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

$549,900
5 Beds ⋅ 4 Baths
“Pioneer Heights Colonial” - Welcome to this beautifully maintained colonial in the desirable Pioneer Heights neighborhood, ideally situated just off Route 7 for easy commuter access. Offering five bedrooms and 3.5 baths, this spacious home has been thoughtfully updated and improved over the years, providing a comfortable blend of classic character and modern convenience. The heart of the home is the updated kitchen, featuring custom cabinetry, granite countertops, stainless steel appliances, and plenty of workspace for everyday living and entertaining. Throughout the home, you'll find updated bathrooms, newer carpeting, and numerous additional improvements that make this home truly move-in ready. The finished basement adds valuable living space and versatility, complete with a walkout, comfortable living area, fifth bedroom, and full bathroom. Ample storage space provides plenty of room for seasonal items, hobbies, or household needs. Step outside and enjoy multiple spaces designed for relaxing and entertaining. A rear porch leads to a deck and backyard patio, creating an easy flow for outdoor gatherings, morning coffee, or quiet evenings. The meticulously manicured front yard is a standout, featuring lush green grass, thoughtfully maintained mulch beds, and beautiful flower gardens—all complemented by an underground sprinkler system for easy lawn care. With generous living space, numerous updates, attractive outdoor amenities, and a convenient location close to Route 7, this Pioneer Heights home offers the space, comfort, and accessibility you've been looking for. Schedule your appointment to see it today!

223 Asbury Rd, Winchester

Listing courtesy of Real Broker LLC- Winchester. Contact:

$355,000
2 Beds ⋅ 2 Baths
Come see what makes Willow Lawn, a 55+ community, such a desirable place to call home! This inviting one owner Winchester home offers a comfortable blend of charm, functionality, and everyday convenience. The Floorplan is open and contemporary. The Great Room has Cathedral Ceilings and is very spacious. The grounds are taken care of by the community so life is easy. One level living w/ newer HVAC, a 4 year old roof, LVP flooring, updated bath, 2 bedrooms + 2 full bath. The 1 car garage is heated and cooled for year round comfort. There is space for a car and small workshop. You'll feel welcomed in this neighborly community where people walk, socialize and have planned activities at the well appointed Community Center. It is right around the corner from this home. Also, this home is located near the Abrams Creek Wetlands Preserve, perfect for walking + biking. Hospital + Down Town Winchester are 10 minutes away. Priced well and ready for you, come take a look today.

1847 Melvor Ln, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$375,000
3 Beds ⋅ 2 Baths
265 McDonald Rd is a 1-story Winchester home built in 1974 with a lower level and connected outdoor spaces. The kitchen includes cabinet storage, a preparation counter, and an adjoining area for dining. The main living room provides space for seating, with an additional finished room on the lower level. The primary bedroom includes a walk-in closet with shelving for organization and an adjoining bathroom with a shower and vanity. A rear deck connects to the home through sliding doors, extending the usable space outdoors. A dedicated laundry area includes cabinetry and a folding counter. The layout combines everyday living with practical storage.

265 Mcdonald Rd, Winchester

Listing courtesy of Open Door Brokerage, LLC. Contact: 4804625392
$409,000
4 Beds ⋅ 1 Baths
Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless character meets modern sophistication in one of Winchester’s most convenient and walkable locations. The large covered front porch immediately sets the tone—an inviting space for morning coffee or relaxed evening conversation. Inside, natural light fills the home, highlighting refinished hardwood floors, fresh interior and exterior paint, and preserved architectural details including original wide wood baseboard trim and classic pocket doors. The well‑proportioned bedrooms offer comfortable retreats with the same warm character found throughout the home. Also added for efficient heating and cooling year‑round, a new ductless mini‑split system has been installed for your comfort. The renovated kitchen features new cabinetry, granite countertops, trending black stainless‑steel appliances, and a pantry with built‑in cabinetry, providing excellent storage and everyday functionality. Thoughtful upgrades and custom touches enhance each living space, creating an atmosphere that is both refined and inviting. Step outside to a covered back porch with new maintenance‑free decking, overlooking an open backyard ideal for relaxing, entertaining, gardening, or unwinding at the end of the day. Additional conveniences include off‑street parking and an oversized single‑car detached garage. The neighborhood continues to shine with recent street repaving and new sidewalks, enhancing curb appeal and walkability. Ideally located just a short stroll from Winchester’s vibrant downtown pedestrian mall, you’ll enjoy easy access to restaurants, coffee shops, boutiques, breweries, and community events. Mature trees, walkable streets, and proximity to commuter routes, parks, schools, and everyday amenities make this location truly exceptional. This is a rare opportunity to own a handsome, thoughtfully updated home that captures the best of Winchester living—where character, comfort, and location come together beautifully.

322 E Piccadilly, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$435,000
3 Beds ⋅ 2 Baths
No HOA in the heart of Winchester! This charming brick rancher features three bedrooms, two baths, tall ceilings, fresh paint, hardwood floors, and a fireplace on the main level. The layout includes a versatile sunroom with a private entrance and a kitchen equipped with stainless steel appliances. The basement expands your living space with a wet bar, separate entrance, and another fireplace! This home provides timeless construction and incredible potential. Walk outside to the spacious, fully fenced backyard with a storage shed. Enjoy ample parking with an oversized attached garage. Don’t miss the opportunity to own this home in an excellent location, just steps from Winchester Country Club and minutes to shopping, dining, and commuter routes. *Seller is also offering a one-year Home Warranty with the sale of the property!

131 Country Club Cir, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$317,265
3 Beds ⋅ 2 Baths
Welcome to this charming three-bedroom, two-bathroom raised ranch nestled on a quiet, tree-lined street in one of the area’s most close-knit neighborhoods. Full of character and potential, this home boasts a classic floor plan just waiting for your cosmetic updates and personal design vision. The main level features a bright living area filled with natural light, a dedicated dining space, and original hardwood flooring. Three comfortably sized bedrooms complete the upper level, including a primary bedroom with its own private en-suite bath. The full basement offers so much room to expand with a laundry area, a finished area for a possible sleeping room, ample heavy shelving units for crafting, storage or a workshop, and a walkout with sliding doors. Beyond the front door lies a vibrant, amenity-rich community known for its warm atmosphere. Neighborhood residents enjoy access to a spring-fed/man-made lake featuring a sandy beach area, swimming, fishing, and a boat ramp (gas motors are not permitted). Cherokee Beach is open to residents without a beach pass, additional smaller ponds and scenic streams located throughout the community, two community playgrounds, wooded nature walks and trails, pavilion spaces, open sports areas, and picnic spots, and covered/lighted mailbox stations and covered school bus stops.

148 Doe Trl, Winchester

Listing courtesy of Keller Williams Realty Advantage. Contact: 3049014886
$515,000
2 Beds ⋅ 3 Baths
Welcome to 100 Gooseberry Drive, located in Winchester's established Cross Creek Village community! This meticulously maintained brick rancher offers true main-level living in one of the communities most spacious and sought-after floor plans. The main level features formal living and dining rooms, a kitchen with breakfast nook, and a bright bonus sunroom. The generous primary suite is filled with natural light and features its own cozy gas fireplace, spacious en-suite bath, and walk-in closet. A guest bedroom, additional full-bath, and dedicated laundry complete the main level. The attached two-car garage provides direct access to the home as well as a private side-entrance leading upstairs to a thoughtfully designed guest suite- ideal for visitors, a home studio or additional climate controlled storage! Enjoy easy outdoor living on a quiet corner lot, with a private fenced in back-patio perfect for enjoying morning coffee or summer grilling! Set within a vibrant 55+ community, this home offers comfort, convenience and low-maintenance living just minutes from major shopping, dining & more! Schedule your private tour today!

100 Gooseberry Dr, Winchester

Listing courtesy of Hunt Country Sotheby's International Realty. Contact:

$805,000
4 Beds ⋅ 4 Baths
CARRINGTON HOMES AT FALL RIDGE ESTATES- 5 Acre Wooded LOTS WITH MOUNTAIN VIEWS. Choose from 7 different floorplans including our Main Level Owners Suite floorplan the Boxwood Farm model with standard 10' Main Level Ceilings Model Home Open on Weekends from 11-5 at 156 Covey Lane Winchester Va

Tumble Leaf Lane, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com
$439,000
5 Beds ⋅ 3 Baths
Welcome to this newly renovated and thoughtfully designed 5-bedroom, 3-full-bath home offering exceptional flexibility for modern living or rental income. Featuring two full kitchens, two dining areas, and potentially two separate living spaces, this home provides a unique opportunity to create two distinct living areas under one roof. Bottom level has two separate entrances in front and rear and for privacy and convenience, the layout ideal for extended family, guests, roommates, or potential rental use. Newly renovated, this home combines the comfort of modern updates with the versatility buyers are looking for. Whether you're seeking a spacious primary residence or an investment opportunity with potential rental income, this property offers the space and flexibility to make it your own. Don't miss this rare opportunity to own a beautifully renovated home with multiple living possibilities!

300 Pembridge Dr, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$699,000
7 Beds ⋅ 5 Baths
Welcome to 2700 Loyalty Court—a beautifully maintained showcase home offering nearly 5,000 square feet of unmatched versatility in one of Winchester City’s most coveted locations. Commanding a prime corner lot on a peaceful cul-de-sac, this residence immediately captivates with its timeless stone-and-vinyl exterior, inviting covered front porch, and unmistakable curb appeal. Step inside to a soaring two-story foyer flowing into a light-filled interior boasting fresh paint, newer carpet, refined architectural details, and abundant natural light throughout. Designed for both grand scale entertaining and effortless everyday living, the main level features a dedicated office behind French doors, a formal dining room accented by elegant wainscoting, a den and a full bath. At the heart of the home, the sprawling family room makes a bold statement with architectural pillars and a floor-to-ceiling stone gas fireplace. It connects seamlessly to a chef-friendly kitchen complete with granite countertops, upgraded cabinetry, stainless steel appliances, a center island, pantry, built-in desk area, and a bright breakfast nook opening directly to the rear deck. A handy mudroom with laundry off the garage completes this level's intuitive floor plan. The impressive layout continues upstairs, offering abundant accommodations for family and guests across five generously sized bedrooms. The massive primary retreat serves as a true private sanctuary, complete with a dedicated sitting area, large walk-in closet, and a spa-like ensuite bath featuring a glass walk-in shower and a corner soaking tub. Two bedrooms are connected by a convenient Jack-and-Jill bath, alongside two more spacious bedrooms and another full bathroom. The real showstopper continues downstairs in the fully finished, walkout lower level—a massive multi-functional footprint that expands your living options exponentially. This lower level provides endless flexibility, featuring an expansive recreation room for hosting game days or movie nights, a full bath and two additional bedrooms perfect for guests, and multiple finished rooms ready to serve as a home gym, playroom, or hobby space—plus a storage area to keep it all organized. Offering extraordinary scale on a premier corner cul-de-sac lot, this move-in-ready home represents Winchester living at its finest and stands ready to welcome its next proud owners.

2700 Loyalty Ct, Winchester

Listing courtesy of Colony Realty. Contact:

$525,000
4 Beds ⋅ 4 Baths
Welcome to a home that gives you room for all the things that matter—working from home, hosting friends, relaxing at the end of the day, and making the space truly your own. Located in Senseny Glen, this 4-bedroom, 3.5-bath, three-level Colonial offers an ideal blend of comfort, flexibility, and location. The recently remodeled main level features luxury vinyl plank flooring throughout, along with a dedicated office, dining room, breakfast area, and inviting family room with a gas fireplace and updated kitchen. And then there’s the front porch—the perfect spot for morning coffee, an evening glass of wine, or simply enjoying the neighborhood. Upstairs, the spacious primary suite offers a private retreat with double vanity, separate shower, and jetted tub. Three additional bedrooms, a full bath, plus access to a floored attic provide plenty of space for guests, hobbies, or storage. The lower level takes entertaining to another level with a generous rec room, built-ins, wet bar, windows, and walk-up access to the backyard. Think movie nights, game nights, a home gym, creative space—or simply a place to spread out. Outside, the fully fenced backyard features a deck and mature trees, creating a private setting for outdoor dining, relaxing, gardening, or spending time with friends and family. This location makes life easy. Senseny Glen is close to schools, shopping, restaurants, and everyday conveniences, giving you the space of a neighborhood without feeling far from everything. A home with room to work, relax, entertain, and grow—while still feeling connected to the things you love. This is more than having more space. It’s having the flexibility to make the space work for you.

302 Canyon Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$430,000
3 Beds ⋅ 2 Baths
This is the one you have been waiting for!! Well cared for home, one story living in desirable Briarwood Estates...east side location convenient to commuter routes, shopping and Old Towne Winchester. Open floor plan with close to 1700 square feet. Three bedrooms, two full baths with hardwood floors in living/family room and dining area. Gas fireplace in family room, two walk in closets in master suite. Two car garage, two decks (enjoy your morning coffee on deck off of master bedroom!!) and large fenced backyard with storage shed.

310 Goldenrod Rd, Winchester

Listing courtesy of Hunt Country Sotheby's International Realty. Contact: (540) 687-8500
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