Homes Under $300K in Winchester, VA

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3 beds New construction With a pool

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24 of 39 Listings

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Homes Under $300K in Winchester, VA

24 of 39 Listings

27Active

39 listings

Homes Under $300K in Winchester, VA

Hide Map

24 of 39 Listings

Map

Homes Under $300K in Winchester, VA

24 of 39 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

27Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

$220,000

2 bd · 1 ba · 560 sqft

610 Puma Trl, Winchester, VA

James Podoley · EXP Realty, LLC

25Active

$299,500

3 bd · 2 ba · 1,138 sqft

621 Watson Ave, Winchester, VA

Caleb Christen Fowler · Samson Properties

23Active

$260,000

2 bd · 1 ba · 900 sqft

107 Little River Dr, Winchester, VA

Erin M Kavanagh · EXP Realty, LLC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

2Active

$300,000

3 bd · 1 ba · 1,008 sqft

111 Haven Ter, Winchester, VA

Erin M Kavanagh · EXP Realty, LLC

54Active

$295,000

2 bd · 3 ba · 2,148 sqft

159 Aspen Trl, Winchester, VA

Kimberly C Baggett · EXP Realty, LLC

4Active

$290,000

2 bd · 3 ba · 1,868 sqft

323 Copperfield Ln, Winchester, VA

Rebecca Sims · Century 21 Redwood Realty

15Active

$287,000

3 bd · 1 ba · 1,104 sqft

700 Tomahawk Trl, Winchester, VA

Stacy Priddy · Berkshire Hathaway HomeServices PenFed Realty

25Active

$250,000

2 bd · 1 ba · 870 sqft

1125 Conway St, Winchester, VA

Curtis W Siever · NextHome Realty Select

42Active

$175,000

1 bd · 1 ba · 384 sqft

305 Raccoon Dr, Winchester, VA

William Fitzgerald Dixon · Dandridge Realty Group, LLC

17Active

$240,000

2 bd · 1 ba · 997 sqft

187 Valley Mill Rd, Winchester, VA

Heloisa P Amar · Samson Properties

8Active

$289,900

2 bd · 2 ba · 1,024 sqft

2640 Limestone Ct, Winchester, VA

Meridee A Powars · Link Realty Services LLC

Price Reduced13Active

$274,000

3 bd · 2 ba · 1,161 sqft

519 Virginia Ave, Winchester, VA

Katherine Smalts Solenberger · Colony Realty

27Active

$239,000

2 bd · 1 ba · 1,014 sqft

1024 Front Royal Pike, Winchester, VA

Daniel J Whitacre · Colony Realty

31Active

$279,000

2 bd · 1 ba · 1,577 sqft

611 Fawn Dr, Winchester, VA

Kathrin Donovan · Keller Williams Realty

37Active

$280,000

3 bd · 1 ba · 1,058 sqft

2810 N Frederick Pike, Winchester, VA

Jonathan C. Fleming III · Weichert Realtors - Blue Ribbon

57Active

$115,000

0 bd · 0 ba · 528 sqft

403 Stag Trl, Winchester, VA

Christopher W Roszko · Colony Realty

Price Reduced24Active

$275,000

2 bd · 2 ba · 1,200 sqft

207 Banbury Ter, Winchester, VA

Kristen Kerns · Roberts Realty Group, LLC

Price Reduced17Active

$289,000

3 bd · 1 ba · 960 sqft

1314 S Braddock St, Winchester, VA

Verria Hairston · Open Door Brokerage, LLC

Price Reduced18Active

$250,000

1 bd · 1 ba · 740 sqft

135 S Kent St #202, Winchester, VA

Sharon Farinholt · Realty ONE Group Old Towne

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

18Active

$290,000

3 bd · 2 ba · 1,232 sqft

132 Geronimo Trl, Winchester, VA

Shane Price · Long & Foster Real Estate, Inc.

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

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: 2026-09-16 03:14:29 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 26, 2026

Median sale price: $387,990$285,000–$541,000 typical range
Price per sq. ft.: $236
Sales: 85
Paid in cash: 31.8%

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: 2026-09-16 03:14:29 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 26, 2026

Median sale price: $387,990$285,000–$541,000 typical range
Price per sq. ft.: $236
Sales: 85
Paid in cash: 31.8%

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.

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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 26, 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 26, 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