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Winchester VA MLS Search

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View All Latest Winchester 4000+ Sq. Ft. Properties for Sale

135 Mascouten St, Winchester image
135 Mascouten St, Winchester $600,000

Welcome home to 135 Mascouten St!!! Walk in to find a lovely foyer and flex space, proceeding to an large open and welcoming floor plan with living/dining and kitchen wit...

  • 6 Beds
  • 5 Baths
  • Retreat At Winding Creek SubDv.
  • 22602 Zip Code
  • COMING SOON Status
150 Harvest Ridge Dr, Winchester image
150 Harvest Ridge Dr, Winchester $689,900

Enjoy the best of low-maintenance living in one of the larger homes in this desirable 55+ community, tucked away yet just minutes from all that Winchester has to offer! L...

  • 4 Beds
  • 3 Baths
  • The Village At Harvest Ridge SubDv.
  • 22601 Zip Code
  • ACTIVE Status
1281 Merrimans Ln, Winchester image
1281 Merrimans Ln, Winchester $2,500,000

This exceptional French Country estate enjoys privacy and architectural delight on five acres of dense, mature, professional landscaping. Beyond the stone gates and circu...

  • 4 Beds
  • 7 Baths
  • Roscommon SubDv.
  • 22602 Zip Code
  • ACTIVE 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
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
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
961 Meadow Ct, Winchester image
961 Meadow Ct, Winchester $709,000 ▼

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
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
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
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
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
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
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
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
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
175 Shields Dr, Winchester image
175 Shields Dr, Winchester $739,000 ▼

Recent major updates, 2 private acres, and space to spread out! This beautiful 5-bedroom, 2.5-bath brick-front home offers a wonderful blend of comfort, privacy, and func...

  • 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
308 Huntersridge Rd, Winchester image
308 Huntersridge Rd, Winchester $630,000

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
  • CLOSED 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
160 Wilton Dr, Winchester image
160 Wilton Dr, Winchester $840,000

Welcome to this Beautiful 4 bedroom, 4.5 Bath All Brick Home where traditional character and modern charm meet together all nestled on a Picturesque 4.18-Acre Estate in t...

  • 4 Beds
  • 5 Baths
  • Mcguire Hills SubDv.
  • 22603 Zip Code
  • CLOSED Status
342 Canyon Rd, Winchester image
342 Canyon Rd, Winchester $699,900 ▼

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
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
517 Merrimans Ln, Winchester image
517 Merrimans Ln, Winchester $875,000

None

  • 4 Beds
  • 3 Baths
  • Meadow Branch SubDv.
  • 22601 Zip Code
  • CLOSED 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
1022 Heth Pl, Winchester image
1022 Heth Pl, Winchester $1,239,000

This amazing property is ready for you! Located close to Winchester Medical Center, Churches, Shopping, Historic Downtown Winchester, John Kerr Elementary School, and ...

  • 4 Beds
  • 8 Baths
  • Meadow Branch SubDv.
  • 22601 Zip Code
  • ACTIVE Status
231 Rebecca Dr, Winchester image
231 Rebecca Dr, Winchester $675,000

NEW PRICE! Offering an exceptional blend of elegance, comfort, and modern updates, this meticulously maintained home is designed to impress. An impressive two-story foye...

  • 6 Beds
  • 5 Baths
  • Fieldstone SubDv.
  • 22602 Zip Code
  • CLOSED Status
136 Cahille Dr, Winchester image
136 Cahille Dr, Winchester $724,900 ▼

This home is where space, comfort and flexibility come together in a home designed to grow with you. Tucked away on a quiet dead-end street, this spacious home offers roo...

  • 5 Beds
  • 5 Baths
  • Raven Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
102 Triangle Ct, Winchester image
102 Triangle Ct, Winchester $830,000

This home was purchased by the current owner after a buyer backed out and because interest rates were high in 2023 so there was a slow down in the market. The builder gav...

  • 4 Beds
  • 4 Baths
  • Abrams Pointe SubDv.
  • 22602 Zip Code
  • CLOSED Status
118 Aulee Ct, Winchester image
118 Aulee Ct, Winchester $784,900 ▼

This beautiful, well-cared-for home occupies a peaceful setting overlooking a lake and stream directly behind the house. The well-stocked lake has an easily accessible w...

  • 5 Beds
  • 5 Baths
  • Twin Lake Overlook SubDv.
  • 22602 Zip Code
  • ACTIVE Status
211 Flanagan Dr, Winchester image
211 Flanagan Dr, Winchester $590,000 ▼

Pictures coming soon. Prime Location in Raven Wing! This beautiful Colonial home offers the perfect combination of comfort, convenience, and modern updates. Located in ...

  • 4 Beds
  • 4 Baths
  • Ravenwing SubDv.
  • 22602 Zip Code
  • ACTIVE Status
108 Norfolk Ct, Winchester image
108 Norfolk Ct, Winchester $675,000 ▼

MOTIVATED SELLERS!!! Sellers are open to closing cost assistance with the right offer. * Welcome home to Norfolk Ct!!! Oh my, where to begin? If you're looking for a tu...

  • 4 Beds
  • 5 Baths
  • Twin Lakes SubDv.
  • 22602 Zip Code
  • ACTIVE Status
144 Widener Dr, Winchester image
144 Widener Dr, Winchester $899,900 ▼

Exceptional All-Brick Custom Home with Panoramic Mountain Views! Nestled on a private 2-acre cul-de-sac lot in prestigious Butler Estates, this exceptional all-brick 4-b...

  • 4 Beds
  • 5 Baths
  • Butler Estates SubDv.
  • 22603 Zip Code
  • ACTIVE Status
614 Mohawk Trl, Winchester image
614 Mohawk Trl, Winchester $541,000

Welcome to 614 Mohawk Trail in the Shawneeland community! Nestled on 1.67 acres, this spacious 5-bedroom, 4-bath home offers over three levels of flexible living space, m...

  • 5 Beds
  • 4 Baths
  • Shawneeland SubDv.
  • 22602 Zip Code
  • CLOSED Status
295 Huntersridge Rd, Winchester image
295 Huntersridge Rd, Winchester $627,500

Price Drop. Come check this home out. The listing remarks below come directly from the Seller's. This home is a true gem. Hello! Human here! I just want to touch base w...

  • 5 Beds
  • 4 Baths
  • Oakdale Crossing SubDv.
  • 22602 Zip Code
  • CLOSED Status
220 Lehigh, Winchester image
220 Lehigh, Winchester $675,000

Some homes are new. This one is finished. Welcome to 220 Lehigh Drive, where the details have already been thoughtfully completed, allowing you to skip the time, expense,...

  • 5 Beds
  • 4 Baths
  • Senseny Village SubDv.
  • 22602 Zip Code
  • CLOSED Status
110 Grindstone Dr, Winchester image
110 Grindstone Dr, Winchester $527,500

Private pool, half-acre homesite, main-level living, and a fully finished lower-level living suite make this one of Winchester's most unique opportunities. Situated on a ...

  • 4 Beds
  • 4 Baths
  • Red Fox Run SubDv.
  • 22602 Zip Code
  • CLOSED Status
119 Thompson Ct, Winchester image
119 Thompson Ct, Winchester $628,000

Welcome to your dream home in the highly sought-after Twin Lakes Overlook community! This stunning , turn-key 4-bedroom, 3.5-bathroom brick-front colonial offers nearly 4...

  • 4 Beds
  • 4 Baths
  • Twin Lakes Overlook SubDv.
  • 22602 Zip Code
  • CLOSED Status

4000+ Sq. Ft. Winchester Real Estate

Our website features the best real estate search for 4000+ 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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