Winchester Homes for Sale

Winchester Homes for Sale

Welcome to Winchester, Virginia—a charming city steeped in history and surrounded by breathtaking natural beauty. Nestled in the heart of the Shenandoah Valley, Winchester boasts a vibrant community with a rich heritage that dates back to the 18th century. Known for its picturesque landscapes and historic architecture, this city offers a perfect blend of small-town charm and modern amenities.

Winchester is home to a variety of cultural attractions, including the Museum of the Shenandoah Valley, the historic Old Town district with its boutique shops and gourmet dining, and the stunning Shenandoah National Park nearby, perfect for outdoor enthusiasts. The city hosts numerous festivals and events throughout the year, fostering a strong sense of community and connection among its residents.

For those looking to call Winchester home, the real estate market is thriving with an array of homes for sale that cater to diverse tastes and budgets. Whether you’re seeking a cozy single-family home with a white picket fence, a modern townhouse in a vibrant neighborhood, or a sprawling estate with stunning views, Winchester has something for everyone. The local real estate market is characterized by its affordability, making it an attractive option for first-time buyers, families, and retirees alike.

With its friendly atmosphere, excellent schools, and convenient access to major highways, Winchester is not just a place to live; it’s a place to thrive. Explore the homes for sale in this enchanting city and discover the perfect backdrop for your next chapter!

Newest Winchester Homes for Sale

$775,000
4 Beds ⋅ 4 Baths ⋅ VAFV2043652 MLS
Welcome to this exceptional 4-bedroom, 3.5-bath Colonial in the sought-after Raven Pointe subdivision, where luxury living extends well beyond the front door. The backyard is a true showstopper, featuring a one-year-old 20' x 40' heated Hayward OmniLogic saltwater pool with a tanning ledge, sunken spa, and Coverstar automatic safety cover. A covered Trex deck with a porch swing overlooks the private backyard, creating the perfect space for relaxing or entertaining. Inside, the main level offers a private home office with custom built-ins, a formal dining room, a spacious family room with a gas fireplace, and a beautifully appointed kitchen featuring a large center island, butler's pantry, stainless steel appliances, gas cooking, and a bright breakfast room. Upstairs, the spacious primary suite includes luxury vinyl plank flooring, a walk-in closet, and a spa-like bath with a jetted tub, walk-in shower, and dual vanities. Three additional bedrooms, a versatile bonus room, and an upper-level laundry room complete the second floor. The finished walk-up basement is made for entertaining with a large recreation room, wet bar with a built-in ice maker, full bath, storage room, and a flexible bonus room that can serve as a fifth bedroom, home gym, or office. Located in Raven Pointe with sidewalks and streetlights, this home is just minutes from shopping, dining, schools, and commuter routes. Offering an incredible combination of elegant living spaces and a resort-style backyard, this is a home you won't want to miss.

107 Cahille Dr, Winchester
$719,000
7 Beds ⋅ 5 Baths ⋅ VAWI2011262 MLS
Situated on a prominent corner lot in an exclusive cul-de-sac enclave of distinguished homes, this impressive stone-front residence offers exceptional space, comfort, and timeless appeal in one of the area’s most desirable neighborhoods. Ideally located near fine dining, shopping, banks, and everyday conveniences, the home combines luxury living with unmatched accessibility. Built in 2011 and meticulously maintained, freshly painted, with new wall to wall carpet, this expansive residence features 7 bedrooms and 5 full bathrooms thoughtfully designed for both elegant entertaining and comfortable everyday living. A dramatic two-story foyer creates a grand first impression, flanked by formal living and dining rooms that add sophistication and charm. The upper level includes a luxurious owner’s suite with a spacious bedroom and spa-inspired bath, along with generously sized secondary bedrooms, including a Jack-and-Jill bath and an additional hall bath arrangement designed for convenience and privacy. The main level offers a desirable guest suite with a full bath, ideal for multigenerational living or visiting guests. At the heart of the home is a beautifully appointed gourmet kitchen featuring upgraded cabinetry, granite countertops, a center island, breakfast area, and seamless flow into the expansive family room. The finished lower level provides exceptional versatility with a large recreation/family room, an additional suite, and three flexible rooms perfectly suited for guest accommodations, home offices, fitness space, or playrooms. Step outside to the inviting deck overlooking the gently rolling backyard — an ideal setting for relaxing mornings, outdoor dining, and entertaining in a peaceful, private setting. House blueprints provided in this listing are for reference only and may not accurately reflect the current structure. Call your real estate agent and schedule a showing today!

2700 Loyalty Ct, Winchester
$359,900
3 Beds ⋅ 1 Baths ⋅ VAWI2011258 MLS
Welcome to this beautifully updated brick home offering the perfect blend of charm and modern updates. Major improvements completed in 2021 include a new roof, windows, HVAC system, kitchen cabinets with granite countertops, and a renovated main-level bathroom. A new water heater was installed in 2024. In 2026, a city-permitted addition created a spacious new primary bedroom and bathroom, along with new roof framing, siding, and plumbing. Conveniently located close to shopping, dining, and commuter routes, this move-in-ready home is ready for its next owner. Chimney is sealed off. Not useable. *Agent is related to landlord* The information contained herein is for informational purposes only. RE/MAX Roots makes no representation as to the accuracy or reliability of the information. The buyer is to verify information provided and related to the property that is material to a buyer’s decision to purchase the property. All documents and other information attached to this listing are provided as a courtesy and should be researched and verified by the buyer agent.

236 Shawnee Ave, Winchester
$349,000
3 Beds ⋅ 3 Baths ⋅ VAFV2043742 MLS
Nestled in the serene Wilde Acres/Mtn Falls community, this exquisite split foyer home, built in 2020, offers a harmonious blend of modern luxury and natural beauty. Spanning a generous 0.78 acres, the property is enveloped by lush trees, providing a tranquil backdrop that enhances the sense of privacy and peace. Step inside to discover a warm and inviting interior, where laminated flooring flows seamlessly throughout the main living areas. The heart of the home features a spacious living room that effortlessly connects to a well-appointed kitchen, complete with ENERGY STAR appliances, including a built-in microwave, refrigerator, and stove. The pantry offers ample storage, ensuring that your culinary adventures are always well-equipped. With three thoughtfully designed bedrooms and two and a half bathrooms, this residence caters to both comfort and functionality. The master suite is a true retreat, boasting an en-suite bathroom that exudes elegance. The additional bedrooms are versatile, perfect for guests, a home office, or creative spaces. The partially finished basement, accessible via a side entrance, presents endless possibilities-whether you envision a cozy family room, a home gym, or additional storage. The attached two-car garage, featuring a side entry and built-in access, adds convenience to your daily routine. Outside, the expansive lot invites you to embrace the outdoors. Imagine sipping your morning coffee on a private patio, surrounded by the soothing sounds of nature, or hosting gatherings under the shade of towering trees. The level yard is perfect for gardening, play, or simply enjoying the picturesque mountain views that stretch beyond your property. This home is not just a residence; it's a lifestyle. With road maintenance and snow removal included in the association fee, you can enjoy the beauty of the changing seasons without the hassle of upkeep. The surrounding area offers a wealth of outdoor activities, from hiking to exploring nearby parks, making it an ideal setting for those who appreciate an active lifestyle. Experience the perfect blend of luxury, comfort, and nature in this stunning home, where every detail has been thoughtfully curated to create a sanctuary you'll be proud to call your own.

204 Cougar Trl, Winchester
$700,000
4 Beds ⋅ 4 Baths ⋅ VAFV2043616 MLS
Welcome home to this gorgeous custom-designed residence offering exceptional one-level living with quality craftsmanship and thoughtful details throughout. A welcoming foyer with an elegant tray ceiling sets the stage for the beautiful interior. The stunning gourmet kitchen is the heart of the home, featuring a large center island with leathered granite countertops, abundant soft-close cabinetry and drawers, Café-style stainless steel appliances, and generous counter space for cooking and entertaining. The spacious dining area showcases a tray ceiling and sliding glass doors that open to a screened-in covered porch, creating the perfect setting for relaxing or entertaining. The impressive living room features a soaring vaulted ceiling with exposed wood beams, a beautiful fireplace with a custom mantel, and large tinted windows that flood the space with natural light while enhancing energy efficiency and privacy. The private owner's suite is a luxurious retreat featuring a tray ceiling, two walk-in closets, and a spa-inspired en-suite bath with a double-sink vanity, linen closet, and a custom-designed tiled walk-in shower with a built-in seat. The desirable split-bedroom floor plan offers two additional generously sized bedrooms and a well-appointed hall bath with a tub/shower combination, providing comfort and privacy for family and guests. The walk-out lower level is truly in a class of its own and showcases the same exceptional craftsmanship and attention to detail found throughout the home. Filled with abundant natural light, this incredible space features a spacious family room, an attractive wet bar, a private bedroom, a full bath, dedicated office space, and a versatile bonus room currently used as a music room with a full-size window. A large unfinished storage area provides ample room for all your storage needs. Step outside to the concrete patio and unwind while listening to the peaceful sounds of the beautifully designed waterfall nestled within the professionally landscaped backyard. Gorgeous natural stone, thoughtfully planned landscaping, and mature plantings create a tranquil outdoor oasis that perfectly complements this remarkable home. While the photographs beautifully capture this home's stunning features, they simply cannot convey the warmth, quality, and craftsmanship you'll experience in person. This is a home that must be seen to be fully appreciated.

151 Feed Mill Ct, Winchester
$399,000
4 Beds ⋅ 2 Baths ⋅ VAFV2043114 MLS
This charming brick ranch-style home, built in 1971, offers a perfect blend of comfort and functionality. With 2,198 sq. ft. of thoughtfully designed space, this residence features three inviting bedrooms and two full bathrooms, ideal for relaxation and privacy. The traditional floor plan is enhanced by beautiful hardwood and ceramic tile flooring, creating a warm and welcoming atmosphere throughout. The heart of the home is the eat-in kitchen, including a built-in microwave, dishwasher, and electric oven/range. Enjoy cozy meals at the kitchen table or gather around the wood-burning/woodstove & propane fireplace in the living area, perfect for creating lasting memories. Additional features include built-ins, ceiling fans, and a convenient main floor laundry area. Step outside to discover a generous 0.74-acre lot, beautifully landscaped and backing onto serene trees, providing a peaceful retreat. The exterior boasts several porches and ample parking with an oversized attached 5-bay garage and paved/gravel driveway, which is fantastic for car enthusiasts! Located in a rural setting, this home offers picturesque views of the garden and surrounding woods, making it an ideal escape from the hustle and bustle. With its combination of comfort, space, and natural beauty, this property is ready to welcome you home. This is a Special Warranty Deed sale. Call for details on garage measurements!

820 Cedar Grove Rd, Winchester
$349,900
2 Beds ⋅ 1 Baths ⋅ VAFV2043734 MLS
The Perfect Starter or downsize Home Awaits! Current Shawneeland Inventory 208 Beaver Trail 101 Tonto Trail 212 Falcon Trail 211 Inca Trail 107 Pinto Trail 123 Killbuck Trail Comcast/Xfinity available on this street. New plan on almost 1/3 of acre! Affordable new home close to town with full unfinished basement (ruff in future bath) for future needs. Upgrades include: Hardwood floors throughout, tile in bath floors, granite countertops kitchen, upgraded cabinets. Builder upgrade full front covered porch and to be Timbertech. Why buy a townhome when you can have your own home! Discover an incredible opportunity to own a brand-new, single-family home on over 1/3 of an acre, offering unparalleled privacy on short street with little traffic and flat lot. This affordable new construction provides the space and freedom you won't find in a townhome. Key Features & Upgrades: Premium Location: Private, expansive lot (1/3+ acre) located low within a desirable community. Quality Finishes: Enjoy hardwood flooring throughout the main living areas, elegant tile in all bathroom floors, granite countertops in the kitchen, and upgraded cabinetry. Outdoor Living: Relax on the stunning, full front covered porch, upgraded with durable, low-maintenance Timbertech decking. Future Potential: A full, unfinished basement provides a blank canvas for future expansion, storage, or customization to meet your evolving needs. Convenience: Just minutes from town, offering easy access to amenities while maintaining a peaceful residential setting. This home is designed for modern living and exceptional value.

101 Tonto, Winchester
$525,000
5 Beds ⋅ 4 Baths ⋅ VAFV2043592 MLS
Nestled in the charming Apple Ridge community, this stunning Colonial-style home offers a perfect blend of comfort and elegance. Set on a generous 0.4-acre lot, the property backs onto serene open common areas and lush trees, providing a tranquil retreat right in your backyard. Enjoy the luxury of multiple balconies, a spacious deck, and a welcoming porch, ideal for relaxing or entertaining while soaking in the peaceful views of nature. With five spacious bedrooms and four full bathrooms, this home is designed for both relaxation and functionality. The fully finished basement with Kitchen adds extra living space. The main floor laundry adds convenience to your daily routine, while the attached front-entry garage ensures easy access and ample parking. The Apple Ridge neighborhood is known for its friendly atmosphere and community spirit. Excellent local schools are just a short drive away, making this location ideal for those seeking a nurturing environment. With a personal in-ground pool, this home invites you to create lasting memories during warm summer days. Experience the best of suburban living, where comfort meets community, and make this beautiful property your new home.

144 Morning Glory, Winchester
$375,000
3 Beds ⋅ 1 Baths ⋅ VAFV2043688 MLS
Enjoy one-level living with 6.44 partly wooded acres. All-brick 3-bedroom, 1-bath home offering a peaceful country setting with plenty of room to enjoy the outdoors. Relax on the covered rear porch overlooking the property. The home features a paved driveway and a full unfinished basement, providing excellent storage or future expansion potential. New water heater installed in 2022. A wonderful opportunity for those seeking privacy, acreage, and the durability of an all-brick home. Be sure to check out our 3-D tour attached to this listing!

1480 Chestnut Grove Rd, Winchester
$219,900
1 Beds ⋅ 1 Baths ⋅ VAFV2043646 MLS
MUST SEE TO APPRECIATE THIS OFFBEAT RAISED FLAT, 1 BEDROOM 1 BATH, 4 ROOMS FRESHLY PAINTED. EAT IN KITCHEN COMES WITH A STOVE, REFRIGERATOR, MICROWAVE, LOTS OF CABINET SPACE. UPDATED HVAC & NEW ROOF FRESH PAINT. WASHER & DRYER IN THE LOWER-LEVEL GARAGE AREA WITH PLENTY OF ROOM FOR STORAGE. FENCED YARD FOR GARDENING OR PETS, OFF STREET PARKING. PRIVATE, CLOSE TO SHOPPING, DOWNTOWN & RT.37. " INVESTORS TAKE NOTICE THE HOME HAS BEEN PREVIOUSLY RENTED" OWNER IS A VIRGINIA LICENSED REALTOR

1057 Foreman Ln, Winchester
$879,900
5 Beds ⋅ 5 Baths ⋅ VAFV2043702 MLS
Immaculate custom home sitting on a half-acre lot in desirable Raven Pointe! Beautiful hardwood floors flow throughout the main level, leading into a dramatic family room with 20-foot ceilings, custom built-ins, a gas fireplace, and high windows featuring remote-controlled custom shades. The gourmet kitchen boasts granite countertops, soft-close cabinets, stainless steel appliances, double wall ovens, a gas cooktop, and opens seamlessly to a second living area with a warm gas fireplace. Main-level primary suite offers tray ceilings, a custom walk-in closets one with a built-in makeup vanity, and a bathroom with dual vanities and a large walk-in shower. Upstairs, you will find two additional spacious bedrooms, a full bath, plus a private in-law suite with its own en-suite bathroom. The bright walk-out lower level features a spacious rec room, full bathroom, bedroom, and a dedicated office space with a window that can also serve as a versatile bonus room. Enjoy outdoor living from the expansive composite deck or relax on the lower covered patio with ceiling fans giving an outdoor living room feel overlooking a private yard supported by an underground irrigation system. Complete with an oversized 3-car garage and located just minutes from I-81, shopping, and downtown Winchester!

243 Summerfield Dr, Winchester
$619,900
4 Beds ⋅ 5 Baths ⋅ VAFV2043500 MLS
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
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