Homes with a Pool in Winchester, KY

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3 beds New construction With a pool

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8 Listings

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Homes with a Pool in Winchester, KY

8 Listings

63Active

8 listings

Homes with a Pool in Winchester, KY

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8 Listings

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Homes with a Pool in Winchester, KY

8 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

63Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

$785,000

5 bd · 3 ba · 4,676 sqft

217 Wades Mill Road, Winchester, KY

Michelle R Blackburn · RE/MAX Creative, Winchester

50Active

$639,000

5 bd · 4 ba · 5,011 sqft

104 Teal Lane, Winchester, KY

Jenny B Ray · RE/MAX Elite Lexington

26Active

$234,900

3 bd · 2 ba · 1,904 sqft

528 Estes Drive, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

110Active

$724,889

4 bd · 5 ba · 4,255 sqft

132 Lana Lane, Winchester, KY

Rebecca J Harvey · Napier Realtors

82Active

$2,299,000

5 bd · 5 ba · 6,284 sqft

5039 Combs Ferry Road, Winchester, KY

Michael R Hilario · The Agency

Price Reduced120Active

$1,595,000

3 bd · 3 ba · 4,518 sqft

3166 Colby Road, Winchester, KY

Alyssa M Boley · Coldwell Banker McMahan

Price Reduced51Active

$413,000

3 bd · 3 ba · 2,288.72 sqft

20 Edgewood Drive, Winchester, KY

Libby VanMeter · Marshall Lane Real Estate - Lexington

68Active

$2,750,000

8 bd · 8 ba · 13,433 sqft

4664 Lexington Road, Winchester, KY

Adam Boardman · Block + Lot Real Estate

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

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.

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Registered offenders on the map

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 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

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