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View All Latest Winchester 2500+ Sq. Ft. Properties for Sale

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...

  • 4 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
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
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
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
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
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
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
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
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
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
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
4241 Cedar Creek Grade, Winchester image
4241 Cedar Creek Grade, Winchester $799,000

Situated on nearly 3 acres of peaceful, private land, 4241 Cedar Creek Grade offers a truly remarkable retreat framed by sweeping, 360-degree views of rolling hills and l...

  • 4 Beds
  • 4 Baths
  • Granville Estates SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
1529 Dalton Pl, Winchester image
1529 Dalton Pl, Winchester $639,900 ▼

Roof 2017 - Water Heater 2017 - HVAC 2023. Welcome to 1529 Dalton Place, an exceptional home tucked away on a quiet cul-de-sac in one of Winchester's most desirable locat...

  • 4 Beds
  • 4 Baths
  • Williamsburg Heights SubDv.
  • 22601 Zip Code
  • ACTIVE Status
107 Cahille Dr, Winchester image
107 Cahille Dr, Winchester $749,050 ▼

Welcome to this exceptional 4-bedroom, 3.5-bath Colonial in the sought-after Raven Pointe subdivision, where luxury living extends well beyond the front door. The backya...

  • 4 Beds
  • 4 Baths
  • Raven Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
243 Summerfield Dr, Winchester image
243 Summerfield Dr, Winchester $879,900

Immaculate custom home sitting on a half-acre lot in desirable Raven Pointe! Beautiful hardwood floors flow throughout the main level, leading into a dramatic family room...

  • 5 Beds
  • 5 Baths
  • Raven Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
308 Huntersridge Rd, Winchester image
308 Huntersridge Rd, Winchester $619,900

No HOA! Settled at the end of the cul-de-sac and pushed back from the street to give additional privacy and comfort. This home has received several improvements since 20...

  • 4 Beds
  • 5 Baths
  • Oakdale Crossing SubDv.
  • 22602 Zip Code
  • PENDING Status
104 Murphy Ct, Winchester image
104 Murphy Ct, Winchester $555,900 ▼

Gorgeous 4-Bedroom Colonial in Sought-After Sovereign Village! This beautifully maintained home is nestled on a large cul-de-sac, offering privacy, space, and comfort b...

  • 4 Beds
  • 4 Baths
  • Sovereign Village SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
450 Green Spring Rd, Winchester image
450 Green Spring Rd, Winchester $3,500,000

Be Sure to View the Video and 3D Tour to Fully Experience this Stunning Property <br><br> **Briede Family Vineyards** presents an exceptional opportunity to acquire one ...

  • 3 Beds
  • 4 Baths
  • No SubDv.
  • 22603 Zip Code
  • ACTIVE Status
450 Green Spring Rd, Winchester image
450 Green Spring Rd, Winchester $3,500,000

Be sure to see the video and 3D tour to fully explore this property! <br><br> Award-Winning Virginia Winery + Luxury Vineyard Estate + Income-Producing Luxury Short Term...

  • 3 Beds
  • 4 Baths
  • No SubDv.
  • 22603 Zip Code
  • ACTIVE Status
245 Hydrangea Way, Winchester image
245 Hydrangea Way, Winchester $599,990

The Dover by D.R. Horton offers 1,958 square feet of thoughtfully designed, main floor living with 3 bedrooms, 2 full baths, and a 2-car garage. A private flex room with ...

  • 4 Beds
  • 3 Baths
  • Willow Run SubDv.
  • 22602 Zip Code
  • ACTIVE Status
102 Julie Ct, Winchester image
102 Julie Ct, Winchester $829,900 ▼

Opportunities of this caliber in the highly coveted Stonebrook Farms community are exceptionally rare. Positioned on a premium cul-de-sac lot backing directly to mature, ...

  • 5 Beds
  • 5 Baths
  • Stonebrook Farms SubDv.
  • 22602 Zip Code
  • ACTIVE Status
342 Canyon Rd, Winchester image
342 Canyon Rd, Winchester $714,000 ▼

Welcome to 342 Canyon Rd, a spacious and beautifully maintained home in the desirable Twin Lakes Overlook community on Winchester's east side close to Rt 7. Situated on a...

  • 5 Beds
  • 4 Baths
  • Twin Lakes Overlook SubDv.
  • 22602 Zip Code
  • ACTIVE Status
1311 Handley Ave, Winchester image
1311 Handley Ave, Winchester $600,000

Nestled in the charming City of Winchester, this delightful Colonial home, built in 1952, exudes warmth and character. With its classic brick exterior and excellent condi...

  • 3 Beds
  • 2 Baths
  • City Of Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE Status
336 Apple Valley Rd, Winchester image
336 Apple Valley Rd, Winchester $715,000

Spacious contemporary craftsman style home built in 2007 on .5 acre lot with rare 3 car attached side load garage as well as a detached 2 car & 1 car garages behind the h...

  • 3 Beds
  • 4 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
582 Miller Rd, Winchester image
582 Miller Rd, Winchester $1,650,000

Built in 1774, before America was America, this remarkable 31-acre estate has stood through the birth of a nation, and today it's ready for its next chapter. This is his...

  • 4 Beds
  • 5 Baths
  • Belleville Farm SubDv.
  • 22602 Zip Code
  • ACTIVE Status
226 Summerfield Dr, Winchester image
226 Summerfield Dr, Winchester $849,000

UP TO $5000 SELLER CONCESSION FOR PAINT. CALL FOR DETAILS. Welcome to this stunning Colonial estate nestled in the highly sought-after Raven Pointe neighborhood of Winche...

  • 6 Beds
  • 5 Baths
  • Raven Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
730 Merrimans Ln, Winchester image
730 Merrimans Ln, Winchester $3,175,000

A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern Luxury Rarely does a property of this caliber, history, and scale become available within Winchester city ...

  • 6 Beds
  • 7 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status

2500+ Sq. Ft. Winchester Real Estate

Our website features the best real estate search for 2500+ 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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