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 picturesque Shenandoah Valley, Winchester boasts a rich cultural heritage, evident in its well-preserved architecture and vibrant downtown area. With its historic sites, including the renowned Museum of the Shenandoah Valley, and the iconic Old Court House, residents and visitors alike can immerse themselves in the stories that shaped this remarkable city.

Winchester is not just about history; it offers a perfect blend of modern conveniences and a close-knit community feel. With a variety of shops, restaurants, and local events, there’s always something happening in this lively town. Outdoor enthusiasts will appreciate the nearby hiking trails, parks, and the stunning views of the Blue Ridge Mountains, making it an ideal location for those who love to explore nature.

For those looking to make Winchester their home, you’ll find a diverse selection of homes for sale that cater to various lifestyles and budgets. From charming historic homes with character to modern new builds, there’s something for everyone. Families will appreciate the excellent school system, while retirees can enjoy the peaceful ambiance and community activities.

Whether you’re a first-time homebuyer or seeking a serene place to retire, Winchester offers a welcoming environment and a strong sense of community. Come discover why so many are choosing to call this beautiful city home. Your dream home in Winchester awaits!

Newest Winchester Homes for Sale

$409,900
3 Beds ⋅ 3 Baths ⋅ VAFV2043846 MLS
Discover this well-appointed 3-bedroom, 3-bathroom single-family home offering approximately 2,150+ square feet of comfortable living space on a generous 0.44-acre lot. Designed with an open floor plan and practical updates, this residence balances everyday convenience with flexible living options in a highly accessible Winchester location. Main Level: Hardwood flooring flows through the open living areas, creating a bright and inviting atmosphere ideal for both daily living and entertaining. The primary suite features a walk-in closet and private full bathroom. Two additional bedrooms share a full hallway bathroom. Finished Lower Level: The finished basement expands the home’s functionality with a full bathroom, dedicated office, and versatile den—perfect for remote work, a media room, guest space, or family activities. Walk-out access leads directly to the deck. Outdoor Living & Parking Enjoy a walk-out deck overlooking a large backyard, ideal for outdoor dining, recreation, or simply relaxing. A two-car attached garage provides convenient parking and storage. Location & Neighborhood Amenities Situated in a convenient Winchester location with easy access to major routes including I-81, Route 37, and Route 11. Residents enjoy proximity to the charm of Old Town Winchester and its walkable Loudoun Street Pedestrian Mall, filled with local shops, restaurants, and historic character. Nearby amenities include shopping centers, Jim Barnett Park with trails and recreational facilities, the Museum of the Shenandoah Valley, and everyday conveniences. The area also offers access to outdoor recreation throughout the Shenandoah Valley while remaining close to major employers and services. This home combines comfortable main-level living, flexible lower-level space, and a private outdoor setting in a location that supports both convenience and lifestyle. Ideal for those seeking space to grow while remaining connected to everything Winchester has to offer.

101 Fay St, Winchester
$598,895
3 Beds ⋅ 4 Baths ⋅ VAFV2043880 MLS
Enjoy the ease of true main-level living in this meticulously maintained ranch home offering more than 4,300 finished square feet on an oversized 0.37-acre lot in Winchester's desirable Star Fort community | NO HOA | With nearly 2,300 square feet on the main level and an additional 2,100+ finished square feet in the walk-out basement, this home offers an abundance of flexible living space, all complemented by breathtaking panoramic valley views from the expansive 63-foot deck | Covered Front Porch Leads to Welcoming Foyer | Spacious Dining Room w/Triple Window has Room for a Crowd as does the 17' x 15' Family Room w/Gas Fireplace | Immaculate Kitchen w/Updated Appliances, Recessed Lighting, Pantry & Breakfast Nook w/Sliding Doors to Deck | Main Level Primary Suite w/2 Huge Walk-In Closets + French Doors to the Deck + En Suite Bath with Walk-In Jetted Soaking Tub & Separate Shower | 2 Additional Bedrooms w/Great Closet Space on Main Level Share the 2nd Full Bath + 13' x 12' Flex Room for Guests or Home Office | Convenient Main Level Laundry/Mudroom + 2-Car Side-Load Garage | Fully Finished Walkout Basement has Tremendous Space for Anything! 35' x 33' Rec Room w/Built-in Cabinet Storage + 2 Additional Rooms (27' x 16' & 27' x 26') with Endless Possibilities + 3rd Full Bath | Delightful Fenced Back Yard + Covered Storage Under Deck | Numerous recent improvements including Painted Porch/Lead Walk, Interior Paint, New Flooring + Carpet/Padding & Updated Kitchen Appliances as well as a Resealed Deck (2026) + Replaced Deck Surface (2024), New Attic Insulation (2025), New Insulated Garage Door (2023), New Roof (2018), Washer & Dryer (2018/2017) Additional features include a whole-house generator, whole-house water softener, invisible fence + fully fenced back yard, and walk-in bathtub | Fantastic Winchester Location Convenient to Old Town Winchester & 81 + Shopping, Dining & Recreation

142 Fortress Dr, Winchester
$115,000
VAFV2043860 MLS
Escape to your own private A-frame cabin in the woods! Whether you're searching for the perfect weekend retreat, a unique Airbnb opportunity, or a peaceful getaway to enjoy with family, friends, or clients, this charming mountain cabin is ready to enjoy. Tucked away in a quiet, wooded setting with easy year-round access, this hidden gem offers the perfect balance of privacy and convenience. Relax on the spacious front deck surrounded by mature trees, or unwind on the rear deck while taking in breathtaking long-range mountain views that truly feel like a million-dollar backdrop. Inside, the cabin is warm, inviting, and being sold fully furnished, making it move-in or rental ready from day one. The loft provides additional sleeping space while maintaining the classic A-frame charm. Located approximately 30 minutes from Historic Downtown Winchester, about 30 minutes from Front Royal, and roughly 1½ hours from Fairfax, this property is close enough for an easy weekend escape while feeling worlds away from the hustle and bustle. Residents enjoy low real estate taxes, low HOA dues, and access to community amenities including a scenic pond and waterfall. As more homes continue to be built throughout the community, this peaceful mountain neighborhood is becoming one of the area's best-kept secrets. Property is being sold fully furnished and strictly As-Is.

403 Stag Trl, Winchester
$650,000
4 Beds ⋅ 4 Baths ⋅ VAWI2011266 MLS
Welcome to 1529 Dalton Place, an exceptional home tucked away on a quiet cul-de-sac in one of Winchester's most desirable locations. Offering 4 spacious bedrooms, 3.5 bathrooms, and an expansive floor plan, this beautifully designed residence delivers the perfect blend of comfort, style, and functionality. From the moment you enter, you'll appreciate the generous room sizes throughout, including elegant formal living and dining rooms ideal for entertaining. The heart of the home features an inviting open-concept kitchen and family room, creating the perfect space for everyday living and gathering with family and friends. A bright and airy sunroom provides the perfect spot to relax while overlooking the backyard. The finished basement offers exceptional flexibility with abundant space for a recreation room, home theater, fitness area, office, or guest suite. A spacious 2-car garage provides plenty of storage and convenience. Ideally situated in a prime location close to shopping, dining, schools, commuter routes, and all that Winchester has to offer, this impressive home combines space, convenience, and timeless appeal. If you're searching for a move-in-ready home with generous living areas and an unbeatable location, 1529 Dalton Place is one you won't want to miss. All sizes are approximate.

1529 Dalton Pl, Winchester
$375,000
3 Beds ⋅ 2 Baths ⋅ VAWI2011076 MLS
Charming, Updated Rancher in the Heart of Winchester! Welcome home to this impeccably maintained 3-bedroom, 2-bath ranch offering the perfect blend of comfort, character, and convenience—all on one level! From the moment you arrive, you'll appreciate the pride of ownership and thoughtful updates throughout. The spacious kitchen is the heart of the home, offering abundant cabinetry and room to gather with family and friends. Multiple living areas provide the flexibility to create a cozy family room, home office, playroom, or hobby space—giving everyone room to spread out. Major updates provide peace of mind, including a new roof, siding, and side porch—all completed within the last year. Other updates include added storage, updated bathrooms, updated flooring, and lots of other touches throughout. Additional features include a gas furnace, central air conditioning, and an abundance of storage rarely found in homes of this size. Located within the City of Winchester, you'll enjoy the convenience of nearby shopping, dining, parks, and commuter routes while coming home to a property filled with warmth, charm, and timeless character. This lovingly cared-for home is a true hidden gem that's move-in ready and waiting for its next owner. Schedule your private tour today before this one is gone!

1004 Pennsylvania Ave, Winchester
$180,000
3 Beds ⋅ 1 Baths ⋅ VAWI2011268 MLS
Opportunity awaits at 309 Liberty Avenue in Winchester City. This classic Cape Cod offers the chance to create something truly special in an area experiencing continued growth, infrastructure improvements, and neighborhood investment. The property does require substantial work, making cash financing the most likely option; however, the potential is significant for a buyer with the vision to transform it into a distinctive home while building meaningful sweat equity. The level backyard provides plenty of usable outdoor space, and the rear alley creates the possibility of adding a gated entrance for convenient off-street parking behind the home. A rare opportunity to reimagine a well-located Winchester property and make it entirely your own.

309 Liberty Ave, Winchester
$969,000
5 Beds ⋅ 4 Baths ⋅ VAFV2043184 MLS
A rare opportunity to live on Lake Serene - Welcome to your private waterfront retreat on Lake Serene, where resort-style outdoor living meets timeless modern craftsmanship. Rarely does an opportunity like this come along. Tucked among the trees on one of Frederick County's most sought-after private lakes, this beautifully renovated waterfront home offers the perfect balance of luxury, recreation, and everyday comfort. Completely transformed in 2016 with a 2-story addition along with thoughtful updates & remodeling, the home features a stunning custom Chef's kitchen with rich cherry cabinetry, elegant soapstone countertops, and quality finishes include KitchenAid gas range and Viking range hood. Designed for gathering with family and friends we have 5 bedrooms and 3.5 beautifully remodeled bathrooms, numerous living areas on two spacious levels making this THE gathering place! Offering one level living for all daily activity the main level is host to gorgeous family room with soaring ceilings, kitchen, dining room, living room with fireplace, laundry, 3 bedrooms & 2.5 baths. The lower level offers additional space to spread out with game room, recreation room, wet bar and two additional bedrooms and storage. Step outside and discover your own private retreat. Extensive hardscaping, an oval in-ground heated pool, multiple outdoor entertaining spaces, and mature landscaping create a resort-like setting that's perfect for summer afternoons or evening sunsets with views of the lake. A detached 2-bay garage also has a finished area w/ fireplace which was originally utilized as an office now acts as a pool house. Life at Lake Serene is about more than the home itself. Enjoy boating, kayaking, fishing, paddleboarding, or simply relaxing by the water. Inventory on Lake Serene is exceptionally limited, with many properties remaining in the same families for generations. Even more uncommon is finding a home that has already been tastefully updated—allowing you to begin enjoying the lake lifestyle immediately instead of planning years of renovations. Whether you're searching for a full-time residence or the ultimate weekend escape, this exceptional waterfront property offers a rare opportunity to own one of the area's most desirable lake homes. Come experience why life is simply better at Lake Serene.

485 Lake Serene Dr, Winchester
$350,000
4 Beds ⋅ 2 Baths ⋅ VAFV2043554 MLS
Country living without the long commute! This 4-bedroom, 2-bath ranch sits on 2.15 private acres just minutes from Winchester, offering the perfect blend of peaceful surroundings and everyday convenience. Backing to woods with your own private walking paths, this property also enjoys distant mountaintop views that can be appreciated from both the backyard and the primary bedroom. Many of the major improvements have already been completed, including new windows in the original portion of the home (2025), a new water softener (2025), an updated bathroom featuring a walk-in shower and new sink vanity (2025), fresh interior paint (2025), a roof that's approximately five years old, heat pump (2018), siding (2017), and a recent septic inspection with the recommended repairs completed in July 2026 for added peace of mind. Inside, you'll find an eat-in kitchen with stainless steel appliances, a wood stove, four bedrooms, and two full bathrooms, providing comfortable one-level living with plenty of flexibility for guests, or a home office. Step outside to enjoy the spacious fully fenced yard, concrete patio, storage shed, established landscaping, including a variety of wild berries amongst the property. Whether you're exploring your own waling paths, gardening, or simply taking in the peaceful surroundings and mountaintop views, this property offers the space, privacy, and lifestyle you've been looking for. Many of the major improvements have already been completed, allowing the next owner to focus on making the home their own while enjoying the privacy, acreage, and peaceful setting from day one. Located mins from town off of Rt. 50, close to shopping, dining, and Winchester Medical Center. A short drive to the local major highways/I-81.

852 Mcdonald Rd, Winchester
$385,000
3 Beds ⋅ 2 Baths ⋅ VAFV2043714 MLS
New construction one-level home on a spacious 1-acre lot! Currently under construction and anticipated to be completed in early October 2026, this thoughtfully designed 3-bedroom, 2-bath ranch offers the ease of single-level living with an open-concept floor plan, luxury vinyl plank flooring, granite countertops, upgraded stainless steel appliances, and an attached two-car garage. The open kitchen flows seamlessly into the dining and living areas, creating a bright, welcoming space that's ideal for everyday living and entertaining. The private primary suite, spacious secondary bedrooms, modern finishes, and abundant cabinet space combine comfort, style, and functionality throughout the home. Whether you're buying your first home, downsizing, retiring, or simply looking for the convenience of one-level living, this home offers a comfortable, low-maintenance lifestyle on a beautiful 1-acre lot with room to enjoy the outdoors. Construction is anticipated to be completed in early October 2026. Buyers may still have the opportunity to make certain finish selections, depending on the stage of construction. Contact the listing agent for current construction updates, available selections, and additional details. Taxes currently reflect the land only.

300 Panther, Winchester
$235,000
2 Beds ⋅ 2 Baths ⋅ VAFV2043818 MLS
This home includes two bedrooms, each with an attached bathroom, and is over 1,500 square feet. It features an open floor plan with cathedral ceilings, exposed beams, and hardwood floors. The front family room boasts winter mountain views. The rear sunroom is perfect for enjoying the backyard wildlife. Shawneeland offers a private community beach, lake, playgrounds, and trails. The property was built before 1978; lead-based paint may be present.

114 Inca Trl, Winchester
$635,690
3 Beds ⋅ 4 Baths ⋅ VAFV2043794 MLS
Rare Dual Primary Suites on the Main Level! Backing to trees, this stunning new Matisse at Hiatt Pointe at Snowden Bridge offers the perfect blend of comfort and flexibility for active adults 55+. Personalize your finishes and move in this spring! Enjoy a gourmet kitchen with SS appliances including hood, quartz countertops, an oversized island, and walk-in pantry. The open layout features 10' ceilings, a gas fireplace, and a screened porch overlooking the wooded homesite. The finished lower level adds a rec room, third bedroom, and full bath. Enjoy resort-style amenities including a gated entrance, clubhouse, fitness center, pickleball, bocce, pool, and hot tub. Ask about builder incentives!

3168 Ruby Royce Dr, Winchester
$465,000
2 Beds ⋅ 2 Baths ⋅ VAFV2043772 MLS
Move-In Ready Luxury in an Intimate 55+ Boutique Community! Crafted in 2022, this exquisite Craftsman-style residence combines main-level luxury with low-maintenance living in serene Abram’s Chase. Perfectly positioned on a quiet cul-de-sac backing to tranquil, partly wooded green space, this turn-key home offers an exceptional lifestyle just minutes from Historic Downtown Winchester, Winchester Medical Center, shopping, and dining—all with a remarkably low HOA fee of just $150/month. Step inside to a bright, open-concept layout designed for seamless living and entertaining. The gourmet kitchen serves as the heart of the home, showcasing sleek quartz countertops, an expansive center island, and clear sightlines to the cozy gas fireplace in the adjacent living area. Built for year-round comfort, the interior is highlighted by energy-efficient double-pane windows, a whole-house humidifier, and a beautiful combination of luxury vinyl plank, ceramic tile, and plush carpeting. The main level provides ultimate flexibility, featuring two spacious bedrooms plus a private study. The primary suite acts as a true retreat, offering a tray ceiling and a spa-inspired bath complete with upgraded tile, a walk-in shower with bench seating, a bright transom window, and a generous walk-in closet. Out back, enjoy outdoor relaxation on your private patio equipped with a retractable awning and scenic nature views. Complete with an attached 2-car garage and HOA-covered lawn care, mulching, snow removal, and trash pick-up, this home offers effortless, main-level living at its finest. professional photos to be uploaded by Tuesday.

131 Amberfield Ct, Winchester
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