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Tollesboro, KY Homes for Sale | Realty.com

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Homes for Sale in Tollesboro, KY

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3 Listings

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3 Listings

Price Reduced55Active

Homes for Sale in Tollesboro, KY

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Homes for Sale in Tollesboro, KY

3 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced55Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

$299,900

3 bd · 2 ba · 1,553 sqft

444 May Hollow Road, Tollesboro, KY

Keith Cooper · CENTURY 21 Advantage Realty

Price Reduced24Active

$165,000

2 bd · 1 ba · 1,446 sqft

10861 Ky-57, Tollesboro, KY

Kelley Bane · CENTURY 21 Advantage Realty

55Active

$295,000

2 bd · 1 ba · 1,000 sqft

98 Bolton Lane, Tollesboro, KY

Kevin Boling · Kevin Boling Auction & Real Estate

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.

Tollesboro housing market

October 2026 · This period is still settling

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

Median home size: 1,280 sq. ft.

Tollesboro, KY community profile

Area: 57.7 sq. mi.

Source: HJN community data

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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.

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.

Tollesboro, KY community profile

Area: 57.7 sq. mi.

Source: HJN community data

Tollesboro housing market

October 2026 · This period is still settling

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

Median home size: 1,280 sq. ft.