Keller Williams
  • Home
  • Home Value
  • Buyers
  • Sellers
  • Rental Search
  • About
  • Webinars
  • Seminars
  • Downsizing
  • Blog
  • FL Listings
  • VA, MD & DC Listings
Login
1.888.840.5553

Sign in to your account

Need to reset your phone number?

Don't have an account with us?

Click here to sign up.

Winchester VA MLS Search

TO
Advanced Search

Address Search

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

Tumble Leaf Lane, Winchester image
Tumble Leaf Lane, Winchester $805,000

CARRINGTON HOMES AT FALL RIDGE ESTATES- 5 Acre Wooded LOTS WITH MOUNTAIN VIEWS. Choose from 7 different floorplans including our Main Level Owners Suite floorplan the Box...

  • 4 Beds
  • 4 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
2700 Loyalty Ct, Winchester image
2700 Loyalty Ct, Winchester $699,000

Welcome to 2700 Loyalty Court—a beautifully maintained showcase home offering nearly 5,000 square feet of unmatched versatility in one of Winchester City’s most coveted l...

  • 7 Beds
  • 5 Baths
  • Rolling Hills SubDv.
  • 22601 Zip Code
  • ACTIVE Status
110 Bentpath Ct, Winchester image
110 Bentpath Ct, Winchester $710,000

Welcome to 110 Betpath Ct, nestled within the premier Twin Lakes Overlook (TLO) enclave of exclusively single-family homes by Toll Brothers and Richmond American, this ex...

  • 5 Beds
  • 4 Baths
  • Twin Lake Overlook SubDv.
  • 22602 Zip Code
  • ACTIVE Status
116 Magpie Ln, Winchester image
116 Magpie Ln, Winchester $595,390

NEW BUILD, move in ready single-family home at Hiatt Pointe, 55+ community at Snowden Bridge by Van Metre Homes! The Sierra 39-F2 at Hiatt Pointe is stunning! This home o...

  • 3 Beds
  • 3 Baths
  • Hiatt Pointe At Snowden Bridge SubDv.
  • 22603 Zip Code
  • ACTIVE Status
337 Canyon Rd, Winchester image
337 Canyon Rd, Winchester $674,000

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
  • COMING SOON Status
200 Fairfield Dr, Winchester image
200 Fairfield Dr, Winchester $645,000

Come and discover this impressive beauty where easy main-level living meets exceptional indoor-outdoor entertaining. This beautifully appointed Cape Cod offers the conven...

  • 4 Beds
  • 4 Baths
  • Oakdale Crossing SubDv.
  • 22602 Zip Code
  • ACTIVE Status
394 Old Baltimore Rd, Winchester image
394 Old Baltimore Rd, Winchester $625,000

Coming Soon! A truly special property in a gorgeous, peaceful setting! This charming 1911 farmhouse sits on 2.75 acres and offers the perfect opportunity for a small farm...

  • 4 Beds
  • 4 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • COMING SOON 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
224 Sharp St, Winchester image
224 Sharp St, Winchester $750,000

Rare Historical Winchester Investment Opportunity – Three Properties in One Location An outstanding investment opportunity awaits in the heart of Winchester City. This un...

  • 22601 Zip Code
  • ACTIVE Status
854 Valley Mill Rd, Winchester image
854 Valley Mill Rd, Winchester $1,170,000

Unique 5+ acre property in Winchester. Beautiful home with plenty of space for everyone's interests. 5 bedrooms- all with en suite bathrooms. High end kitchen designed by...

  • 5 Beds
  • 6 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
101 Poe Dr, Winchester image
101 Poe Dr, Winchester $624,990

Welcome to this lovely 4 Bedroom, 2.5 Bath Craftsman Style Home where modern design meets everyday comfort! This beautifully maintained home & unique designs include an ...

  • 4 Beds
  • 3 Baths
  • Raven Oaks 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 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 $760,000

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
2216 Laurel Grove Rd, Winchester image
2216 Laurel Grove Rd, Winchester $1,300,000

Welcome to 2216 Laurel Grove Rd, an exceptional custom-built modern farmhouse offering privacy, beautiful views, and relaxed country living on 30 unrestricted acres, all ...

  • 4 Beds
  • 3 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
218 Babbs Mountain Rd, Winchester image
218 Babbs Mountain Rd, Winchester $935,000 ▼

A PRIVATE CUSTOM-BUILT ESTATE SURROUNDED BY NATURE — WITH YOUR OWN RESORT-STYLE POOL! Set on an extraordinary 6.44 private acres, this exquisite custom-built residence of...

  • 5 Beds
  • 3 Baths
  • Babbs Mountain SubDv.
  • 22603 Zip Code
  • ACTIVE UNDER CONTRACT Status
313 Lehigh Dr, Winchester image
313 Lehigh Dr, Winchester $630,000

***Very motivated Sellers*** Set within the desirable Senseny Village community, 313 Lehigh Drive offers an exceptional blend of refined living and effortless comfort. Th...

  • 5 Beds
  • 4 Baths
  • Senseny Village SubDv.
  • 22602 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
  • ACTIVE Status
175 Shields Dr, Winchester image
175 Shields Dr, Winchester $749,900 ▲

Beautiful 5 bedroom, 2.5-bath brick-front home situated on 2 private acres, offering the perfect blend of space, comfort, and recent updates. Shower on the main floor in...

  • 5 Beds
  • 4 Baths
  • Equestrian Estates SubDv.
  • 22602 Zip Code
  • ACTIVE Status
194 Glendobbin Ln, Winchester image
194 Glendobbin Ln, Winchester $1,350,000

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
  • ACTIVE UNDER CONTRACT Status
146 Stonebrook Rd, Winchester image
146 Stonebrook Rd, Winchester $649,900 ▼

Spacious ranch home on a beautiful 1-acre lot in the highly desirable Stonebrook Farms community! Surrounded by mature trees and offering a peaceful setting, this home co...

  • 5 Beds
  • 3 Baths
  • Stonebrook Farms SubDv.
  • 22602 Zip Code
  • ACTIVE Status
4241 Cedar Creek Grade, Winchester image
4241 Cedar Creek Grade, Winchester $799,000

Situated on nearly 3 acres of peaceful, private land, 4241 Cedar Creek Grade offers a truly remarkable retreat framed by sweeping, 360-degree views of rolling hills and l...

  • 4 Beds
  • 4 Baths
  • Granville Estates SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
1529 Dalton Pl, Winchester image
1529 Dalton Pl, Winchester $639,900 ▼

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
107 Cahille Dr, Winchester image
107 Cahille Dr, Winchester $749,050 ▼

Welcome to this exceptional 4-bedroom, 3.5-bath Colonial in the sought-after Raven Pointe subdivision, where luxury living extends well beyond the front door. The backya...

  • 4 Beds
  • 4 Baths
  • Raven Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
243 Summerfield Dr, Winchester image
243 Summerfield Dr, Winchester $879,900

Immaculate custom home sitting on a half-acre lot in desirable Raven Pointe! Beautiful hardwood floors flow throughout the main level, leading into a dramatic family room...

  • 5 Beds
  • 5 Baths
  • Raven Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
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
  • PENDING 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
102 Julie Ct, Winchester image
102 Julie Ct, Winchester $829,900 ▼

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 $714,000 ▼

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
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
  • 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
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
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 UNDER CONTRACT 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 $629,000 ▼

Seller is offering a $2,500 credit toward the purchaser's closing costs, mortgage rate buy-down, prepaid expenses, moving costs, or other allowable buyer expenses. Situat...

  • 4 Beds
  • 3 Baths
  • Farms At Frog Hollow SubDv.
  • 22603 Zip Code
  • ACTIVE Status
104 Bramble Ct, Winchester image
104 Bramble Ct, Winchester $624,900 ▼

Welcome to this beautifully maintained 3-level Colonial tucked away on a quiet cul-de-sac in sought-after Oakdale Crossing. With 4 bedrooms, 2.5 baths, a remodeled kitche...

  • 4 Beds
  • 3 Baths
  • Oakdale Crossing SubDv.
  • 22602 Zip Code
  • ACTIVE 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
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 $610,000 ▼

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 $647,000 ▼

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 $949,000 ▼

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
165 Carroll Ridge Ln, Winchester image
165 Carroll Ridge Ln, Winchester $945,000 ▼

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
  • 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!

Like or Share

Address Search

Anne Nouri headshot
Anne Nouri

keller william luxury
1.888.840.5553
Contact Me

Browse Winchester Homes by Features

  • Styles
  • Subdivisions
  • Buildings

Browse Winchester Homes by Property Type

  • Single Family
  • Townhouses
  • Land
  • Manufactured Homes
  • Historical Homes
  • Foreclosures
  • Short Sales
  • Just Listed
  • Homes with Pool

Browse Winchester Homes by Price Range

  • Under $200K
  • $200K-$300K
  • $300K-$400K
  • $400K-$500K
  • $500K-$600K
  • $600K-$700K
  • $700K-$800K
  • $800K-$900K
  • $900K-$1 Million
  • $1 Million-$2 Million
  • $2 Million-$3 Million
  • $3 Million-$4 Million
  • $4 Million-$5 Million
  • Above $5 Million

Browse Winchester Homes by # of Bedroom

  • 1
  • 2
  • 3
  • 4
  • 5
  • 6+

Browse Winchester Homes by # of Bathroom

  • 1
  • 2
  • 3
  • 4
  • 5
  • 6+

Browse Winchester Homes by Lot Size

  • 1 Acre
  • 2+ Acres
  • 3+ Acres
  • 4+ Acres
  • 5+ Acres
  • 6+ Acres

Browse Winchester Homes by Square Feet

  • 500+ Sqft
  • 700+ Sqft
  • 1000+ Sqft
  • 1250+ sqft
  • 1500+ Sqft
  • 1750+ Sqft
  • 2000+ Sqft
  • 2250+ Sqft
  • 2500+ Sqft
  • 2750+ Sqft
  • 3000+ Sqft
  • 3500+ Sqft
  • 4000+ Sqft
  • 5000+ Sqft
  • 7500+ Sqft

Winchester Real Estate Market Reports

  • Winchester

Mortgage Calculator

Amount of Loan
Annual Interest Rate
%
Term of Loan
Years
Calculate

Does not include any taxes or fees.
Please consult a financial professional.

  • Home
  • Advanced Search
  • Sellers
  • Buyers
  • Rental Search
  • About
  • Blog
  • Connect

  • Alexandria
  • Arlington
  • Ashburn
  • Fairfax
  • Leesburg
  • Mclean
  • Middleburg
  • Purcellville
  • Reston
  • Round Hill
  • Springfield
  • Sterling
  • Upperville
  • Vienna
  • Waterford
  • Winchester
  • Woodbridge
  • Delray Beach
  • Jupiter
  • Lake Park
  • North Palm Beach
  • Palm Beach
  • Palm Beach Gardens
  • Palm Springs
  • Royal Palm Beach
  • West Palm Beach
  • Washington DC
IDX Real Estate Websites by
• Accessibility • Terms • Privacy