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Homes with a Pool in Middlesboro, KY

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3 listings

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3 beds New construction With a pool

Homes with a Pool in Middlesboro, KY

Homes with a Pool in Middlesboro, KY

3 Listings

Homes with a Pool in Middlesboro, KY

3 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #221881

12Active
$215,000
3 bd · 2 ba · 1,352 sqft
209 S 19th Street, Middlesboro, KY
Megan Stanaford · Black Diamond Realty
Price Reduced46Active
$315,000
5 bd · 2 ba · 2,664 sqft
926 Doncaster Avenue, Middlesboro, KY
Kevin Bisceglia · Coldwell Banker Bisceglia Realty & Auction Co
Price Reduced17Active
$230,000
3 bd · 2 ba · 1,320 sqft
156 Wellington Drive, Middlesboro, KY
Megan Stanaford · Black Diamond Realty

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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.

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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.

By feature

New construction
With a pool

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #221881

Middlesboro, KY community profile

Area: 73.6 sq. mi.

Source: HJN community data

Middlesboro housing market

August 2026 · This period is still settling

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,186 sq. ft.