Luxury Homes in Winchester, VA

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10 Listings

Map

10 Listings

40Active

10 listings

Luxury Homes in Winchester, VA

Show Map

10 Listings

Map

Luxury Homes in Winchester, VA

10 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

40Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

$2,200,000

5 bd · 6 ba · 6,342 sqft

261 Merrifield Ln, Winchester, VA

Lisa A Behr · Hunt Country Sotheby's International Realty

97Active

$1,100,000

6 bd · 6 ba · 6,789 sqft

1030 Breckinridge Ln, Winchester, VA

Joleen Ritter Haymaker · Samson Properties

111Active

$2,599,000

4 bd · 6 ba · 4,753 sqft

144 Robinson Dr, Winchester, VA

Daniel J Whitacre · Colony Realty

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

67Active

$3,500,000

3 bd · 4 ba · 4,421 sqft

450 Green Spring Rd, Winchester, VA

Phyllis Guthrie · Keller Williams Realty

76Active

$1,650,000

4 bd · 5 ba · 6,183 sqft

582 Miller Rd, Winchester, VA

Elizabeth Anne Cossette · ERA Oakcrest Realty, Inc.

83Active

$1,239,000

4 bd · 8 ba · 5,662 sqft

1022 Heth Pl, Winchester, VA

Cynthia Butler · Samson Properties

127Active

$3,175,000

6 bd · 7 ba · 8,593 sqft

730 Merrimans Ln, Winchester, VA

Justin Mistretta · Berkshire Hathaway HomeServices PenFed Realty

Price Reduced14Active

$4,900,000

1 bd · 1 ba · 44,000 sqft

1116 Woodstock Ln, Winchester, VA

Meridee A Powars · Link Realty Services LLC

83Active

$2,200,000

5 bd · 5 ba · 5,884 sqft

2230 Jones Rd, Winchester, VA

Jennifer Sacco · RE/MAX Roots

66Active

$1,150,000

4 bd · 4 ba · 5,425 sqft

Lot 1 Keval Gyan Way, Winchester, VA

Jim Thomson · Realty ONE Group Old Towne

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: 2026-09-28 23:47:53 UTC

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 · 90 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 18, 2026

Median sale price: $397,500$310,275–$536,250 typical range
Price per sq. ft.: $257
Sales: 50
Paid in cash: 32.0%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $422,495

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

Explore Winchester homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

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: 2026-09-28 23:47:53 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 · 90 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 18, 2026

Median sale price: $397,500$310,275–$536,250 typical range
Price per sq. ft.: $257
Sales: 50
Paid in cash: 32.0%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $422,495

Homes for sale

334

Median days on market

32 days

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

Year-over-year: -6.3%

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.