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3 beds New construction With a pool

2 Bedroom Homes in Winchester, VA

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14 of 38 Listings

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14 of 38 Listings

Price Reduced47Active

2 Bedroom Homes in Winchester, VA — Page 2

38 listings

2 Bedroom Homes in Winchester, VA

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14 of 38 Listings

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2 Bedroom Homes in Winchester, VA

14 of 38 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

Price Reduced47Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

$459,990

2 bd · 2 ba · 1,564 sqft

107 Lawford Way, Winchester, VA

Elizabeth Ellis · Brookfield Mid-Atlantic Brokerage, LLC

Price Reduced11Active

$579,990

2 bd · 2 ba · 2,658 sqft

159 Williamson Rd, Winchester, VA

Greta Mirly Fernandez · New Home Star Virginia, LLC

Price Reduced37Active

$400,000

2 bd · 2 ba · 1,431 sqft

1826 Kershaw Ln, Winchester, VA

Roxanna D Grimes · RE/MAX Roots

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

Price Reduced28Active

$244,900

2 bd · 2 ba · 1,173 sqft

136-6 Brookland Ct #6, Winchester, VA

Jeffrey W Konrady · Realty ONE Group Old Towne

Price Reduced32Active

$239,000

2 bd · 2 ba · 1,257 sqft

157-6 Brookland Ter #6, Winchester, VA

Kimberly D Hurst · MarketPlace REALTY

Price Reduced25Active

$177,000

2 bd · 2 ba · 896 sqft

313 Avon Ct, Winchester, VA

Sophia Alam · AMN Realty, LLC.

Price Reduced40Active

$289,000

2 bd · 2 ba · 1,173 sqft

110 Brookland Ct #10, Winchester, VA

Traci J. Shoberg · Samson Properties

Price Reduced87Active

$790,000

2 bd · 3 ba · 3,446 sqft

210 Jackson Dr, Winchester, VA

Elizabeth D. McDonald · Dandridge Realty Group, LLC

Price Reduced29Active

$265,000

2 bd · 1 ba · 1,734 sqft

11 W Germain St, Winchester, VA

Magnolia L Halkowitz · ERA Oakcrest Realty, Inc.

Price Reduced37Active

$349,900

2 bd · 2 ba · 1,219 sqft

1856 Melvor Ln, Winchester, VA

Natasha Roberts · Realty ONE Group Old Towne

Price Reduced27Active

$244,900

2 bd · 2 ba · 1,173 sqft

136-8 Brookland Ct #8, Winchester, VA

Amy A Longerbeam · Re/Max Roots

Price Reduced32Active

$399,900

2 bd · 2 ba · 1,419 sqft

118 1/2 E Cork St, Winchester, VA

Janet M. Flaherty · Keller Williams Realty

30Active

$379,900

2 bd · 2 ba · 1,186 sqft

711 E Cork St, Winchester, VA

Marco Novillo · Spring Hill Real Estate, LLC.

Price Reduced45Active

$260,000

2 bd · 1 ba · 997 sqft

108 Martin Dr, Winchester, VA

Heloisa P Amar · Samson Properties

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: 2026-09-21 21:44:59 UTC

Winchester housing market

August 2026

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 31, 2026

Median sale price: $382,500$283,750–$562,175 typical range
Price per sq. ft.: $234
Sales: 112
Paid in cash: 30.4%

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: -3.8%

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

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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: 2026-09-21 21:44:59 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

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 31, 2026

Median sale price: $382,500$283,750–$562,175 typical range
Price per sq. ft.: $234
Sales: 112
Paid in cash: 30.4%

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: -3.8%

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.