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$300,000
3 Beds ⋅ 1 Baths
Charming 3-Bedroom Rambler on a Spacious Lot! Welcome to 111 Haven Terrace, a conveniently located 3-bedroom, 1-bath rambler situated on approximately 0.26 acres. This single-level home offers a practical layout with comfortable living spaces and plenty of potential to make it your own. The main-level living design provides easy access throughout the home, making this property a great fit for first-time buyers, downsizers, or anyone looking for a manageable home without stairs. The level lot offers space for outdoor enjoyment, gardening, entertaining, or future improvements. With three bedrooms, a full bath, and a manageable footprint, this home offers an excellent opportunity for a buyer looking for affordability and convenience. Bring your vision and add your personal touches to create the home you've been looking for.

111 Haven Ter, Winchester

Listing courtesy of EXP Realty, LLC. Contact: 8668257169
$230,000
2 Beds ⋅ 1 Baths
Investor opportunity in Winchester! This 2-bedroom, 1-bath home offers 1,112 finished square feet above grade, plus a full unfinished basement with additional space for storage, renovation, or future improvements. The home also features two fireplaces and a convenient carport. Located within the City of Winchester, this property presents an excellent opportunity for an investor, renovator, or buyer looking to bring their vision to life. With the right updates, this home has the potential to shine. Property is being sold strictly AS-IS. Seller will make no repairs.

214 Molden Dr, Winchester

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$380,000
4 Beds ⋅ 3 Baths
Nestled in the serene Wilde Acres community, this exquisite Colonial-style residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. Built in 2007 and thoughtfully renovated in 2019, this home boasts a pristine condition and modern amenities that cater to the discerning homeowner. Step inside to discover an inviting open floor plan that seamlessly connects the family room, dining area, and gourmet kitchen. The heart of the home features upgraded countertops, a spacious pantry, and energy-efficient appliances, including a self-cleaning oven and an ENERGY STAR dishwasher. The kitchen's breakfast area is bathed in natural light, making it an ideal spot for morning coffee or casual meals. Recessed lighting and ceiling fans throughout enhance the ambiance, while the cozy gas fireplace with glass doors in the family room invites relaxation on cooler evenings. With four generously sized bedrooms, including a primary suite complete with a luxurious en-suite bathroom and walk-in closet, this home provides ample space for both privacy and togetherness. The additional bathrooms are elegantly designed, featuring a tub shower combination that adds a touch of sophistication. The exterior of the property is equally impressive, situated on a corner lot of 0.3 acres that adjoins open space, offering both tranquility and scenic mountain views. Enjoy outdoor living on the expansive deck, perfect for entertaining or unwinding in the fresh air. The property is equipped with secure storage options and exterior lighting, ensuring both convenience and safety. Additional features include a full unfinished basement with outside and side entrances, providing endless possibilities for customization, whether as a workshop or additional living space. The gravel driveway accommodates up to six vehicles, making hosting gatherings effortless. Residents of Wilde Acres enjoy exclusive access to community amenities, including a community center, picnic area, and a picturesque lake, fostering a sense of community and connection. The association also takes care of road maintenance and snow removal, allowing you to focus on enjoying your home. This property is not just a house; it's a lifestyle. Experience the perfect blend of luxury, comfort, and community in this stunning Wilde Acres residence, where every detail has been thoughtfully curated for your enjoyment.

900 Enfield Dr, Winchester

Listing courtesy of Spring Hill Real Estate, LLC.. Contact: 7038914520
$350,000
3 Beds ⋅ 2 Baths
Nestled in a charming neighborhood, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 1954, this brick beauty exudes timeless appeal while providing modern living spaces that cater to today's lifestyle. With 1,507 square feet of thoughtfully designed space, this residence features three cozy bedrooms and one and a half bathrooms, making it an ideal retreat for anyone seeking a warm and inviting atmosphere. As you step inside, you'll be greeted by a spacious layout that encourages both relaxation and entertaining. The partially finished basement offers endless possibilities-whether you envision a cozy family room, a home office, or a play area, the choice is yours! The main living areas are bathed in natural light, creating a welcoming ambiance that feels like home. The exterior of the property is equally inviting, with a classic brick façade that stands the test of time. Enjoy the convenience of on-street parking, ensuring that you and your guests always have a place to park. The surrounding neighborhood is a tapestry of tree-lined streets and friendly faces, fostering a sense of community that is hard to find. Location is key, and this home does not disappoint. Situated in a vibrant area, you'll find an array of local amenities just a stone's throw away. Explore nearby parks for leisurely strolls or picnics, and take advantage of local shops and eateries that add character to the community. Whether you're grabbing a morning coffee or enjoying a weekend brunch, the neighborhood offers a delightful selection of options to satisfy your cravings. For those who appreciate the outdoors, the proximity to parks and recreational areas provides ample opportunities for hiking, biking, and enjoying nature. The community is well-connected, making it easy to access nearby attractions and essential services. This charming ranch-style home is more than just a property; it's a place where memories are made and cherished. With its inviting atmosphere, convenient location, and potential for personalization, this residence is ready to welcome you home. Don't miss the chance to make this delightful space your own!

1048 Woodland Ave, Winchester

Listing courtesy of Re/Max Roots. Contact: (540) 686-7362
$710,000
5 Beds ⋅ 4 Baths
Welcome to 110 Betpath Ct, nestled within the premier Twin Lakes Overlook (TLO) enclave of exclusively single-family homes by Toll Brothers and Richmond American, this exceptional 2019-built executive estate offers an unmatched lifestyle in Winchester. Spanning nearly 4,000 square feet of refined living space, this property combines high-end craftsmanship with an extraordinary, functional layout. The Main & Upper Levels Designed for effortless entertaining and daily comfort, the main level features an expansive formal dining room and a sophisticated living room. The heart of the home is a gourmet chef's kitchen showcasing sleek silver appliances, abundant custom cabinetry, and premium granite countertops throughout. This space flows seamlessly into a sprawling great room and family room framing serene views of the private, tree-lined backyard. Upstairs, the residence offers five spacious bedrooms, highlighted by a true primary sanctuary featuring an expansive master suite complete with a luxurious ensuite bath, indulgent Jacuzzi soaking tub, and a separate stand-up shower. The Lower Level & Outdoor Living The fully finished lower level functions as a self-contained apartment space, offering ultimate flexibility for guests or multi-generational living. It includes an expansive sixth bedroom (NTC), a luxury full bath with a soaking tub, a practical kitchenette equipped with a sink and refrigerator, and convenient all-in-one laundry hookups. A private walk-up leads directly out to the generous, beautifully treed backyard, creating a secluded outdoor haven. Residents of TLO also enjoy exclusive neighborhood perks, including private community lake access and scenic walking/running trails just steps from your door. Prime Location Conveniently situated just minutes from historic downtown Winchester’s vibrant shops and dining, this home places you in close proximity to the renowned Winchester Hospital and the expansive 170-acre Jim Barnett Park and Family Sports facilities. Blending executive elegance with everyday practicality, this property delivers a premier Northern Virginia living experience. Schedule your private tour today!

110 Bentpath Ct, Winchester

Listing courtesy of Realty Aspire. Contact: 7034290188
$429,000
3 Beds ⋅ 2 Baths
Awesome Interior Photo's Coming Soon! Step inside this tastefully renovated brick ranch and feel instantly at home. Offering three comfortable bedrooms and two full baths, this property blends classic charm with thoughtful updates throughout. The main level features a bright, welcoming layout perfect for everyday living, while the lower level opens the door to exceptional flexibility — complete with its own entrance, a full bath, and a kitchenette. It’s an ideal setup for multi‑generational living, extended guests, or a turnkey investment opportunity ready for rental income. Outside, the large fenced yard provides space to relax, play, garden, or gather, and the off‑street parking adds everyday convenience. The location couldn’t be better: close to schools, the college campus, Historic Downtown Winchester, and a wide range of shopping and commuter routes. A move‑in‑ready home with options, comfort, and character — schedule your tour today and see how perfectly it fits your needs. Schedule your tour today!Awe

1412 S Loudoun St, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$499,900
3 Beds ⋅ 2 Baths
Looking for one-level living with acreage, a detached workshop/garage, RV/camper parking, and no HOA? Welcome to 1960 Siler Road, a custom-built ranch situated on 5 fenced acres in Winchester. The home offers a comfortable and functional floor plan with hardwood flooring throughout much of the home, Corian countertops, stainless steel appliances, and a sunroom located just off the primary bedroom. Outside, the property offers plenty of versatility with an attached two-car garage plus an approximately 23'6" x 29'11" detached workshop/garage with its own electric service, roll-up door, covered storage areas, dedicated RV parking, and a 30-amp RV hookup. With no HOA or restrictive covenants, there’s room to make the acreage your own. Bring the chickens, create a garden, or simply enjoy the extra space. Recent improvements include an updated shower, new dishwasher, new mini blinds, and a LeafFilter gutter protection system. Additional features include a tankless water heater, owned propane tank, and whole-house generator. With one-level living, 5 fenced acres, no HOA, RV/camper accommodations, and substantial garage and workshop space, 1960 Siler Road offers a combination of features that can be difficult to find in the Winchester area.

1960 Siler Rd, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$549,900
4 Beds ⋅ 3 Baths
Fully Renovated Winchester-Area Retreat on 3.24 Acres with Two Garages! Rarely does a property come along that offers this combination of extensive renovations, usable acreage, incredible storage, multiple garages, and a peaceful established neighborhood, all just minutes from everything Winchester has to offer. Welcome to 127 Mountain View Rd, where quiet living meets modern convenience, and nearly everything has been thoughtfully updated for today's buyer. Inside, extensive updates include fresh paint, new LVP flooring, refinished hardwood floors, updated fixtures and lighting, and 2-inch recessed lighting. The luxury kitchen features a large 5-foot island, quartz countertops, stainless-steel appliances, and under-cabinet lighting, plus a convenient pop-up electrical outlet/device charger in the island. Major improvements provide exceptional peace of mind, including a new roof (2025), new Rheem HVAC system (2026), new baseboard heat (2026), new water heater (2026), and completely new septic system with tank, distribution box, and lines (2026). Newer windows add to the home's efficiency and appeal. Enjoy outdoor living on the freshly stained 48' x 12' deck, perfect for entertaining, grilling, or relaxing. The oversized attached garage offers abundant storage and features a new garage door and opener. A second 26' x 17' detached garage with its own basement provides exceptional workshop, hobby, equipment, and storage space. With the right vision, the detached structure offers a variety of opportunities. Fresh landscaping and a newly graded oversized driveway provide plenty of parking and a welcoming approach. Located just minutes from downtown Winchester, shopping, restaurants, the hospital, gyms, and schools. Enjoy a quiet neighborhood setting with an established community feel while remaining close to everything you need. Homes in this great neighborhood are a rarity, don't miss your opportunity to see this one. 3.24 acres | Extensive 2025–2026 updates | Luxury kitchen | Two garages | Workshop potential | New septic | New HVAC | New roof | Large deck | No HOA | Minutes to Winchester.

127 Mountain View Rd, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$350,000
Open ground that is prime for investment, livestock or build your future home. Fully unrestriced, this property sits a long the Virginia/West Virginia border but calls Virginia home. Accessed via a 50 foot wide right of way from Dominion Road, a home site could be tucked back into the field giving you privacy and mountain views. Along the front portion of the property is a patch of timber that would make for a great homesite or place to create an oasis under the trees canopy. Looking to own a large farm? The adjoining 91+/- acres is also available making the possibilities on these two tracts endless.

Dominion Rd, Winchester

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact: 2172859000
$175,000
1 Beds ⋅ 1 Baths
Cozy 1-bedroom, 1-bathroom cabin located on a level, nicely shaded lot, ready for your enjoyment. Offering the perfect combination of rustic character, comfort, and natural beauty. Step outside onto the screened-in porch and enjoy your morning coffee, unwind with a good book, or simply take in the sights and sounds of the surrounding woods. This peaceful setting offers a wonderful opportunity to slow down and enjoy nature while still having all the comfort you need. Whether you're searching for a weekend getaway, a cozy full-time residence, or an investment property with rental potential, this versatile cottage is full of possibilities. Newer upgrades include an electrical panel, UV light, and exterior and interior painting/siding. Won’t last long at this price point!

305 Raccoon Dr, Winchester

Listing courtesy of Dandridge Realty Group, LLC. Contact: 3048857645
$984,900
4 Beds ⋅ 4 Baths
Nestled in the prestigious Midland Heights community, this exquisite Colonial-style residence offers a harmonious blend of luxury and comfort, set against a breathtaking mountainous backdrop. Built in 2019, this home boasts an impressive 3,317 square feet of meticulously designed living space, perfect for those who appreciate both elegance and functionality. The kitchen is a culinary dream, featuring high-end appliances including a built-in microwave, electric cooktop, and self-cleaning wall oven, all complemented by ample table space and a cozy eat-in area. Beautiful built-ins and walk-in closets provide both style and practicality, ensuring that every inch of this home is utilized to its fullest potential. The main level also features a thoughtfully designed entry-level bedroom and a luxurious bathroom with a walk-in shower, catering to convenience and comfort. Ascend to the upper levels to find two additional spacious bedrooms with its own spacious full bathroom, promising tranquility and relaxation. The fully finished basement offers endless possibilities, a forth bedroom or office with a full bathroom, daylight windows and walkout access to the serene outdoors, making it perfect for a home gym, media room, or additional living space. There is also an expansive storage area for all your needs. Outside, the property spans over 5 acres of beautifully cleared and landscaped grounds, providing a private oasis that backs to lush trees. Enjoy the tranquility of nature from your beautiful wrap-around porch, where you can unwind and soak in the stunning mountain views. The lower level offers a concrete area with a hot tub. There is a beautiful large detached 3 car garage for all of your cars, motorcycles or mowers. This home is not just a residence; it's a lifestyle. Experience the luxury of modern living in a serene mountain setting, where every detail has been thoughtfully curated to create a warm and inviting atmosphere. With its exceptional features and prime location, this property is a rare gem that promises to be a cherished sanctuary for years to come. Generator hook up wired for electric outages and Outside water bib running hot and cold water for dog baths and other use. Come see it today!

236 Delmas Trl Trl, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$595,390
3 Beds ⋅ 3 Baths
NEW BUILD, move in ready single-family home at Hiatt Pointe, 55+ community at Snowden Bridge by Van Metre Homes! The Sierra 39-F2 at Hiatt Pointe is stunning! This home offers 3 bedrooms, 3 full bathrooms, a 2-car front load garage, a finished basement and much more! As you enter the home you are greeted with 9' ceilings, luxury vinyl plank flooring, recessed lighting throughout, programmable thermostat, tankless gas water heater, solar panel ready, open floor plan, huge rec room on the lower level, all spanning over 3200 sq ft. The kitchen is a chef's dream with all stainless-steel appliances, white quartz counters, a spacious island and a walk-in pantry with solid shelving. Off the great room is your 20x12 deck, making it easy to entertain your family and friends! Cozy up by your electric fireplace to unwind or enjoy a good book. The primary suite offers a large bath with quartz counters, dual vanities, soaking tub and a roll -in frameless tile shower. On the lower level of the home, you will find a finished rec room, the third bedroom and the third full bath. Don't miss your opportunity to live in Hiatt Pointe at Snowden Bridge, a gated 55+ active adult community! Enjoy all the amenities to include a full clubhouse, fitness center, pickleball, outdoor pool and hot tub, fire tables and outdoor kitchens! Located near restaurants, shopping and downtown Winchester. Close to Rt 7, I-81 and I-66, making it a great commuter location. Schedule your showing today!

116 Magpie Ln, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$295,000
2 Beds ⋅ 3 Baths
**Investor & Fixer-Upper Special Endless Potential on Nearly 1 Acre!** Calling all visionaries, weekend warriors, and Airbnb hosts! This secluded retreat in Shawneeland is your chance to create the mountain getaway, rental, or private homestead you've been dreaming of customized entirely to your style. Offering an estimated 2,000+ sq ft of finished living space with the potential for over 2,400 total sq ft, this home has great bones to build on: new foundation repairs, porch, roof, HVAC, and well pump/bladder (all 2012), hot water heater (2019), and washer/dryer (2016). The spacious porch was even framed with a hot tub in mind just add your finishing touches! A walk-out basement leads to an oversized attached 2-car garage, offering great flexibility for storage, a workshop, or extra living space. Set on a corner lot that was once two separate parcels and is now combined into just shy of 1 acre, this is one of the largest lots you'll find in Shawneeland with room to roam and privacy to spare. And despite the tranquil, wooded setting, you're only about 15 miles from historic, charming downtown Winchester, a destination growing fast in popularity. Bring your tools, your creativity, and your vision, this one is priced for opportunity and sold strictly As Is. No HOA

159 Aspen Trl Trl, Winchester

Listing courtesy of EXP Realty, LLC. Contact: 8668257169
$287,000
3 Beds ⋅ 1 Baths
Located in the desirable Shawneeland community, this freshly updated three bedroom home is situated on a great corner lot with scenic views and plenty of possibilities to make it your own. The home features an updated kitchen, breakfast area, along with a detached two story garage/shed offering additional parking and storage. Step outside and enjoy relaxing evenings on the deck while taking in peaceful surroundings. Shawneeland offers an array of community amenities, including fishing, private access, playgrounds, and a four-hole golf course. With it's spacious lot, thoughtful updates, versatile outdoor space, and inviting setting, this quaint home is ready for it's next owner to make it their very own.

700 Tomahawk Trl, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 5403717653
$385,000
3 Beds ⋅ 2 Baths
Coming soon in Winchester! Welcome to this beautifully maintained 3-bedroom, 2-bath brick rambler in a convenient location. This move-in-ready home offers comfortable one-level living and features an updated kitchen with quartz countertops and stainless steel appliances, updated bathrooms, attractive flooring throughout, and a detached side-entry garage. The current owner has carefully maintained the property, making it ready for its next owner to enjoy. Conveniently located near shopping, dining, commuter routes, and everyday amenities. Professional photos and showing availability coming soon!

108 Williamson Rd, Winchester

Listing courtesy of Spring Hill Real Estate, LLC.. Contact: 7038914520
$334,000
3 Beds ⋅ 3 Baths
Nestled in the charming Wilde Acres community, this delightful Colonial home offers a perfect blend of comfort and style. Built in 2009, this residence features 3 spacious bedrooms and 2.5 bathrooms, providing ample space for relaxation and daily living. The inviting layout encompasses 1,680 sq. ft. of thoughtfully designed living space, ideal for both entertaining and quiet evenings at home. Enjoy the serene outdoor setting on a generous 0.65-acre lot, perfect for gardening or outdoor activities. The detached garage and driveway provide convenient parking options. Inside, the home boasts a warm ambiance, ready for your personal touch. Experience the tranquility of Wilde Acres while being just a short drive from local amenities. This home is not just a place to live; it's a place to thrive. Don't miss the opportunity to make it yours!

308 Fawn Dr, Winchester

Listing courtesy of Coldwell Banker Premier. Contact: 990007.lead@leads.leadrouter.com
$675,000
2 Beds ⋅ 1 Baths
Discover a rare opportunity to own a piece of Frederick County history with this unique farmette property offering approximately 9.79 acres, a charming farmhouse, extensive outbuildings, and an established farm market setup. Originally built in the 1800s with later additions, the home offers character that is difficult to replicate while providing the space and functionality today's buyers appreciate. Beyond the residence, this property truly shines through its improvements, including a large approximately 2,400-square-foot wooden barn with three stalls, multiple storage buildings, workshop space, greenhouse/storage building, orchard and garden area, and a separate farm market building. The farm market features separate electric service, insulation, gas heaters, refrigerators, counters, shelving, and a layout that has supported farm market operations. (Buyer to verify all intended uses with Frederick County.) Whether your vision includes homesteading, raising animals, growing produce, operating a farm market, or simply enjoying the beauty of country living, this property offers exceptional flexibility. Located just minutes from Winchester while providing the privacy and space of rural living, this is a property where history, agriculture, and opportunity come together. Properties offering this combination of history, acreage, agricultural infrastructure, and farm market potential rarely become available. Schedule your private showing and experience everything this unique property has to offer. Highlights Approximately 9.79 acres Historic farmhouse 2,400± sq ft barn with 3 stalls Separate farm market building Orchard & garden area Multiple outbuildings Workshop Greenhouse/storage Convenient Winchester location

531 Cedar Grove Rd, Winchester

Listing courtesy of Virginia Real Estate. Contact: 5406452999
$759,900
5 Beds ⋅ 5 Baths
This spectacular, move-in-ready home shows like a professional model, showcasing exquisite designer touches, custom window treatments (included), and premium finishes throughout. Built in 2023, the residence offers the ultimate convenience of main-level living with a bright, open-concept layout that beautifully blends comfortable luxury with timeless appeal. Nestled on a spacious .28-acre lot with a deep setback from the street, the property provides a serene sense of arrival and added privacy. The fully finished lower level significantly expands your living space, offering a versatile recreation area, a private guest suite, and an additional room perfect for a home office or extra bedroom. Step outside to the beautiful patio, ideal for relaxing or entertaining. Every detail of this home reflects extraordinary care and pristine taste—truly a model-home experience ready for its new owners. *Also offering a one-year Home Warranty with the sale of the home.

174 Williamson Rd, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$308,000
2 Beds ⋅ 2 Baths
This charming cottage in the heart of the City of Winchester is poised for a remarkable transformation with major renovations slated for 2026. Built in 1950, this detached home offers a unique opportunity for investors seeking to capitalize on a revitalized property in a desirable location. With two spacious bedrooms and two full bathrooms, the layout is perfect for modern living. The full basement provides ample storage or potential for additional living space, enhancing the property's value. Set on a generous 0.34-acre lot, there's plenty of room for outdoor enjoyment or future enhancements. The vinyl siding ensures low maintenance, while the inviting architectural style adds character. Investors will appreciate the potential for significant returns as the renovations breathe new life into this home, making it an attractive option for renters or future buyers. With its warm ambiance and promising upgrades, this property is a sound investment in a thriving community. Don't miss the chance to be part of its exciting journey!

2519 Hockman Ave, Winchester

Listing courtesy of Link Realty Services LLC. Contact:

$434,900
3 Beds ⋅ 4 Baths
The lot you’ve been waiting for—without giving up the convenience of townhouse living! This exceptional end-unit townhome sits on a rare, double-sized lot, offering the kind of space, privacy, and breathing room that is hard to find in a community setting. Tucked at the edge of the neighborhood with open space beside and behind, this home feels remarkably private while still being close to the community playground and everyday conveniences. With over 2,200 finished square feet across three levels, this beautifully maintained home offers 3 bedrooms, 3.5 baths, and a layout designed for both comfortable living and easy entertaining. The main level features hardwood floors, an inviting family room with gas fireplace and built-in bookcases, and a spacious kitchen and dining area that open directly to the large rear deck. Granite countertops and thoughtfully selected finishes add a polished touch throughout. Upstairs, the spacious primary suite offers a tray ceiling, walk-in closet, and a generous walk-in shower. The finished lower level provides additional living space along with plenty of flexibility for a home office, recreation room, guests, or whatever fits your lifestyle. The attached garage adds everyday convenience, while the oversized end-unit setting provides something truly special: more privacy, more parking, less traffic, and more outdoor space than the typical townhouse. Step onto the deck, look around, and you’ll immediately appreciate the difference. Rarely does a townhouse offer this much lot, this much privacy, and this much living space in one package. Come see why this end-unit gem is one you won’t want to miss!

142 Sequoia Dr, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$674,000
5 Beds ⋅ 4 Baths
Welcome to 337 Canyon Road, a spacious brick-front home offering more than 4,600 finished square feet in desirable Twin Lakes Overlook. The open-concept main level features beautiful hardwood floors, a cozy gas fireplace, and a stunning kitchen with quartz countertops, abundant cabinetry, and plenty of space for gathering and entertaining. Generously sized bedrooms provide room for everyone, while the finished basement, with a full bathroom, offers incredible flexibility and can be used as an in-law suite, theater room, home gym, recreation area, or private guest retreat. Step outside onto the Trex deck and enjoy the peaceful setting overlooking mature trees, or relax on the lower patio, ready for a future hot tub. Just steps away, the community trail leads to the stocked lake, where residents can enjoy canoeing and kayaking. Conveniently located on Winchester’s east side near shopping, restaurants, and major commuter routes, this home offers an exceptional combination of space, comfort, convenience, and natural beauty.

337 Canyon Rd, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$379,900
2 Beds ⋅ 2 Baths
This charming Cape Cod home in Winchester City, built in 1950 and beautifully renovated in 2026, offers a perfect blend of classic character and modern convenience. With 2 spacious bedrooms and 2 full bathrooms, including a luxurious walk-in shower, this residence is designed for comfort. The heart of the home features a bright kitchen equipped with stainless steel appliances, including a refrigerator, dishwasher, microwave, and stove, making meal prep a delight. A generous size family room just off the kitchen. Enjoy the convenience of main-floor laundry and a partially finished basement, perfect for a cozy retreat on gameday, or even possible 3rd bedroom, & couple extra rooms for storage. The attic could also add potential living space.(possible 4th) The inviting outdoor space is ideal for relaxation, Brand New Garage while the driveway provides ample off-street parking. Nestled in a vibrant community, residents benefit from nearby parks, excellent schools, Shenandoah University and convenient public services. Experience the warmth of neighborhood gatherings and the charm of local shops. This home is not just a place to live; it's a place to thrive. Embrace the lifestyle you've been dreaming of!

1414 S Braddock St, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$645,000
4 Beds ⋅ 4 Baths
Come and discover this impressive beauty where easy main-level living meets exceptional indoor-outdoor entertaining. This beautifully appointed Cape Cod offers the convenience of a spacious main-level primary suite, while the heart of the home flows seamlessly from the well-appointed kitchen to a covered rear porch overlooking the sparkling inground pool and hot tub. With ceiling fans and a TV, the covered porch is an inviting gathering space for morning coffee, lazy summer afternoons, or movie night—truly an extension of the home all year long. Inside, the main level offers an ideal blend of an open floorplan and defined rooms with gleaming hardwood floors, soaring ceilings, crown molding, beautiful fresh paint, and an abundance of natural light. The kitchen features generous cabinet storage and prep space,a gas cook top, double ovens, built in microwave, a center island, and breakfast nook with direct access to the covered porch and expansive patio & pool area, making indoor-outdoor entertaining effortless. From the kitchen flow into the spacious living room with charming built-ins to find a warm and inviting place to relax and watch TV while being part of the action. This home also has a formal dining and living room (currently used as office) that flank the welcoming and generously sized foyer. The large main-level primary suite offers a private retreat with a relaxing en-suite bath featuring a soaking tub, step in shower, and huge walk-in closet. The main level is also home to laundry room and gorgeous powder room. Upstairs, three generously sized bedrooms share a full bath, providing comfortable accommodations for family and guests along with a loft area perfect as play area or reading nook. The versatile lower level expands the living space with ceramic tile throughout, a spacious recreation area, full bath, and finished room with closet that could serve as a fifth bedroom, home office, guest space, gym, media room, or game room. Outside, the covered rear porch, expansive patio, inground pool, and hot tub create a backyard designed for enjoying home to the fullest. The inviting front porch adds another charming outdoor space, perfect for morning coffee or winding down at the end of the day. A two-car garage, newer roof (2025), two-zone HVAC, and desirable corner-lot setting add to the home's appeal. Meaningful updates include new pool cover (3 years old), pool pump (2 years old) and brand new sand filter. Located in the quiet, Oakdale Crossing neighborhood, this home offers convenient access to Jim Barnett Park, Shenandoah University, Schools, Costco, Apple Blossom Mall, Winchester Country Club, and everyday amenities. Whether you're looking for the ease of main-level living, a comfortable home for entertaining, or your own private backyard retreat, 200 Fairfield Drive offers a wonderful combination of comfort, convenience, and lifestyle.

200 Fairfield Dr, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$420,000
4 Beds ⋅ 4 Baths
Don't miss this nearly new townhouse in Rossum Crossing! With 4 bedrooms, 3.5 bathrooms, over 2,000 square feet of finished space, and a one-car garage, this home offers plenty of room and a great layout for everyday living. The lower level features a private bedroom with its own full bathroom, including a tiled walk-in shower, along with direct access to the rear yard. Upstairs, you'll find a bright, open floor plan with a spacious living room that flows right into the kitchen. The kitchen features upgraded white quartz countertops, white cabinetry, stainless steel appliances, a center island, pantry, and counter space for bar seating. Just beyond the kitchen is a half bathroom and a convenient area for a dining table, along with a door leading to a future deck. The upper level includes a primary suite with a walk-in closet and private bathroom featuring a tiled walk-in shower. Two additional bedrooms share a full hall bathroom, making this a practical setup for family or guests. A laundry closet with a stacked washer and dryer completes the upper level. Don't worry about mowing again! This HOA includes mowing in front and rear as well as trash service. This home is conveniently located near many shopping and dining options and close to all major commuting routes for easy access to many areas.

109 Marlow Ct, Winchester

Listing courtesy of ERA Liberty Realty. Contact: (304) 728-2000
$899,000
152± BEAUTIFUL ACRES IN WINCHESTER, VA! This outstanding property offers an incredible opportunity to build your dream home, cabin, or private retreat. The property features beautiful views, a cleared building site, an approved five-bedroom perc site, and electric has been run to the property, providing an excellent foundation for future development. Outdoor enthusiasts will appreciate the great hunting opportunities, with abundant wildlife including deer, turkey, and more. A stream flows through the property, adding to the natural beauty and creating a peaceful setting. An established road provides access into the property, with access from a deeded right-of-way off Laurel Grove Road. Located just 13 miles from Winchester and less than 9 miles from I-81 and Route 11, the property offers convenient access for commuting while maintaining a private, rural setting. Dulles International Airport is approximately 80 minutes away, with Washington, D.C. approximately 90 minutes away. Whether you're looking to build a home or cabin, enjoy great hunting, or create your own private getaway, this property offers an exceptional opportunity. Come and make this your next great adventure! Buyer is responsible for all due diligence regarding building suitability, permits, zoning, permitted uses, utilities, and any other intended use of the property. This property will be offered at auction on Friday, October 16, 2026, at 1:00 PM. The list price in no way represents a minimum, starting, or acceptable bid. This property will be offered in a multi-parcel auction, giving buyers the flexibility to purchase Tract 1, Tract 2, or both tracts. Tract 1: 152.44+/- Acres Tract 2: 158.43+/- acres

TRACT 1: 152.44+/- ACRES Off Of Laurel Grove Rd, Winchester

Listing courtesy of Hurley Real Estate & Auctions. Contact: (717) 729-5501
$899,000
158.43± BEAUTIFUL ACRES IN WINCHESTER, VA! This outstanding property offers an incredible opportunity to build your dream home, cabin, or private retreat. The property features beautiful views, a cleared building site, an approved five-bedroom perc site, and electric is near to the property, providing an excellent foundation for future development. Outdoor enthusiasts will appreciate the great hunting opportunities, with abundant wildlife including deer, turkey, and more. A stream flows through the property, adding to the natural beauty and creating a peaceful setting. An established road provides access into the property, with access from a deeded right-of-way off Laurel Grove Road. Located just 13 miles from Winchester and less than 9 miles from I-81 and Route 11, the property offers convenient access for commuting while maintaining a private, rural setting. Dulles International Airport is approximately 80 minutes away, with Washington, D.C. approximately 90 minutes away. Whether you're looking to build a home or cabin, enjoy great hunting, or create your own private getaway, this property offers an exceptional opportunity. Come and make this your next great adventure! Buyer is responsible for all due diligence regarding building suitability, permits, zoning, permitted uses, utilities, potential utility projects, and any other intended use of the property. The property is crossed by existing power lines, and there may be a project to add an additional power line to the existing lines. At this time, the potential project has not been confirmed, and buyers should conduct their own due diligence regarding any proposed utility projects. This property will be offered at auction on Friday, October 16, 2026, at 1:00 PM. The list price in no way represents a minimum, starting, or acceptable bid. This property will be offered in a multi-parcel auction, giving buyers the flexibility to purchase Tract 1, Tract 2, or both tracts. Tract 1: 152.44+/- Acres Tract 2: 158.43+/- acres

TRACT 2: 158.43+/- ACRES Laurel Grove Rd, Winchester

Listing courtesy of Hurley Real Estate & Auctions. Contact: (717) 729-5501
$575,000
3 Beds ⋅ 2 Baths
Like NEW built in 2020 on 2.49 acres. partly wooded, partly cleared. Walkout basement with windows ready for finishing, with rough-in for bath! Add a 4th bedroom - Septic rated for the additional bedroom. Close to town (approx 5 mins to hospital) Hi Speed Internet. Main level living with high ceilings, oversized windows and modern finishes. LVP floor, island kitchen with granite countertops, extended‑height cabinetry, and stainless steel appliances. Primary with en suite and walk‑in closet. Located just off Route 50 West, this home offers country living without the commute—only minutes from the hospital, shopping, dining, and all Winchester amenities.

584 Mcdonald Rd, Winchester

Listing courtesy of Coldwell Banker Realty. Contact: 7034717220
$1,025,000
5 Beds ⋅ 4 Baths
Opportunities in Stonymeade don't come along often—and once you arrive, it's easy to understand why. Tucked away on 3.2 beautifully maintained acres with a wooded perimeter, this custom-built Joe Mohr home feels wonderfully removed from the world, yet shops, restaurants and Winchester Medical Center are just 5–7 minutes away and Old Town Winchester is only 10 minutes from your door. Elegant without being formal, this home offers over 3,800 finished square feet and exceptional one-level living, with three bedrooms and 2.5 baths on the main floor plus two bedrooms and a full bath on the finished walkout lower level. At the heart of the home is a showstopping gourmet kitchen designed for those who love to cook, gather and entertain. A massive center island anchors the space, surrounded by Thermador appliances including a gas cooktop, double wall ovens and built-in microwave, Sub-Zero refrigeration, wine cooler and an oversized walk-in pantry. The adjoining family room features a gas fireplace flanked by custom built-ins and an expansive plate-glass window framing the peaceful backyard. A second oversized picture window in the dining room brings the outdoors in, while stunning hardwood floors, plantation shutters throughout and abundant natural light create a sense of warmth and understated elegance. The main-level primary suite is a true retreat. At 19' x 17', the bedroom is spacious and filled with natural light, complemented by a large walk-in closet and private bath with dual vanities and an oversized walk-in shower. Downstairs, the walkout lower level was made for entertaining. A generous living area with wet bar provides plenty of room for game days, movie nights and gatherings, while two additional bedrooms and a full bath comfortably accommodate family and overnight guests. And then there's the wine cellar. With capacity for approximately 1,000 bottles, this extraordinary climate-controlled brick-and-wood cellar feels like something discovered in a private wine country retreat. A dedicated tasting area creates a memorable space for opening a favorite bottle or sharing an evening with friends.* Outdoor living is every bit as inviting. Just off the main level, the spacious deck offers a built-in gas grill and plenty of room for dining and gathering while overlooking the grounds. Below, the walkout lower level opens to a patio with both covered and open-air spaces and a built-in fire pit. From summer dinners on the deck to wine by the fire on a cool evening, there are spaces here for every season. The gently sloping 3.2 acres offer a beautiful balance of mature trees and open lawn, with a wooded perimeter providing remarkable privacy and plenty of room to play, garden or simply enjoy the quiet. Even the three-car attached garage has been thoughtfully finished with extensive built-in cabinetry and wall organization, while a custom drop zone just inside keeps everyday life organized. Fresh interior paint and new carpet make this home ready for its next chapter. For those who have been waiting for something special in Stonymeade, this is a rare combination: custom construction, main-level living, exceptional entertaining spaces, acreage and privacy—all just minutes from the heart of Winchester. Some homes impress you. This one invites you to stay. *Wine cellar cooling unit is currently non-operational and conveys as-is.

632 Stonymeade Dr, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$597,000
5 Beds ⋅ 3 Baths
Welcome to this beautifully maintained home in the established Stonebrook Farms community, perfectly situated on a quiet cul-de-sac and surrounded by mature trees and landscaping. This inviting home offers a spacious and versatile floor plan, including a main-level bedroom and full bath—ideal for guests, multigenerational living, or anyone needing convenient main-level accommodations. At the heart of the home is a large family room featuring a wood-burning fireplace, creating a warm and welcoming space for gathering with family and friends. The home has been lovingly cared for, with pride of ownership evident throughout. One of the home's standout features is the beautiful covered and screened-in back porch, offering the perfect place for morning coffee, outdoor dining, or relaxing at the end of the day while overlooking the peaceful and beautifully maintained backyard. With its desirable cul-de-sac setting, flexible main-level living space, spacious family room, and wonderful outdoor living area, this well-maintained Stonebrook Farms home is ready to welcome its next owners!

102 Forest Valley Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$250,000
2 Beds ⋅ 1 Baths
Welcome to 1125 Conway Ave, a charming bungalow in Winchester City that's move-in ready and full of character! This cozy 2-bedroom, 1-bath home features beautiful hardwood floors and numerous recent updates, including a new roof, fresh interior paint, kitchen remodel, hallway and bathroom flooring, and a new stainless steel refrigerator. The deck has also been restored, providing a great spot to relax or entertain. Conveniently located near shopping, dining and everyday amenities, with quick access to I-81 from Winchester's east side—making it an excellent option for commuters. Whether you're a first-time buyer, downsizing, or looking for a low-maintenance home in the city, this bungalow is worth a look. Schedule your showing today!

1125 Conway St, Winchester

Listing courtesy of NextHome Realty Select. Contact: (540) 667-9097