Luxury Homes in Winchester, VA

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3 beds New construction With a pool

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15 Listings

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Luxury Homes in Winchester, VA

15 Listings

83Active

15 listings

Luxury Homes in Winchester, VA

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15 Listings

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Luxury Homes in Winchester, VA

15 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

83Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

$1,025,000

5 bd · 4 ba · 3,870 sqft

632 Stonymeade Dr, Winchester, VA

Katrina M Smith · Samson Properties

71Active

$1,170,000

5 bd · 6 ba · 3,846 sqft

854 Valley Mill Rd, Winchester, VA

Linden McLean · Samson Properties

97Active

$1,100,000

6 bd · 6 ba · 6,789 sqft

1030 Breckinridge Ln, Winchester, VA

Joleen Ritter Haymaker · Samson Properties

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

111Active

$2,599,000

4 bd · 6 ba · 4,753 sqft

144 Robinson Dr, Winchester, VA

Daniel J Whitacre · Colony Realty

107Active

$1,300,000

4 bd · 3 ba · 3,922 sqft

2216 Laurel Grove Rd, Winchester, VA

Jennifer Nichole Burn · Real Broker, LLC

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

Price Reduced55Active

$1,050,000

4 bd · 5 ba · 4,188 sqft

1015 Redbud Rd, Winchester, VA

Ryan Rice · Keller Williams Capital Properties

50Active

$1,179,000

4 bd · 5 ba · 4,970 sqft

1004 Heth Pl, Winchester, VA

Kathryn R Hallett · Long & Foster Real Estate, Inc.

59Active

$1,150,000

4 bd · 4 ba · 5,425 sqft

Lot 1 Keval Gyan Way, Winchester, VA

Jim Thomson · Realty ONE Group Old Towne

Price Reduced7Active

$1,025,000

3 bd · 3 ba · 2,947 sqft

Lot 60 Gravenstein Ct, Winchester, VA

Daniel A. Boris · Pearson Smith Realty, LLC

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: 2026-09-11 17:02:00 UTC

Winchester housing market

August 2026 · This period is still settling

Selling at 99.0% of asking price

Buyers here are paying below asking. MLS · 86 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 21, 2026

Median sale price: $388,990$289,250–$566,725 typical range
Price per sq. ft.: $250
Sales: 74
Paid in cash: 29.7%

Homes on the market · MLS, as of Aug 31, 2026

Median list price: $429,450
Homes for sale: 326
Median days on market: 37 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -2.5%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,620 sq. ft.

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: 2026-09-11 17:02:00 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

August 2026 · This period is still settling

Selling at 99.0% of asking price

Buyers here are paying below asking. MLS · 86 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 21, 2026

Median sale price: $388,990$289,250–$566,725 typical range
Price per sq. ft.: $250
Sales: 74
Paid in cash: 29.7%

Homes on the market · MLS, as of Aug 31, 2026

Median list price: $429,450
Homes for sale: 326
Median days on market: 37 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -2.5%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,620 sq. ft.

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Winchester housing market

Homes that sold · County records, as of Aug 21, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Winchester, VA community profile

Explore Winchester homes

Your local brokerage

Listing data & MLS disclosures

Winchester, VA community profile

Winchester housing market

Homes that sold · County records, as of Aug 21, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026