Winchester Homes for Sale

Winchester Homes for Sale

Welcome to Winchester, Virginia – a charming city steeped in history and bursting with modern conveniences. Nestled in the picturesque Shenandoah Valley, Winchester is known for its stunning landscapes, vibrant community, and rich heritage. With its quaint downtown area, lined with boutiques, cafes, and historic sites, Winchester offers a unique blend of small-town charm and urban amenities, making it an ideal place to call home.

This welcoming city is surrounded by the breathtaking Blue Ridge Mountains, offering outdoor enthusiasts a plethora of activities, from hiking and biking to exploring the nearby national parks. Winchester is also home to a variety of annual events and festivals that celebrate its culture, including the renowned Shenandoah Apple Blossom Festival, which draws visitors from near and far.

For those considering a move to this enchanting locale, you’ll be pleased to discover a diverse selection of homes for sale. Whether you’re looking for a cozy bungalow, a spacious family home, or a luxurious estate, Winchester has something to suit every taste and budget. Many properties boast beautiful yards, modern amenities, and easy access to local schools and parks, making it a fantastic choice for families and individuals alike.

With a strong sense of community and a commitment to preserving its historic charm, Winchester is not just a place to live; it’s a place to thrive. Explore the homes for sale in this vibrant city and take the first step toward making Winchester your new home sweet home!

Newest Winchester Homes for Sale

$619,900
4 Beds ⋅ 5 Baths
No HOA! Settled at the end of the cul-de-sac and pushed back from the street to give additional privacy and comfort. This home has received several improvements since 2020. Including a whole new kitchen (Dec 2025), soft close cabinets, quartz countertop and backsplash, Stainless Steel appliances, the kitchen island was enlarged for more countertop space and additional storage, seats 2-3 people comfortably. Kitchen includes a large pantry with upgraded doors (2025). Both HVAC Systems were replaced and a humidifier was added (Spring 2026). Ducts were professionally cleaned (2020). Custom Blinds (2025). The spacious back yard has an aluminum 5ft fence with 2 single gates and 1 double gate (2024). Trex Deck 12x16ft with gate at top of stairs (2021). Custom built 10x12ft swing for 3 people or a hammock. Trees and bushes and fencing makes the back yard feel very private. Interior and exterior professionally painted (2020/21). Large 12x16ft shed added (2023). New carpet in basement and upper level (2020). Updated both half bathrooms (2022-23). Primary bathroom has a heated tile floor, walk-in shower with rain fall shower head and 4 body sprayers, large jacuzzi tub, double vanity, chandelier, and linen closet. Primary bedroom has two walk-in closets. One with a chandelier and upgraded closet system. Garage has a Mini Split heating/cooling system as well as its own attic with flooring for storage. All interior and exterior light fixtures have been updated. Both gas fireplaces were professionally serviced (2023). Basement is wired for surround sound, has upgraded dry bar with soft close cabinets, quartz countertop to match kitchen, and floating shelves, the basement also has two windows for natural light, and walk-up basement stairs. Upstairs bedrooms have a Jack-n-Jill bathroom between them with an updated double vanity (2025). The rear bedroom has a walk-in closet with a laundry shoot. Professional landscaping in front of home (2021). Home is wired with ADT security but isn't currently in use. Location is excellent, almost everything you'd need is 5-10 minutes away including Winchester Country Club, Costco, Shopping Centers, Downtown walking mall, commuter routes like rt. 50, rt. 7, rt. 522, and Interstate 81.

308 Huntersridge Rd, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$625,000
5 Beds ⋅ 3 Baths
COMING SOON! Being beautifully remodeled and updated, this home is getting a fresh new look inside and out! Enjoy relaxing times on the expansive front porch and entertain year-round on the covered rear deck in private back yard. More details, professional photos, and a full list of features are coming soon—stay tuned for this exciting opportunity in Winchester!

139 Darby Dr, Winchester

Listing courtesy of Coldwell Banker Realty. Contact: chrissi.chapman@cbmove.com
$408,000
3 Beds ⋅ 2 Baths
Welcome to 120 Hawk Trail, a beautifully maintained home offering the perfect blend of modern comfort, peaceful surroundings, and the relaxed mountain lifestyle that makes Shawneeland such a special place to call home. Surrounded by mature trees and nature, this inviting retreat provides privacy and serenity while still being conveniently located near Winchester. Built in 2014, this thoughtfully designed home offers the benefits of newer construction with a warm and comfortable feel. Step inside to a spacious living room featuring a high tray ceiling that adds character and an open, airy feel. Hardwood flooring flows throughout the main living and dining areas while large double windows in both areas provide abundant natural light. The kitchen is designed for both functionality and everyday enjoyment, featuring stainless steel appliances, abundant cabinetry, and plenty of workspace for meal preparation. A comfortable breakfast area near the large sliding glass door provides the perfect spot for a kitchen table, morning coffee, casual meals, or simply relaxing while enjoying peaceful views of the backyard. The flexible floor plan includes two spacious bedrooms and a primary suite featuring its own private full bathroom. A second full bathroom is conveniently located near the living areas and bedrooms, providing easy access for family and guests. The unfinished basement with a rough-in bathroom offers endless possibilities for future expansion. Create a recreation room, home gym, workshop, office, guest area, or additional living space tailored to your needs. Until then, it provides exceptional storage and a great opportunity to customize the home over time. This move-in ready home has been lovingly cared for by its original owner with thoughtful features throughout, including updated lighting and bathroom fixtures, ceiling fans for added comfort, and an attached two-car garage offering convenience and additional storage. Outside, the backyard provides a peaceful setting with plenty of space for outdoor enjoyment. Whether you're firing up the grill, gardening, relaxing with a good book, or simply enjoying the sounds of nature, this private setting creates a wonderful place to unwind. Life in Shawneeland offers a unique mountain community experience with amenities that make everyday living feel like a getaway. Residents enjoy access to a spring-fed lake, private Cherokee Beach, fishing ponds, hiking trails, playgrounds, picnic areas, sports courts, and beautiful mountain scenery. The community is maintained through the Shawneeland Sanitary District rather than a traditional homeowners association, with fees supporting road maintenance, snow removal, and upkeep of shared amenities. Nature lovers will appreciate the nearby access to George Washington National Forest, while Winchester provides shopping, dining, medical services, entertainment, wineries, and historic charm just a short drive away. Commuters will appreciate convenient access to major routes connecting to the Washington, DC metro area. Whether you are looking for a new home, weekend getaway, or peaceful place to reconnect with nature, 120 Hawk Trail offers the opportunity to enjoy the best of mountain living while staying connected to modern conveniences. Here, fresh air, quiet evenings, and the beauty of the outdoors become part of your everyday lifestyle.

120 Hawk Trl, Winchester

Listing courtesy of Samson Properties. Contact: 7033788810
$429,000
4 Beds ⋅ 2 Baths
Turn-key and move-in ready! This beautifully updated 4-bedroom, 2-bath home features a modern kitchen with recently updated appliances, a new HVAC system, and a new hot water heater for added peace of mind. Enjoy the spacious backyard, perfect for outdoor entertaining, along with convenient off-street parking and the freedom of no HOA. Nestled in an established neighborhood with large yards and a charming community park, this home is ideally located just minutes from Winchester Medical Center, the Museum of the Shenandoah Valley, and Old Town Winchester's restaurants, shops, and entertainment.

1310 Whittier Ave, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$586,900
4 Beds ⋅ 4 Baths
Gorgeous 4-Bedroom Colonial in Sought-After Sovereign Village! This beautifully maintained home is nestled on a large cul-de-sac, offering privacy, space, and comfort both inside and out. This home boasts a well-designed layout perfect for everyday living and entertaining. The bright, open main level with shining hardwood floors creates a warm and inviting atmosphere. Cozy up by the gas fireplace in the living area or enjoy meals in the spacious bay window style dining area overlooking the backyard. The chef's kitchen with large island, granite countertops and stainless steel appliances (brand new refrigerator!) opens seamlessly to the living spaces and offers plenty of room for meal prep and gatherings. Step outside to the fantastic private deck, patio and backyard, ideal for outdoor entertaining, gardening, or simply relaxing in your own peaceful oasis. On the second level, the spacious primary suite has a large walk-in closet, ensuite with a jacuzzi tub, and recessed high ceilings that add so much character. The two additional bedrooms are bright, generously sized and share a full hallway bathroom. The laundry room is right outside of the large 4th bedroom with its own private bathroom and walk in closet. The mostly finished basement has abundant storage space and the main area has so many possibilities! Additional highlights include: New Water Softener & New Water Heater and access to the Community Pool and Common Areas. (Pool membership for Sovereign Village residents is $210 as long as in good standing with the HOA. Senior Passes for those 55+ is $176.) Located on a cul-de-sac and walking distance to the elementary school.

104 Murphy Ct, Winchester

Listing courtesy of Epic Realty, LLC.. Contact: (703) 328-3000
$500,900
4 Beds ⋅ 3 Baths
Welcome to 609 Quartzite Circle! A beautifully maintained 4-bedroom, 3-bath home offering a spacious and functional layout designed for modern living. The main level features inviting living spaces, hardwood flooring, and an open kitchen with ample cabinetry and table space. The primary suite includes a walk-in closet and a private bath with a soaking tub, while the finished lower level provides a generous recreation room, an additional bedroom, and a full bath, offering flexible space for guests, a home office, or everyday living. Enjoy the fully fenced backyard with a patio, perfect for relaxing or entertaining, along with the convenience of an attached 2-car garage. Ideally located near shopping, dining, schools, parks, and major commuter routes, this home combines comfort, versatility, and a convenient Winchester location.

609 Quartzite Cir, Winchester

Listing courtesy of Samson Properties. Contact: 7033788810
$329,000
3 Beds ⋅ 2 Baths
Charming, meticulously maintained brick rancher in the heart of Winchester City! This move-in-ready home features 3 spacious bedrooms, 1 full bath, and a convenient half bath. Step inside to find gorgeous hard wood floors and several rooms boasting fresh, modern paint. The fully finished basement ( with radon system installed) offers incredible bonus square footage, perfect for a family room, home office, or recreation space. Outdoor living is a breeze on the private backyard brick patio, situated on a peaceful, quiet street. Driveway provides convenient off-street parking. New Refrigerator, washer and dryer convey. Location is everything! Enjoy the convenience of in-town living while staying just minutes away from major commuting routes, shopping, and dining. Don't miss this Winchester gem—schedule your tour today!

912 Allen Dr, Winchester

Listing courtesy of Colony Realty. Contact:

$229,000
3 Beds ⋅ 1 Baths
Set on 1.4 acres with beautiful long-range views, this well-built home is ready for someone to bring it back to life. A strong structure, a covered front porch, and a generous lot give you space to breathe, all just minutes from downtown Winchester and Winchester Medical Center. With a little vision and renovation, this could become someone's dream home, whether that's a full modern transformation or a labor-of-love restoration that honors its original character. The real bonus is the rear outbuilding with three rooms. A blank canvas ready to become a guest suite, studio, home office, or whatever your imagination needs it to be. A second shed adds extra storage, so there's room for tools, toys, or projects. Location seals the deal, quick access to Old Town Winchester's shops and restaurants just down the road and route 37 minutes away makes for easy commuting. Schedule your showing today!

269 Poorhouse Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$379,999
3 Beds ⋅ 3 Baths
This lovely 3 bedroom 2 and 1/2 bath home in the Apple Ridge neighborhood of Winchester is not far from shopping and dining. Close to Route 81 and Route 7 it's an easy commute . The home has a great covered deck for outdoor entertaining and a large shed for your storage needs. Step into the home by way of a welcoming entryway and comfortable living room. Stainless appliances and granite countertops in the kitchen make it a pleasurable place to prepare all your favorites to serve in the formal dining room. There is a separate laundry room/ mud room with a washer and dryer that convey and lead to the garage. The upstairs landing has an arched window leading to 3 bedrooms and a hall bath. The spacious primary bedroom has a large private bath. Don't miss out on this wonderful home.

105 Mesquite Ct, Winchester

Listing courtesy of CENTURY 21 New Millennium. Contact: 5406650700
$499,900
3 Beds ⋅ 2 Baths
Stately rambler on gorgeous 1-acre lot in prestigoius Stonebrook Farms. Major remodel in 2016 includes new kitchen and both full baths. New windows & Sliding Glass Door replaced with Renewal by Anderson in April 2024 ($41,856). HVAC 2022, Water heater 2025. Kitchen features granite colunters, stainless steel appliances, added pantry, recessed lighing, under cabinet lighing, and pendant lighing, soft-close cabinets w/ pull-out shelves and soft-close drawers. Brand new carpeting being installed Sat July 25 on main level (Living Room, Family Room, & all 3 Bedrooms), hardwood flooring in kitchen and dining room in great shape. Huge unfinished basement offers tons of space to expand. Other updates include asphalt drivway (2018), Gutter guards (2014), Culligan water softener (2022), and ducts cleaned in Oct 2025. Beautiful landscaping includes azaleas, boxwoods, and Japanese maple tree. Large patio-style porch in front looks out onto lush green lawn, and 3-season enclosed sunroom in back looks out to trees and grass, very private! Do not miss this rare opportunity to buy into Wincheter's most prestigious neighborhood. And purchase an optional membership at Stonebook Club (Indoor & outdoor tennis, huge pool, raquetball courts, reception hall, and dining facilities, less than 1/2 mile away.

112 Beverly Dr, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com
$3,500,000
3 Beds ⋅ 4 Baths
Be Sure to View the Video and 3D Tour to Fully Experience this Stunning Property <br><br> **Briede Family Vineyards** presents an exceptional opportunity to acquire one of Virginia's distinguished boutique vineyard estates. Offering far more than beautiful real estate, it provides the new owners the opportunity to continue a well-established legacy within the Commonwealth's thriving wine industry. Combining an award-winning vineyard and winery brand with an elegant country residence currently operating as a licensed short-term rental, this remarkable property is ideally suited for those seeking both a lifestyle investment and an established business. The property's total acreage also includes three additional building lots (with approved Well and Septic), providing exceptional opportunities for future residential development, guest accommodations, or investment, subject to applicable approvals.<br><br> For years, Briede Family Vineyards has earned recognition for producing award-winning wines while cultivating a reputation for offering intimate, highly personalized guest experiences. Unlike larger commercial wineries, the vineyard has become known for its thoughtfully curated tastings, signature Champagne experiences, and imported French cheese pairings, creating a destination that guests return to year after year. The recognized brand, loyal clientele, and respected presence within Virginia's wine community provide an invaluable foundation for future ownership.<br><br> The beautifully appointed tasting room and adjoining great room provide an inviting setting for tastings, private gatherings, and special events. Guests can also enjoy the charming covered pavilion overlooking the vineyard, offering an ideal outdoor venue for relaxing, live entertainment, special events, and taking in the surrounding views. Complementing the vineyard experience, the beautifully maintained residence offers guests the opportunity to experience life among the vines. Surrounded by sweeping vineyard vistas and tranquil countryside, the home serves equally well as a private estate residence, luxury guest accommodations, or an expanded hospitality venue, offering exceptional flexibility for a variety of ownership goals.<br><br> The property encompasses established vineyards, meticulously maintained grounds, and the infrastructure necessary to continue current operations while providing opportunities for future growth. This is a true turnkey opportunity, allowing a new owner to step into an established vineyard operation with recognized branding and a well-developed hospitality experience, while providing an exceptional foundation for future growth and continued success. Whether expanding wine production, enhancing agritourism, hosting private events, or preserving the vineyard's boutique character, the possibilities are exceptional.<br><br> Conveniently located in Frederick County, Virginia, with easy access to Northern Virginia, Washington, D.C., and the Shenandoah Valley, Briede Family Vineyards represents a rare opportunity to acquire a recognized vineyard destination where years of dedicated ownership, reputation, and hospitality come together in one remarkable offering.

450 Green Spring Rd, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$360,000
3 Beds ⋅ 3 Baths
Welcome home to 117 E Pall Mall St! Ideally located within a mile of Shenandoah University and historic downtown Winchester! This 3 bedroom, 2.5 bath has lots of updates and upgrades! Updated kitchen and baths, stainless steel appliances, & a fenced in backyard! 2023 - Roof, siding, & electrical panel (and all breakers), updated kitchen and all baths, 2024 - repaired sump pump & new hot water heater, 2025 - new sewer line under driveway & from driveway to street, new LVP in kitchen, 2026 - replaced / leveled living room floor & subfloor, new LVP. Schedule your tour today!

117 E Pall Mall St, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com
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