Winchester Homes for Sale

Winchester Homes for Sale

Welcome to Winchester, Virginia—a charming city steeped in history and nestled in the picturesque Shenandoah Valley. Known for its vibrant downtown, stunning architecture, and rich Civil War heritage, Winchester offers a unique blend of small-town warmth and modern amenities. The historic Old Town district is a treasure trove of boutique shops, delightful eateries, and cultural attractions, making it a perfect spot for leisurely strolls and community gatherings.

Winchester is not just a place to visit; it’s a place to call home. With a variety of neighborhoods that cater to diverse lifestyles, you’ll find everything from quaint historic homes to contemporary developments. The real estate market here is thriving, with homes for sale that boast charming features, spacious layouts, and beautiful outdoor spaces. Whether you’re a first-time buyer, looking to downsize, or searching for a family-friendly abode, Winchester has something to offer everyone.

Outdoor enthusiasts will appreciate the abundance of parks and recreational areas, including the scenic Jim Barnett Park and the nearby Appalachian Trail, perfect for hiking and exploring the natural beauty of the region. Families can take advantage of excellent schools and community resources, ensuring a nurturing environment for children.

In Winchester, you’re not just buying a home; you’re investing in a lifestyle rich with history, community spirit, and endless opportunities for adventure. Explore our current listings today and discover your dream home in this enchanting city!

Newest Winchester Homes for Sale

5 Beds ⋅ 4 Baths

223 Fairfield Dr, Winchester

Listing courtesy of Samson Properties. Contact: 7033788810

5 Beds ⋅ 5 Baths

**Freshly Updated Estate on 3.46 Acres with Mountain Views | Now $749,900** Freshly reintroduced to the market with significant new upgrades and a new price! This exceptional 5-bedroom, 4.5-bath estate offers over 3,700 finished sq. ft. on 3.46 private acres with beautiful mountain views. Recent improvements give the home a fresh, elevated feel, including new interior paint, coffered ceilings, recessed lighting, an updated double-sided fireplace, new basement flooring, and new French doors. The gormet kitchen features Thor appliances, modern cabinetry, updated countertops, flooring, and fixtures. A spacious main-level primary suite offers a soaking tub, dual vanities, and separate shower. The fully finished walkout basement provides incredible flexibility with two additional bedrooms, two full baths, and a large recreation area—perfect for guests, multigenerational living, a home gym, office, or entertaining. Outside, enjoy a Trex deck, multiple patios, built-in firepit, and peaceful mountain views. Additional updates include a newer well pump, pressurized water tank, water softening system, and upstairs AC condensing unit. Adding to its one-of-a-kind story, the home was once owned by NFL MVP and Washington Redskins legend Mark Moseley. Now offered at $749,900—an incredible opportunity for this much space, acreage, character, and recent updates. Fresh look. Fresh price. Ready for its next chapter!

199 Meeting House Dr, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

2 Beds ⋅ 2 Baths

Set on nearly two acres just minutes from historic downtown Winchester, this beautifully maintained one-level home delivers the rare combination of open country space and everyday convenience. A classic covered front porch welcomes you in, opening to a bright, open-concept kitchen and living with 10' ceilings. This central living area is designed for easy flow — cooking, gathering, and relaxing all in one connected space. Two comfortable bedrooms and two full baths include a spa-inspired retreat. One with a luxurious walk-in shower and the other with a step-up soaking tub. Out back, a covered patio overlooks the wide, level lawn — a quiet spot for morning coffee or evening entertaining, framed by mature trees and open sky. Storage and workspace are never an issue here: a two-car attached garage plus a separate detached garage offer room for vehicles, tools, hobbies, or a workshop. Manicured landscaping, crisp white siding, and a white-fenced property line complete the picture. Move-in ready, meticulously cared for, and surrounded by room to breathe — all within a short drive of Winchester's shops, dining, and Old Town district.

211 Marple Rd, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact: (301) 365-0664

3 Beds ⋅ 2 Baths

Welcome home to this beautifully maintained 3-bedroom, 2-bath home offering comfort, convenience, and exceptional outdoor living. Ideally located just minutes from shopping, schools, the hospital, and other everyday amenities, this home combines a prime location with thoughtful updates. Inside, you'll find two recently remodeled bathrooms featuring modern finished and stylish upgrades. The functional layout provides comfortable living spaces perfect for everyday life. Step outside to enjoy the fully fenced backyard, offering privacy and plenty of space for children, pets, or entertaining. The extensive hardscaping creates a beautiful, low-maintenance outdoor retreat, while the paver driveway adds outstanding curb appeal. An above-ground pool provides the perfect place to cool off on warm summer days, and the storage shed offers ample space for lawn equipment, tools, and seasonal items. Move-in ready and conveniently located, this home offers the perfect blend of comfort, style. and accessibility. Don't miss your opportunity to make it yours-schedule your private showing today!

153 Fox Dr, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

3 Beds ⋅ 1 Baths

Charming 1932 Craftsman Near Downtown Winchester! Step into this classic 1932 Craftsman home, where timeless historic character perfectly meets modern updates. Stunning original craftsman style windows in every room. Boasting an abundance of original woodwork and original wood floors throughout, this home radiates warmth, style, and craftsmanship. The main level highlights Large, open rooms designed for seamless living and entertaining. Bright and open kitchen enjoys newer double ovens, dishwasher, new cooktop and SS hood, new kitchen sink and faucet. The Sunroom features beautiful, heated terracotta tile floors and new double pane windows that flood the space with natural light. Outdoor boasts your classic front porch spanning the width of the house, perfect for relaxing with your favorite beverage. The main floor hosts a 1/2 bath and convenient laundry room. The second level with three generous bedrooms, each equipped with spacious closets, also features a large hall linen closet. The renovated Full Bath comes with custom tile flooring and a sleek, walk-in glass shower. Enjoy the perfect blend of neighborhood charm and urban convenience. If outdoors is your vibe, relaxing on the stone patio with plenty of room for outdoor furniture and a deep yard for kids and pets to enjoy! This home sits just minutes from vibrant downtown restaurants, shopping, and entertainment. Don't miss the opportunity to own a piece of history featuring the perfect balance of original 1930s details and thoughtful modern updates! Call me today to arrange your private showing. PROFESSIONAL PHOTOS COMING SOON.

633 Pennsylvania Ave, Winchester

Listing courtesy of Colony Realty. Contact:

3 Beds ⋅ 2 Baths

Permitted and delivery 4 months. Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house (new PIN OAK model); it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle of single-level living in this immaculate, brand-new residence, meticulously designed with a flowing 2,488 sq. ft. open floor plan. The builder has redefined "standard features," integrating premium elements throughout the home that others typically label as costly upgrades. Key Features & Elegant Finishes: Striking Curb Appeal: A distinguished full brick front complemented by durable cement siding creates a timeless exterior, highlighted by a large, welcoming concrete front porch and lead walk. Exquisite Main Level: Rich, stained Early American hardwood flooring flows seamlessly across the entire main level, excluding the elegant tiled bathrooms and laundry room, creating a warm, inviting atmosphere. Seamless Indoor/Outdoor Entertaining: Step through to your private outdoor oasis. A covered and screened deck provides an ideal spot for year-round relaxation, extending onto an attached open deck perfect for grilling and sunbathing. This exquisite home represents a unique blend of craftsmanship, luxury, and exclusivity. Don't miss the chance to claim your spot in this premier community.

lot 12 Keval Gyan Way, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475

5 Beds ⋅ 3 Baths

Beautiful 5-bedroom, 2.5-bath brick-front home situated on 2 private acres, offering the perfect blend of space, comfort, and recent updates. Major updates provide peace of mind, including a new roof (2025), HVAC systems replaced in 2023, 2024, and 2025, a new pressure tank, water heater, sump pump, Culligan water softener, and updated light fixtures Enjoy outdoor living on the spacious deck and paver patio, ideal for entertaining or relaxing. Inside, the kitchen features hardwood flooring, Corian countertops, a pantry, and ample cabinet space. The main level showcases elegant crown molding, a convenient laundry room with a shower, and freshly painted rooms that give the home a bright, refreshed feel. The oversized primary suite includes a huge walk-in closet for exceptional storage. . Full, unfinished, walkout level basement. Enjoy the privacy of country living while still being conveniently located to nearby amenities.

175 Shields Dr, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362

3 Beds ⋅ 1 Baths

Lovingly maintained, this charming brick rancher is the perfect starter home or investment opportunity! The main level offers three comfortable bedrooms, one full bath, a bright eat-in kitchen, and a spacious living room filled with natural light. The full unfinished basement provides endless potential for additional finished living space, while an existing hobby room is already in place—perfect for sewing, crafts, a workshop, or a home office. A unique bonus is the custom-built "catio" just off the back of the home, creating a safe outdoor retreat for your feline friends. Outside, enjoy a private backyard with mature landscaping and a detached one-car garage. Ideally located just minutes from Old Town Winchester, the Walking Mall, the Museum of the Shenandoah Valley, Winchester Medical Center, shopping, dining, and commuter routes, this home offers both convenience and charm. Major updates completed in 2016 include new windows, HVAC, roof, driveway, and beautifully refinished hardwood floors. The home is served by public water and a private septic system.

805 Pennsylvania Ave, Winchester

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

3 Beds ⋅ 3 Baths

Charming Country Farmhouse with Modern Updates & Unrestricted Property! Welcome to this charming 1940's farmhouse, thoughtfully renovated and expanded in 2006 to blend timeless character with modern convenience. Offering 3 bedrooms and 3 full bathrooms, this inviting home provides a flexible layout that's perfect for a variety of lifestyles. The main level features a kitchen that flows seamlessly into the living room, creating the perfect gathering space. Two bedrooms and two full bathrooms are conveniently located on the main floor, including a comfortable primary suite complete with a generously sized walk-in closet and private ensuite bath. Upstairs, you'll find a spacious landing area leading to the third bedroom, which boasts its own ensuite full bath and access to a private outdoor deck—an ideal spot to enjoy your morning coffee or unwind at the end of the day. The walk-up attic offers excellent potential to finish and create additional living space, whether you envision a home office, bonus room, or hobby area. Comfort is ensured year-round with a central HVAC system, supplemented by a mini-split system and propane heater for added flexibility. The home also includes both an interior-access cellar and a traditional exterior root cellar, providing abundant storage options. Situated on a quarter-acre lot, the property also features a 24' x 24' detached two-car garage with automatic door openers and 30-amp electrical service, making it ideal for vehicles, a workshop, or recreational equipment. With no restrictions, this property offers many possibilities. Whether you're looking for modern living in a peaceful rural setting, homestead living, or simply room to create your own, this unique property is ready to welcome you home.

2346 Welltown Rd, Winchester

Listing courtesy of Touchstone Realty, LLC. Contact:

4 Beds ⋅ 4 Baths

Welcome to an extraordinary custom-built all-brick estate nestled on five beautifully manicured acres in the highly sought-after Apple Pie Ridge area. This exceptional property blends timeless elegance, quality craftsmanship, and modern updates to create a truly one-of-a-kind retreat. From the moment you arrive, the winding approach and picturesque setting set the stage for what's inside. Designed for both grand entertaining and everyday comfort, the home features three spacious bedrooms, three full bathrooms, and two half baths, with flexible living spaces that can easily accommodate a bedroom, guest suite, or recreation room. The heart of the home is the spectacular gourmet kitchen, where culinary enthusiasts will appreciate granite countertops, a commercial-size refrigerator, two Wolf wall ovens, a cooktop with downdraft ventilation, an expansive multi-level island with prep sink, and instant hot water. The kitchen flows effortlessly into the inviting family room with custom built-ins and a cozy gas fireplace, while the adjoining sunroom fills the home with natural light and offers panoramic views of the backyard oasis. Outside, resort-style living awaits. The inground pool is the centerpiece of the backyard, creating the perfect setting for relaxing afternoons, gatherings, and unforgettable summer entertaining. A brick patio overlooks the beautifully landscaped grounds, offering a peaceful space to unwind and enjoy the privacy of your surroundings. The primary suite is a private sanctuary complete with its own gas fireplace, cedar-lined walk-in closets with custom built-ins, and an impressive spa-inspired bath featuring a jetted soaking tub and separate shower. Additional bedrooms are generously sized, while a spacious office with custom built-ins provides the ideal work-from-home space. A large bonus room with a full bath offers endless possibilities and the fourth-floor bedroom is an incredible private retreat that any teenager or overnight guest will love. Movie nights become an event in the dedicated theater room, while the expansive unfinished basement offers tremendous potential for additional finished living space, a home gym, workshop, or recreation area. Car collectors, hobbyists, and outdoor enthusiasts will appreciate the attached and detached garages with room for up to six vehicles. The detached heated and cooled three-bay garage includes a full bath, separate septic system, and unfinished space above offering endless possibilities. This meticulously maintained home has been thoughtfully updated with two new HVAC systems, a new hot water heater, a new water softener, a new dishwasher, and a new washer and dryer. The original portion of the home also features premium Andersen windows with upgraded screens, enhancing both energy efficiency and timeless appeal. Properties of this caliber rarely become available.

194 Glendobbin Ln, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099

5 Beds ⋅ 3 Baths

Spacious ranch home on a beautiful 1-acre lot in the highly desirable Stonebrook Farms community! Surrounded by mature trees and offering a peaceful setting, this home combines the space of country living with the convenience of being just minutes from shopping, dining, medical facilities, and all that Winchester has to offer. Designed with flexibility in mind, this home features 5 bedrooms and 3 full baths, including a private wing tucked behind the garage with a bedroom, full bath, and adjoining den. Located just off the kitchen, this space is ideal for an in-law suite, guest quarters, home office, or multi-generational living. The finished lower level provides even more living space with an additional bedroom, full bath, kitchen, and dining area, creating endless possibilities for recreation, extended family, or entertaining. Step outside to enjoy the spacious backyard, mature landscaping, and patio, offering plenty of room to relax, garden, or host gatherings. Stonebrook Farms is one of Winchester's most sought-after neighborhoods, offering the opportunity to join the optional Stonebrook Club, featuring swimming, tennis, pickleball, and social activities. With its combination of generous living space, a beautiful setting, and an exceptional location, this home is ready for its next chapter.

146 Stonebrook Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360

2 Beds ⋅ 2 Baths

Welcome to easy one-level living in Willow Lawn Cottages, a popular 55+ community in Winchester! This well-maintained home has been freshly painted and offers 2 bedrooms and 2 full bathrooms. The open floor plan feels bright and spacious, with vaulted ceilings, plenty of natural light, and luxury vinyl plank flooring throughout. The kitchen includes granite countertops, updated cabinets, stainless steel appliances, and a built-in microwave. The primary bedroom has a walk-in closet and a private bathroom with a walk-in shower. You’ll also find main-level laundry, an attached one-car garage, a covered front porch, and a rear patio where you can relax outdoors. The HOA takes care of lawn maintenance and snow removal and provides access to the community clubhouse, gathering spaces, and sidewalks. Located close to Winchester Medical Center, shopping, restaurants, and historic downtown Winchester, this home offers comfort and convenience in a welcoming community.

1853 Rosser Ln, Winchester

Listing courtesy of Realty FC. Contact: (540) 931-0144

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