Winchester, KY Homes for Sale

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Homes for Sale in Winchester, KY

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24 of 114 Listings

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Homes for Sale in Winchester, KY

24 of 114 Listings

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Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

New50Active
$249,900
3 bd · 1 ba · 1,250 sqft
215 Robyn Drive, Winchester, KY
Joshua Wood · Freedom Realty & Property Management
New23Active
$225,000
4 bd · 2 ba · 1,400 sqft
522 Acadia Way, Winchester, KY
Tyler I Back · The Brokerage
New30Active
$249,900
3 bd · 3 ba · 1,416 sqft
330 Vanover Way, Winchester, KY
Darrell Tackett · Dream Maker Realty, LLC

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

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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

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.

Safety & registry resources

Safety & registry resources

Safety & registry resources

Homes for Sale in Winchester, KY

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

Listing data & MLS disclosures

Your local brokerage

Your local brokerage

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