Winchester, VA homes for sale & real estate

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NEW 9 HRS AGO

ABOUT THIS HOME
Winchester, VA Homes for Sale
Completely renovated and move-in ready, this charming 3 bedroom, 1 bath home is ideally located just minutes from downtown Winchester's shops, dining, and entertainment. Inside, you'll find beautiful hardwood floors throughout and a brand new kitchen and fully renovated bathroom. Major updates to the home include a new roof, new windows, new HVAC system, new hot water heater and new electric all installed in 2025. Outside there is an oversized garage with ample storage and a spacious backyard with privacy. A rare opportunity to own a turnkey home in a prime location - schedule your showing today!

$320,000

3 beds1 bath1,134 sq ft

27 Jackson Ave, Winchester, VA 22601

New kitchen • New hot water heater • New roof

(540) 665-0360

ABOUT THIS HOME
Winchester, VA Homes for Sale
Spacious 5BR/3BA with Primary BR on main floor. This Cape Cod is located on 5 level acres with mountain views along historic Apple Pie Ridge Road. Built in 2001, this property offers a comfortable layout filled with natural light and peaceful rural surroundings just minutes from Winchester. Enjoy open space, privacy, and scenic Shenandoah Valley vistas while remaining conveniently close to shopping, dining, schools, and major commuter routes. A perfect blend of country living and everyday convenience with no HOA!

$715,000

5 beds3 baths2,354 sq ft

3915 Apple Pie Ridge Rd, Winchester, VA 22603

Level acres • Open space • Natural light

(540) 773-8475

ABOUT THIS HOME
Winchester, VA Homes for Sale
Exceptional opportunity to enjoy one-level, low maintenance living in this all-brick rancher nestled in beautifully maintained neighborhood across from the Medical Center. Finished basement provides additional bedroom and full bath for guests or family. One-owner home with recently updated HVAC and tankless water heater. Level basement walkout opens to back yard backed by trees.

$569,900

4 beds3 baths2,644 sq ft

436 Westside Station Dr, Winchester, VA 22601

2 garage spots • Built 1996 • Listed 3 days

(540) 348-4911

ABOUT THIS HOME
Winchester, VA Homes for Sale
* * * VA assumable loan at an incredible 3.375%! * * * Welcome to this stunning 4-bedroom, 3-bath luxury residence offering over 4,000 square feet of thoughtfully designed living space, including 586 square feet of customizable unfinished area. From the moment you step inside, the grand entryway impresses, leading either upstairs to a bright, expansive loft or downstairs to a spacious family room. The main level features an open-concept design that seamlessly connects the living room—highlighted by a sleek recessed in-wall electric fireplace—to the chef’s kitchen, complete with quartz countertops, a natural gas range, a large island with sink, and a walk-in pantry. Th

$684,900

4 beds2.5 baths4,092 sq ft

128 Raven Oaks Dr, Winchester, VA 22602

Open-concept design • Quartz countertops • Grand entryway

(540) 662-3484

ABOUT THIS HOME
Winchester, VA Homes for Sale
New roof and decking make this Orchard Hill town home a great buy—Hardwood floors, a fireplace in the family room, along with built-in cabinets and bookshelves: full walk-out basement and large yard.

$375,900

3 beds2.5 baths1,728 sq ft

2116 Stoneleigh Dr, Winchester, VA 22601

Bookshelves • Built-in cabinets • Walk-out basement

(540) 662-0323

Property at 403 Tudor Dr, Winchester, VA 22603, 2 beds, 1.5 baths

$269,900

2 beds1.5 baths1,200 sq ft

403 Tudor Dr, Winchester, VA 22603

(540) 722-0477

Property at 125 Lakota St, Winchester, VA 22602, 4 beds, 3.5 baths

$399,990

4 beds3.5 baths1,889 sq ft

125 Lakota St, Winchester, VA 22602

(804) 510-9139

Property at 179 Munsee Cir, Winchester, VA 22602, 4 beds, 3.5 baths

$414,990

4 beds3.5 baths1,889 sq ft

179 Munsee Cir, Winchester, VA 22602

(804) 510-9139

Property at 718 Panther Dr, Winchester, VA 22602, 3 beds, 2.5 baths

$350,000

3 beds2.5 baths1,512 sq ft

718 Panther Dr, Winchester, VA 22602

(540) 227-4416

Property at 521 Hidden Valley Ln, Winchester, VA 22603, 3 beds, 3 baths

$659,000

3 beds3 baths2,973 sq ft

521 Hidden Valley Ln, Winchester, VA 22603

(540) 686-7362

Property at 229 Soldiers Rest Ln, Winchester, VA 22602, 6 beds, 4.5 baths

$925,000

6 beds4.5 baths3,725 sq ft

229 Soldiers Rest Ln, Winchester, VA 22602

(540) 227-4416

Property at 123 Old Bethel Ln, Winchester, VA 22603, 3 beds, 2.5 baths

$175,000

3 beds2.5 baths2,090 sq ft

123 Old Bethel Ln, Winchester, VA 22603

(540) 341-1000

Property at 534 N Kent St, Winchester, VA 22601, 3 beds, 1.5 baths

$300,000

3 beds1.5 baths1,152 sq ft

534 N Kent St, Winchester, VA 22601

(540) 348-4911

Property at 113 Williamson Rd, Winchester, VA 22602, 3 beds, 2.5 baths

$434,900

3 beds2.5 baths2,547 sq ft

113 Williamson Rd, Winchester, VA 22602

(540) 686-7362

Property at 218 Flanagan Dr, Winchester, VA 22602, 4 beds, 4.5 baths

$655,000

4 beds4.5 baths4,354 sq ft

218 Flanagan Dr, Winchester, VA 22602

(681) 252-3002

Property at 313 Beaver Trl, Winchester, VA 22602, 3 beds, 2.5 baths

$379,000

3 beds2.5 baths1,631 sq ft

313 Beaver Trl, Winchester, VA 22602

(703) 818-0111

Property at 115 Alpine Meadow Rd, Winchester, VA 22602, 3 beds, 3.5 baths

$450,000

3 beds3.5 baths2,486 sq ft

115 Alpine Meadow Rd, Winchester, VA 22602

(540) 450-2747

Property at 199 Meeting House Dr, Winchester, VA 22602, 5 beds, 4.5 baths

$849,900

5 beds4.5 baths3,767 sq ft

199 Meeting House Dr, Winchester, VA 22602

(540) 259-4090

Property at 309 W Tevis St, Winchester, VA 22601, 3 beds, 2 baths

$349,900

3 beds2 baths1,419 sq ft

309 W Tevis St, Winchester, VA 22601

(877) 328-4400

Property at 126 N Euclid Ave, Winchester, VA 22601, 4 beds, 3 baths

$370,000

4 beds3 baths1,868 sq ft

126 N Euclid Ave, Winchester, VA 22601

(855) 450-0442

Property at 461 Skylar Lanes Way, Winchester, VA 22603, 6 beds, 4.5 baths

$699,900

6 beds4.5 baths4,124 sq ft

461 Skylar Lanes Way, Winchester, VA 22603

(540) 348-4911

Property at 420 Russelcroft Rd, Winchester, VA 22601, 3 beds, 2 baths

$399,900

3 beds2 baths1,580 sq ft

420 Russelcroft Rd, Winchester, VA 22601

(540) 773-8475

Property at 133 Meade Dr, Winchester, VA 22602, 3 beds, 3 baths

$400,000

3 beds3 baths2,550 sq ft

133 Meade Dr, Winchester, VA 22602

(540) 686-7362

Property at 415 Quail Dr, Winchester, VA 22602, 3 beds, 2.5 baths

$359,000

3 beds2.5 baths1,719 sq ft

415 Quail Dr, Winchester, VA 22602

(540) 686-7362

Property at 17 E Leicester St, Winchester, VA 22601, 4 beds, 2 baths

$430,000

4 beds2 baths2,100 sq ft

17 E Leicester St, Winchester, VA 22601

(540) 450-2747

Property at 3339 N Frederick Pike, Winchester, VA 22603, 5 beds, 2 baths

$329,000

5 beds2 baths3,378 sq ft

3339 N Frederick Pike, Winchester, VA 22603

(540) 635-8000

Property at Homesite 199 Malbec, Winchester, VA 22602, 4 beds, 2.5 baths

$585,990

4 beds2.5 baths2,682 sq ft

Homesite 199 Malbec, Winchester, VA 22602

(703) 967-2073

Property at 236 Bentley Ave, Winchester, VA 22602, 3 beds, 2 baths

$449,000

3 beds2 baths1,791 sq ft

236 Bentley Ave, Winchester, VA 22602

(540) 662-0323

Property at 407 Jefferson St, Winchester, VA 22601, 3 beds, 2 baths

$476,500

3 beds2 baths2,568 sq ft

407 Jefferson St, Winchester, VA 22601

(540) 662-9937

Property at 405 1/2 Elm St, Winchester, VA 22601, 3 beds, 2 baths

$299,990

3 beds2 baths1,152 sq ft

405 1/2 Elm St, Winchester, VA 22601

(703) 787-7903

Property at 1619 Tomahawk Trl, Winchester, VA 22602, 3 beds, 3 baths

$349,900

3 beds3 baths1,850 sq ft

1619 Tomahawk Trl, Winchester, VA 22602

(540) 773-8475

Property at 204 Shenandoah Ave, Winchester, VA 22601, 2 beds, 1 bath

$265,000

2 beds1 bath882 sq ft

204 Shenandoah Ave, Winchester, VA 22601

(703) 669-0099

Property at 687 Woodland Ave, Winchester, VA 22601, 4 beds, 4 baths

$564,900

4 beds4 baths2,489 sq ft

687 Woodland Ave, Winchester, VA 22601

(703) 533-8660

Property at 24 Williamson Rd, Winchester, VA 22602, 3 beds, 2 baths

$598,990

3 beds2 baths3,056 sq ft

24 Williamson Rd, Winchester, VA 22602

(703) 967-2073

Property at 127 Shirley St, Winchester, VA 22601, 4 beds, 2 baths

$365,000

4 beds2 baths1,780 sq ft

127 Shirley St, Winchester, VA 22601

(540) 665-0360

Property at 681 Hillman Dr, Winchester, VA 22601, 5 beds, 4 baths

$600,000

5 beds4 baths3,550 sq ft

681 Hillman Dr, Winchester, VA 22601

(703) 679-1700

Property at 109 Glen Ridge Dr, Winchester, VA 22602, 3 beds, 3 baths

$439,900

3 beds3 baths1,935 sq ft

109 Glen Ridge Dr, Winchester, VA 22602

(540) 665-0700

Property at 711 E Cork St, Winchester, VA 22601, 2 beds, 1.5 baths

$384,900

2 beds1.5 baths1,186 sq ft

711 E Cork St, Winchester, VA 22601

(703) 891-4520

Property at 318 E Piccadilly St, Winchester, VA 22601, 4 beds, 1.5 baths

$399,000

4 beds1.5 baths1,953 sq ft

318 E Piccadilly St, Winchester, VA 22601

(540) 662-0323

Property at Homesite 25 Williamson Rd, Winchester, VA 22602, 3 beds, 2 baths

$549,990

3 beds2 baths1,658 sq ft

Homesite 25 Williamson Rd, Winchester, VA 22602

(703) 967-2073

Property at 111 Meadowview Ct, Winchester, VA 22602, 3 beds, 1.5 baths

$356,000

3 beds1.5 baths1,164 sq ft

111 Meadowview Ct, Winchester, VA 22602

(540) 665-0360

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Average home prices near Winchester, VA

Cities

Ranson homes for sale
$388,490
Shawneeland homes for sale
$376,950
Lake Holiday homes for sale
$426,500
Charles Town homes for sale
$374,990
Strasburg homes for sale
$299,900
Shenandoah Farms homes for sale
$425,000
Gore homes for sale
$274,900
Martinsburg homes for sale
$285,000
Front Royal homes for sale
$374,950
Berryville homes for sale
$649,000
Boyce homes for sale
$450,000
Capon Bridge homes for sale
$404,999
Stephens City homes for sale
$417,945
Middletown homes for sale
$453,000
Inwood homes for sale
$291,500

Neighborhoods
Zip Codes

Historic District homes for sale
$449,900
Kernstown homes for sale
$434,990

Winchester, VA real estate trends

All Home Types trends in Winchester, VA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$377,500

+0.7% YoY | Nov 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Nov 2025

Growth

% YoY

Winchester, VA

$377,500

+0.7%

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