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View All Latest Winchester 3500+ Sq. Ft. Properties for Sale

109 Scotch Bonnet Dr, Winchester image
109 Scotch Bonnet Dr, Winchester $724,990

New main‑level primary bedroom home is under construction for year end move in! The main level features luxury vinyl plank flooring and an open, light‑filled layout. The ...

  • 5 Beds
  • 5 Baths
  • Snowden Bridge SubDv.
  • 22603 Zip Code
  • ACTIVE Status
1214 Martinsburg Pike, Winchester image
1214 Martinsburg Pike, Winchester $674,927

Solid 1957 custom Cape Cod home now fully renovated! 4 bedroom, 2.5 bath home on .66 acre! All new windows! Freshly painted! Mini splits and hardwood flooring throughout!...

  • 4 Beds
  • 3 Baths
  • Martinsburg Pike SubDv.
  • 22603 Zip Code
  • ACTIVE Status
606 Pritchards Hill Ct, Winchester image
606 Pritchards Hill Ct, Winchester $579,000

Have you been looking for houses that just lack the one thing you really wanted or needed? I think I can confidently say, the search is over. Allow me to present 606 Prit...

  • 4 Beds
  • 4 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • PENDING Status
1010 Breckinridge Ln, Winchester image
1010 Breckinridge Ln, Winchester $1,065,000

Winchester’s established Meadow Branch neighborhood invites you to the first ever offering of 1010 Breckinridge Lane! A thoughtfully designed residence offering generous...

  • 5 Beds
  • 6 Baths
  • Meadow Branch SubDv.
  • 22601 Zip Code
  • ACTIVE Status
219 Darby Dr, Winchester image
219 Darby Dr, Winchester $569,900

Welcome to 219 Darby Dr, tucked onto a quiet cul-de-sac in Ravenwing, where through traffic is kept to a minimum. Step inside to a wide entrance with wood flooring, with ...

  • 4 Beds
  • 3 Baths
  • Ravenwing SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
718 Academy Cir, Winchester image
718 Academy Cir, Winchester $673,000

Quiet Brick Cape Cod in the heart of Winchester, VA with over 4 thousand sqft and 6 bedrooms, there is plenty of space for everyone - growing family or combining house ho...

  • 6 Beds
  • 4 Baths
  • Academy Heights SubDv.
  • 22601 Zip Code
  • ACTIVE Status
105 Okeefe Dr, Winchester image
105 Okeefe Dr, Winchester $575,000

WOW! This exceptional home perfectly blends country charm with city convenience, ideally located between Rock Harbor Gof Club and the Medical center. Possible main floor ...

  • 4 Beds
  • 4 Baths
  • Merrimans Chase SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
451 Lake Serene Dr, Winchester image
451 Lake Serene Dr, Winchester $759,000 ▼

Custom built brick English Tudor offering breathtaking views of the lake in a private lake community. This distinctive three-level home features architectural character, ...

  • 2 Beds
  • 4 Baths
  • Lake Serene SubDv.
  • 22603 Zip Code
  • ACTIVE Status
220 Amherst St, Winchester image
220 Amherst St, Winchester $749,000

Downtown living at its finest! Welcome to 220 Amherst Street, a stunning brick residence nestled in Winchester’s prestigious historic district. This home blends timeless ...

  • 4 Beds
  • 4 Baths
  • Historic Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE Status
119 Cheifton Pl, Winchester image
119 Cheifton Pl, Winchester $799,900

Boasting timeless architectural charm and sweeping countryside views, 119 Cheifton Place offers an extraordinary lifestyle on an expansive two plus acre lot. Frame-worthy...

  • 4 Beds
  • 4 Baths
  • The Orchard SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
151 Travis Ct, Winchester image
151 Travis Ct, Winchester $524,900

SPACE, PRIVACY & CUL-DE-SAC LIVING IN RED FOX RUN! Discover an exceptional opportunity at 151 Travis Court in Winchester! Situated on one of the larger lots in the commun...

  • 5 Beds
  • 4 Baths
  • Red Fox Run SubDv.
  • 22602 Zip Code
  • ACTIVE Status
961 Meadow Ct, Winchester image
961 Meadow Ct, Winchester $719,000

Warm, elegant, and beautifully maintained, this 5-bedroom, 4.5-bath home offers gracious living in a desirable City of Winchester neighborhood with no HOA. Step into the ...

  • 5 Beds
  • 5 Baths
  • Harvest Ridge Estates SubDv.
  • 22601 Zip Code
  • ACTIVE Status
159 Lavender Hills Ln, Winchester image
159 Lavender Hills Ln, Winchester $764,900 ▼

Welcome to 159 Lavender Hills Lane, where space, comfort, and a peaceful setting come together in a home designed for both everyday living and entertaining. With approxim...

  • 4 Beds
  • 4 Baths
  • Apple Glen Estates SubDv.
  • 22603 Zip Code
  • ACTIVE Status
159 Abrams Pointe Blvd, Winchester image
159 Abrams Pointe Blvd, Winchester $724,900

***SELLER IS WILLING TO CONTRIBUTE UP TO $20,000.00 IN CONCESSIONS TOWARD BUYER CLOSING COSTS OR POINT BUY-DOWN WITH AN ACCEPTABLE OFFER.*** Better than new in coveted Ab...

  • 5 Beds
  • 5 Baths
  • Abrams Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
116 Cardigan Way, Winchester image
116 Cardigan Way, Winchester $704,990 ▲

This 4‑bedroom Torrington home with a main‑level primary suite is under construction for year end move in! The main level features luxury vinyl plank flooring and an open...

  • 4 Beds
  • 4 Baths
  • Snowden Bridge SubDv.
  • 22603 Zip Code
  • ACTIVE Status
440 N Braddock St, Winchester image
440 N Braddock St, Winchester $529,000

An exceptional multifamily investment opportunity awaits in the heart of historic downtown Winchester! Located at 440 N Braddock St, this turnkey property features a time...

  • 22601 Zip Code
  • ACTIVE UNDER CONTRACT Status
146 Darby Dr, Winchester image
146 Darby Dr, Winchester $659,900 ▼

FRESH UPDATES & NEARLY 4,000 FINISHED SQ. FT.—COME TAKE ANOTHER LOOK AT 146 DARBY DRIVE! New flooring has just been installed in the kitchen, family room AND finished low...

  • 4 Beds
  • 4 Baths
  • Raven Wing SubDv.
  • 22602 Zip Code
  • ACTIVE Status
261 Merrifield Ln, Winchester image
261 Merrifield Ln, Winchester $2,200,000

Privately sited on 6.11 acres just outside Winchester, 261 Merrifield Lane pairs classic Georgian architecture with extensive recent improvements throughout its approxima...

  • 5 Beds
  • 6 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
25 W Boscawen St, Winchester image
25 W Boscawen St, Winchester $625,000

Awesome income-producing multi-unit property in the heart of downtown Winchester. This stately red brick building delivers immediate cash flow with a great documented CAP...

  • 22601 Zip Code
  • PENDING Status
922 Armistead St, Winchester image
922 Armistead St, Winchester $839,000

Welcome to 922 Armistead Street, a spacious brick Colonial in Winchester's established Morlyn Hills neighborhood offering approximately 4,697 finished square feet across ...

  • 4 Beds
  • 5 Baths
  • Morlyn Hills SubDv.
  • 22601 Zip Code
  • ACTIVE Status
540 Monticello St, Winchester image
540 Monticello St, Winchester $605,000

Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location! Presenting a Triplex in the heart of Downtown Winches...

  • 22601 Zip Code
  • ACTIVE Status
132 Darby Dr, Winchester image
132 Darby Dr, Winchester $625,000 ▼

Welcome to this beautiful single-family home in the sought-after Ravenwing neighborhood of Winchester, Virginia. The sellers are open to offers that include credits towar...

  • 4 Beds
  • 4 Baths
  • Ravenwing SubDv.
  • 22602 Zip Code
  • ACTIVE Status
416 Briarmont Dr, Winchester image
416 Briarmont Dr, Winchester $748,900

Classic all-brick home in a highly desirable Winchester location! Well maintained and thoughtfully designed, this five bedroom, three full bath home offers timeless chara...

  • 5 Beds
  • 3 Baths
  • Voyne B Omps SubDv.
  • 22601 Zip Code
  • ACTIVE Status
314 Huntersridge Rd, Winchester image
314 Huntersridge Rd, Winchester $634,900

Your Next Chapter Starts Here! Space, style, flexibility, and a backyard made for entertaining — all tucked away on a quiet cul-de-sac in desirable Oakdale Crossing. Thi...

  • 5 Beds
  • 4 Baths
  • Oakdale Crossing SubDv.
  • 22602 Zip Code
  • ACTIVE Status
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 UNDER CONTRACT Status
2700 Loyalty Ct, Winchester image
2700 Loyalty Ct, Winchester $699,000

If you are looking for space to spread out, look no further! This home offers 7 bedrooms and 5 full baths. Commanding a prime corner lot on a peaceful cul-de-sac, this re...

  • 7 Beds
  • 5 Baths
  • Rolling Hills SubDv.
  • 22601 Zip Code
  • ACTIVE Status
110 Bentpath Ct, Winchester image
110 Bentpath Ct, Winchester $699,000 ▼

HUGE BUYER INCENTIVES — $10,000 TOWARD CLOSING COSTS PLUS SELLER-PAID 1-POINT PERMANENT MORTGAGE RATE BUYDOWN! OFFERED AT $699,000 | 5 BEDROOMS | 3.5 BATHROOMS | 3,946...

  • 5 Beds
  • 4 Baths
  • Twin Lake Overlook SubDv.
  • 22602 Zip Code
  • ACTIVE Status
337 Canyon Rd, Winchester image
337 Canyon Rd, Winchester $639,000 ▼

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
  • ACTIVE 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 UNDER CONTRACT 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
854 Valley Mill Rd, Winchester image
854 Valley Mill Rd, Winchester $1,075,000 ▼

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 UNDER CONTRACT Status
136 Travis Ct, Winchester image
136 Travis Ct, Winchester $580,000

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
  • CLOSED 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
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 UNDER CONTRACT 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
769 Seldon Dr, Winchester image
769 Seldon Dr, Winchester $700,000 ▼

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 $1,200,000

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
  • CLOSED Status
217 Ashland Dr, Winchester image
217 Ashland Dr, Winchester $725,000

WOW!!! Sellers are offering a temporary buy-down rate with a qualified buyer and offer... Want a MUCH lower rate for your first two or three years? It's possible at Ashla...

  • 4 Beds
  • 4 Baths
  • Ashland Meadows SubDv.
  • 22603 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
  • PENDING 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
  • CLOSED Status
175 Shields Dr, Winchester image
175 Shields Dr, Winchester $739,000 ▼

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 $1,325,000

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
  • CLOSED Status
146 Stonebrook Rd, Winchester image
146 Stonebrook Rd, Winchester $599,900 ▼

Spacious ranch home on a beautiful 1-acre lot in the highly desirable Stonebrook Farms community, offering generous living space, a flexible floor plan, and numerous impo...

  • 5 Beds
  • 3 Baths
  • Stonebrook Farms SubDv.
  • 22602 Zip Code
  • ACTIVE Status
142 Fortress Dr, Winchester image
142 Fortress Dr, Winchester $582,500

Enjoy the ease of true main-level living in this meticulously maintained ranch home offering more than 4,300 finished square feet on an oversized 0.37-acre lot in Winches...

  • 3 Beds
  • 4 Baths
  • Star Fort SubDv.
  • 22603 Zip Code
  • CLOSED Status
1529 Dalton Pl, Winchester image
1529 Dalton Pl, Winchester $625,000 ▼

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
485 Lake Serene Dr, Winchester image
485 Lake Serene Dr, Winchester $939,000 ▼

A rare opportunity to live on Lake Serene - Welcome to your private lakefront retreat on Lake Serene, where lake-life meets timeless craftsmanship. Tucked among the trees...

  • 5 Beds
  • 4 Baths
  • Lake Serene SubDv.
  • 22603 Zip Code
  • ACTIVE UNDER CONTRACT Status

3500+ Sq. Ft. Winchester Real Estate

Our website features the best real estate search for 3500+ 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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