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Browse All Winchester VA Single Family Properties for Sale

120 Comanche Trl, Winchester image
120 Comanche Trl, Winchester $349,999

Welcome to 120 Comanche Trail in Shawneeland! Offering over 1,800 finished sq. ft., this 4-bedroom, 2-bath home combines thoughtful updates with plenty of space inside an...

  • 4 Beds
  • 2 Baths
  • Shawneeland SubDv.
  • 22602 Zip Code
  • ACTIVE Status
109 Julee Dr, Winchester image
109 Julee Dr, Winchester $479,900

This lovingly maintained two-owner Colonial has been thoughtfully cared for and improved since 1994, offering the character of an established home with many of the update...

  • 4 Beds
  • 3 Baths
  • Mill Race Estates SubDv.
  • 22602 Zip Code
  • COMING SOON Status
991 Front Royal Pike, Winchester image
991 Front Royal Pike, Winchester $459,900

Enjoy easy one-level living in this well-maintained ranch home conveniently located in Winchester, close to commuter routes, shopping, restaurants, and everyday amenities...

  • 3 Beds
  • 2 Baths
  • Bufflick Heights SubDv.
  • 22602 Zip Code
  • ACTIVE Status
805 S Kent St, Winchester image
805 S Kent St, Winchester $325,000

Welcome home! This beautifully maintained two-level home offers 4 bedrooms and 2 full bathrooms in the heart of Winchester. Warm and inviting, the home features a comfort...

  • 4 Beds
  • 2 Baths
  • City Of Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE Status
100 Winns Cir, Winchester image
100 Winns Cir, Winchester $552,000

Beautifully remodeled Colonial in Pioneer Heights. Designed with primary suite; ideal home office configuration. All large bedrooms, large hardwood living room with stone...

  • 4 Beds
  • 3 Baths
  • Pioneer Heights SubDv.
  • 22602 Zip Code
  • ACTIVE Status
178 Payne Rd, Winchester image
178 Payne Rd, Winchester $395,600

You are going to love this spacious, one-level ranch located on a half-acre lot in a great location! Here are some of the key features and recent updates: - Huge 20x26 fa...

  • 4 Beds
  • 2 Baths
  • Russell's Paradise SubDv.
  • 22603 Zip Code
  • ACTIVE Status
223 Asbury Rd, Winchester image
223 Asbury Rd, Winchester $549,900

“Pioneer Heights Colonial” - Welcome to this beautifully maintained colonial in the desirable Pioneer Heights neighborhood, ideally situated just off Route 7 for easy com...

  • 5 Beds
  • 4 Baths
  • Pioneer Heights SubDv.
  • 22602 Zip Code
  • ACTIVE Status
1847 Melvor Ln, Winchester image
1847 Melvor Ln, Winchester $355,000

Come see what makes Willow Lawn, a 55+ community, such a desirable place to call home! This inviting one owner Winchester home offers a comfortable blend of charm, funct...

  • 2 Beds
  • 2 Baths
  • Willow Lawn Cottages SubDv.
  • 22601 Zip Code
  • ACTIVE Status
265 Mcdonald Rd, Winchester image
265 Mcdonald Rd, Winchester $375,000

265 McDonald Rd is a 1-story Winchester home built in 1974 with a lower level and connected outdoor spaces. The kitchen includes cabinet storage, a preparation counter, a...

  • 3 Beds
  • 2 Baths
  • Canter Estates L-313 SubDv.
  • 22602 Zip Code
  • ACTIVE Status
322 E Piccadilly, Winchester image
322 E Piccadilly, Winchester $409,000

Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless ch...

  • 4 Beds
  • 1 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
131 Country Club Cir, Winchester image
131 Country Club Cir, Winchester $435,000

No HOA in the heart of Winchester! This charming brick rancher features three bedrooms, two baths, tall ceilings, fresh paint, hardwood floors, and a fireplace on the ma...

  • 3 Beds
  • 2 Baths
  • A Melvin Lewis SubDv.
  • 22602 Zip Code
  • COMING SOON Status
148 Doe Trl, Winchester image
148 Doe Trl, Winchester $317,265

Welcome to this charming three-bedroom, two-bathroom raised ranch nestled on a quiet, tree-lined street in one of the area’s most close-knit neighborhoods. Full of charac...

  • 3 Beds
  • 2 Baths
  • Shawneeland SubDv.
  • 22602 Zip Code
  • COMING SOON Status
100 Gooseberry Dr, Winchester image
100 Gooseberry Dr, Winchester $515,000

Welcome to 100 Gooseberry Drive, located in Winchester's established Cross Creek Village community! This meticulously maintained brick rancher offers true main-level livi...

  • 2 Beds
  • 3 Baths
  • Cross Creek Village SubDv.
  • 22602 Zip Code
  • ACTIVE Status
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
300 Pembridge Dr, Winchester image
300 Pembridge Dr, Winchester $439,000

Welcome to this newly renovated and thoughtfully designed 5-bedroom, 3-full-bath home offering exceptional flexibility for modern living or rental income. Featuring two ...

  • 5 Beds
  • 3 Baths
  • Pembridge Heights 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
302 Canyon Rd, Winchester image
302 Canyon Rd, Winchester $525,000

Welcome to a home designed for the way you live, with room to work, entertain, relax, and make the space your own. Located in Senseny Glen, this 4-bedroom, 3.5-bath, thre...

  • 4 Beds
  • 4 Baths
  • Senseny Glen SubDv.
  • 22602 Zip Code
  • ACTIVE Status
310 Goldenrod Rd, Winchester image
310 Goldenrod Rd, Winchester $430,000

This is the one you have been waiting for!! Well cared for home, one story living in desirable Briarwood Estates...east side location convenient to commuter routes, shopp...

  • 3 Beds
  • 2 Baths
  • Briarwood Estates SubDv.
  • 22602 Zip Code
  • ACTIVE Status
128 Alliance Ct, Winchester image
128 Alliance Ct, Winchester $550,000

Welcome to 128 Alliance Court, a beautifully maintained, move-in-ready home built in 2021 and offering over 3,200 finished square feet across three spacious levels. The o...

  • 4 Beds
  • 4 Baths
  • Freedom Manor SubDv.
  • 22602 Zip Code
  • ACTIVE Status
111 Haven Ter, Winchester image
111 Haven Ter, Winchester $300,000

Charming 3-Bedroom Rambler on a Spacious Lot! Welcome to 111 Haven Terrace, a conveniently located 3-bedroom, 1-bath rambler situated on approximately 0.26 acres. This si...

  • 3 Beds
  • 1 Baths
  • Heritage Hills SubDv.
  • 22602 Zip Code
  • ACTIVE Status
214 Molden Dr, Winchester image
214 Molden Dr, Winchester $230,000

Investor opportunity in Winchester! This 2-bedroom, 1-bath home offers 1,112 finished square feet above grade, plus a full unfinished basement with additional space for s...

  • 2 Beds
  • 1 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
900 Enfield Dr, Winchester image
900 Enfield Dr, Winchester $380,000

Nestled in the serene Wilde Acres community, this exquisite Colonial-style residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevate...

  • 4 Beds
  • 3 Baths
  • Wilde Acres SubDv.
  • 22602 Zip Code
  • ACTIVE Status
1048 Woodland Ave, Winchester image
1048 Woodland Ave, Winchester $350,000

Nestled in a charming neighborhood, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 1954, this brick beauty exudes timeless a...

  • 3 Beds
  • 2 Baths
  • None Available 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
1412 S Loudoun St, Winchester image
1412 S Loudoun St, Winchester $429,000

Awesome Interior Photo's Coming Soon! Step inside this tastefully renovated brick ranch and feel instantly at home. Offering three comfortable bedrooms and two full baths...

  • 3 Beds
  • 2 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
1960 Siler Rd, Winchester image
1960 Siler Rd, Winchester $499,900

Looking for one-level living with acreage, a detached workshop/garage, RV/camper parking, and no HOA? Welcome to 1960 Siler Road, a custom-built ranch situated on 5 fence...

  • 3 Beds
  • 2 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE Status
127 Mountain View Rd, Winchester image
127 Mountain View Rd, Winchester $549,900

Fully Renovated Winchester-Area Retreat on 3.24 Acres with Two Garages! Rarely does a property come along that offers this combination of extensive renovations, usable ac...

  • 4 Beds
  • 3 Baths
  • Indian Lake SubDv.
  • 22603 Zip Code
  • ACTIVE Status
305 Raccoon Dr, Winchester image
305 Raccoon Dr, Winchester $175,000

Cozy 1-bedroom, 1-bathroom cabin located on a level, nicely shaded lot, ready for your enjoyment. Offering the perfect combination of rustic character, comfort, and natur...

  • 1 Beds
  • 1 Baths
  • Wilde Acres SubDv.
  • 22602 Zip Code
  • ACTIVE Status
236 Delmas Trl Trl, Winchester image
236 Delmas Trl Trl, Winchester $984,900

Nestled in the prestigious Midland Heights community, this exquisite Colonial-style residence offers a harmonious blend of luxury and comfort, set against a breathtaking ...

  • 4 Beds
  • 4 Baths
  • Midland Heights SubDv.
  • 22602 Zip Code
  • COMING SOON 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
159 Aspen Trl Trl, Winchester image
159 Aspen Trl Trl, Winchester $295,000 ▲

**Investor & Fixer-Upper Special Endless Potential on Nearly 1 Acre!** Calling all visionaries, weekend warriors, and Airbnb hosts! This secluded retreat in Shawneeland i...

  • 2 Beds
  • 3 Baths
  • Shawneeland SubDv.
  • 22602 Zip Code
  • ACTIVE Status
700 Tomahawk Trl, Winchester image
700 Tomahawk Trl, Winchester $287,000

Located in the desirable Shawneeland community, this freshly updated three bedroom home is situated on a great corner lot with scenic views and plenty of possibilities to...

  • 3 Beds
  • 1 Baths
  • Shawneeland SubDv.
  • 22602 Zip Code
  • ACTIVE Status
108 Williamson Rd, Winchester image
108 Williamson Rd, Winchester $385,000

Coming soon in Winchester! Welcome to this beautifully maintained 3-bedroom, 2-bath brick rambler in a convenient location. This move-in-ready home offers comfortable one...

  • 3 Beds
  • 2 Baths
  • Senseny Heights SubDv.
  • 22602 Zip Code
  • COMING SOON Status
308 Fawn Dr, Winchester image
308 Fawn Dr, Winchester $334,000

Nestled in the charming Wilde Acres community, this delightful Colonial home offers a perfect blend of comfort and style. Built in 2009, this residence features 3 spacio...

  • 3 Beds
  • 3 Baths
  • Wilde Acres SubDv.
  • 22602 Zip Code
  • ACTIVE Status
452 Valley Mill Rd, Winchester image
452 Valley Mill Rd, Winchester $299,900

SOLD AS IS, CASH ONLY! Investor special on this great home that is on .55 Acre lot (2 lots make this up). Outbuildings, wood floors, fireplace, 3 generous size bedrooms,...

  • 3 Beds
  • 1 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • PENDING Status
531 Cedar Grove Rd, Winchester image
531 Cedar Grove Rd, Winchester $675,000

Discover a rare opportunity to own a piece of Frederick County history with this unique farmette property offering approximately 9.79 acres, a charming farmhouse, extensi...

  • 2 Beds
  • 1 Baths
  • Cedar Grove Road SubDv.
  • 22603 Zip Code
  • ACTIVE Status
174 Williamson Rd, Winchester image
174 Williamson Rd, Winchester $759,900

This spectacular, move-in-ready home shows like a professional model, showcasing exquisite designer touches, custom window treatments (included), and premium finishes thr...

  • 5 Beds
  • 5 Baths
  • Abrams Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
2519 Hockman Ave, Winchester image
2519 Hockman Ave, Winchester $308,000

This charming cottage in the heart of the City of Winchester is poised for a remarkable transformation with major renovations slated for 2026. Built in 1950, this detache...

  • 2 Beds
  • 2 Baths
  • City Of Winchester SubDv.
  • 22601 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
124 Dinkle Dr, Winchester image
124 Dinkle Dr, Winchester $345,000

Amazing and ready for new owner. New kitchen, new baths, newly refinished hardwood floors, new appliances, new HVAC. Come and check out this great 3 bedroom/2 bath home...

  • 3 Beds
  • 2 Baths
  • Shannon Hills SubDv.
  • 22601 Zip Code
  • ACTIVE UNDER CONTRACT Status
1414 S Braddock St, Winchester image
1414 S Braddock St, Winchester $379,900

This charming Cape Cod home in Winchester City, built in 1950 and beautifully renovated in 2026, offers a perfect blend of classic character and modern convenience. With ...

  • 2 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • ACTIVE 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
938 Wayne Dr, Winchester image
938 Wayne Dr, Winchester $499,900

Beautifully maintained and updated home located in popular area close to Medical Center, schools , services and amenities and with easy access to commuter thoroughfares. ...

  • 4 Beds
  • 3 Baths
  • Meadow Branch South SubDv.
  • 22601 Zip Code
  • PENDING Status
584 Mcdonald Rd, Winchester image
584 Mcdonald Rd, Winchester $575,000 ▼

Like NEW built in 2020 on 2.49 acres. partly wooded, partly cleared. Walkout basement with windows ready for finishing, with rough-in for bath! Add a 4th bedroom - Sept...

  • 3 Beds
  • 2 Baths
  • The View SubDv.
  • 22602 Zip Code
  • ACTIVE Status
632 Stonymeade Dr, Winchester image
632 Stonymeade Dr, Winchester $1,025,000

Opportunities in Stonymeade don't come along often—and once you arrive, it's easy to understand why. Tucked away on 3.2 beautifully maintained acres with a wooded perimet...

  • 5 Beds
  • 4 Baths
  • Stonymeade SubDv.
  • 22602 Zip Code
  • ACTIVE Status
352 Woodchuck Ln, Winchester image
352 Woodchuck Ln, Winchester $299,900

Welcome to 352 Woodchuck Lane in Winchester, VA! This charming 3-bedroom, 2-bath home sits on .92 flat acres, offering plenty of room to create the small homestead you’ve...

  • 3 Beds
  • 2 Baths
  • Cather SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
102 Forest Valley Rd, Winchester image
102 Forest Valley Rd, Winchester $597,000 ▼

Welcome to this beautifully maintained home in the established Stonebrook Farms community, perfectly situated on a quiet cul-de-sac and surrounded by mature trees and lan...

  • 5 Beds
  • 3 Baths
  • Stonebrook Farms SubDv.
  • 22602 Zip Code
  • ACTIVE Status
1125 Conway St, Winchester image
1125 Conway St, Winchester $250,000

Welcome to 1125 Conway Ave, a charming bungalow in Winchester City that's move-in ready and full of character! This cozy 2-bedroom, 1-bath home features beautiful hardwoo...

  • 2 Beds
  • 1 Baths
  • Shannon Hill SubDv.
  • 22601 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
  • ACTIVE Status
182 Mason St, Winchester image
182 Mason St, Winchester $349,990

Welcome to this adorable 3-bedroom, 2-full-bath cottage rancher home located on the East side of Winchester with NO HOA! Offering approximately 1,024 finished square feet...

  • 3 Beds
  • 2 Baths
  • C M Lockhart SubDv.
  • 22602 Zip Code
  • ACTIVE Status

Winchester Single Family Real Estate

Our website features the best real estate search for single family 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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