Winchester, VA homes for sale & real estate

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107 E Monmouth St, Winchester, VA 22601
107 E Monmouth St, Winchester, VA 22601
107 E Monmouth St, Winchester, VA 22601
ABOUT THIS HOME
Winchester, VA Homes for Sale
Price Reduction!! Charming Historic Home in Downtown Winchester – Move-In Ready! If you love timeless craftsmanship—think original wood floors, custom built-ins, and vintage doors—but still want the ease of modern living, this beautifully updated downtown Winchester home is calling your name! From the moment you step onto the inviting covered porch and through the front door, you’ll feel right at home. Warm wood tones complement freshly painted crisp white walls, creating a perfect blend of cozy and fresh. The living room showcases a gorgeous staircase, beautifully refinished white oak floors, and an eye-catching wall of custom built-in shelving—ideal for your

$344,900

3 beds1.5 baths1,178 sq ft

107 E Monmouth St, Winchester, VA 22601

1,464 sq ft lot • Very walkable

(540) 662-0323

1503 Valley Ave, Winchester, VA 22601
1503 Valley Ave, Winchester, VA 22601
1503 Valley Ave, Winchester, VA 22601
ABOUT THIS HOME
Winchester, VA Homes for Sale
Active again, Buyer's loan fell through. Charming Colonial located in the heart of Winchester. Only a few minutes walk to the Old Town Mall. This home features 5 bedrooms and 3 1/2 baths with 4 levels. There's a Primary Bedroom and Bathroom located on the main level with doors that open onto the back deck. The family room boasts hardwood floors and a wood burning fireplace. The kitchen is spacious with a formal dinning room adjoining. Enjoy evenings on the large back deck with a fenced yard for the kids or fur babies in your life.

$425,000

5 beds3.5 baths3,333 sq ft

1503 Valley Ave, Winchester, VA 22601

8,494 sq ft lot • Somewhat walkable

(540) 662-3484

NEW CONSTRUCTION

120 Magpie Ln, Winchester, VA 22603
120 Magpie Ln, Winchester, VA 22603
120 Magpie Ln, Winchester, VA 22603

$669,409

3 beds3 baths3,200 sq ft

120 Magpie Ln, Winchester, VA 22603

Car-dependent

Listing provided by Zillow

109 Aulee Ct, Winchester, VA 22602
109 Aulee Ct, Winchester, VA 22602
109 Aulee Ct, Winchester, VA 22602
ABOUT THIS HOME
Winchester, VA Homes for Sale
If you’re looking for a home that truly checks all the boxes, space, setting, style, and room to grow, this is the one you’ve been waiting for. Perfectly perched on a quiet cul-de-sac in the sought-after Twin Lakes Overlook neighborhood, this Toll Brothers built beauty offers more than curb appeal. It boasts a premium lot backing to the lake, with tranquil views that just might make you forget you’re so close to town. Inside, the heart of the home is a showstopper kitchen with rich wood cabinetry, single wall oven, built in microwave, a gas cooktop, and gleaming granite counters. Whether you’re cooking up a storm or simply rinsing dishes, the woodsy view might have y

$660,000

4 beds2.5 baths3,165 sq ft

109 Aulee Ct, Winchester, VA 22602

0.26 acre lot • $85 HOA • 2 garage spots

(703) 430-9008

103 Fenwick Ct, Winchester, VA 22602
103 Fenwick Ct, Winchester, VA 22602
103 Fenwick Ct, Winchester, VA 22602
ABOUT THIS HOME
Winchester, VA Homes for Sale
5 bedroom, 3.5 bathroom detached home! It's located in a neighborhood on a quiet cul-de-sac and convenient to route 7 and Route 81 for commuters. Large private 6 car new paved driveway -so plenty of off-street parking! Whole length of house rear deck for entertaining! Featuring rare main level bedroom with attached full bathroom. Plus, primary bedroom/primary full bathroom and 3 more bedrooms plus another full bathroom upstairs! Half bath, eat-in kitchen, plus separate dining room, living room, and laundry on main level. Also has level rear exterior access and a rear French door that opens to dining room. Many updates and upgrades, like HVAC, appliances, lighting and much more throughout

$445,900

4 beds3.5 baths1,776 sq ft

103 Fenwick Ct, Winchester, VA 22602

9,147 sq ft lot • $7 HOA • Car-dependent

(703) 378-8810

Property at 113 Pangborne Ct, Winchester, VA 22602, 4 beds, 4.5 baths

$674,900

4 beds4.5 baths4,395 sq ft

113 Pangborne Ct, Winchester, VA 22602

(540) 773-8475

Property at 109 Boone Ct, Winchester, VA 22602, 3 beds, 2.5 baths

$398,985

3 beds2.5 baths1,989 sq ft

109 Boone Ct, Winchester, VA 22602

(703) 967-2073

Property at 105 Boone Ct, Winchester, VA 22602, 3 beds, 2.5 baths

$395,985

3 beds2.5 baths1,989 sq ft

105 Boone Ct, Winchester, VA 22602

(703) 967-2073

Property at 117 Boone, Winchester, VA 22602, 3 beds, 2.5 baths

$399,480

3 beds2.5 baths1,989 sq ft

117 Boone, Winchester, VA 22602

(703) 967-2073

Property at 540 Monticello St, Winchester, VA 22601, 9 beds, 4 baths

$615,000

9 beds4 baths4,396 sq ft

540 Monticello St, Winchester, VA 22601

(540) 450-2747

Property at Lot 60 Gravenstein Ct, Winchester, VA 22602, 3 beds, 3 baths

$1,045,000

3 beds3 baths2,875 sq ft

Lot 60 Gravenstein Ct, Winchester, VA 22602

(571) 386-1075

Property at 111 Sovereign Ct, Winchester, VA 22602, 4 beds, 3.5 baths

$559,000

4 beds3.5 baths2,884 sq ft

111 Sovereign Ct, Winchester, VA 22602

(540) 665-0360

Property at 129 Jalapa Trl, Winchester, VA 22602, 3 beds, 2 baths

$540,000

3 beds2 baths2,400 sq ft

129 Jalapa Trl, Winchester, VA 22602

(703) 790-1850

Property at 1460 Pitcock Ln, Winchester, VA 22602, 4 beds, 4 baths

$1,125,000

4 beds4 baths4,949 sq ft

1460 Pitcock Ln, Winchester, VA 22602

(540) 686-7362

Property at 2431 Cedar Creek Grade, Winchester, VA 22602, 3 beds, 1.5 baths

$400,000

3 beds1.5 baths1,036 sq ft

2431 Cedar Creek Grade, Winchester, VA 22602

(540) 667-1130

Property at 700 Miller Rd, Winchester, VA 22602, 5 beds, 6 baths

$1,074,900

5 beds6 baths5,058 sq ft

700 Miller Rd, Winchester, VA 22602

(540) 662-0323

Property at 320 Highland Ave, Winchester, VA 22601, 3 beds, 2 baths

$299,900

3 beds2 baths1,313 sq ft

320 Highland Ave, Winchester, VA 22601

(540) 348-4911

Property at 112 Fairway Dr, Winchester, VA 22602, 3 beds, 1 bath

$379,000

3 beds1 bath1,200 sq ft

112 Fairway Dr, Winchester, VA 22602

(540) 686-7362

Property at 3980 Middle Rd, Winchester, VA 22602, 4 beds, 3.5 baths

$765,000

4 beds3.5 baths3,504 sq ft

3980 Middle Rd, Winchester, VA 22602

(540) 348-4911

Property at 400 Great Mountain Ln, Winchester, VA 22602, 2 beds, 2 baths

$799,000

2 beds2 baths1,600 sq ft

400 Great Mountain Ln, Winchester, VA 22602

(540) 686-7362

Property at 355 Fishel Rd, Winchester, VA 22602, 4 beds, 3.5 baths

$669,000

4 beds3.5 baths3,008 sq ft

355 Fishel Rd, Winchester, VA 22602

(540) 686-7362

Property at 224 Lauck Dr, Winchester, VA 22603, 3 beds, 2.5 baths

$525,000

3 beds2.5 baths2,328 sq ft

224 Lauck Dr, Winchester, VA 22603

(540) 662-4500

Property at 109 Gilmore Trl, Winchester, VA 22602, 3 beds, 3 baths

$389,900

3 beds3 baths1,850 sq ft

109 Gilmore Trl, Winchester, VA 22602

(540) 773-8475

Property at 525 Pheasant Dr, Winchester, VA 22602, 3 beds, 2.5 baths

$349,900

3 beds2.5 baths1,362 sq ft

525 Pheasant Dr, Winchester, VA 22602

(540) 665-0700

Property at 126 Armstrong Pl, Winchester, VA 22602, 4 beds, 3 baths

$399,000

4 beds3 baths1,617 sq ft

126 Armstrong Pl, Winchester, VA 22602

(540) 662-0323

Property at 291 Lake Serene Dr, Winchester, VA 22603, 4 beds, 4.5 baths

$1,485,000

4 beds4.5 baths5,754 sq ft

291 Lake Serene Dr, Winchester, VA 22603

(540) 348-4911

Property at 1380 Magruder Ct, Winchester, VA 22601, 4 beds, 2.5 baths

$564,000

4 beds2.5 baths3,263 sq ft

1380 Magruder Ct, Winchester, VA 22601

(540) 665-0360

Property at 908 Cedar Creek Grade, Winchester, VA 22601, 12 beds

$2,098,000

12 beds— baths7,190 sq ft

908 Cedar Creek Grade, Winchester, VA 22601

(540) 450-0142

Property at 113 Shockey Cir, Winchester, VA 22602, 4 beds, 3 baths

$939,000

4 beds3 baths3,363 sq ft

113 Shockey Cir, Winchester, VA 22602

(540) 662-5794

Property at 230 W Boscawen St, Winchester, VA 22601

$649,000

— beds— baths7,650 sq ft

230 W Boscawen St, Winchester, VA 22601

(540) 662-9937

Property at 103 Oak Ridge Ln, Winchester, VA 22602, 5 beds, 6 baths

$1,499,000

5 beds6 baths9,447 sq ft

103 Oak Ridge Ln, Winchester, VA 22602

(540) 662-0323

Property at DELMAR II Plan, Winchester, VA 22602, 3 beds, 2.5 baths

$364,990

3 beds2.5 baths1,509 sq ft

DELMAR II Plan, Winchester, VA 22602

Listing provided by Zillow

Property at ADAMS Plan, Winchester, VA 22602, 4 beds, 3.5 baths

$429,990

4 beds3.5 baths1,889 sq ft

ADAMS Plan, Winchester, VA 22602

Listing provided by Zillow

Property at DELMAR Plan, Winchester, VA 22602, 3 beds, 2.5 baths

$364,990

3 beds2.5 baths1,500 sq ft

DELMAR Plan, Winchester, VA 22602

Listing provided by Zillow

Property at 3336 Hunting Ridge Rd, Winchester, VA 22603, 4 beds, 2.5 baths

$574,900

4 beds2.5 baths3,036 sq ft

3336 Hunting Ridge Rd, Winchester, VA 22603

(703) 669-0099

Property at 146 Broomsedge Ln, Winchester, VA 22602, 3 beds, 2.5 baths

$679,000

3 beds2.5 baths1,800 sq ft

146 Broomsedge Ln, Winchester, VA 22602

(540) 450-0142

Property at 482 Diamondback Ln, Winchester, VA 22602, 3 beds, 2 baths

$385,000

3 beds2 baths880 sq ft

482 Diamondback Ln, Winchester, VA 22602

(540) 686-7362

Property at 127 S Euclid Ave, Winchester, VA 22601, 3 beds, 2 baths

$312,000

3 beds2 baths1,120 sq ft

127 S Euclid Ave, Winchester, VA 22601

(703) 264-0000

Property at Grouse Dr, Winchester, VA 22602, 3 beds, 2 baths

$310,000

3 beds2 baths1,333 sq ft

Grouse Dr, Winchester, VA 22602

(540) 348-4911

Property at 205 Eastside, Winchester, VA 22602, 4 beds, 3.5 baths

$319,000

4 beds3.5 baths1,840 sq ft

205 Eastside, Winchester, VA 22602

(540) 662-4500

Property at 531 Washout Ln, Winchester, VA 22603, 6 beds, 4.5 baths

$519,900

6 beds4.5 baths3,612 sq ft

531 Washout Ln, Winchester, VA 22603

(540) 665-0700

Viewing page 6 of 8

Average home prices near Winchester, VA

Cities

Ranson homes for sale
$314,370
Shawneeland homes for sale
$384,900
Lake Holiday homes for sale
$507,450
Charles Town homes for sale
$409,000
Strasburg homes for sale
$349,950
Gore homes for sale
Martinsburg homes for sale
$322,450
Front Royal homes for sale
$395,000
Berryville homes for sale
$439,250
Boyce homes for sale
$582,400
Capon Bridge homes for sale
Apple Mountain Lake homes for sale
$526,325
Stephens City homes for sale
$400,500
Middletown homes for sale
$497,000
Inwood homes for sale
$319,000

Neighborhoods
Zip Codes

Historic District homes for sale
$474,500
Old Town homes for sale
Kernstown homes for sale
$455,000

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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