Winchester 12-month median sale price trend

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3 beds New construction With a pool

60 listings

3 Bedroom Homes in Winchester, KY

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24 of 60 Listings

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3 Bedroom Homes in Winchester, KY

24 of 60 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced37

Active

$249,000

3 bd · 2 ba · 1,386 sqft

33 Bon-Haven Avenue, Winchester, KY

Erika Beatty · Plum Tree Realty

New48Active

$1,500,000

3 bd · 2 ba · 1,860 sqft

4578 Combs Ferry Road, Winchester, KY

Joshua A Davis · The Agency

58Active

$309,900

3 bd · 2 ba · 2,138 sqft

118 College Street, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

Price Reduced50Active

$239,900

3 bd · 2 ba · 1,533 sqft

377 Crescent Avenue, Winchester, KY

Bill VanWinkle · Joyce Marcum Realty

33Active

$225,000

3 bd · 3 ba · 1,522 sqft

115 Quail Ridge Road, Winchester, KY

Michelle R Blackburn · RE/MAX Creative, Winchester

26Active

$249,900

3 bd · 2 ba · 1,492 sqft

317 Vanover Way, Winchester, KY

Austina Bruton · Rector Hayden Realtors

Price Reduced29Active

$275,000

3 bd · 2 ba · 1,500 sqft

103 Southern Court, Winchester, KY

Mila J Ensor · Ensor Real Estate, LLC

32Active

$275,000

3 bd · 2 ba · 1,444 sqft

204 Lindsey Court, Winchester, KY

Michelle R Blackburn · RE/MAX Creative, Winchester

29Active

$150,000

3 bd · 1 ba · 1,842 sqft

5 S Burns Avenue, Winchester, KY

Tirza Howard · The Howard Realty Co

64Active

$359,900

3 bd · 3 ba · 1,846 sqft

420 Calmes Boulevard, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

60Active

$259,900

3 bd · 1 ba · 2,249 sqft

11304 Irvine Road, Winchester, KY

Darrell Tackett · Dream Maker Realty, LLC

19Active

$350,000

3 bd · 3 ba · 2,592 sqft

135 E Broadway Street, Winchester, KY

Dale Hatton · Dream Maker Realty, LLC

Price Reduced31Active

$275,000

3 bd · 2 ba · 1,512 sqft

4305 Old Boonesboro Road, Winchester, KY

Brenda H Sipes · WEICHERT REALTORS - ABG Properties

25Active

$165,000

3 bd · 1 ba · 1,249 sqft

209 E Washington Street, Winchester, KY

Michelle R Blackburn · RE/MAX Creative, Winchester

Price Reduced24Active

$189,900

3 bd · 2 ba · 915 sqft

225 Buffalo Trace, Winchester, KY

Tyler I Back · The Brokerage

60Active

$235,000

3 bd · 1 ba · 1,272 sqft

119 Tower Lane, Winchester, KY

Shawna Wever · Wever Realty LLC

Price Reduced18Active

$355,000

3 bd · 2 ba · 1,990 sqft

11 Stoney Brook Drive 1, Winchester, KY

Garry H Milton · Milton and Associates Real Estate

Price Reduced30Active

$219,900

3 bd · 3 ba · 1,416 sqft

330 Vanover Way, Winchester, KY

Darrell Tackett · Dream Maker Realty, LLC

40Active

$244,000

3 bd · 2 ba · 1,692 sqft

54 Locust Drive, Winchester, KY

Natalie Avant · Berkshire Hathaway HomeServices Foster Realtors

26Active

$234,900

3 bd · 2 ba · 1,904 sqft

528 Estes Drive, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

65Active

$359,900

3 bd · 2 ba · 2,269 sqft

15 Moundale Avenue, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

Price Reduced24Active

$229,900

3 bd · 1 ba · 1,100 sqft

125 Kittison Drive, Winchester, KY

Kathryn M Cheuvront · Coldwell Banker McMahan

7Active

$365,900

3 bd · 2 ba · 1,558 sqft

204 Jett Drive, Winchester, KY

Mila J Ensor · Ensor Real Estate, LLC

Price Reduced23Active

$215,000

3 bd · 2 ba · 1,319 sqft

3 Nunnelly Court, Winchester, KY

Yasir Ahmed · Black Mountain Realty

Listing data & MLS disclosures

Imagine MLS (Bluegrass REALTORS): The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) Program of Bluegrass REALTORS®. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Real estate listings held by IDX brokerage firms other than Realty.com, are marked with the IDX logo or the IDX thumbnail logo and detailed information about them includes the name of the listing IDX brokers. Information deemed reliable but not guaranteed. Copyright © 2026 Bluegrass REALTORS®. All Rights Reserved.

Winchester housing market

July 2026 · This period is still settling

Selling at 99.6% of asking price

Sales here are closing essentially at asking. MLS · 50 sales · as of Jul 31, 2026

Homes that sold · County records, as of Jul 14, 2026

Median sale price: $241,250$196,175–$368,750 typical range
Price per sq. ft.: $160
Sales: 28
Paid in cash: 57.1%

Homes on the market · MLS, as of Jul 21, 2026

Median list price: $319,900
Homes for sale: 113

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

Year-over-year: -3.0%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026

Median home size: 1,544 sq. ft.

Winchester, KY community profile

Population: 19,583
Median income: $57,052
Housing units: 9,262
People per sq. mi.: 81.2
Area: 241.2 sq. mi.

Source: HJN community data

Explore Winchester homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Listing data & MLS disclosures

Imagine MLS (Bluegrass REALTORS): The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) Program of Bluegrass REALTORS®. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Real estate listings held by IDX brokerage firms other than Realty.com, are marked with the IDX logo or the IDX thumbnail logo and detailed information about them includes the name of the listing IDX brokers. Information deemed reliable but not guaranteed. Copyright © 2026 Bluegrass REALTORS®. All Rights Reserved.

Winchester, KY community profile

Population: 19,583
Median income: $57,052
Housing units: 9,262
People per sq. mi.: 81.2
Area: 241.2 sq. mi.

Source: HJN community data

Winchester housing market

July 2026 · This period is still settling

Selling at 99.6% of asking price

Sales here are closing essentially at asking. MLS · 50 sales · as of Jul 31, 2026

Homes that sold · County records, as of Jul 14, 2026

Median sale price: $241,250$196,175–$368,750 typical range
Price per sq. ft.: $160
Sales: 28
Paid in cash: 57.1%

Homes on the market · MLS, as of Jul 21, 2026

Median list price: $319,900
Homes for sale: 113

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

Year-over-year: -3.0%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026

Median home size: 1,544 sq. ft.

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Listing data & MLS disclosures

Winchester housing market

Homes that sold · County records, as of Jul 14, 2026

Homes on the market · MLS, as of Jul 21, 2026

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

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026

Winchester, KY community profile

Explore Winchester homes

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Winchester, KY community profile

Winchester housing market

Homes that sold · County records, as of Jul 14, 2026

Homes on the market · MLS, as of Jul 21, 2026

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

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026