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

112 Killaney Ct, Winchester image
112 Killaney Ct, Winchester $620,000

Pride of ownership exudes from this cul-de-sac Colonial in Raven Pointe. From the moment you walk up to the brick porch to start your tour imagine relaxing in your rocki...

  • 4 Beds
  • 4 Baths
  • Raven Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
134 Wilkins Dr, Winchester image
134 Wilkins Dr, Winchester $399,900

Welcome to this spacious 4-bedroom, 2-full-bath split-level home in Winchester! Offering 2,556 square feet of living space, there's plenty of room to spread out and enjoy...

  • 4 Beds
  • 2 Baths
  • Green Acres SubDv.
  • 22602 Zip Code
  • ACTIVE Status
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
113 Malbec Ct, Winchester image
113 Malbec Ct, Winchester $677,130

UNDER CONSTRUCTION – THE BIRMINGHAM | WINTER DELIVERY AT ABRAMS POINTE! Welcome to Abrams Pointe! Discover the perfect blend of space, style, and functionality with the B...

  • 4 Beds
  • 3 Baths
  • Abrams Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
29 Williamson Rd, Winchester image
29 Williamson Rd, Winchester $549,990

TO BE BUILT – THE ROCKFORD | SPACIOUS THREE-LEVEL LIVING AT ABRAMS POINTE! Welcome to Abrams Pointe! Discover the perfect blend of comfort, style, and functionality with ...

  • 4 Beds
  • 3 Baths
  • Abrams Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
18 Williamson Rd, Winchester image
18 Williamson Rd, Winchester $598,990

TO BE BUILT – THE DREXEL | SPACIOUS RANCH-STYLE LIVING! Discover the perfect blend of comfort, style, and functionality with the Drexel, offering 3,213 square feet of tho...

  • 3 Beds
  • 2 Baths
  • Abrams Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
2018 Colin Dr, Winchester image
2018 Colin Dr, Winchester $499,000

Modern updates, cozy charm, and inviting spaces come together beautifully in this thoughtfully refreshed 3-bedroom, 2.5-bath home in one of Winchester’s hidden-gem neighb...

  • 3 Beds
  • 3 Baths
  • Westside Station 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
460 Cattail Rd, Winchester image
460 Cattail Rd, Winchester $624,000

Stunning Custom-Built Home on 5.43 Acres Near Winchester! Welcome to this amazing custom-built home, nestled on 5.43 beautiful acres with easy access to the City of Winc...

  • 4 Beds
  • 4 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE Status
757 Seldon Dr, Winchester image
757 Seldon Dr, Winchester $867,500

SOARING CEILINGS, EFFORTLESS MAIN-LEVEL LIVING & EXPANSIVE SPACE Welcome to 757 Seldon Drive in Meadow Branch, one of Winchester’s established and coveted communities. O...

  • 4 Beds
  • 4 Baths
  • Meadow Branch South SubDv.
  • 22601 Zip Code
  • ACTIVE Status
1151 Wardensville Grade, Winchester image
1151 Wardensville Grade, Winchester $700,000

Enjoy the best of country living with this spacious 4-bedroom, 5-full-bath home nestled on over 7 acres in Frederick County! Surrounded by mountain views and wooded beaut...

  • 4 Beds
  • 5 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
127 Wappinger Ter, Winchester image
127 Wappinger Ter, Winchester $559,990

Move-In Ready! The Hayden is a spacious two-story home offering 6 bedrooms, 4 bathrooms, and more than 3,100 square feet of thoughtfully designed living space. The main l...

  • 6 Beds
  • 4 Baths
  • Retreat At Winding Creek SubDv.
  • 22602 Zip Code
  • ACTIVE Status
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
1564 Perry Rd, Winchester image
1564 Perry Rd, Winchester $579,900

Peaceful country living with everyday conveniences just minutes away! Tucked away from the hustle and bustle of main roads, yet less than 10 minutes from shopping, groce...

  • 4 Beds
  • 3 Baths
  • Winchester SubDv.
  • 22602 Zip Code
  • ACTIVE Status
327 Ridge Ave, Winchester image
327 Ridge Ave, Winchester $639,900

STUNNING BRICK-FRONT COLONIAL IN SOUGHT-AFTER WHITTIER ACRES — Amazing renovations have been done so the home is absolutely move-in ready!!! Welcome to 327 Ridge Avenue,...

  • 4 Beds
  • 3 Baths
  • Whittier Acres SubDv.
  • 22601 Zip Code
  • ACTIVE Status
130 Country Club Cir, Winchester image
130 Country Club Cir, Winchester $325,000

Opportunity in Winchester! This home offers a convenient location, practical living space, and the chance to make updates to suit your preferences. The property is being ...

  • 4 Beds
  • 3 Baths
  • A Melvin Lewis SubDv.
  • 22602 Zip Code
  • ACTIVE Status
407 Tamarack Cir, Winchester image
407 Tamarack Cir, Winchester $499,000

*Short Sale*Beautiful colonial located on a quiet cul-de-sac. The formal living and dining rooms feature hardwood floors, crown molding, and chair rail. The light-filled,...

  • 6 Beds
  • 4 Baths
  • Apple Ridge SubDv.
  • 22602 Zip Code
  • ACTIVE Status
490 Devland Dr, Winchester image
490 Devland Dr, Winchester $900,000

Enjoy space, privacy, and refreshed country living at 490 Devland Drive! Situated on 6.7 acres, this renovated Colonial offers 4 bedrooms, 3.5 bathrooms, and a striking f...

  • 4 Beds
  • 4 Baths
  • Devland Farms SubDv.
  • 22603 Zip Code
  • ACTIVE Status
1214 Martinsburg Pike, Winchester image
1214 Martinsburg Pike, Winchester $649,927 ▼

Put this unique property on the top of your list! Solid 1957 custom Cape Cod home now fully renovated! 4 bedroom, 2.5 bath home on .66 acre! How often can you buy a tenn...

  • 4 Beds
  • 3 Baths
  • Martinsburg Pike SubDv.
  • 22603 Zip Code
  • ACTIVE Status
124 Ruby Royce Dr, Winchester image
124 Ruby Royce Dr, Winchester $649,990

Ready for Move In this year at Hiatt Pointe at Snowden Bridge—a vibrant 55+ gated community! This brand-new Matisse, backing to tree line, offers effortless, elegant livi...

  • 4 Beds
  • 4 Baths
  • Hiatt Pointe At Snowden Bridge 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
243 Hydrangea Way, Winchester image
243 Hydrangea Way, Winchester $559,990

The Dover by D.R. Horton offers 2,712 square feet of thoughtfully designed, main-level 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
241 Hydrangea Way, Winchester image
241 Hydrangea Way, Winchester $589,990

The Dover by D.R. Horton offers 2,712 square feet of thoughtfully designed, main-level 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
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
1 Plaid Hill Dr Unit SHELDON 40-F2, Winchester image
1 Plaid Hill Dr Unit SHELDON 40-F2, Winchester $572,990

Discover new SINGLE FAMILY HOMES by Van Metre Homes at SNOWDEN BRIDGE in Stephenson, VA that will be ready for you to move in EARLY-MID 2027 based on build time. Say hell...

  • 4 Beds
  • 3 Baths
  • Snowden Bridge SubDv.
  • 22603 Zip Code
  • ACTIVE Status
432 N Loudoun St, Winchester image
432 N Loudoun St, Winchester $699,000

432 North Loudoun Street sits a half block up from the historic fort and 2 blocks from the Winchester Mall. This completely redeveloped 1915 Craftsman style house in Winc...

  • 4 Beds
  • 3 Baths
  • Historic Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE Status
999 Dicks Hollow Rd, Winchester image
999 Dicks Hollow Rd, Winchester $439,000

Experience effortless main-level living in this charming rancher set on over an acre of scenic, usable land. Inside, an inviting open-concept layout connects the primary ...

  • 3 Beds
  • 3 Baths
  • Charles Conrad SubDv.
  • 22603 Zip Code
  • ACTIVE Status
3336 Hunting Ridge Rd, Winchester image
3336 Hunting Ridge Rd, Winchester $524,990

Colonial home 21 yrs young on 5 acres in Frederick county 4 bedroom 2 full baths with 1 half bath ., Whole house freshly painted in Jan/Feb 2025, laundry on main level ...

  • 5 Beds
  • 3 Baths
  • Chestnut Grove Estates SubDv.
  • 22603 Zip Code
  • ACTIVE Status
205 Crestleigh Dr, Winchester image
205 Crestleigh Dr, Winchester $630,000

Extensively updated and thoughtfully maintained, this beautiful Colonial in the prestigious Oakdale Crossing community offers 2,884 square feet of living space, impressiv...

  • 4 Beds
  • 3 Baths
  • Oakdale Crossing SubDv.
  • 22602 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
107 Oak Ridge Ln, Winchester image
107 Oak Ridge Ln, Winchester $440,000 ▼

Come to one of Winchester's premier neighborhoods - Fairway Estates - bordering the Winchester Country Club! Homes are seldom listed in this community so here is your cha...

  • 4 Beds
  • 4 Baths
  • Fairway Estates SubDv.
  • 22602 Zip Code
  • ACTIVE Status
637 Treys Dr, Winchester image
637 Treys Dr, Winchester $850,000

Exceptional Winchester living with TWO primary suites, an incredible covered outdoor living space, and a private in-ground pool! This beautifully appointed home offers an...

  • 4 Beds
  • 5 Baths
  • Williamsburg Heights SubDv.
  • 22601 Zip Code
  • COMING SOON Status
225 Hydrangea Way, Winchester image
225 Hydrangea Way, Winchester $649,990

Experience effortless living in our Willow Run Active Adult community! 225 Hydrangea Way is a thoughtfully designed ranch home blending style and functionality in a singl...

  • 4 Beds
  • 3 Baths
  • Willow Run SubDv.
  • 22602 Zip Code
  • PENDING Status
306 Longview Ave, Winchester image
306 Longview Ave, Winchester $540,000 ▲

Built in 2023 and offering the feel of new construction without the new construction price tag, this spacious three-level home in the WEA-VILLA community has so much to o...

  • 5 Beds
  • 3 Baths
  • Wea-Villa SubDv.
  • 22601 Zip Code
  • PENDING 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
150 Abrams Pointe Blvd, Winchester image
150 Abrams Pointe Blvd, Winchester $699,900

Welcome to 150 Abrams Pointe Blvd, a beautifully appointed 3-bedroom, 3.5 bath home offering approximately 2700+ square feet of finished living space in desirable Abrams ...

  • 3 Beds
  • 4 Baths
  • Abrams Pointe SubDv.
  • 22602 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
123 Likens Way, Winchester image
123 Likens Way, Winchester $450,000

One level living in a very easy location, with disability access to the front door and privacy in your back yard! Enjoy the best of both worlds with this charming rambler...

  • 4 Beds
  • 3 Baths
  • Carlisle Heights SubDv.
  • 22602 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 $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 $749,000 ▼

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

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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