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View All Latest Winchester 2250+ Sq. Ft. Properties for Sale

114 Nassau Dr, Winchester image
114 Nassau Dr, Winchester $525,000

Offering three luxuriously finished levels, extensive upgrades, and a backyard designed for entertaining, this 4 bed/3.5 bath colonial is a MUST-SEE! Step inside to a gra...

  • 4 Beds
  • 4 Baths
  • Fieldstone SubDv.
  • 22602 Zip Code
  • ACTIVE Status
109 Julee Dr, Winchester image
109 Julee Dr, Winchester $479,900

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 update...

  • 5 Beds
  • 3 Baths
  • Mill Race Estates SubDv.
  • 22602 Zip Code
  • COMING SOON Status
100 Winns Cir, Winchester image
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
223 Asbury Rd, Winchester image
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
100 Gooseberry Dr, Winchester image
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 image
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 image
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
110 Bentpath Ct, Winchester image
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 image
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 image
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 image
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
337 Canyon Rd, Winchester image
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 image
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
938 Wayne Dr, Winchester image
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 image
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 image
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 image
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
291 Huntersridge Rd, Winchester image
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
224 Sharp St, Winchester image
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
854 Valley Mill Rd, Winchester image
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 image
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
101 Poe Dr, Winchester image
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
922 Wayne Dr, Winchester image
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 image
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 image
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 image
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 image
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
414 N Braddock St, Winchester image
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
3135 Eton Pl, Winchester image
3135 Eton Pl, Winchester $400,000

Lofts at Creekside is one of the newest walkable communities in the city of Winchester with proximity to the upscale Creekside Station. Offering eateries, clothing store...

  • 3 Beds
  • 3 Baths
  • Lofts At Creekside SubDv.
  • 22601 Zip Code
  • ACTIVE Status
102 Primrose Pl, Winchester image
102 Primrose Pl, Winchester $499,900

Nestled in the charming Apple Ridge community, this delightful Colonial home offers a perfect blend of comfort and convenience. With 2,528 sq. ft. of living space, this r...

  • 5 Beds
  • 3 Baths
  • Apple Ridge SubDv.
  • 22602 Zip Code
  • ACTIVE Status
2643 Middle Rd, Winchester image
2643 Middle Rd, Winchester $499,999

Location, Location, Location! NO HOA!!! Priced below assessed value! Hardwood floors on the main level. Formal living and dining room leads to the Family room with sto...

  • 4 Beds
  • 4 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
185 Hannah Ct, Winchester image
185 Hannah Ct, Winchester $649,500 ▼

SELLER OFFERING $5000 CREDIT! Welcome home to your private 2-acre sanctuary! This charming 1997 Colonial seamlessly blends classic warmth, modern convenience, and unforge...

  • 4 Beds
  • 4 Baths
  • Ashland Meadows SubDv.
  • 22603 Zip Code
  • ACTIVE UNDER CONTRACT Status
1605 Fort Braddock Ct, Winchester image
1605 Fort Braddock Ct, Winchester $530,000

Fort Braddock Heights (Winchester City) - Detached Two-Level Home with Five (5) Bedrooms + Three (3) Full Bathrooms + One (1) Half Bathroom *Approx. 2,417 Finished Square...

  • 5 Beds
  • 4 Baths
  • Fort Braddock Heights SubDv.
  • 22601 Zip Code
  • ACTIVE Status
1950 Jones Rd, Winchester image
1950 Jones Rd, Winchester $1,750,000

Tucked away on a private lane bordered by an elegant stone wall, this impressive all-brick residence offers approximately 8,000 square feet of exceptional living space in...

  • 4 Beds
  • 6 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • PENDING Status
144 Robinson Dr, Winchester image
144 Robinson Dr, Winchester $2,599,000

This upscale custom home blends clean, modern comfort with rustic charm—and does it sublimely with nearly 5,000 finished square feet on one level, including a separate in...

  • 4 Beds
  • 6 Baths
  • Roscommon SubDv.
  • 22602 Zip Code
  • ACTIVE Status
158 Old Forest Cir, Winchester image
158 Old Forest Cir, Winchester $665,000 ▼

NEW PRICE — NOW $665,000! An exceptional opportunity to make 158 Old Forest your new home. With a $10,000 price improvement, this property offers even more value. If you'...

  • 4 Beds
  • 3 Baths
  • Stonebrook Farms SubDv.
  • 22602 Zip Code
  • ACTIVE Status
103 Renee Ln, Winchester image
103 Renee Ln, Winchester $710,000 ▼

Welcome to this gorgeous single family home with custom details galore in the lovely Lynnehaven community! Approaching the home you are welcomed by a spacious front porch...

  • 5 Beds
  • 4 Baths
  • Lynnehaven SubDv.
  • 22602 Zip Code
  • ACTIVE Status
141 Poe Dr, Winchester image
141 Poe Dr, Winchester $589,900

Discover this impressive Hopewell home, ready for quick move-in! Included features: a quiet study with French doors; a spacious great room with an electric fireplace; a d...

  • 4 Beds
  • 4 Baths
  • Raven Oaks SubDv.
  • 22602 Zip Code
  • ACTIVE Status
769 Seldon Dr, Winchester image
769 Seldon Dr, Winchester $760,000

Welcome to 769 Seldon Drive—an elegant brick-front colonial situated on nearly half an acre in one of Winchester’s most desirable neighborhoods. Offering over 4,500 finis...

  • 5 Beds
  • 5 Baths
  • Meadow Branch SubDv.
  • 22601 Zip Code
  • ACTIVE Status
2216 Laurel Grove Rd, Winchester image
2216 Laurel Grove Rd, Winchester $1,300,000

Welcome to 2216 Laurel Grove Rd, an exceptional custom-built modern farmhouse offering privacy, beautiful views, and relaxed country living on 30 unrestricted acres, all ...

  • 4 Beds
  • 3 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
217 Ashland Dr, Winchester image
217 Ashland Dr, Winchester $725,000

Welcome home to Ashland Dr! This very well maintained ranch, is simply waiting for you to move in and make your own. From fresh paint throughout, new carpet in the prima...

  • 4 Beds
  • 4 Baths
  • Ashland Meadows SubDv.
  • 22603 Zip Code
  • ACTIVE Status
107 Ardeyth Ln, Winchester image
107 Ardeyth Ln, Winchester $529,900

Welcome to 107 Ardeyth Lane! This well-maintained 4-bedroom, 3.5-bath Colonial offers generous living space, thoughtful updates, and an inviting backyard retreat. The bri...

  • 4 Beds
  • 4 Baths
  • Steeplechase SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
218 Babbs Mountain Rd, Winchester image
218 Babbs Mountain Rd, Winchester $935,000 ▼

A PRIVATE CUSTOM-BUILT ESTATE SURROUNDED BY NATURE — WITH YOUR OWN RESORT-STYLE POOL! Set on an extraordinary 6.44 private acres, this exquisite custom-built residence of...

  • 5 Beds
  • 3 Baths
  • Babbs Mountain SubDv.
  • 22603 Zip Code
  • ACTIVE UNDER CONTRACT Status
313 Lehigh Dr, Winchester image
313 Lehigh Dr, Winchester $630,000

***Very motivated Sellers*** Set within the desirable Senseny Village community, 313 Lehigh Drive offers an exceptional blend of refined living and effortless comfort. Th...

  • 5 Beds
  • 4 Baths
  • Senseny Village SubDv.
  • 22602 Zip Code
  • ACTIVE Status
223 Fairfield Dr, Winchester image
223 Fairfield Dr, Winchester $725,000

Beautifully remodeled with exceptional care and attention to detail by its current owners, this stunning 5-bedroom, 3-bath home offers over 4,400 finished square feet on ...

  • 5 Beds
  • 4 Baths
  • Oakdale Crossing SubDv.
  • 22602 Zip Code
  • ACTIVE Status
199 Meeting House Dr, Winchester image
199 Meeting House Dr, Winchester $699,000 ▼

3.46 ACRES • MOUNTAIN VIEWS • NO HOA • MAIN-LEVEL PRIMARY Discover a different kind of Winchester living at 199 Meeting House Drive. Tucked at the end of a quiet cul-de-...

  • 5 Beds
  • 5 Baths
  • Fawcett Gap Farm SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
lot 12 Keval Gyan Way, Winchester image
lot 12 Keval Gyan Way, Winchester $849,900

Four month build time from contract. Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Appl...

  • 3 Beds
  • 2 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE Status
175 Shields Dr, Winchester image
175 Shields Dr, Winchester $749,900 ▲

Beautiful 5 bedroom, 2.5-bath brick-front home situated on 2 private acres, offering the perfect blend of space, comfort, and recent updates. Shower on the main floor in...

  • 5 Beds
  • 4 Baths
  • Equestrian Estates SubDv.
  • 22602 Zip Code
  • ACTIVE Status
194 Glendobbin Ln, Winchester image
194 Glendobbin Ln, Winchester $1,350,000

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 pr...

  • 4 Beds
  • 4 Baths
  • Glendobbin Hills SubDv.
  • 22603 Zip Code
  • ACTIVE UNDER CONTRACT Status
146 Stonebrook Rd, Winchester image
146 Stonebrook Rd, Winchester $649,900 ▼

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 co...

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

2250+ Sq. Ft. Winchester Real Estate

Our website features the best real estate search for 2250+ sq. ft. properties available in Winchester and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

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Anne Nouri

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