundry room with existing space and hookups already in place. Outside, the possibilities are endless with a 30' x 50' detached workshop featuring 14' ceilings, a newly built barn, chicken coop, private pond, two attached garage spaces, four detached garage spaces, and multiple outbuildings equipped with water spigots. With AG zoning, this exceptional property is ideal for hobbies, animals, equipment, or simply enjoying the space and privacy of country living. Conveniently located with easy access to both I-66 and I-81 while offering the tranquility of a private rural setting.**Photos may be virtually staged**

354 Guard Hill Rd, Middletown

Listing courtesy of Keller Williams Realty. Contact: (703) 679-1700

$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.

7927 Main St, Middletown

Listing courtesy of Coldwell Banker Premier. Contact:

$774,900

6 Beds ⋅ 5 Baths

Offering just over 3900 finished square feet, 6 bedrooms, 5 full bathrooms, a main level bedroom with access to a full bath, a 1-acre lot, no HOA, and a peaceful setting in a golf course community, this home is designed for both everyday living and entertaining. Mountain views, an 880 square foot Trex deck, a roof that's only 5 years old, and a flexible floor plan complete the package. The main level features hardwood floors through most of the living areas, a bedroom with convenient access to a full bath, formal living and dining rooms, a two story (18ft tall) foyer, laundry room, and a spacious kitchen. The updated kitchen features quartz countertops, subway tile backsplash, freshly painted cabinetry, and stainless steel appliances. Upstairs you'll find five bedrooms, including a spacious primary suite with a jetted garden tub, tiled shower, double vanity, and walk in closet. Three additional bedrooms share a full bath with double sinks. There's also a junior suite at the end of the hall with its own private full bath, making it a great option for guests or multigenerational living. The partially finished walkout basement offers even more flexible living space with two finished rooms, a full bathroom, and a large unfinished storage and mechanical room. The current media room and game room setup provides plenty of possibilities for entertaining, hobbies, a home office, or guest space. Outside, the fully fenced backyard offers plenty of open space for entertaining, recreation, pets, or simply enjoying the peaceful setting. The spacious Trex deck, completed in 2024, offers plenty of room for outdoor dining, relaxing, or gathering with family and friends. A side porch extends the outdoor living space and opens to its own separate fenced area, creating a private space that's ideal for pets, young children, or even a garden. Recent improvements include the 2024 Trex deck, backyard and side yard fencing, refinished and expanded hardwood flooring (including the main staircase), fresh interior paint, fireplace surround and mantel, quartz countertops, updated lighting, insulated garage doors and openers, extensive HVAC and plumbing improvements, radon mitigation, and smart home features including Nest thermostats, Ring cameras, and a Schlage smart lock. The extensive list of recent improvements reflects the care and investment the current owners have made throughout the home. (See attached document for full detailed list of improvements.) Located in an established neighborhood surrounded by Sly Fox Golf Club, the home offers a peaceful setting while remaining just five minutes from I-66 and ten minutes from I-81. The sellers would also consider selling the home fully furnished (to include the basement theater equipment, seating, game tables and riding lawn mower) through a separate agreement, creating a true move in ready opportunity. (See attached document for full detailed list of items.) Shown by appointment only.

80 Little Sorrel Dr, Middletown

Listing courtesy of Real Broker, LLC. Contact: 8504500442

$420,000

3 Beds ⋅ 2 Baths

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

Listing courtesy of Real Broker, LLC. Contact: 8504500442

$379,000

4 Beds ⋅ 2 Baths

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

Listing courtesy of Coldwell Banker Premier. Contact:

$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!

209 Mineral St, Middletown

Listing courtesy of Sager Real Estate. Contact:

$949,999

5 Beds ⋅ 6 Baths

PRICED BELOW APPRAISED VALUE!! Nestled on an expansive 6.84-acre lot just minutes from shopping, dining, and commuter routes, this stunning colonial exudes elegance and comfort. Built in 2013, the home features a harmonious blend of vinyl siding and stone, creating a timeless façade that invites you in. Step inside to discover five spacious bedrooms and six bathrooms. The heart of the home boasts a cozy fireplace, perfect for intimate gatherings or quiet evenings. With the primary suite on the main level along with your laundry, the home proves to be extremely functional on all levels. A fully finished basement offers endless possibilities for entertainment or relaxation, with both interior access and an outside entrance for convenience. Grab a seat at the bar, pick your spot on the couch to watch TV, work out, or play games in the game room. Enjoy the serenity of your private retreat, complete with an attached side-entry garage and ample driveway space. This property is not just a home; it's a lifestyle, offering the perfect balance of sophistication and warmth. Experience the tranquility and exclusivity that this remarkable residence has to offer, where every detail has been crafted for your comfort and enjoyment.

228 Mercys Dr, Middletown

Listing courtesy of Keller Williams Realty. Contact: 7036690099

$639,900

3 Beds ⋅ 3 Baths

Privacy, space, and convenience come together in this all-brick ranch on just over 7 acres with no HOA. All brick and offering more than 2,700 sq. ft. on the main level, this home is ready for you. The property features 3 spacious bedrooms, 2.5 baths, a living room with a brick fireplace and wood stove insert, a family room, and a large mudroom off the kitchen. The unfinished walk-out basement offers excellent potential for additional living space, storage, or a workshop. Major updates include a roof replaced in 2020, dual HVAC zones with units replaced in 2010 and 2015, septic tank pumped in fall 2025, and an new rear deck. Enjoy plenty of room for indoor and outdoor living, all while being close to everything. Please note: property has a shared driveway with deeded right of way.

298 Mcdaniel Ln, Middletown

Listing courtesy of Colony Realty. Contact:

$729,900

3 Beds ⋅ 4 Baths

Coming Soon! Interior Photos will be uploaded July 9th. First time offered on the market, this 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

Listing courtesy of Colony Realty. Contact:

$549,900

3 Beds ⋅ 2 Baths

Tucked away in a peaceful setting, this 3-bedroom, 2-bath home offers the perfect blend of comfort, functionality, and space both inside and out. The spacious kitchen features abundant cabinet and counter space, providing plenty of storage for everyday living, along with a brand-new dishwasher. The inviting living room is centered around a cozy gas fireplace and flows directly into a beautiful glass sunroom overlooking the backyard. The home features a fully renovated bathroom with a stylish walk-in shower, while the second full bath offers a relaxing jacuzzi tub. Downstairs, the walk-out basement provides additional living and entertaining space complete with a bar, mini fridge, and wine cooler. Step outside to the multi-level patio, ready for outdoor entertaining, relaxing, or the future addition of a hot tub, all while enjoying the peaceful surroundings. The property truly shines with its incredible detached garage space. The oversized 40' x 30' garage with 18-foot ceilings is a dream for car enthusiasts, boat owners, RV storage, hobbyists, or anyone in need of a workshop. Complete with its own power, heat, and water, the possibilities are endless. In addition, a second detached garage provides even more space for vehicles, equipment, storage, or projects and has its own electrical service as well. The property is also equipped with a whole-house generator, providing reliable backup power when needed. Recent updates give added peace of mind, including a new roof in 2023, brand-new flooring, fresh paint, updated trim and doors, a fully renovated full bathroom, refrigerator replaced in 2025, a commercial-grade dryer, Whirlpool washer, a hot water heater replaced in 2018, and recent landscaping and power washing that enhance the home's curb appeal and overall presentation. Prior to installing the new basement flooring, a moisture barrier underlayment was installed for added protection. This unique property offers the perfect combination of comfortable living, exceptional garage space, and a peaceful country setting. Enjoy the privacy and tranquility of rural living while remaining just minutes from shopping, dining, and convenient access to Route 66.

3586 Reliance Rd, Middletown

Listing courtesy of Samson Properties. Contact: 7033788810

$465,999

4 Beds ⋅ 3 Baths

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

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$1,900,000

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

Listing courtesy of Hunt Country Sotheby's International Realty. Contact:

$874,900

6 Beds ⋅ 6 Baths

Welcome to this stunning house offering 6,000 square feet to enjoy and PRICED BELOW assessment! Bring your design ideas because with an acceptable offer, sellers are including a credit at closing to add your personal touch or use to assist with closing costs. This expansive 6-bedroom, 6 bath home has a lot to offer, from the grand entryway to the soaring ceilings, dual staircases, beautiful crown molding, abundant natural light, 3-car garage, in-ground pool and sits on an acre. The gourmet kitchen features plenty of counter space, upgraded cherry cabinets, newer appliances, and opens to spacious living and dining areas ideal for entertaining. The main level also includes a laundry/mud room, guest bath, den/office, a bedroom with its own outside entrance, en-suite bathroom and walk in closet. Choose which staircase, walk upstairs and you will find the enormous primary suite with a spa-like bath, large walk-in closet and sitting room. Three additional bedrooms provide generous space for family, guests, or home office use, each offering direct access to an updated bathroom appointed with new quartz countertops. The basement has a bedroom, full bathroom, and flexible living spaces which can accommodate a gym, media room, or bonus rooms as desired. It is also prewired, including plumbing, for a wet bar and includes a storage room. Step outside to your backyard retreat featuring a custom-designed heated in-ground gunite pool with colorful lights for evening swims, a diving board and an attached 8 person spa. The home’s ideal location near I-66 and I-81 ensures an easy commute, while outdoor enthusiasts will appreciate being close to Skyline Drive, the Shenandoah River, local wineries and breweries, golf courses, and more. This home has been well maintained including replacing several items: new roof with upgraded 50 year shingles 9/2022, HVAC 7/2020, hot water heater 12/2023, dishwasher, refrigerator, cooktop replaced 12/2016, pool sand filter replaced 5/2017. Ask your agent for the entire list of updates and upgrades. This home is ready for you!

4 Jackson Pl, Middletown

Listing courtesy of CENTURY 21 New Millennium. Contact: 5406650700

$549,000

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

Listing courtesy of Sager Real Estate. Contact:

$725,000

Options galore! Purchase or ground lease with potential seller financing for a qualified purchaser. I-81 Exit #302 is the Gateway entrance into the Historic Town of Middletown, Virginia. This is the last remaining lot at the corner of Reliance Road and Valley Ave (Rt #11). We have 3.84 acres zoned B2 highway commercial. You are surrounded by The Village at Middletown by Ryan Homes. Richmond American Homes are building 90 additional single family homes on the south end of town. Middletown is home to Historic Wayside Inn, circa 1797, Laurel Ridge Community College with 3,500 students and staff. Immediate neighbors include; Comfort Inn, McDonalds, Dollar General, 7-11, Liberty C-store with fuel depot, Sheetz C-store with fuel depot has recently opened on the east side of the interstate. Locate your successful business venture where the growth is happening.

Reliance, Middletown

Listing courtesy of Commercial Specialists. Contact:

$3,100,000

3 Beds ⋅ 3 Baths

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

Listing courtesy of Mountains Edge Realty LLC. Contact: 5406831891

$3,100,000

3 Beds ⋅ 3 Baths

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

Listing courtesy of Mountains Edge Realty LLC. Contact: 5406831891

$385,000

RARE opportunity to own 20 private acres with approximately 400 feet of Shenandoah River frontage in the heart of the Shenandoah Valley. Recently reduced and now aggressively priced, this extraordinary property offers the perfect setting to build a luxury riverfront estate, private retreat, vacation getaway, or investment property. Tucked away in the scenic River Ridge community, this wooded parcel combines privacy, mountain views, and direct river access while remaining conveniently located near Middletown, Winchester, I-81, wineries, hiking, and outdoor recreation. Imagine mornings overlooking the river, kayaking from your own property, evenings around a firepit under the stars, and the peaceful escape of Shenandoah Valley living just a short drive from Northern Virginia and DC. With multiple potential homesite options and breathtaking natural surroundings, this property offers endless possibilities for a custom home, modern mountain retreat, or weekend escape. Properties with this combination of acreage, privacy, and Shenandoah River frontage rarely become available, especially at this price point. Bring your vision and create something truly special.

River Ridge Dr, Middletown

Listing courtesy of Samson Properties. Contact: (540) 348-4911

$1,300,000

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

Listing courtesy of RE/MAX Allegiance. Contact:

$645,000

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

Listing courtesy of Sager Real Estate. Contact:

$110,000

If you are in search of the perfect building lot that provides seclusion, yet has easy access to state maintained roads nearby. You've found it! Tremendous views of the Signal Knob Mountain from various lots! Perfect Dream Home Lot for the commuter looking to escape from the hustle of the city! Whether you want a House-on-the-Hillside Lot surrounded by seclusion, or a lot located close to the Private Common Use area for Lake Access, we have exactly what you're looking for. This is the developers last lot remaining out of 41!

Comforter Ln, Middletown

Listing courtesy of Skyline Team Real Estate. Contact:

Middletown VA Homes For Sale

Middletown VA Homes For Sale VA Homes For Sale