View All Latest Winchester 5000+ Sq. Ft. Properties for Sale

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 $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

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

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

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 $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

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

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

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 $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 $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

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 $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

128 Babbs Run Ln, Winchester $960,000

Luxury custom home with a primary bedroom on the main floor. 5 partially wooded acres with an in-ground saltwater pool, upper-level Trex decks, screened porch, outdoor f...

5 Beds
5 Baths
Ridgeview SubDv.
22603 Zip Code
CLOSED Status

2230 Jones Rd, Winchester $2,200,000

Set on 21.5 acres just minutes from downtown Winchester, this 5-bedroom home offers over 5,800 finished square feet with a blend of space, functionality, and outdoor livi...

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

125 Skyjes Ln, Winchester $829,000

Nestled on 2 private acres, this custom-built Modern Farmhouse offers the perfect blend of luxury, flexibility, and exceptional multigenerational living. From the momen...

4 Beds
6 Baths
Shady Elm Farms SubDv.
22602 Zip Code
CLOSED Status

170 Graystone Ln, Winchester $790,000

NEW PRICE! Welcome to your luxurious oasis in the woods! Private, but near Winchester, this French influenced home sits on five acres, features a covered front porch, st...

6 Beds
5 Baths
Graystone Estates SubDv.
22603 Zip Code
CLOSED Status

186/190 Hawthorne Dr, Winchester $882,000

Designed by renowned local architect, Keith Williams, and built by Furman and Kathy Perry of Perry Engineering, this stunning contemporary home sits on a lot of over one ...

4 Beds
5 Baths
Hawthorne Acres SubDv.
22601 Zip Code
CLOSED Status

120 Ballygar Dr, Winchester $1,400,000

Don't miss this very unique opportunity to own a gorgeous estate home in the highly sought after neighborhood of Roscommon Estates on 5+ acres of flat land with beautiful...

4 Beds
5 Baths
Roscommon SubDv.
22602 Zip Code
CLOSED Status

2660 N Frederick Pike, Winchester $1,670,000

Don't miss your chance to own this remarkable contemporary home in Winchester. This stunning property is in pristine condition and combines modern elegance on a beautiful...

6 Beds
5 Baths
None Available SubDv.
22603 Zip Code
CLOSED Status

164 Creola Dr, Winchester $932,000

Hello I am done! A whole lot of house! Sits private off the road . This home boosts 3100 sq. ft. of open floor plan on main floor AND 3,000 sq. ft finished in basement to...

4 Beds
4 Baths
Hunting Ridge Estates SubDv.
22603 Zip Code
CLOSED Status

547 Apple Pie Ridge Rd, Winchester $950,000

Discover a sanctuary on Apple Pie Ridge! Positioned on 19+ picturesque acres just outside the heart of Winchester, this custom-built haven is a dream come true for those ...

4 Beds
7 Baths
None Available SubDv.
22603 Zip Code
CLOSED Status

410 Valley View Dr, Winchester $985,000

Discover Your Private Estate: 9.83 Acres of Country Charm with Resort-Style Amenities. NO HOA! AND with ANOTHER Price Improvement! Step into the unexpected with this exc...

5 Beds
5 Baths
Valley View SubDv.
22603 Zip Code
CLOSED Status

530 Laurel Grove Rd, Winchester $999,900

If you’re looking for a truly impressive property with unexpected benefits, welcome to 530 Laurel Grove Road. With nearly 6,000 finished square feet and five bedrooms and...

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

700 Miller Rd, Winchester $1,025,000

Situated on a 2.5 acre lot in highly desirable area, this stunning Colonial home offers an open floor plan perfect for entertaining. Thoughtfully designed with a main-le...

5 Beds
7 Baths
Belleville Farm SubDv.
22602 Zip Code
CLOSED Status

217 W Boscawen St, Winchester — None Available $1,014,300

Historic Water Street Inn a magnificent legacy residence, profitable Bed & Breakfast, or sophisticated professional office opportunity! Located in Winchester's Historic...

6 Beds
5 Baths
Winchester Historic District SubDv.
22601 Zip Code
CLOSED Status

189 Babbs Mountain Rd, Winchester $900,000

Stunning 4 Bed / 3.5 Bath Chalet on 3.26 Acres with Over 6,300 Sq Ft — Minutes from Winchester This exceptional chalet-style home offers over 6,300 sq ft of living space...

4 Beds
4 Baths
Estates At Claytons Rest SubDv.
22603 Zip Code
CLOSED Status

819 Armistead St, Winchester $1,149,000

Welcome to 819 Armistead Street. Located in the prestigious Meadow Branch neighborhood, this Colonial Revival style home has a nice Georgian flair to it. Marble floor...

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

121 Keval Gyan Way, Winchester $1,150,000 ▲

Four months build time from contract. Foundation dug and construction to begin soon. To have finished basement. Seize a rare opportunity to own one of just fifteen prem...

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

212 Fairfield Dr, Winchester $545,000

Welcome to 212 Fairfield Drive, a sprawling, all-brick rancher offering an incredible amount of space and comfort in a highly sought-after Winchester location. This home ...

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

112 Heath Ct, Winchester $700,000

Nestled in the tranquil community of Twin Lakes Overlook, this stately home offers 5500 square feet of finished living space, with 5 bedrooms and 5 bathrooms. Walk up to ...

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

1877 Clayton Ridge Dr, Winchester $695,000

From the moment you arrive, this home welcomes you in. A spacious covered front porch—perfect for rocking chairs and quiet mornings—sets the stage for the warmth and comf...

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

821 Apple Pie Ridge Rd, Winchester image

821 Apple Pie Ridge Rd, Winchester $2,000,000

This extraordinary 5-bedroom, 6-bathroom estate sits on 14.44 acres across two parcels—5.0 acres on the front lot and 9.44 acres with the residence—just minutes from Winc...

5 Beds
6 Baths
None Available SubDv.
22603 Zip Code
CLOSED Status

2411 Hunting Ridge Rd, Winchester $800,000

This is the one you've been waiting for! Welcome to 2411 Hunting Ridge Rd. This large and private classic colonial is ready for you. With over 5000 sq ft and more than...

4 Beds
4 Baths
Creek View Farms SubDv.
22603 Zip Code
CLOSED Status

2530 Goldenfield Ln, Winchester $685,000

Gorgeous home in the sought after Harvest Ridge neighborhood. Make this immaculately kept and updated home yours. Walk through the front door and be welcomed by a grand...

4 Beds
5 Baths
Harvest Ridge SubDv.
22601 Zip Code
CLOSED Status

1205 Caroline St, Winchester $750,000

**Do Not Miss This One!** Don’t miss this rare opportunity in the heart of Winchester! Offered for the first time since it was custom built in 2001, this stunning all-bri...

4 Beds
4 Baths
Whittier Acres SubDv.
22601 Zip Code
CLOSED Status

331 N Braddock St, Winchester $1,025,000

This circa 1863 Italianate home is located in the heart of Winchester's historic district within a short walk to Handley Library and downtown. The home has been elegantly...

5 Beds
6 Baths
Historic District SubDv.
22601 Zip Code
CLOSED Status

325 Windsor Ln, Winchester $1,200,000

Welcome to 325 Windsor Ln, a stately brick Georgian-style home on 5 open and wooded acres in Winchester’s desirable Long Meadows community. This timeless residence offers...

5 Beds
5 Baths
Long Meadows SubDv.
22602 Zip Code
CLOSED Status

202 S Washington St, Winchester $1,150,000

Back on the market due to NO fault of the Seller! You have to see this $1M renovation by an architect out of NYC. Currently a single family home with a private “guest a...

7 Beds
7 Baths
Winchester Historic District SubDv.
22601 Zip Code
CLOSED Status

220 Anna Margaret Dr, Winchester $1,071,134

Just minutes from town, this impressive all-brick residence in the sought-after Granville Estates offers the perfect blend of space, elegance, and versatility. Situated o...

4 Beds
5 Baths
Granville Estates SubDv.
22602 Zip Code
CLOSED Status

101 Winterberry Ct, Winchester $675,000

Well-maintained home available in Oakdale Crossing. Great layout, very spacious, and an abundance of natural light permeates every room in the house!! Finished basement w...

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

1509 Stone House Ct, Winchester $920,000

Perched on the edge of the walking trail with fall views of the lake, and host to a private oasis in the back yard, you'll find 1509 Stone House Court, one of the largest...

4 Beds
5 Baths
Morlyn Hills SubDv.
22601 Zip Code
CLOSED Status

105 Braxton Ct, Winchester $675,000

Welcome to 105 Braxton Ct, Winchester VA! This stunning Colonial-style home offers over 3,500 square feet of beautifully updated living space with modern features through...

4 Beds
4 Baths
Fieldstone SubDv.
22602 Zip Code
CLOSED Status

939 Buckner Dr, Winchester $782,000

Priced to se!!! Listed well below market value, this stunning all-brick home in the sought-after Meadow Branch community was built in 2000 and has undergone extensive ren...

5 Beds
5 Baths
Meadowbranch SubDv.
22601 Zip Code
CLOSED Status

1517 Brookdale Ct, Winchester $850,000

A rare opportunity to own the largest model in the Morlyn Hills neighborhood--more than 6500 square feet when including the fully finished basement. Situated on a premie...

4 Beds
5 Baths
Morlyn Hills SubDv.
22601 Zip Code
CLOSED Status

132 Wilton Dr, Winchester $775,000

Beautifully Conceived Custom Colonial on 2.59 manicured acres with mature trees and landscaping. Versatile floor plan with Main Floor Primary and generous room sizes for ...

4 Beds
4 Baths
Mcguire Hills SubDv.
22603 Zip Code
CLOSED Status

118 Saint Andrews Ct, Winchester $1,429,000

This beautiful home boasts an ideal floor plan with spacious rooms and luxurious finishes. The main level features large rooms with 10' ceilings, including a two-story fa...

4 Beds
5 Baths
Roscommon SubDv.
22602 Zip Code
CLOSED Status

191 Old Baltimore Rd, Winchester $1,202,501

Perched on 2.75 private acres with panoramic valley and mountain views, this extraordinary estate is a true showpiece among Winchester’s finest homes. With over 6,000 fin...

6 Beds
6 Baths
Frederick County SubDv.
22603 Zip Code
CLOSED Status

1013 Armistead St, Winchester $777,000

Stunning Custom Colonial in the Coveted Meadow Branch Neighborhood This beautifully maintained colonial home offers the perfect combination of timeless elegance, modern ...

5 Beds
5 Baths
Morlyn Hills At Meadow Branch SubDv.
22601 Zip Code
CLOSED Status

422 Canyon Rd, Winchester $769,000

Stunning Huge Dream home over 5000 sq ft of upscale living. Wonderful Gourmet Kitchen with Stainless Steel Appliances and Granite Counters. Upscale Flooring covers the en...

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

5000+ Sq. Ft. Winchester Real Estate

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