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View All Latest Winchester 2250+ 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
1907 Martinsburg Pike, Winchester image
1907 Martinsburg Pike, Winchester $390,000

Beautiful Cape Cod home situated on approximately 0.57 acres, featuring 3 bedrooms, 2 full bathrooms, 1 half bath, a 2-car garage, and ample driveway parking. The home of...

  • 3 Beds
  • 3 Baths
  • Stephenson SubDv.
  • 22603 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
Homesite 91 Shuoner Court, Winchester image
Homesite 91 Shuoner Court, Winchester $374,990

🏡 Winter Delivery – St. Paul 4 Bedrooms | 3.5 Bathrooms | Finished Lower Level | Larger Deck | 🔥 Beautiful wooded homesites are available! Enjoy up to 2,250 sq. ft. of...

  • 4 Beds
  • 5 Baths
  • Abrams Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
Homesite 90 Shuoner Court, Winchester image
Homesite 90 Shuoner Court, Winchester $389,990

🏡 Winter Delivery – St. Paul LAST END UNIT!! 4 Bedrooms | 3.5 Bathrooms | Finished Lower Level | Larger Deck | 🔥 Beautiful wooded homesites are available! Enjoy up to...

  • 4 Beds
  • 5 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
134 Hudson Ave, Winchester image
134 Hudson Ave, Winchester $375,000

Enjoy the perfect blend of country peace and convenience to town in this beautiful brick Colonial. Nestled on two park-like lots with no HOA, this 4-bedroom, 2-bathroom h...

  • 4 Beds
  • 2 Baths
  • Edwards SubDv.
  • 22603 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
108 Oleander Ct, Winchester image
108 Oleander Ct, Winchester $509,990

asy living starts here, and this home is ready for you now! Discover the freedom of low-maintenance living in Hiatt Pointe at Snowden Bridge, a gated 55+ active adult com...

  • 3 Beds
  • 3 Baths
  • Hiatt Pointe At Snowden Bridge SubDv.
  • 22603 Zip Code
  • ACTIVE Status
205 Pond View Ln, Winchester image
205 Pond View Ln, Winchester $669,000

Professional photos coming soon! Enjoy 5 acres of peaceful country living without sacrificing convenience. With no HOA, no gravel roads, and a paved driveway, this spaci...

  • 3 Beds
  • 3 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • COMING SOON Status
1113 Apple Pie Ridge Rd, Winchester image
1113 Apple Pie Ridge Rd, Winchester $699,000

Custom-designed by architect Crawford Horne and built by local builder Ritter Homes, this 3 BR / 3.5 BA home draws on Frank Lloyd Wright's belief that a house should live...

  • 3 Beds
  • 4 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • PENDING 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
411 W Cecil St, Winchester image
411 W Cecil St, Winchester $645,000

This home is not just a property; it's a place where memories are made and cherished. Don't miss the opportunity to make this delightful residence your own. Metal roof (2...

  • 4 Beds
  • 2 Baths
  • City SubDv.
  • 22601 Zip Code
  • ACTIVE Status
310 Mountain Falls Blvd, Winchester image
310 Mountain Falls Blvd, Winchester $419,900

Set on a beautiful, level lot of more than half an acre, this inviting two-level Colonial a paved road. A must see inside, with beautiful windows that make a bright, air...

  • 4 Beds
  • 3 Baths
  • Wilde Acres SubDv.
  • 22602 Zip Code
  • ACTIVE Status
Homesite 30 Shuoner Court, Winchester image
Homesite 30 Shuoner Court, Winchester $395,990

🏡 Winter Delivery – St. Paul LAST END UNIT!! 4 Bedrooms | 3.5 Bathrooms | Finished Lower Level | Larger Composite Deck | 🔥 Beautiful wooded homesites are available! E...

  • 4 Beds
  • 5 Baths
  • Abrams Pointe 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
104 Scotch Bonnet Dr, Winchester image
104 Scotch Bonnet Dr, Winchester $599,990

Brand-new Pendleton backing to trees offers a rare move-in ready opportunity with main-level living at Snowden Bridge! The open main level features low-maintenance LVP fl...

  • 4 Beds
  • 4 Baths
  • Snowden Bridge 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
Homesite 61 Shuoner Court, Winchester image
Homesite 61 Shuoner Court, Winchester $384,990 ▼

🏡 YOUR NEW HOME THIS WINTER — ST. PAUL TOWNHOME ✨ Room to Gather. Space to Unwind. A Wooded Setting to Love. 4 Bedrooms | 3.5 Bathrooms | Up to 2,250 Sq. Ft. Finished L...

  • 4 Beds
  • 4 Baths
  • Abrams Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
Homesite 60 Shuoner Court, Winchester image
Homesite 60 Shuoner Court, Winchester $349,999

🏡 110 SHUONER Ct – Model Home | We Have MOVE IN READY 2026 Delivery Available St. Paul TBB | 3 BR | 2.5 BA | Finished Lower Level 🔥 Beautiful wooded homesites available!...

  • 3 Beds
  • 3 Baths
  • Abrams Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
Homesite 52 Shuoner Court, Winchester image
Homesite 52 Shuoner Court, Winchester $379,990 ▼

🏡 YOUR NEW HOME THIS WINTER — ST. PAUL TOWNHOME ✨ Room to Gather. Space to Unwind. A Wooded Setting to Love. 4 Bedrooms | 3.5 Bathrooms | Up to 2,250 Sq. Ft. Finished L...

  • 4 Beds
  • 4 Baths
  • Abrams Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
104 Monet Ter, Winchester image
104 Monet Ter, Winchester $549,999

Opportunities like this don't come around often! Lovingly owned and cared for by the original owners for over 20 years, this beautiful brick Colonial in a highly desirabl...

  • 4 Beds
  • 3 Baths
  • Sovereign Village SubDv.
  • 22602 Zip Code
  • ACTIVE Status
626 Bruce St, Winchester image
626 Bruce St, Winchester $399,044

Thoughtfully renovated home in the City, (although the backyard feels more like a private oasis) This one has all the renovations! Gorgeous Kitchen complete with Custom ...

  • 3 Beds
  • 2 Baths
  • None Available SubDv.
  • 22601 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
115 Garnett Ct, Winchester image
115 Garnett Ct, Winchester $859,000

Welcome to this beautifully crafted new construction home offering approximately 2,400 square feet of high-quality living space, perfectly situated on 2 peaceful acres at...

  • 3 Beds
  • 3 Baths
  • Jackson's Retreat SubDv.
  • 22602 Zip Code
  • ACTIVE Status
1 Swansong Pl Unit TEAGAN 24-F2, Winchester image
1 Swansong Pl Unit TEAGAN 24-F2, Winchester $399,990

New personalized TOWNHOMES by Van Metre Homes at SNOWDEN BRIDGE in Stephenson, VA that will be ready for move in MID 2027 based on build time. Discover the Teagan 24-F2—a...

  • 3 Beds
  • 4 Baths
  • Snowden Bridge SubDv.
  • 22603 Zip Code
  • ACTIVE Status
615 Mahlon Dr, Winchester image
615 Mahlon Dr, Winchester $675,000

Welcome to 615 Mahlon Drive, Winchester, VA. Custom-built 2023 home offering the perfect blend of modern comfort, thoughtful upgrades, privacy, and country living on 5 un...

  • 4 Beds
  • 3 Baths
  • Earl Haines-Shanholtz 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

2250+ Sq. Ft. Winchester Real Estate

Our website features the best real estate search for 2250+ 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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