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View All Latest Winchester 2750+ Sq. Ft. Properties for Sale

308 Huntersridge Rd, Winchester image
308 Huntersridge Rd, Winchester $619,900

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
  • COMING SOON 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> **Briede Family Vineyards** presents an exceptional opportunity to acquire one of Virginia'...

  • 3 Beds
  • 4 Baths
  • No SubDv.
  • 22603 Zip Code
  • ACTIVE Status
140 Stonebrook Rd, Winchester image
140 Stonebrook Rd, Winchester $675,000

🏡 Professional Interior Photos Coming Soon! Experience the ease of one-level living in the highly desirable Stonebrook Subdivision, just minutes from Winchester! Situate...

  • 4 Beds
  • 3 Baths
  • Stonebrook Farms SubDv.
  • 22602 Zip Code
  • COMING SOON Status
160 Wilton Dr, Winchester image
160 Wilton Dr, Winchester $839,900

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
  • COMING SOON Status
102 Julie Ct, Winchester image
102 Julie Ct, Winchester $889,900

Opportunities of this caliber in the highly coveted Stonebrook Farms community are exceptionally rare. Positioned on a premium cul-de-sac lot backing directly to mature, ...

  • 5 Beds
  • 5 Baths
  • Stonebrook Farms SubDv.
  • 22602 Zip Code
  • ACTIVE Status
342 Canyon Rd, Winchester image
342 Canyon Rd, Winchester $724,000

Welcome to 342 Canyon Rd, a spacious and beautifully maintained home in the desirable Twin Lakes Overlook community on Winchester's east side. Situated on a beautifully l...

  • 5 Beds
  • 4 Baths
  • Twin Lakes Overlook SubDv.
  • 22602 Zip Code
  • COMING SOON Status
336 Apple Valley Rd, Winchester image
336 Apple Valley Rd, Winchester $715,000

Spacious contemporary craftsman style home built in 2007 on .5 acre lot with rare 3 car attached side load garage as well as a detached 2 car & 1 car garages behind the h...

  • 3 Beds
  • 4 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • COMING SOON 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
608 Bellview Ave, Winchester image
608 Bellview Ave, Winchester $580,000

Open House Sunday, July 19th from 12pm - 2pm!  Welcome home to this spacious single-family home in the sought-after Williamsburg Heights community! This great home, locat...

  • 4 Beds
  • 3 Baths
  • Williamsburg Heights SubDv.
  • 22601 Zip Code
  • PENDING Status
226 Summerfield Dr, Winchester image
226 Summerfield Dr, Winchester $849,000

UP TO $5000 SELLER CONCESSION FOR PAINT. CALL FOR DETAILS. Welcome to this stunning Colonial estate nestled in the highly sought-after Raven Pointe neighborhood of Winche...

  • 6 Beds
  • 5 Baths
  • Raven Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
139 Panarama Dr, Winchester image
139 Panarama Dr, Winchester $799,900

A rare opportunity to own a beautifully updated and meticulously maintained home set on an incredibly beautiful 5‑acre property with perennial gardens, a fountain, mature...

  • 4 Beds
  • 3 Baths
  • Glen E Russell SubDv.
  • 22603 Zip Code
  • PENDING 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 $695,000 ▼

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
  • ACTIVE Status
136 Cahille Dr, Winchester image
136 Cahille Dr, Winchester $750,000

Nestled towards the end of a quiet dead-end street in the sought-after Raven Pointe community, this stunning 5-bedroom, 4.5-bath home offers the perfect blend of elegance...

  • 5 Beds
  • 5 Baths
  • Raven Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
115 Marion Dr, Winchester image
115 Marion Dr, Winchester $639,000 ▼

**Seller is offering a $2,500 credit with an acceptable offer, giving the purchaser added flexibility toward closing costs, a mortgage rate buy-down, prepaid expenses, mo...

  • 4 Beds
  • 3 Baths
  • Farms At Frog Hollow SubDv.
  • 22603 Zip Code
  • ACTIVE Status
297 Huntersridge Rd, Winchester image
297 Huntersridge Rd, Winchester $709,900

Executive Living in Oakdale Crossing Nestled in the highly desirable Oakdale Crossing community, this exceptional brick-front residence offers an impressive blend of ele...

  • 4 Beds
  • 5 Baths
  • Oakdale Crossing SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
112 Hites St, Winchester image
112 Hites St, Winchester $419,900 ▼

This beautiful home features two primary suites, one on each level, offering flexibility and convenience. The upper-level primary suite includes a versatile flex space, p...

  • 4 Beds
  • 4 Baths
  • Shenandoah Hills SubDv.
  • 22602 Zip Code
  • ACTIVE Status
104 Bramble Ct, Winchester image
104 Bramble Ct, Winchester $649,000 ▼

Welcome home to this beautifully maintained 3-level Colonial, perfectly situated on a quiet cul-de-sac in the highly desirable Oakdale Crossing community. Offering 4 bedr...

  • 4 Beds
  • 3 Baths
  • Oakdale Crossing SubDv.
  • 22602 Zip Code
  • ACTIVE Status
114 Nassau Dr, Winchester image
114 Nassau Dr, Winchester $565,000

4 bed/ 3.5 bath colonial in a prime commuter location just minutes from I-81 and Route 7. Enjoy outdoor living with a fenced backyard, low-maintenance composite decking, ...

  • 4 Beds
  • 4 Baths
  • Fieldstone SubDv.
  • 22602 Zip Code
  • COMING SOON Status
118 Aulee Ct, Winchester image
118 Aulee Ct, Winchester $789,900

This beautiful, well-cared-for home overlooks a lake and stream directly behind the house. The owners have painted the entire interior, added new lighting fixtures, new ...

  • 5 Beds
  • 5 Baths
  • Twin Lake Overlook SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
137 Old Forest Cir, Winchester image
137 Old Forest Cir, Winchester $989,000

Nestled in the highly sought-after Stonebrook neighborhood, this incredibly quiet wooded property offers the perfect blend of privacy and convenience. This 2.6 acre estat...

  • 4 Beds
  • 4 Baths
  • Stonebrook Farms SubDv.
  • 22602 Zip Code
  • ACTIVE Status
211 Flanagan Dr, Winchester image
211 Flanagan Dr, Winchester $630,000

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 $690,000 ▼

Welcome home to Norfolk Ct!!! Oh my, where to begin? If you're looking for a turnkey home with ample space and lots of room for your dreams, then this is the home for yo...

  • 4 Beds
  • 5 Baths
  • Twin Lakes SubDv.
  • 22602 Zip Code
  • ACTIVE Status
256 Skylar Lanes Way, Winchester image
256 Skylar Lanes Way, Winchester $669,000 ▼

Welcome to this beautifully maintained home in the highly sought-after Walnut Springs Estates subdivision, offering exceptional space,comfort, and versatility on a privat...

  • 7 Beds
  • 4 Baths
  • Walnut Springs Estates SubDv.
  • 22603 Zip Code
  • ACTIVE Status
144 Widener Dr, Winchester image
144 Widener Dr, Winchester $989,000

Exceptional Custom Home with Panoramic Mountain & Pastoral Views in Butler Estates. Nestled in a scenic valley on a private 2-acre cul-de-sac lot in the prestigious Butl...

  • 4 Beds
  • 5 Baths
  • Butler Estates SubDv.
  • 22603 Zip Code
  • ACTIVE Status
614 Mohawk Trl, Winchester image
614 Mohawk Trl, Winchester $580,000

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
  • ACTIVE UNDER CONTRACT Status
165 Carroll Ridge Ln, Winchester image
165 Carroll Ridge Ln, Winchester $975,000

Modern farmhouse living meets peaceful acreage on 2.75 acres right on Cedar Creek Grade. Built just two years ago by owner/builder Stephen Carroll, this thoughtfully desi...

  • 4 Beds
  • 3 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
161 Skylar Lanes Way, Winchester image
161 Skylar Lanes Way, Winchester $824,900 ▼

PRICED BELOW RECENT APPRAISAL>> Gorgeous Country Home on Two Acres — Nearly 5,000 Sq Ft of Well-Appointed Living!! Welcome to 161 Skylar Lanes Way, a thoughtfully-updated...

  • 6 Beds
  • 5 Baths
  • Walnut Springs Estates SubDv.
  • 22603 Zip Code
  • ACTIVE Status
3105 Apple Pie Ridge Rd, Winchester image
3105 Apple Pie Ridge Rd, Winchester $699,999

Situated on a beautiful tract of land with scenic views in every season, this charming farmhouse offers the space, tranquility, and rural lifestyle that buyers dream abou...

  • 4 Beds
  • 2 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • COMING SOON Status
295 Huntersridge Rd, Winchester image
295 Huntersridge Rd, Winchester $627,102 ▼

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
  • ACTIVE Status
300 Tavistock Dr, Winchester image
300 Tavistock Dr, Winchester $899,990 ▼

Discover the perfect blend of space, privacy and convenience this expansive 3500 sq ft plus ranch home situated on 7.12 beautiful acres. Located just 10 mins from shoppin...

  • 4 Beds
  • 4 Baths
  • Tavistock Estates SubDv.
  • 22602 Zip Code
  • ACTIVE Status
801 Armistead St, Winchester image
801 Armistead St, Winchester $1,150,000

There are homes that simply provide shelter. And then there are homes like this—homes that make you slow down, take a deep breath, and picture the life you've been worki...

  • 5 Beds
  • 5 Baths
  • Meadowbranch SubDv.
  • 22601 Zip Code
  • ACTIVE Status
3336 Hunting Ridge Rd, Winchester image
3336 Hunting Ridge Rd, Winchester $539,000 ▼

Price Improvement . 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, l...

  • 4 Beds
  • 3 Baths
  • Chestnut Grove Estates SubDv.
  • 22603 Zip Code
  • ACTIVE Status
220 Lehigh, Winchester image
220 Lehigh, Winchester $685,000 ▼

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
  • ACTIVE Status
116 Magpie Ln, Winchester image
116 Magpie Ln, Winchester $599,990 ▼

READY FOR IMMEDIATE DELIVERY! The Sierra 39-F2 at Hiatt Pointe (55+) delivers single-family living at its finest — 3 bedrooms, 3 full baths, 2-car front-load garage, an...

  • 3 Beds
  • 3 Baths
  • Hiatt Pointe At Snowden Bridge SubDv.
  • 22603 Zip Code
  • ACTIVE Status
108 Nevermore Dr, Winchester image
108 Nevermore Dr, Winchester $671,625 ▼

Practicality meets long-term value with a $70,000 IN UPGRADE to install a 32 PANEL SOLAR SYSTEM., that that virtually reduces monthly electric bills. An additional $30...

  • 4 Beds
  • 3 Baths
  • Raven Oaks SubDv.
  • 22602 Zip Code
  • ACTIVE Status
974 Wayne Dr, Winchester image
974 Wayne Dr, Winchester $614,999

Finally, a five-bedroom, 3.5 bath home in the city of Winchester with over 4200 sq ft of living space within minutes of Valley Health and shopping. Beautifully landscaped...

  • 5 Beds
  • 4 Baths
  • Meadow Branch South SubDv.
  • 22601 Zip Code
  • ACTIVE UNDER CONTRACT Status
1004 Heth Pl, Winchester image
1004 Heth Pl, Winchester $1,179,000

Stepping onto the Southern style covered front porc.h you enter the large foyer with a Schoenbek chandelier. There is a living room to the left which opens to a separate...

  • 4 Beds
  • 5 Baths
  • Meadow Branch SubDv.
  • 22601 Zip Code
  • ACTIVE Status
159 Abrams Pointe Blvd, Winchester image
159 Abrams Pointe Blvd, Winchester $749,900 ▼

***You could get up to $3,000 with use of preferred lender for closing cost assistance or use funds for a rate buy-down (restrictions apply and not all will qualify, cont...

  • 5 Beds
  • 5 Baths
  • Abrams Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
146 Darby Dr, Winchester image
146 Darby Dr, Winchester $674,900

Beautiful brick-front home in sought-after Ravenwing offering three finished levels and exceptional space throughout! This 4-bedroom, 3.5-bath home features a welcoming m...

  • 4 Beds
  • 4 Baths
  • Raven Wing SubDv.
  • 22602 Zip Code
  • ACTIVE Status
769 Seldon Dr, Winchester image
769 Seldon Dr, Winchester $799,000

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
1564 Perry Rd, Winchester image
1564 Perry Rd, Winchester $605,000 ▼

Discover the perfect blend of comfort and contemporary living in this stunning detached home, nestled on a generous 1.35-acre lot. Built in 2009, this residence boasts a ...

  • 4 Beds
  • 3 Baths
  • Winchester SubDv.
  • 22602 Zip Code
  • ACTIVE Status
2230 Jones Rd, Winchester image
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
1460 Pitcock Ln, Winchester image
1460 Pitcock Ln, Winchester $1,050,000

Escape to Your Private Retreat – Just 10 Minutes from Winchester! Don’t miss the 3D tour attached to this listing! Welcome to a truly one-of-a-kind property offering 27....

  • 4 Beds
  • 4 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
125 Skyjes Ln, Winchester image
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
  • ACTIVE UNDER CONTRACT Status
230 Conifer Ln, Winchester image
230 Conifer Ln, Winchester $824,900 ▼

WOW - what a price improvement - schedule your viewing now!! Perched on a picturesque knoll with sweeping mountain views, this thoughtfully designed modern farmhouse co...

  • 4 Beds
  • 3 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
1400 Valley Ave, Winchester image
1400 Valley Ave, Winchester $575,000 ▼

Versatile on Valley! So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful original hardwood floors, t...

  • 6 Beds
  • 4 Baths
  • Henry Land SubDv.
  • 22601 Zip Code
  • ACTIVE Status
1400 Valley Ave, Winchester image
1400 Valley Ave, Winchester $575,000 ▼

Versatile on Valley! So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful wood floors, tall ceilings,...

  • 22601 Zip Code
  • ACTIVE Status

2750+ Sq. Ft. Winchester Real Estate

Our website features the best real estate search for 2750+ 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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