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Winchester VA MLS Search

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

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
  • COMING SOON 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
  • COMING SOON Status
1214 Martinsburg Pike, Winchester image
1214 Martinsburg Pike, Winchester $674,927

Solid 1957 custom Cape Cod home now fully renovated! 4 bedroom, 2.5 bath home on .66 acre! All new windows! Freshly painted! Mini splits and hardwood flooring throughout!...

  • 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
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
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 comfortable and elegant...

  • 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
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
  • ACTIVE 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
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 $719,000

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 $774,900

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
25 W Boscawen St, Winchester image
25 W Boscawen St, Winchester $625,000

Awesome income-producing multi-unit property in the heart of downtown Winchester. This stately red brick building delivers immediate cash flow with a great documented CAP...

  • 22601 Zip Code
  • PENDING Status
922 Armistead St, Winchester image
922 Armistead St, Winchester $839,000

Welcome to 922 Armistead Street, a spacious brick Colonial in Winchester's established Morlyn Hills neighborhood offering approximately 4,697 finished square feet across ...

  • 4 Beds
  • 5 Baths
  • Morlyn Hills SubDv.
  • 22601 Zip Code
  • ACTIVE Status
540 Monticello St, Winchester image
540 Monticello St, Winchester $605,000

Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location! Presenting a Triplex in the heart of Downtown Winches...

  • 22601 Zip Code
  • ACTIVE Status
Lot 60 Gravenstein, Winchester image
Lot 60 Gravenstein, Winchester $1,035,000

MAIN LEVEL LIVING in an Idyllic Setting - Welcome to Stonymeade ! -2 acre Home Site in Winchester Virginia Base price shown is for the Boxwood MAIN LEVEL Owners Suite FL...

  • 4 Beds
  • 4 Baths
  • Stoneymeade SubDv.
  • 22602 Zip Code
  • ACTIVE Status
151 Nevermore Dr, Winchester image
151 Nevermore Dr, Winchester $619,900

***Seller has an assumable VA loan with a 4.99% interest rate. Contact listing agent for details!*** Welcome to 151 Nevermore Drive, a home that truly has it all! Built i...

  • 4 Beds
  • 4 Baths
  • Raven Oaks SubDv.
  • 22602 Zip Code
  • ACTIVE Status
Winchester image
Winchester $545,000 ▼

Beautiful hardwood floors and ceramic tile throughout, complemented by a spacious open floor plan. Enjoy a private rear yard, with shopping and commuter routes just minut...

  • 4 Beds
  • 4 Baths
  • Park Place SubDv.
  • 22601 Zip Code
  • ACTIVE Status
409 Fortress Dr, Winchester image
409 Fortress Dr, Winchester $499,900 ▼

Big, beautiful, and ideally located, this spacious three-level Colonial offers 4 bedrooms, 3.5 baths, over 3,100 finished square feet, a 2-car garage, and a fully finishe...

  • 4 Beds
  • 4 Baths
  • Star Fort SubDv.
  • 22603 Zip Code
  • ACTIVE UNDER CONTRACT Status
101 Poe Dr, Winchester image
101 Poe Dr, Winchester $619,900 ▼

Marry the house, but date the rate! *****SELLER WILL PAY for a 1-1 TEMPORARY BUYDOWN with use of preferred lender!! That means YOU save 1% on your mortgage rate for TWO Y...

  • 4 Beds
  • 3 Baths
  • Raven Oaks SubDv.
  • 22602 Zip Code
  • ACTIVE Status
112 Wappinger Ter, Winchester image
112 Wappinger Ter, Winchester $589,990 ▼

Situated on a desirable cul-de-sac homesite backing to community open space, this thoughtfully designed home offers the perfect blend of comfort and functionality. The ma...

  • 5 Beds
  • 5 Baths
  • Retreat At Winding Creek SubDv.
  • 22602 Zip Code
  • ACTIVE Status
132 Darby Dr, Winchester image
132 Darby Dr, Winchester $625,000 ▼

Welcome to this beautiful single-family home in the sought-after Ravenwing neighborhood of Winchester, Virginia. The sellers are open to offers that include credits towar...

  • 4 Beds
  • 4 Baths
  • Ravenwing SubDv.
  • 22602 Zip Code
  • ACTIVE Status
143 Wappinger Ter, Winchester image
143 Wappinger Ter, Winchester $579,990 ▼

Rare cul-de-sac home! The Hayden offers 6 bedrooms, 4 bathrooms, and over 3,100 square feet of beautifully designed living space. The open-concept main level features a f...

  • 6 Beds
  • 4 Baths
  • Retreat At Winding Creek SubDv.
  • 22602 Zip Code
  • ACTIVE Status
114 Settlers Cir, Winchester image
114 Settlers Cir, Winchester $539,900

Welcome to 114 Settlers Circle, a spacious 5-bedroom, 3.5-bathroom home nestled on a quiet street in a prime east-side Winchester location. Classic curb appeal greets you...

  • 5 Beds
  • 4 Baths
  • Pioneer Heights SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
507 S Stewart St, Winchester image
507 S Stewart St, Winchester $629,000

If you've been waiting for a home that offers both character and modern convenience, this one deserves a close look. This all-brick, charming Cape Cod is located on a b...

  • 4 Beds
  • 3 Baths
  • City Of Winchester SubDv.
  • 22601 Zip Code
  • PENDING Status
416 Briarmont Dr, Winchester image
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
111 Alliance Ct, Winchester image
111 Alliance Ct, Winchester $550,000

Get ready for this elegant and a beautiful Colonial home in the sought-after Freedom Manor community. Built in 2021, this residence boasts a spacious 2,904 sq. ft. layout...

  • 4 Beds
  • 3 Baths
  • Freedom Manor SubDv.
  • 22602 Zip Code
  • ACTIVE Status
229 Taggart Dr, Winchester image
229 Taggart Dr, Winchester $817,252

None

  • 4 Beds
  • 3 Baths
  • Raven Pointe SubDv.
  • 22602 Zip Code
  • CLOSED 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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