Middletown VA Real Estate & Homes for Sale

154 Dursley Cir, Middletown, VA 22645 is a single-family home that contains 1,680 sq ft and was built in 2023 by Ryan Homes. It contains 4 bedrooms and 2.5 bathrooms. It is housed in a very nice neighborhood. House has vinyl flooring on first floor, ceiling fan fittings in all bedrooms and living room, bathroom fitted for completion of basement. Makes a great first-time buyer home. Owner willing to leave all furniture if first time buyer to allow for instant move in for free (not part of price).

Tucked into the woods along the banks of Dry Run, this 21.78-acre property delivers the kind of privacy, usable land, and outdoor lifestyle that delivers complete comfort. The driveway follows the rocky streambed and natural beauty of Dry Run before proceeding through mature hardwoods that surround this secluded all-brick ranch, rich with wildlife, trails, and recreational opportunity. The land itself is a standout feature. Hunters, hikers, foragers, homesteaders, and outdoor enthusiasts will appreciate the trails that run throughout the property. You'll find abundant wildlife activity and natural food sources that include strawberries, raspberries, wine berries, and blackberries. This property provides excellent mushroom foraging, including Chicken of the Woods and Hen of the Woods. A well-positioned tree stand offers incredible overlook possibilities and has easily transitioned into a fabulous treehouse setup, while a partially built "she-shed" adds even more opportunity for creative or recreational use. Enjoy one-level living with a spacious covered front porch, attached 2-car garage, concrete rear patio, and an open interior design. Hardwood flooring runs throughout the main level, while the kitchen offers hardwood cabinetry and workspace plus new appliances replaced in 2025 (refrigerator, range, built-in microwave/exhaust fan). Major value updates also include a new roof, HVAC system, and water filtration system, providing peace of mind for years to come. The walk-out lower level is already roughed-in and offers approximately 1,664 additional square feet, ready to fully finish into recreation space, guest quarters, gym, office, or media room. Double doors lead directly outside toward the impressive 3-bay detached garage/workshop, complete with 12' ceilings, 3-10'x10' garage doors, electric and water service, plus a metal roof 12'x24' carport ideal for tractors, classic vehicles, ATVs, trailers, boats, or outdoor gear. Currently enrolled in Warren County's Forestal Land Use Program, this property benefits from a program designed to help preserve the land's natural setting while offering potential tax advantages. Whether your passions include hunting, trail riding, homesteading, gardening, workshop projects, or simply having room to create, explore, and enjoy the outdoors, 906 Cauthorn Mill Road makes it possible. Despite its private woodland setting, the location is exceptionally convenient with quick access to both Interstate 66 and Interstate 81, placing Northern Virginia, Winchester, Front Royal, Strasburg, and the Shenandoah Valley within easy reach. Properties combining a meticulously maintained home, wooded acreage, trails, streamside beauty, recreational opportunity, garage workspace, and commuter accessibility are increasingly a rare-find!

Elegant Colonial on 3.47 Acres. Situated on a cul-de-sac in the lovely Chimney Hill Estates in Middletown. 4 bedrooms on 2nd level with 2 full bathrooms. Main floor offers a bedroom or office and half bath. Spacious family room off of the kitchen has a gorgeous stone hearth from floor to ceiling with a pellet stove. Paved neighborhood and driveway. Black board fencing in rear of property. Mature landscaping, deck off of the kitchen and wonderful front porch. Shed & Unfinished basement with plenty of storage. Walk Out Basement is plumbed with rough in for a future bathroom. NEW ROOF and NEW FLOORING upstairs and in the main floor bedroom or office. New water heater and new pressure tank. HVAC was serviced in April 2025. Radon Remediation Installed. Installed 240 V Hook Up for an electric car (needs charger cord). 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. Professional pictures coming soon!

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.

Find yourself at home in Middletown, in a five bedroom home with a fully finished basement!! The upper level showcases 5 bedrooms provide comfortable accommodations for family or guests. The main level you will find an open floor plan that seamlessly connects the kitchen and living room, creating a warm and welcoming atmosphere perfect for daily life and entertaining. Downstairs, the finished basement significantly extends your living space with an additional 2 Dens and full bathroom. The outdoor space is perfect for play, relaxation, and enjoying the peaceful surroundings. Parking are covered with an attached 2-car garage The combination of space, layout, community make it the Perfect Home for your Family!

Privacy, space, and convenience come together in this all-brick ranch on just over 7 acres with no HOA. Built in 1989 and offering more than 2,700 sq. ft. on the main level, this home is ready for your personal updates and style. 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 updated 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.

FINAL HOUSE FOR SALE! This new construction ranch home by Richmond American is move in ready! Three bedrooms and 2 full baths. The primary suite has a large walk-in closet and a private bath. Laundry is situation near the master suite offering ultimate convenience. Large kitchen island, fireplace, deck off the great room and an unfinished basement with a 3-piece plumbing rough-in for future bathroom, ready for your personal touches! Inquire about limited-time incentives. Call today to schedule your tour of this beautiful home. Middletown Place is conveniently located just 15 minutes from Winchester and is a must see for house hunters in the Shenandoah Valley! Located directly off Valley Pike, residents will enjoy easy access to I-81 and I-66.

Nestled in a serene setting, this charming ranch-style home offers a perfect blend of comfort and functionality. Built in 1965, this well-maintained residence spans 1,560 square feet and features three inviting bedrooms and two full bathrooms, making it an ideal retreat for those seeking a cozy yet spacious living environment. Step inside to discover a warm and welcoming atmosphere, accentuated by beautiful wood flooring that flows throughout the home. The traditional floor plan seamlessly connects the living spaces, creating an inviting flow for both everyday living and entertaining. The living room, conveniently located off the kitchen, is perfect for gatherings, while the family room addition features a wood-burning fireplace, adding a touch of warmth and ambiance during cooler evenings. An air filter system enhances indoor air quality, ensuring a fresh and comfortable environment year-round. Outside, the property sits on a generous one-acre lot, providing ample space for outdoor activities or gardening. Enjoy the fresh air on the deck, perfect for morning coffee or evening relaxation. The detached garage offers additional storage and parking options, while the gravel driveway accommodates multiple vehicles. This home is not just a place to live; it's a sanctuary where memories are made. With its inviting interior, functional layout, and outdoor space, it's ready to welcome you home. Don't miss the opportunity to make this delightful property your own! Pre-listing title review completed confirming clear and marketable title. Seller prefers Brindley Ross Title for settlement; title report fee waived if buyer closes with them.

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.

SELLER REDUCED PRICE. Join us at our open house on Sunday 6/7 from 1-4. Nestled within the serene enclave of River Ridge on the Shenandoah, this exquisite ranch-style home built in 2022, offers a harmonious blend of modern luxury and natural beauty. Spanning an impressive 20 acres, the property is enveloped by a lush, wooded landscape. This home provides a tranquil retreat with breathtaking sunsets and mountain views that inspire relaxation and rejuvenation from your wrap-around porch. Step inside to discover an open floor plan that seamlessly connects the living spaces, perfect for both entertaining and everyday living. The heart of the home is the open kitchen, featuring stainless steel appliances. The spacious kitchen island invites gatherings, while the adjacent eat-in area offers a cozy spot for casual meals. Ample built-in cabinetry and a separate walk-in pantry ensures that storage is never a concern, keeping your kitchen organized and stylish. The living area is enhanced by recessed lighting and a handcrafted built-in entertainment center. The home boasts three well-appointed bedrooms, including a primary suite with a spacious walk-in closet and an en-suite bathroom featuring a walk-in shower, dual sink vanity, and custom made shelving. Additional features include 10' ceilings, a bonus room that would make a perfect home office, and a dedicated laundry area equipped with an electric dryer, washer, sink, upright freezer and cabinetry for additional storage. The property is designed with modern living in mind, ensuring comfort and functionality at every turn. Outside, the expansive lot offers endless possibilities for outdoor activities, gardening, or simply enjoying the peaceful surroundings. This property is a hunter's paradise with an abundance of trophy whitetail deer and turkey. This house has private access to the Shenandoah river within the subdivision for the fishing or outdoor enthusiasts. The rural setting enhances the sense of privacy, while the stunning mountain views serve as a picturesque backdrop for your daily life. This home is not just a residence; it's a lifestyle choice that embraces the beauty of nature while offering all the modern conveniences you desire. This home and property was recently appraised in February 2026. This home is located just minutes away from interstate 81 and 66, providing an easy commute to all areas of northern Virginia. Experience the perfect blend of luxury and tranquility in this remarkable property, where every detail has been thoughtfully curated to meet the needs of discerning buyers. Don't miss the opportunity to make this stunning home your own.

Welcome to this stunning house offering 6,000 square feet to enjoy and PRICED BELOW county tax assessment! 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 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 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. This home is ready for you!

4 -bedroom, 1.5-bath single-story home with 1,439 sq ft on a 0.14-acre lot. Features living room, second living space, dining area, kitchen, and two storage shops. Roof functional; siding and gutters may need updates. Appliances included: fridge, freezer, stove. Window AC units and wood stove. Public water & sewer, electricity by REC. Conveniently located near Frederick County schools.

Have you been looking for the perfect sophisticated and elegant historic home? Do you want everything; a gracious home, amazing space, acreage, a place for chickens, but also walkable and close to town? It sounds impossible, but you've found it! Welcome to historic Maplewood, circa 1872, know colloquially as The Tower. With no HOA and business B-1 zoning, this property presents endless possibilities, allowing dozens of potential uses! With stunning Italianate architecture and over an acre of land, this property is one in a million. This landmark home located in the heart of lovely downtown Middletown is a piece of history with all the modern conveniences. Rich with history, this amazing property was once the home and studio of John Chumley, a famous local artist. (The current owners have tons of photos and information about the history of the home that they'd love to share with you!) Too many amazing features to list; gorgeous high ceilings, original hardwood floors, wrap around built ins, huge windows, original millwork throughout, a generous kitchen and huge walk in pantry, fabulous mudroom, several outbuildings for storage and work space, an amazing chicken coop; the list goes on and on! Featuring four large bedrooms and two and half bathrooms, this home is spacious, beautiful, and elegant. The panoramic mountain views will take your breath away, especially from the tower studio room. And the home sits on a fantastic level lot behind public memorial land! All of this, located right in the center of town, so shopping and restaurants are just steps away. Middletown is an ideal location for commuters, with Rt 37, I-66 and I-81 within just a few minutes drive, not to mention all the natural beauty, activities, and amenities of the Shenandoah Valley. This is the one!!!

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.

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.