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Start here

Homes for sale by state
Home buying tips
Before you start looking
The buying timeline

Afford it

Today's mortgage rates
Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

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Selling Options

What's my home worth?
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Get an instant cash offer
Buy before you sell

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What's worth fixing first
Find a seller's agent

3 beds New construction

Homes Under $600K in Winchester, VA

265 listings

Homes Under $600K in Winchester, VA

Homes Under $600K in Winchester, VA

24 of 265 Listings

Homes Under $600K in Winchester, VA

24 of 265 Listings

New72

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #0225245042

Active

$535,000

5 bd · 3 ba · 2,540 sqft

306 Longview Ave, Winchester, VA

Lauren C. Seaton · Charis Realty Group

$255,000

3 bd · 2 ba · 1,386 sqft

329 Fairview Ave, Winchester, VA

Verria Hairston · Open Door Brokerage, LLC

$289,000

2 bd · 2 ba · 1,580 sqft

606 Elk Trl, Winchester, VA

Philip Virgil Asper · Keller Williams Realty/Lee Beaver & Assoc.

$429,900

3 bd · 2 ba · 1,820 sqft

182 Front Dr, Winchester, VA

Susan Susan Raburn · Long & Foster Real Estate, Inc.

$420,000

3 bd · 4 ba · 2,250 sqft

105 Biscane Ct, Winchester, VA

Ismael Carino · MarketPlace REALTY

$339,900

3 bd · 2 ba · 1,570 sqft

121 Duwamish Trl, Winchester, VA

Harry T Hamilton · CENTURY 21 New Millennium

$299,900

3 bd · 1 ba · 2,228 sqft

1308 Commerce, Winchester, VA

Jeanne Mezzatesta · Colony Realty

$298,900

2 bd · 2 ba · 1,079 sqft

828 Woodland Ave, Winchester, VA

Sylvia R Stoneberger · Samson Properties

$399,900

4 bd · 3 ba · 1,932 sqft

111 Glendale Cir, Winchester, VA

Josh W Feltner · Realty ONE Group Old Towne

$374,990

3 bd · 3 ba · 2,000 sqft

118 Shuoner Ct, Winchester, VA

James Thomas · New Home Star Virginia, LLC

$399,999

4 bd · 4 ba · 2,250 sqft

Homesite 40 Shuoner Ct, Winchester, VA

James Thomas · New Home Star Virginia, LLC

$409,990

4 bd · 4 ba · 2,026 sqft

140 Swansong Pl, Winchester, VA

Elizabeth Ellis · Brookfield Mid-Atlantic Brokerage, LLC

$249,900

2 bd · 2 ba · 1,173 sqft

136-9 Brookland Ct #9, Winchester, VA

Daniel J Whitacre · Colony Realty

$299,900

3 bd · 2 ba · 1,648 sqft

1013 Orchard Hill Dr, Winchester, VA

Josh W Feltner · Realty ONE Group Old Towne

$419,900

3 bd · 4 ba · 2,424 sqft

138 Copeley Cir, Winchester, VA

Christopher R Hild · Realty FC

$385,000

3 bd · 2 ba · 2,193 sqft

119 Meadowbrooke Pl, Winchester, VA

Michele E Bonner · Keller Williams Realty

$376,990

3 bd · 4 ba · 1,806 sqft

Homesite 3 Monteith Dr, Winchester, VA

Brittany Newman · DRB Group Realty, LLC

$529,900

4 bd · 4 ba · 2,452 sqft

448 Canyon Rd, Winchester, VA

David K Spence · RE/MAX Roots

$225,000

2 bd · 1 ba · 0 sqft

132 White Pine Ln, Winchester, VA

Shannon N Willett · Long & Foster Real Estate, Inc.

$284,900

2 bd · 3 ba · 1,540 sqft

5 E Hart St, Winchester, VA

Leah Stafford Marabella · Realty ONE Group Old Towne

$305,500

3 bd · 2 ba · 1,350 sqft

3 S Euclid Ave, Winchester, VA

Tina Marie Jacobin · Main Street Realty

$299,900

4 bd · 3 ba · 1,680 sqft

1 E Hart St, Winchester, VA

Leah Stafford Marabella · Realty ONE Group Old Towne

$329,000

3 bd · 2 ba · 2,103 sqft

129 Rappahannock Trl, Winchester, VA

Alexandra H Chism · Loudoun Ridge Realty, LLC

Price Reduced34Active

$357,000

4 bd · 3 ba · 2,050 sqft

621 Patterson Ave, Winchester, VA

Leslie A. Webb · Long & Foster Real Estate, Inc.

1 2…12

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #0225245042

Listing data & MLS disclosures

Bright MLS: The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-10-03 03:06:02 UTC

Winchester, VA community profile

Population: 27,805
Median income: $66,091
Housing units: 12,270
People per sq. mi.: 128.8
Area: 215.8 sq. mi.

Source: HJN community data

Winchester housing market

September 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 77 sales · as of Sep 28, 2026

Homes that sold · County records, as of Sep 11, 2026

Median sale price: $386,773$287,500–$523,750 typical range
Price per sq. ft.: $255
Sales: 34
Paid in cash: 29.4%

Homes on the market · MLS, as of Sep 27, 2026–Sep 28, 2026

Median list price: $422,495
Homes for sale: 334
Median days on market: 28 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: -12.1%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026

Median home size: 1,620 sq. ft.