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

$349,999
4 Beds ⋅ 2 Baths
Welcome to 120 Comanche Trail in Shawneeland! Offering over 1,800 finished sq. ft., this 4-bedroom, 2-bath home combines thoughtful updates with plenty of space inside and out. Recent improvements include a NEW roof, newer HVAC, new flooring, fresh paint, updated lighting, and updated bathrooms. The primary bedroom features a walk-in closet and private en-suite bath, creating a comfortable retreat. The fully finished walkout basement expands the living space with a huge additional bedroom, bonus room and plenty of storage. Ideal for guests, a home office, recreation space, or multi-generational living. Outside, enjoy a large private lot surrounded by mature trees with established garden beds and a fire pit. A 1-car garage and spacious driveway provide plenty of parking for guests. Located on the lower end of Shawneeland, approximately 15 minutes from Winchester Medical Center, Downtown Winchester, shopping, dining, and major commuter routes. Community amenities include a lake, private beach, playgrounds, sports fields, and more. NO HOA - Shawneeland is a sanitary district maintained by Frederick County. The septic system was completely redone in November of 2024 for additional buyer peace of mind. Updated, spacious, private, and conveniently located—this home is ready for its next owner!

120 Comanche Trl, Winchester

Listing courtesy of NextHome Realty Select. Contact: (540) 667-9097
$479,900
4 Beds ⋅ 3 Baths
This lovingly maintained two-owner Colonial has been thoughtfully cared for and improved since 1994, offering the character of an established home with many of the updates today's buyers are looking for. Homes in this sought-after neighborhood rarely come to market, making this a special opportunity in one of the area's most convenient commuter locations. Inside, you'll find a comfortable blend of hardwood, tile, and carpet flooring, built-in shelving, fresh paint in many areas, and charming details including chair rail and crown molding in select rooms. The living area features an antique stained-glass mantle that has been beautifully refinished and incorporated above the gas fireplace, creating a distinctive focal point. The kitchen is designed for both everyday living and entertaining, with an oversized island offering abundant storage, a butcher block top, and an eat-up bar area. Granite countertops are complemented by a white subway tile backsplash and a dramatic floor-to-ceiling accent wall. Recent improvements include a new water softener, a 2018 water heater, and a new washer and dryer installed in 2026. The HVAC systems are approximately two and three years old and have been recently serviced. The roof is less than five years old, while newer HardieBoard siding and windows provide additional peace of mind. Step outside to the large covered rear porch, finished with beadboard and a ceiling fan, overlooking the spacious fenced backyard. Mature trees and established landscaping create a private setting that is ideal for relaxing, entertaining, or enjoying outdoor time. The paved driveway adds convenience, while the no-HOA neighborhood provides added flexibility. Perfectly positioned close to town, schools, and everyday amenities while offering quick access to Route 7 for commuters, this home combines a well-established neighborhood setting with an exceptionally convenient location. A home with genuine character, meaningful improvements, and a level of care that is evident throughout.

109 Julee Dr, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$459,900
3 Beds ⋅ 2 Baths
Enjoy easy one-level living in this well-maintained ranch home conveniently located in Winchester, close to commuter routes, shopping, restaurants, and everyday amenities. The inviting front porch is the perfect spot to relax and enjoy warm evenings. Inside, hardwood floors flow through the living room, kitchen, and dining area, while the bedrooms feature comfortable carpeting. A dedicated laundry room adds convenience, and the unfinished basement provides plenty of storage and future possibilities. Step outside to the backyard, where a deck offers the perfect setting for entertaining, relaxing, or enjoying outdoor gatherings. A shed provides additional storage, while the two-car garage offers plenty of parking and workspace. A great combination of comfort, convenience, and outdoor living!

991 Front Royal Pike, Winchester

Listing courtesy of Re/Max Roots. Contact: (540) 686-7362
$325,000
4 Beds ⋅ 2 Baths
Welcome home! This beautifully maintained two-level home offers 4 bedrooms and 2 full bathrooms in the heart of Winchester. Warm and inviting, the home features a comfortable, functional layout with classic charm and thoughtful updates throughout. Pride of ownership is evident in every detail, both inside and out. Enjoy spacious living areas, a fully fenced yard perfect for relaxing or entertaining, and a private driveway for convenient off-street parking. Ideally located close to downtown Winchester, shopping, dining, and commuter routes. Move-in ready and waiting for you to make it your own!

805 S Kent St, Winchester

Listing courtesy of Weichert, REALTORS. Contact: (703) 850-4771
$552,000
4 Beds ⋅ 3 Baths
Beautifully remodeled Colonial in Pioneer Heights. Designed with primary suite; ideal home office configuration. All large bedrooms, large hardwood living room with stone wood fireplace, new natural gas upstairs furnace and a/c, upgraded insulation in attic, oversized garage and large deck. New paint, LVPk flooring in baths and kitchen. Must see.

100 Winns Cir, Winchester

Listing courtesy of NetRealtyNow.com, LLC. Contact: 7035818605
$395,600
4 Beds ⋅ 2 Baths
You are going to love this spacious, one-level ranch located on a half-acre lot in a great location! Here are some of the key features and recent updates: - Huge 20x26 family room with Red Oak hardwood floors, a brick fireplace, and newly replaced French doors that open onto a large L-shaped front deck. - Bedrooms & Baths: New paint and new flooring throughout bedrooms and bathrooms master bath features a new vanity and new ceramic tile flooring, which is also featured in the hallway bath. master bedroom has full bath -Laundry: 8x8 laundry room complete with washer, dryer, cabinets, and counter space. -Kitchen and living room has Bruce flooring All new painting through out house - Upgrades: New ceiling fans in all rooms. The water pump, septic tank, and attic air handler for the AC unit have all been replaced. Both decks have been recently remodeled and resealed. - Garaging & Parking: Oversized 20x28 garage with front and back entry doors, plus a second attached garage in the rear. Large driveway with a 10+ car capacity and turnaround area. - Outdoor Space: Fenced backyard with a 10x12 back deck and beautiful pastoral views in both the front and back. Large L-shaped deck on front of house This home offers peaceful country living while remaining convenient to local grocery stores, restaurants, gas stations, schools, and major commuter routes this ranch offers the space & amenities you been dreaming of....... LOOK NO FURTHER!

178 Payne Rd, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$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
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