Winchester, VA homes for sale & real estate

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NEW 2 MINS AGO

222 Liberty Ave, Winchester, VA 22601
222 Liberty Ave, Winchester, VA 22601
222 Liberty Ave, Winchester, VA 22601
ABOUT THIS HOME
Winchester, VA Homes for Sale
Investor, builder, or renovation enthusiast—this is the opportunity you’ve been waiting for! This 2-bedroom, 1-bath home is a true fixer-upper with serious potential. Whether you’re looking to take on a full gut renovation or tear it down and start from scratch, this property is a blank canvas ready for your vision. With 882 square feet of interior space and sitting on a generously sized lot, there's room to reimagine, expand, or build new entirely. Located in a transitioning neighborhood that’s seeing steady growth and redevelopment, this is an ideal location for a smart long-term investment. With rising property values and increased demand in the area, the upside h

$90,000

2 beds1 bath882 sq ft

222 Liberty Ave, Winchester, VA 22601

Somewhat walkable

COMING SOON

114 Nassau Dr, Winchester, VA 22602
ABOUT THIS HOME
Winchester, VA Homes for Sale
Beautifully updated 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, brick patio, outdoor fireplace, and a storage shed. The spacious primary suite includes a large walk-in closet. The finished basement is ideal for entertaining, featuring a full bath and wet bar. Recent upgrades include new siding and roof (2022), new HVAC systems, composite deck, sump pump, attic insulation (2021), water heater (2021), water softener (2021), and an irrigation system. This home also features a radon mitigation system and Vivint/Blink security systems for peace of mind. Professionally lan

$629,900

4 beds3.5 baths3,829 sq ft

114 Nassau Dr, Winchester, VA 22602

0.28 acre lot • $42 HOA • 2 garage spots

(540) 686-7362

NEW 3 HRS AGO

815 Woodland Ave, Winchester, VA 22601
815 Woodland Ave, Winchester, VA 22601
815 Woodland Ave, Winchester, VA 22601
ABOUT THIS HOME
Winchester, VA Homes for Sale
TWO HOMES FOR THE PRICE OF ONE! Welcome to a unique investment or multi-generational living opportunity with two separate homes on one property! Front House (815 Woodland Ave): On-street parking - 1400 Fin Sq Ft This charming 1920s Craftsman-style Cape Cod offers 3 bedrooms and 1 full bathroom, featuring a welcoming large front porch, original hardwood floors, updated electrical systems, and dual-zoned heating & air conditioning. Original built-ins in the kitchen and upstairs hallway, as well as an unfinished basement perfect for storage or future finishing. Rear House (815 ½ Woodland Ave): Driveway - off-street parking - 747 Fin Sq Ft Tucked behind the main home, this delightf

$425,000

5 beds— baths1,298 sq ft

815 Woodland Ave, Winchester, VA 22601

9,017 sq ft lot • Somewhat walkable

(540) 686-7362

COMING SOON

208 Opossum Trl, Winchester, VA 22602
208 Opossum Trl, Winchester, VA 22602
208 Opossum Trl, Winchester, VA 22602
ABOUT THIS HOME
Winchester, VA Homes for Sale
Welcome to this charming two-story home nestled in a peaceful country setting, surrounded by mature trees, vibrant flower beds, and a majestic weeping willow that graces the front yard. The cozy and convenient main-level primary suite features a spacious double-door walk-in closet, and the open floor plan offers the perfect blend of comfort and function—flooded with natural light and ideal for both everyday living and entertaining. Upstairs, you’ll find two generously sized bedrooms, each with its own closet and serene views of the treetops. Step outside to a lovely patio and attached sidewalk, where you can host gatherings or unwind while soaking in the tranquil surroundings. R

$255,000

3 beds1 bath946 sq ft

208 Opossum Trl, Winchester, VA 22602

0.52 acre lot • $66 HOA • Car-dependent

(540) 722-9300

NEW 6 HRS AGO

629 Laurelwood Cir, Winchester, VA 22601
629 Laurelwood Cir, Winchester, VA 22601
629 Laurelwood Cir, Winchester, VA 22601
ABOUT THIS HOME
Winchester, VA Homes for Sale
Fall Move-In Poplar Available at Laurelwood Commons! This home features 3 bedrooms, 2.5 baths, 1,442 sq. ft. , upgraded kitchen with white cabinets, quartz counters, island, LVP throughout the main level & more! Plus, enjoy all closing costs paid with use of NVR Mortgage! * . Learn more!

$345,950

3 beds2.5 baths1,442 sq ft

629 Laurelwood Cir, Winchester, VA 22601

Garage • Car-dependent

Listing provided by Zillow

Property at 101 Etnam St, Winchester, VA 22602, 3 beds, 2.5 baths

$385,000

3 beds2.5 baths1,870 sq ft

101 Etnam St, Winchester, VA 22602

(703) 754-1770

Property at 109 Senseny Glen Dr, Winchester, VA 22602, 3 beds, 2.5 baths

$434,900

3 beds2.5 baths2,047 sq ft

109 Senseny Glen Dr, Winchester, VA 22602

(703) 582-1321

Property at 101 Rosewood Ln, Winchester, VA 22602, 2 beds, 2 baths

$390,000

2 beds2 baths1,692 sq ft

101 Rosewood Ln, Winchester, VA 22602

(540) 686-7362

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

$355,000

3 beds2.5 baths1,719 sq ft

415 Quail Dr, Winchester, VA 22602

(540) 662-3484

Property at 128 Parkside Dr, Winchester, VA 22602, 3 beds, 1.5 baths

$249,942

3 beds1.5 baths1,200 sq ft

128 Parkside Dr, Winchester, VA 22602

(703) 858-9108

Property at 108 Meadowbrooke Pl, Winchester, VA 22602, 4 beds, 2 baths

$379,900

4 beds2 baths1,768 sq ft

108 Meadowbrooke Pl, Winchester, VA 22602

(540) 722-9300

Property at 566 N Loudoun St, Winchester, VA 22601, 4 beds, 2 baths

$299,000

4 beds2 baths2,058 sq ft

566 N Loudoun St, Winchester, VA 22601

(540) 662-0323

Property at 101 Dutton Pl, Winchester, VA 22601, 3 beds, 2 baths

$565,000

3 beds2 baths2,517 sq ft

101 Dutton Pl, Winchester, VA 22601

(540) 662-9937

Property at 325 Windsor Ln, Winchester, VA 22602, 5 beds, 4.5 baths

$1,300,000

5 beds4.5 baths5,117 sq ft

325 Windsor Ln, Winchester, VA 22602

(540) 635-8000

Property at 110 Webster Ct, Winchester, VA 22603, 3 beds, 2.5 baths

$556,464

3 beds2.5 baths2,263 sq ft

110 Webster Ct, Winchester, VA 22603

Listing provided by Zillow

Property at 108 Webster Ct, Winchester, VA 22603, 3 beds, 2.5 baths

$551,724

3 beds2.5 baths2,263 sq ft

108 Webster Ct, Winchester, VA 22603

Listing provided by Zillow

Property at 122 Deer Trl, Winchester, VA 22602, 3 beds, 3 baths

$389,900

3 beds3 baths1,910 sq ft

122 Deer Trl, Winchester, VA 22602

(540) 773-8475

Property at 341 Warm Springs Rd, Winchester, VA 22603, 4 beds, 2.5 baths

$537,900

4 beds2.5 baths1,958 sq ft

341 Warm Springs Rd, Winchester, VA 22603

(703) 522-0500

Property at 143 Harvest Ridge Dr, Winchester, VA 22601, 3 beds, 2 baths

$575,000

3 beds2 baths2,233 sq ft

143 Harvest Ridge Dr, Winchester, VA 22601

(540) 450-2747

Property at 103 Woodbury Ct, Winchester, VA 22602, 3 beds, 3 baths

$445,000

3 beds3 baths2,268 sq ft

103 Woodbury Ct, Winchester, VA 22602

(304) 582-1852

Property at 214 Cavalry Dr, Winchester, VA 22602, 4 beds, 2.5 baths

$439,900

4 beds2.5 baths2,543 sq ft

214 Cavalry Dr, Winchester, VA 22602

(540) 450-2747

Property at 718 Chelsea Dr, Winchester, VA 22601, 3 beds, 2 baths

$589,900

3 beds2 baths2,271 sq ft

718 Chelsea Dr, Winchester, VA 22601

(540) 662-0400

Property at 115 Etnam St, Winchester, VA 22602, 4 beds, 2.5 baths

$410,000

4 beds2.5 baths1,800 sq ft

115 Etnam St, Winchester, VA 22602

(540) 686-7362

Property at 601 Fall Run Ln, Winchester, VA 22602, 3 beds, 2 baths

$870,000

3 beds2 baths2,175 sq ft

601 Fall Run Ln, Winchester, VA 22602

(703) 595-2100

Property at 114 Scented Rose Way, Winchester, VA 22601, 4 beds, 3 baths

$616,990

4 beds3 baths2,712 sq ft

114 Scented Rose Way, Winchester, VA 22601

(804) 510-9139

Property at 111 Scented Rose Way, Winchester, VA 22601, 4 beds, 3 baths

$636,990

4 beds3 baths2,865 sq ft

111 Scented Rose Way, Winchester, VA 22601

(804) 510-9139

Property at 115 Scented Rose Way, Winchester, VA 22601, 4 beds, 3 baths

$626,990

4 beds3 baths2,818 sq ft

115 Scented Rose Way, Winchester, VA 22601

(804) 510-9139

Property at 254 Whistlewood Ln, Winchester, VA 22602, 5 beds, 6.5 baths

$939,950

5 beds6.5 baths4,301 sq ft

254 Whistlewood Ln, Winchester, VA 22602

(571) 386-1075

Property at 242 Footstone Ln, Winchester, VA 22603, 1 bed, 1 bath

$350,000

1 bed1 bath1,348 sq ft

242 Footstone Ln, Winchester, VA 22603

(540) 635-8000

Property at 216 Monticello Sq, Winchester, VA 22602, 3 beds, 2.5 baths

$350,000

3 beds2.5 baths2,436 sq ft

216 Monticello Sq, Winchester, VA 22602

(540) 662-3484

Property at 125 Alliance Ct, Winchester, VA 22602, 4 beds, 3.5 baths

$460,000

4 beds3.5 baths1,676 sq ft

125 Alliance Ct, Winchester, VA 22602

(540) 665-0360

Property at 122 Poe Dr, Winchester, VA 22602, 6 beds, 3.5 baths

$718,999

6 beds3.5 baths4,365 sq ft

122 Poe Dr, Winchester, VA 22602

(703) 680-2631

Property at 117 Wagtail Ln, Winchester, VA 22603, 3 beds, 2.5 baths

$496,129

3 beds2.5 baths2,195 sq ft

117 Wagtail Ln, Winchester, VA 22603

(571) 386-1075

Property at 115 Wagtail Ln, Winchester, VA 22603, 3 beds, 2.5 baths

$513,579

3 beds2.5 baths2,181 sq ft

115 Wagtail Ln, Winchester, VA 22603

(571) 386-1075

Property at 103 Wagtail Ln, Winchester, VA 22603, 4 beds, 3 baths

$734,610

4 beds3 baths3,567 sq ft

103 Wagtail Ln, Winchester, VA 22603

(571) 386-1075

Property at 220 Flanagan Dr, Winchester, VA 22602, 5 beds, 4.5 baths

$679,900

5 beds4.5 baths4,755 sq ft

220 Flanagan Dr, Winchester, VA 22602

(703) 319-3344

Property at 112 Hites St, Winchester, VA 22602, 4 beds, 3.5 baths

$445,000

4 beds3.5 baths2,892 sq ft

112 Hites St, Winchester, VA 22602

(571) 386-2272

Property at 109 Lake Sever Dr, Winchester, VA 22603, 3 beds, 2 baths

$325,000

3 beds2 baths1,232 sq ft

109 Lake Sever Dr, Winchester, VA 22603

(304) 229-9359

Property at 2623 Middle Rd, Winchester, VA 22601, 3 beds, 2.5 baths

$515,000

3 beds2.5 baths1,984 sq ft

2623 Middle Rd, Winchester, VA 22601

(540) 662-4500

Property at 410 Valley View Dr, Winchester, VA 22603, 5 beds, 4.5 baths

$1,195,000

5 beds4.5 baths5,426 sq ft

410 Valley View Dr, Winchester, VA 22603

(540) 450-2747

Property at 107 Fay St, Winchester, VA 22602, 3 beds, 1.5 baths

$379,999

3 beds1.5 baths1,560 sq ft

107 Fay St, Winchester, VA 22602

(540) 686-7362

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Average home prices near Winchester, VA

Cities

Ranson homes for sale
$339,950
Shawneeland homes for sale
$389,900
Lake Holiday homes for sale
$472,500
Charles Town homes for sale
$409,500
Strasburg homes for sale
$369,900
Gore homes for sale
$360,000
Martinsburg homes for sale
$300,000
Front Royal homes for sale
$415,000
Berryville homes for sale
$525,000
Boyce homes for sale
$782,450
Capon Bridge homes for sale
$379,900
Apple Mountain Lake homes for sale
$526,325
Stephens City homes for sale
$427,450
Middletown homes for sale
$479,999
Inwood homes for sale
$319,000

Neighborhoods
Zip Codes

Historic District homes for sale
$434,000
Old Town homes for sale
$369,500
Kernstown homes for sale
$450,000

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)

$399,500

-0.37% YoY | Jun 2025

1 year
3 year
5 year

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

Location

Data

Jun 2025

Growth

% YoY

Winchester, VA

$399,500

-0.37%

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