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3 beds New construction

5 Bedroom Homes in Winchester, VA

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12 of 36 Listings

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12 of 36 Listings

Price Reduced103Active

5 Bedroom Homes in Winchester, VA — Page 2

36 listings

5 Bedroom Homes in Winchester, VA

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12 of 36 Listings

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5 Bedroom Homes in Winchester, VA

12 of 36 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

Price Reduced103Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

$739,900

5 bd · 5 ba · 4,731 sqft

136 Cahille Dr, Winchester, VA

Victoria Davis · Century 21 Redwood Realty

Price Reduced53Active

$549,000

5 bd · 3 ba · 2,368 sqft

440 Canyon Rd, Winchester, VA

Tami Rene' Woerl · ERA Oakcrest Realty, Inc.

Price Reduced57Active

$784,900

5 bd · 5 ba · 5,310 sqft

118 Aulee Ct, Winchester, VA

George W Glaize Jr. · George W. Glaize, Jr., Inc. REALTOR

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

Price Reduced37Active

$377,000

5 bd · 3 ba · 2,387 sqft

303 Pembridge Dr, Winchester, VA

Rebecca Sims · Century 21 Redwood Realty

Price Reduced96Active

$439,999

5 bd · 3 ba · 1,887 sqft

419 Summit Ave, Winchester, VA

Waqas A Abbasi · Lifestyle Realty, LLC.

Price Reduced22Active

$599,950

5 bd · 2 ba · 1,948 sqft

446 N Loudoun St, Winchester, VA

Lawrence M. Lessin · Homes By Owner, Inc.

83Active

$2,200,000

5 bd · 5 ba · 5,884 sqft

2230 Jones Rd, Winchester, VA

Jennifer Sacco · RE/MAX Roots

Price Reduced83Active

$749,900

5 bd · 4 ba · 3,800 sqft

107 Launchris Dr, Winchester, VA

Laura D White · ERA Oakcrest Realty, Inc.

Price Reduced22Active

$620,990

5 bd · 4 ba · 2,967 sqft

219 Lehigh, Winchester, VA

Tim N Tieff · Keller Williams Realty

Price Reduced56Active

$849,900

5 bd · 3 ba · 3,057 sqft

Lot 10 Desant Cir, Winchester, VA

Jim Thomson · Realty ONE Group Old Towne

15Active

$435,000

5 bd · 4 ba · 2,014 sqft

122 Cherry Hill Cir, Winchester, VA

Jen L Moore · ERA Oakcrest Realty, Inc.

Price Reduced79Active

$850,000

5 bd · 6 ba · 6,256 sqft

150 Ewell Dr, Winchester, VA

Sherry Lee Santmyer · Hunt Country Sotheby's International Realty

1 2

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: 2026-10-09 22:04:55 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 · 91 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 23, 2026

Median sale price: $400,000$304,350–$606,625 typical range
Price per sq. ft.: $254
Sales: 87
Paid in cash: 36.8%

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: 33 days

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

Year-over-year: -5.4%

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.

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

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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.

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: 2026-10-09 22:04:55 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 · 91 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 23, 2026

Median sale price: $400,000$304,350–$606,625 typical range
Price per sq. ft.: $254
Sales: 87
Paid in cash: 36.8%

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: 33 days

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

Year-over-year: -5.4%

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.