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$474,900
4 Beds ⋅ 3 Baths
"Beautiful On Birmingham" This 4-bedroom, 2 1/2 bath colonial style home is ready for you to move right in! As you enter, you'll be welcomed by the open floor plan! With a large island and plenty of cabinet space the kitchen was built for everyday life and entertainment. Spacious family room, eating area and first floor flex room perfect for a home office! Upstairs you'll find a large primary bedroom with a walk-in-closet and private bathroom. 3 additional bedrooms on the upper level as well as a full hallway bathroom and upstairs laundry room. Unfinished walk-out basement with a full rough-in for the possibility of adding an additional bathroom. Two car garage that was painted and has wooden ceiling shelves that were added. Step out back to a massive deck that was just added in 2026 and a wooden fence that was added in 2023. Additional upgrades include hardware added to the kitchen cabinets, basement staircase painted, board and batten design added to laundry room as well as laundry room cabinets added. Close to I-81 and Rt. 66 making commuting a dream!

122 Birmingham Dr, Middletown

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$389,900
4 Beds ⋅ 1 Baths
This charming ranch-style home, beautifully renovated in 2018, offers a perfect blend of comfort and modern living. Nestled on a serene half-acre lot, the property features a welcoming interior with four spacious bedrooms and a thoughtfully designed layout. Enjoy the warmth of hardwood floors throughout, complemented by upgraded countertops in the eat-in kitchen, which seamlessly connects to the dining area-ideal for gatherings. The main level includes a convenient entry-level bedrooms and a luxurious walk-in shower in the bathroom. Step outside to discover a private oasis with an above-ground pool, surrounded by lush landscaping and mature trees, providing a tranquil view of the pasture and woods. The exterior is enhanced by thoughtful features such as exterior lighting and flood lights, ensuring safety and ambiance. Located in a peaceful rural setting, this home is part of a friendly community that values connection and outdoor living. Nearby parks offer recreational opportunities, while local schools are known for their commitment to education. With easy access to public services and a gravel driveway accommodating up to four vehicles, convenience is at your fingertips. This property is not just a house; it's a place to create lasting memories. Experience the joy of living in a home that combines modern amenities with the charm of nature.

1810 Chapel Rd, Middletown

Listing courtesy of Colony Realty. Contact:

$409,900
3 Beds ⋅ 2 Baths
Adorable 5-year-young rancher backing to common area in quaint Middletown! This beautifully maintained home feels practically brand new with luxury vinyl plank flooring throughout the main living areas, brand-new carpet in the bedrooms, and fresh paint throughout. Enjoy easy one-level living with a desirable split-bedroom floor plan. The spacious kitchen opens to the dining and living areas and features stainless steel appliances, pantry, and large island—perfect for everyday living and entertaining. The generously sized primary suite offers a lovely en-suite bath and huge walk-in closet. Step outside to the beautiful composite rear deck with stairs leading to the fully fenced backyard with privacy fencing. With common area behind the home and no home directly beside you on one side, you’ll enjoy a nice sense of privacy. The full walk-out basement offers excellent potential for additional living space, a recreation room, home office, or whatever suits your needs. One room is already framed and just needs drywall, and rough-in plumbing is in place for a potential third bathroom. Sliding glass doors lead to a composite patio and backyard. A concrete driveway and two-car garage add convenience, while one of the home’s standout features is the solar panel system, valued at approximately $50,000 and included in the sales price! Enjoy the potential for significantly reduced electric bills, along with the option to sell excess solar energy you don’t use, subject to the applicable utility agreement. If you’re looking for one-level living, a two-car garage, energy savings, outdoor space, privacy, and room to grow, this home checks all the boxes! A wonderful opportunity in a charming Middletown setting with thoughtful updates and plenty of potential to make it your own.

131 Emmet St, Middletown

Listing courtesy of Colony Realty. Contact:

$700,000
3 Beds ⋅ 4 Baths
FIRST TIME ON THE MARKET! Discover the exceptional charm of this custom-built, one-owner home, gracefully positioned on a picturesque 2.33-acre knoll in desirable Chimney Hills Estates. Beautifully maintained and thoughtfully designed, this 2017 custom home built by Donald Adams, offers a wonderful blend of elegance, comfort, and easy living. The home is heated and cooled with a heatpump and the there is propane fueled backup for the heat. The inviting main level features a welcoming foyer, private office, dining room, and an impressive great room showcasing a cathedral ceiling and fireplace. The thoughtfully designed split-bedroom floorplan provides privacy, with the spacious primary suite and bath on one side of the home and two additional bedrooms and a full bath on the opposite side. The beautifully appointed kitchen is sure to impress, featuring quartz countertops, a quartz-topped island, stainless steel appliances, tile flooring, a large pantry, and a convenient breakfast bar. An additional sitting/breakfast area overlooks the expansive rear yard and provides a seamless connection to the outdoors. Hickory flooring graces the main living areas, adding warmth and timeless appeal. A true highlight is the welcoming sunroom, where beautiful views of the rear grounds create a peaceful retreat year-round. Step outside onto the private deck—perfect for morning coffee, entertaining, or simply enjoying the tranquil setting. The deck is conveniently accessible from both the sunroom and primary bedroom. The lower level offers a finished recreation room with doors leading directly to the rear of the property, while the unfinished portion provides abundant storage and exciting possibilities for future expansion. Set on a beautiful 2.33-acre homesite with a peaceful, elevated setting, this lovingly maintained custom home offers a rare opportunity to enjoy quality construction, thoughtful design, privacy, and beautiful surroundings—all in one exceptional property. A truly special home, ready for its next chapter!

440 Chimney Cir, Middletown

Listing courtesy of Colony Realty. Contact:

$334,000
3 Beds ⋅ 2 Baths
ROOMY RANCHER ON MORE THAN HALF AN ACRE! IN MIDDLETOWN, COMMUTER CONVENIENT TO I-81, I-66, Winchester, Stephens City, Strasburg and Front Royal. Near historic Belle Grove Plantation and Cedar Creek Battlefield, Laurel Ridge Community College, the Blue Ridge Mountains and the Shenandoah River. Don't let this one get away! So much bigger than it looks! This 3-bedroom rancher at the end of a cul-de-sac awaits your remodeling and reimagination. Glass-enclosed double porches overlook the private back yard. Full basement features a gas fireplace with a brick hearth and a large space that longs to be finished as a family room. The rear carport and basement garage are perfect for those with hobbies or who like to work on cars. Carport can double as a covered patio for backyard picnics. Large kitchen with gas cooktop and an electric wall oven. Whole house fan. Hot water heater with expansion tank 2025. Uninstalled window air conditioning unit (still in box) conveys. Roof with architectural shingles 2013. Sold as-is.

2111 Shawn Dr, Middletown

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$995,000
Rare opportunity to own 63.48± acres in northern Warren County featuring a scenic mix of open fields, mature woodlands, and West Run Creek winding through the property. Whether you're seeking a private estate, recreational retreat, hunting property, or long-term land investment, this property offers exceptional privacy and natural beauty with potential for future low-density residential development and subdivision opportunities subject to county approvals. Existing well, septic, electric service, and a 1,430 SF manufactured home convey as-is. Enjoy a secluded rural setting while remaining conveniently located near Front Royal, Middletown, Strasburg, and Winchester, with excellent access to Route 522, I-66, I-81, shopping, restaurants, and regional employment centers.

105 Ridgemont Rd, Middletown

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$815,000
6 Beds ⋅ 4 Baths
Discover a rare opportunity to own an exceptional custom residence where timeless craftsmanship, refined comfort, and peaceful natural surroundings come together. Nestled on five picturesque wooded acres within an exclusive lake community in Middletown, this remarkable estate offers over 4,700 square feet of beautifully designed living space, creating the perfect balance of luxury, privacy, and everyday functionality. Thoughtfully designed, the home features six bedrooms and three-and-a-half bathrooms, providing exceptional flexibility. A dedicated office on the main level creates an elegant work-from-home space, while an expansive loft offers endless possibilities as a library, media lounge, or additional gathering area. The spacious primary suite is conveniently located on the first floor, featuring access to the deck, a stone fireplace and private ensuite bathroom. At the heart of the home, the chef-inspired kitchen is equipped with newer appliances—all less than five years old—and seamlessly flows into generous living and dining spaces designed for effortless entertaining. The walk-out lower level is partially finished and already plumbed for a future full bath, offering exceptional potential to create a luxury guest suite, fitness studio, wine cellar, home theater, or recreation space tailored to your vision. Step outside to experience the home's true sanctuary. A custom multi-level deck overlooks the wooded landscape, providing multiple outdoor living spaces for entertaining or quiet relaxation. A reinforced section has already been engineered to accommodate a hot tub, creating the perfect setting for enjoying peaceful evenings beneath the stars. Exceptional features continue with an oversized two-car garage and the added confidence of a whole-home gas generator, ensuring comfort and peace of mind in every season. Residents enjoy access to the community's private lake, offering opportunities for fishing, kayaking, and embracing the beauty of the surrounding countryside. Despite its serene setting, the property remains conveniently located near commuter routes, historic Middletown, wineries, outdoor recreation, and all that the Shenandoah Valley has to offer. Offering an extraordinary combination of luxury, privacy, and room to grow, this distinguished estate is more than a home—it's a lifestyle.

816 Great Lake Dr, Middletown

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$649,000
THE FINANCING MAY BE AS IMPRESSIVE AS THE HOME! Offered at $649,000 with the potential opportunity for a qualified purchaser to assume the seller's existing VA loan. A VA assumption could offer a tremendous financing advantage compared with obtaining an entirely new mortgage, depending upon the existing loan terms and the buyer's financing structure. Veteran status is not necessarily required to assume a VA loan. Assumption is subject to buyer qualification and approval by the loan servicer/VA. Ask about the VA ASSUMABLE LOAN opportunity when scheduling your showing! Rare commercial opportunity in the heart of Middletown, ideally located directly across the street from the famous Wayside Theater and just minutes from I-81 with excellent accessibility and visibility. Zoned B-1 Commercial, this versatile property offers endless possibilities for business owners, investors, or developers seeking a unique space with flexible use options. Take advantage of the opportunity to live in or rent the attached apartment while running your business from the main portion of the home. See the attached document that outlines potential uses. The property features a beautifully maintained 1920s building full of character, including an inviting front porch, welcoming foyer, grand staircase, hardwood floors, exposed brick, and multiple decorative fireplaces that create a distinctive setting for a variety of commercial uses. The updated kitchen, numerous private rooms, and multiple bathrooms provide a functional layout well suited for professional offices, boutique retail, medical or wellness practices, hospitality, event space, or other approved commercial ventures. A significant advantage is the attached second unit, complete with its own kitchen, living area, two bedrooms, and two-and-a-half baths, offering exceptional flexibility for additional office space, employee accommodations where permitted, rental income, or complementary business operations. The configuration also allows the spaces to function independently or be integrated into one larger commercial operation. Situated on an expansive lot, the property includes a detached two-car garage with additional storage, a storage shed, abundant off-street parking, and ample outdoor space to accommodate a variety of business needs. Combining historic charm, modern updates, and valuable commercial zoning, this is a rare opportunity to establish or expand your business in a prime Middletown location with outstanding long-term investment potential.

7760 Main St, Middletown

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$649,000
THE FINANCING MAY BE AS IMPRESSIVE AS THE HOME! Offered at $649,000 with the potential opportunity for a qualified purchaser to assume the seller's existing VA loan. A VA assumption could offer a tremendous financing advantage compared with obtaining an entirely new mortgage, depending upon the existing loan terms and the buyer's financing structure. Veteran status is not necessarily required to assume a VA loan. Assumption is subject to buyer qualification and approval by the loan servicer/VA. Ask about the VA ASSUMABLE LOAN opportunity when scheduling your showing! Exceptional investment opportunity in the heart of Middletown, directly across from the famous Wayside Theater, and conveniently located just minutes from I-81. This unique property features two attached living units, offering outstanding income potential, multigenerational living, or the flexibility to occupy one unit while generating rental income from the other. The main residence showcases the timeless charm of a 1920s home with an inviting front porch, welcoming foyer, beautiful staircase, wood floors, exposed brick, and multiple decorative fireplaces. The updated kitchen features modern cabinetry and a center island. The main unit includes two main-level bedrooms with private en-suite baths, while the upper level offers a spacious primary suite with a walk-in closet and attached bath, plus two additional bedrooms that share a hall bath. The attached second unit is fully equipped with its own kitchen, living room, two bedrooms, and two-and-a-half baths, making it ideal for long-term tenants, short-term rental opportunities (subject to local regulations), or extended family. The property's layout also provides the option to combine both units into one expansive residence if desired. Situated on a generous lot, the property includes a detached two-car garage with additional storage, a storage shed, ample off-street parking, and plenty of outdoor space. Whether you're an investor seeking strong rental potential or a buyer looking for a property with flexible living and income opportunities, this one-of-a-kind multifamily property offers exceptional value in a prime location.

7760 Main St, Middletown

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$649,000
7 Beds ⋅ 7 Baths
THE FINANCING MAY BE AS IMPRESSIVE AS THE HOME! Offered at $649,000 with the potential opportunity for a qualified purchaser to assume the seller's existing VA loan. A VA assumption could offer a tremendous financing advantage compared with obtaining an entirely new mortgage, depending upon the existing loan terms and the buyer's financing structure. Veteran status is not necessarily required to assume a VA loan. Assumption is subject to buyer qualification and approval by the loan servicer/VA. Ask about the VA ASSUMABLE LOAN opportunity when scheduling your showing! Single family or multi-family with an approved, attached apartment - directly across from the famous Wayside Theater! This is a rare opportunity to own prime real estate in Middletown on a beautiful, large lot. Nestled in the heart of Middletown and just minutes from I-81, this exceptional 1920s home blends timeless character with modern updates. From the inviting front porch to the welcoming foyer with its stunning staircase, you'll immediately appreciate the home's classic charm. Beautiful wood floors, exposed brick, and multiple decorative fireplaces add warmth and character throughout. The updated kitchen features modern cabinetry, a center island, and ample space for gathering. Two main-level bedrooms each offer private en-suite baths, providing flexible living arrangements. Upstairs, the spacious primary suite includes a walk-in closet and attached bath, along with two additional bedrooms that share a hall bath. A unique highlight of this property is the attached second living unit located at the rear of the home. Complete with two bedrooms, two-and-a-half baths, a full kitchen, and living room, this space offers endless possibilities. It can serve as an in-law suite, guest quarters, or be seamlessly incorporated into the main residence to significantly expand the home's living space. The property also includes a detached two-car garage with additional storage, a storage shed, abundant parking, and plenty of outdoor space to enjoy. This one-of-a-kind property offers historic charm, flexible living options, and an unbeatable location.

7760 Main St, Middletown

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$585,000
THE FINANCING MAY BE AS IMPRESSIVE AS THE HOME! Offered at $585,000 with the potential opportunity for a qualified purchaser to assume the seller's existing VA loan. A VA assumption could offer a tremendous financing advantage compared with obtaining an entirely new mortgage, depending upon the existing loan terms and the buyer's financing structure. Veteran status is not necessarily required to assume a VA loan. Assumption is subject to buyer qualification and approval by the loan servicer/VA. Ask about the VA ASSUMABLE LOAN opportunity when scheduling your showing! Exceptional commercially zoned property in the heart of Middletown, offering outstanding visibility and accessibility on a quiet one-way street just off Main Street and only minutes from I-81. Situated on a beautiful 1-acre lot, this unique property presents endless possibilities for a variety of professional, retail, office, or mixed-use applications. The flexible floor plan provides ample space to customize for your business needs, with multiple large rooms that can easily accommodate private offices, conference areas, client meeting spaces, or collaborative work environments. A convenient half bath on the main level serves customers and staff, while the upper level features additional rooms and two full bathrooms, making the property well-suited for expanded office space, live/work potential or other commercial uses. Inside, the property showcases timeless architectural details that create a distinctive and welcoming atmosphere. Beautiful hardwood floors, impressive thick moldings, custom built-ins, decorative fireplaces, and a grand entrance foyer with a stunning spiral staircase combine historic charm with professional appeal, helping your business make a lasting impression. With abundant space, flexible configuration, exceptional character, and a highly desirable location close to major transportation routes, this is a rare opportunity to establish or expand your business in one of Middletown's most convenient and recognizable locations.

2239 Sixth St, Middletown

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$585,000
4 Beds ⋅ 3 Baths
THE FINANCING MAY BE AS IMPRESSIVE AS THE HOME! Offered at $585,000 with the potential opportunity for a qualified purchaser to assume the seller's existing VA loan. A VA assumption could offer a tremendous financing advantage compared with obtaining an entirely new mortgage, depending upon the existing loan terms and the buyer's financing structure. Veteran status is not necessarily required to assume a VA loan. Assumption is subject to buyer qualification and approval by the loan servicer/VA. Ask about the VA ASSUMABLE LOAN opportunity when scheduling your showing! Welcome to this stunning Circa 1872 farmhouse nestled in the heart of Middletown with a stunning view! Situated on a gorgeous 1-acre lot on a quiet one-way street just off Main Street, this spacious property offers the perfect blend of peaceful living and everyday convenience, with easy access to I-81. Zoned B1, it offers many possibilities for either residential or commercial use, including a Bed and Breakfast! (see attached document). Step inside to discover timeless character and charm, featuring gorgeous period details including thick moldings, custom built-ins, decorative fireplaces, and beautiful hardwood floors. The impressive entrance foyer, featuring a grand spiral staircase, welcomes you and creates a memorable first impression. This home is absolutely perfect for entertaining, also featuring a grand dining room and details throughout that only a home of this era can offer. The thoughtfully designed second level offers four spacious bedrooms and two full bathrooms, providing privacy for family and guests. A convenient half bath on the main level is ideal for entertaining. Complete your journey to the third story overlook and enjoy the most beautiful sunsets you can imagine in the Shenandoah Valley - read, paint, meditate, or just relax and enjoy this very unique space. This exceptional home is ready to welcome its next owner.

2239 Sixth St, Middletown

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$525,000
4 Beds ⋅ 3 Baths
AVAILABLE FOR SALE AND RENT!! Rental listing is VAFV2044396. MOVE IN READY!!! 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

Listing courtesy of Century 21 Redwood Realty. Contact:

$699,999
3 Beds ⋅ 3 Baths
Welcome to 289 Reliance Woods Dr – a thoughtfully designed, all-brick rancher on 3 peaceful acres in the heart of Reliance Woods. Built with long-term comfort in mind, this one-level home offers a spacious, accessible layout ideal for everyday living and aging in place. Wide doorways, minimal steps, and generous room sizes make the home functional without sacrificing warmth or charm. The main living area is bright and open, flowing into the kitchen and dining space—perfect for gathering or unwinding. The primary suite provides a private retreat, while the additional bedrooms offer flexibility for guests, a home office, or hobbies. A full walk-up attic provides abundant storage or potential for future expansion. The oversized two-car garage delivers plenty of space for vehicles, tools, and equipment—with room to spare. Outdoors, enjoy wooded views, open space, and the peaceful rhythm of country living—all within easy reach of town amenities. If you’re looking for a solid, stylish home that’s built to grow with you—this is the one.

289 Reliance Woods Dr, Middletown

Listing courtesy of Samson Properties. Contact: 7033788810
$449,900
3 Beds ⋅ 2 Baths
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:

$1,350,000
4 Beds ⋅ 4 Baths
Upscale Modern Farmhouse To Be Built on 8.75 Acres Experience the perfect balance of refined craftsmanship and modern farmhouse elegance. This exceptional to-be-built custom residence is beautifully positioned on 8.75 primarily cleared picturesque acres with a small band of trees at the center, offering a sophisticated retreat with plenty of room to breathe. Designed for premium country living, the thoughtful layout features 4 bedrooms, 3 full baths, and 1 half bath, matching timeless architecture with high-quality finishes. Inside, soaring 10-foot ceilings and an expansive open floor plan create a bright, welcoming atmosphere. The impressive great room centers around a dramatic stone-surrounded fireplace, while rich architectural details—like the exposed timber beam spanning the kitchen and dining areas—add warmth and distinct character. Built for effortless entertaining, the gourmet kitchen features elegant granite countertops, custom-quality cabinetry, and premium Energy Star® stainless steel appliances. The main-level owner's suite serves as a peaceful private retreat. Its spa-inspired bath offers a beautifully tiled walk-in shower, a deep soaking tub, and a tranquil atmosphere. High-end luxury vinyl plank flooring runs throughout the main living areas, blending premium styling with everyday durability. The striking exterior showcases crisp white smart siding, dramatic black window frames, and a spacious three-car garage. A full unfinished basement provides excellent storage and a blank canvas for future living space. For those looking to further personalize the property, premium upgrade options include a metal roof, a double front entry door, a bonus room above the garage, and upgraded hardwood or tile flooring. Don't miss this rare opportunity to build a custom home tailored to your lifestyle. ------------------------------ Featured Details- * Acreage: 8.75 acres * Bedrooms: 4 spacious bedrooms * Bathrooms: 3 full baths, 1 half bath * Main Living: 10-foot ceilings, open-concept layout, stone fireplace * Kitchen: Granite countertops, custom cabinetry, Energy Star® appliances * Owner's Suite: Tiled walk-in shower, deep soaking tub * Parking: Attached 3-car garage * Basement: Full footprint, unfinished * Upgrades Available: Bonus room, metal roof, hardwood or tile flooring *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
$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:

$369,000
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:

$709,900
3 Beds ⋅ 4 Baths
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:

$535,000
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
$464,999
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:

$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:

$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
20 acres of privacy, peace, and possibilities in the beautiful River Ridge community! If you’ve been looking for acreage where you can create a private retreat, homestead, or custom home surrounded by nature, this property deserves a closer look. The generous acreage and established community restrictions help preserve the spacious, rural character of the area—protecting your investment from becoming a crowded development of smaller homes and multiple structures. Imagine driving through River Ridge and seeing the difference: larger homesites, wooded privacy, open space, and room to breathe. This is an opportunity to build something truly special in a setting designed to maintain its natural beauty and sense of privacy. The property offers the opportunity to create your own private escape while still being within convenient reach of Front Royal and the surrounding Shenandoah Valley. Bring your vision and explore the possibilities this beautiful 20-acre parcel has to offer. Buy the acreage, enjoy the privacy, and invest in a community where the restrictions help protect the character and value of your property for years to come. Buyers should independently verify building requirements, permitted uses, road access, utilities, and all covenants and restrictions with the appropriate authorities and HOA.

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: