View All Latest Winchester 1750+ Sq. Ft. Properties for Sale

991 Front Royal Pike, Winchester $459,900

Enjoy easy one-level living in this well-maintained ranch home conveniently located in Winchester, close to commuter routes, shopping, restaurants, and everyday amenities...

3 Beds
2 Baths
Bufflick Heights SubDv.
22602 Zip Code
ACTIVE Status

172 Sioux Loop, Winchester $360,000

This Adams interior townhouse features 4 bedrooms, 3.5 baths, and a 1-car garage. With a total of 1,889 sqft, there is plenty of space to entertain and live comfortably.<...

4 Beds
4 Baths
Retreat At Winding Creek SubDv.
22602 Zip Code
ACTIVE Status

100 Winns Cir, Winchester $552,000

Beautifully remodeled Colonial in Pioneer Heights. Designed with primary suite; ideal home office configuration. All large bedrooms, large hardwood living room with stone...

4 Beds
3 Baths
Pioneer Heights SubDv.
22602 Zip Code
ACTIVE Status

178 Payne Rd, Winchester $395,600

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 fa...

4 Beds
2 Baths
Russell's Paradise SubDv.
22603 Zip Code
ACTIVE Status

223 Asbury Rd, Winchester $549,900

“Pioneer Heights Colonial” - Welcome to this beautifully maintained colonial in the desirable Pioneer Heights neighborhood, ideally situated just off Route 7 for easy com...

5 Beds
4 Baths
Pioneer Heights SubDv.
22602 Zip Code
ACTIVE Status

322 E Piccadilly, Winchester $409,000

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 ch...

4 Beds
1 Baths
None Available SubDv.
22601 Zip Code
ACTIVE Status

100 Gooseberry Dr, Winchester $515,000

Welcome to 100 Gooseberry Drive, located in Winchester's established Cross Creek Village community! This meticulously maintained brick rancher offers true main-level livi...

2 Beds
3 Baths
Cross Creek Village SubDv.
22602 Zip Code
ACTIVE Status

Tumble Leaf Lane, Winchester $805,000

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 Box...

4 Beds
4 Baths
None Available SubDv.
22602 Zip Code
ACTIVE Status

2700 Loyalty Ct, Winchester $699,000

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 l...

7 Beds
5 Baths
Rolling Hills SubDv.
22601 Zip Code
ACTIVE Status

302 Canyon Rd, Winchester $525,000

Welcome to a home designed for the way you live, with room to work, entertain, relax, and make the space your own. Located in Senseny Glen, this 4-bedroom, 3.5-bath, thre...

4 Beds
4 Baths
Senseny Glen SubDv.
22602 Zip Code
ACTIVE Status

128 Alliance Ct, Winchester $550,000

Welcome to 128 Alliance Court, a beautifully maintained, move-in-ready home built in 2021 and offering over 3,200 finished square feet across three spacious levels. The o...

4 Beds
4 Baths
Freedom Manor SubDv.
22602 Zip Code
ACTIVE Status

900 Enfield Dr, Winchester $380,000

Nestled in the serene Wilde Acres community, this exquisite Colonial-style residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevate...

4 Beds
3 Baths
Wilde Acres SubDv.
22602 Zip Code
ACTIVE Status

110 Bentpath Ct, Winchester $710,000

Welcome to 110 Betpath Ct, nestled within the premier Twin Lakes Overlook (TLO) enclave of exclusively single-family homes by Toll Brothers and Richmond American, this ex...

5 Beds
4 Baths
Twin Lake Overlook SubDv.
22602 Zip Code
ACTIVE Status

236 Delmas Trl Trl, Winchester $984,900

Nestled in the prestigious Midland Heights community, this exquisite Colonial-style residence offers a harmonious blend of luxury and comfort, set against a breathtaking ...

4 Beds
4 Baths
Midland Heights SubDv.
22602 Zip Code
COMING SOON Status

116 Magpie Ln, Winchester $595,390

NEW BUILD, move in ready single-family home at Hiatt Pointe, 55+ community at Snowden Bridge by Van Metre Homes! The Sierra 39-F2 at Hiatt Pointe is stunning! This home o...

3 Beds
3 Baths
Hiatt Pointe At Snowden Bridge SubDv.
22603 Zip Code
ACTIVE Status

174 Williamson Rd, Winchester $759,900

This spectacular, move-in-ready home shows like a professional model, showcasing exquisite designer touches, custom window treatments (included), and premium finishes thr...

5 Beds
5 Baths
Abrams Pointe SubDv.
22602 Zip Code
ACTIVE Status

142 Sequoia Dr, Winchester $434,900 ▼

The lot you’ve been waiting for—without giving up the convenience of townhouse living! This exceptional end-unit townhome sits on a rare, double-sized lot, offering the k...

3 Beds
4 Baths
Fieldstone SubDv.
22602 Zip Code
ACTIVE Status

337 Canyon Rd, Winchester $674,000

Welcome to 337 Canyon Road, a spacious brick-front home offering more than 4,600 finished square feet in desirable Twin Lakes Overlook. The open-concept main level featur...

5 Beds
4 Baths
Twin Lakes Overlook SubDv.
22602 Zip Code
COMING SOON Status

200 Fairfield Dr, Winchester $645,000

Come and discover this impressive beauty where easy main-level living meets exceptional indoor-outdoor entertaining. This beautifully appointed Cape Cod offers the conven...

4 Beds
4 Baths
Oakdale Crossing SubDv.
22602 Zip Code
ACTIVE Status

109 Marlow Ct, Winchester $420,000

Don't miss this nearly new townhouse in Rossum Crossing! With 4 bedrooms, 3.5 bathrooms, over 2,000 square feet of finished space, and a one-car garage, this home offers ...

4 Beds
4 Baths
Rossum Crossing SubDv.
22602 Zip Code
ACTIVE Status

938 Wayne Dr, Winchester $499,900

Beautifully maintained and updated home located in popular area close to Medical Center, schools , services and amenities and with easy access to commuter thoroughfares. ...

4 Beds
3 Baths
Meadow Branch South SubDv.
22601 Zip Code
PENDING Status

632 Stonymeade Dr, Winchester $1,025,000

Opportunities in Stonymeade don't come along often—and once you arrive, it's easy to understand why. Tucked away on 3.2 beautifully maintained acres with a wooded perimet...

5 Beds
4 Baths
Stonymeade SubDv.
22602 Zip Code
ACTIVE Status

102 Forest Valley Rd, Winchester $597,000 ▼

Welcome to this beautifully maintained home in the established Stonebrook Farms community, perfectly situated on a quiet cul-de-sac and surrounded by mature trees and lan...

5 Beds
3 Baths
Stonebrook Farms SubDv.
22602 Zip Code
ACTIVE Status

394 Old Baltimore Rd, Winchester $625,000

Coming Soon! A truly special property in a gorgeous, peaceful setting! This charming 1911 farmhouse sits on 2.75 acres and offers the perfect opportunity for a small farm...

4 Beds
4 Baths
None Available SubDv.
22603 Zip Code
ACTIVE Status

1077 Carpers Dr, Winchester $354,900 ▼

Welcome home to this charming 3-bedroom, 2-bath house nestled on .32 acres, where comfortable living spaces and inviting outdoor areas come together to create a place tha...

3 Beds
2 Baths
None Available SubDv.
22603 Zip Code
ACTIVE Status

291 Huntersridge Rd, Winchester $659,900

Space, style, and room to live your best life come together in this 4-bedroom, 4.5-bath, 3-level Colonial in desirable Oakdale Crossing. With flexible spaces, great indoo...

4 Beds
5 Baths
Oakdale Crossing SubDv.
22602 Zip Code
ACTIVE Status

108 Magpie Ln Unit #HOMESITE 1035, Winchester image

108 Magpie Ln Unit #HOMESITE 1035, Winchester $585,659

Find Homesite 1035, a brand new SINGLE FAMILY HOME designed for Active Adult (55+) living. This never lived-in before, MOVE-IN READY home offers main-level living and low...

3 Beds
3 Baths
Hiatt Pointe At Snowden Bridge SubDv.
22603 Zip Code
ACTIVE Status

224 Sharp St, Winchester $750,000

Rare Historical Winchester Investment Opportunity – Three Properties in One Location An outstanding investment opportunity awaits in the heart of Winchester City. This un...

22601 Zip Code
ACTIVE Status

229 Monteith Dr, Winchester $369,990

The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Possibility of 4th bedroom or f...

3 Beds
4 Baths
Village At Valor Crossing SubDv.
22601 Zip Code
ACTIVE Status

854 Valley Mill Rd, Winchester $1,170,000

Unique 5+ acre property in Winchester. Beautiful home with plenty of space for everyone's interests. 5 bedrooms- all with en suite bathrooms. High end kitchen designed by...

5 Beds
6 Baths
None Available SubDv.
22602 Zip Code
ACTIVE Status

136 Travis Ct, Winchester $589,000

Welcome to 136 Travis Court in Winchester, VA—an impressive, sun-drenched Colonial designed for seamless living and entertaining! An inviting covered front porch welcomes...

4 Beds
5 Baths
Red Fox Run SubDv.
22602 Zip Code
ACTIVE UNDER CONTRACT Status

237 Monteith Dr, Winchester $359,990

The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Home backing to trees for added...

3 Beds
4 Baths
Village At Valor Crossing SubDv.
22601 Zip Code
ACTIVE Status

249 Monteith Dr, Winchester $374,990

END UNIT Luxury 3 level/3-bedroom townhome with 1 car garage located in the heart of Winchester! Possibility of 4th Bedroom/flex base in the basement available! ***OFFER...

3 Beds
4 Baths
Village At Valor Crossing SubDv.
22601 Zip Code
PENDING Status

101 Poe Dr, Winchester $624,990

Welcome to this lovely 4 Bedroom, 2.5 Bath Craftsman Style Home where modern design meets everyday comfort! This beautifully maintained home & unique designs include an ...

4 Beds
3 Baths
Raven Oaks SubDv.
22602 Zip Code
ACTIVE Status

123 Harvest Ridge Dr, Winchester $575,000

Welcome to 123 Harvest Ridge Dr in Winchester, where low-maintenance living, a great location, and the good life all decided to move in together. Located in a desirable 5...

3 Beds
2 Baths
The Village At Harvest Ridge SubDv.
22601 Zip Code
ACTIVE Status

660 Arden Ct, Winchester $385,690

660 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for September move-in. Our modern Adams ...

4 Beds
4 Baths
Abrams Crossing SubDv.
22601 Zip Code
ACTIVE Status

652 Arden Ct, Winchester $381,690

652 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for September move-in. Our modern Adams ...

4 Beds
4 Baths
Abrams Crossing SubDv.
22601 Zip Code
ACTIVE Status

648 Arden Ct, Winchester $385,490 ▲

648 Arden Court is an attractive new 3 level townhome backing to trees with brick in Winchester's premier Meadow Branch community for September move-in. Our modern Adams ...

4 Beds
4 Baths
Abrams Crossing SubDv.
22601 Zip Code
ACTIVE Status

644 Arden Ct, Winchester $379,690

644 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for September move-in. Our modern Adams ...

4 Beds
4 Baths
Abrams Crossing SubDv.
22601 Zip Code
PENDING Status

640 Arden Ct, Winchester $410,190

640 Arden Court is an attractive new 3 level end townhome with brick backing to trees in Winchester's premier Meadow Branch community for September move-in. Our modern Ad...

4 Beds
4 Baths
Abrams Crossing SubDv.
22601 Zip Code
PENDING Status

105 Foxbury Ln, Winchester $550,000

Beautifully maintained by its original owner, this all-brick Colonial in the desirable Windsor Hill community reflects years of thoughtful care and pride of ownership. Se...

4 Beds
4 Baths
Windsor Hill SubDv.
22602 Zip Code
PENDING Status

922 Wayne Dr, Winchester $615,000

Welcome home to this beautifully updated brick-front residence in the City of Winchester, where a thoughtful floor plan, generous living spaces with 9' ceilings on the ma...

5 Beds
4 Baths
Meadow Branch South SubDv.
22601 Zip Code
ACTIVE Status

422 S Loudoun St, Winchester $434,000

Priced at recent appraised value. Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the cha...

3 Beds
3 Baths
City Of Winchester SubDv.
22601 Zip Code
ACTIVE Status

1030 Breckinridge Ln, Winchester $1,100,000

Welcome to this inviting, beautifully maintained 6-bedroom, 4-full-bathroom, 2-half-bathroom all-brick home in the desirable Meadow Branch subdivision in Winchester, Virg...

6 Beds
6 Baths
Meadowbranch SubDv.
22601 Zip Code
ACTIVE Status

1400 Gordon Pl, Winchester $649,500

One level living in The Downs at Meadow Branch, a sought after community convenient to shopping, medical center, and Old Town Winchester. Expansive all-brick home offers ...

3 Beds
2 Baths
Downs At Meadows Branch SubDv.
22601 Zip Code
ACTIVE Status

136 Plaid Hill Dr, Winchester $729,990

Rare cul-de-sac opportunity in sought-after Snowden Bridge! This stunning 5-bedroom Sinclair is under construction for a year-end move-in and offers the perfect blend of ...

5 Beds
5 Baths
Snowden Bridge SubDv.
22603 Zip Code
PENDING Status

107 Heirloom Way, Winchester $389,990

Move-In Ready Villa in Hiatt Pointe at Snowden Bridge's Premier Gated 55+ Community! Experience the ease of low-maintenance living in this beautifully designed home, read...

3 Beds
3 Baths
Hiatt Pointe At Snowden Bridge SubDv.
22603 Zip Code
PENDING Status

100 Keystone Ln Unit #HOMESITE 1090, Winchester image

100 Keystone Ln Unit #HOMESITE 1090, Winchester $456,639 ▲

Discover a new MOVE-IN READY and thoughtfully designed home for active 55+ living. This BRAND NEW END VILLA gives you more time to enjoy what matters most. Main-level liv...

3 Beds
3 Baths
Hiatt Pointe At Snowden Bridge SubDv.
22603 Zip Code
ACTIVE Status

414 N Braddock St, Winchester $550,000

This charming farmhouse-style home,with off street parking, originally built in 1890 and beautifully renovated in 2018 (new windows, doors, HVAC, plumbing, drywall & ins...

3 Beds
3 Baths
None Available SubDv.
22601 Zip Code
ACTIVE UNDER CONTRACT Status

424 Valley Mill Rd, Winchester $474,900 ▼

Welcome to this beautifully updated Colonial in Winchester, where classic curb appeal meets thoughtful modern upgrades. The exterior shines with new Hardie Plank siding, ...

4 Beds
3 Baths
Brentwood Terrace SubDv.
22602 Zip Code
ACTIVE Status

1750+ Sq. Ft. Winchester Real Estate

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