5 Bedroom Homes in Middlesboro, KY

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3 beds New construction With a pool

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6 Listings

Map

5 Bedroom Homes in Middlesboro, KY

6 Listings

33Active

6 listings

5 Bedroom Homes in Middlesboro, KY

Show Map

6 Listings

Map

5 Bedroom Homes in Middlesboro, KY

6 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

33Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

$475,000

5 bd · 3 ba · 2,542 sqft

2004 Twin Fawn Tr, Middlesboro, KY

Virginia Wilder · Century 21 Virginia Wilder Real Estate

Price Reduced35Active

$264,900

5 bd · 3 ba · 3,068 sqft

207 Arthur Heights, Middlesboro, KY

Sheila Durham · Coldwell Banker Bisceglia Realty & Auction Co

Price Reduced49Active

$299,900

5 bd · 2 ba · 2,664 sqft

926 Doncaster Avenue, Middlesboro, KY

Kevin Bisceglia · Coldwell Banker Bisceglia Realty & Auction Co

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced41Active

$120,000

5 bd · 4 ba · 2,844 sqft

215 S 21st Street, Middlesboro, KY

Megan Stanaford · Black Diamond Realty

Price Reduced16Active

$295,000

5 bd · 3 ba · 2,100 sqft

717 Highway 441, Middlesboro, KY

Megan Stanaford · Black Diamond Realty

13Active

$455,000

5 bd · 4 ba · 3,146 sqft

523 N 30th St, Middlesboro, KY

Kevin Carroll · Backwoods Realty & Development

Listing data & MLS disclosures

East Tennessee REALTORS MLS (Knoxville): IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Listing information ©2026 Knoxville Area AOR, Inc®. All Rights Reserved. Last Updated: 2026-09-14 23:50:37 UTC
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.

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.

Middlesboro, KY community profile

Area: 73.6 sq. mi.

Source: HJN community data

Explore Middlesboro homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Listing data & MLS disclosures

East Tennessee REALTORS MLS (Knoxville): IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Listing information ©2026 Knoxville Area AOR, Inc®. All Rights Reserved. Last Updated: 2026-09-14 23:50:37 UTC
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.

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.

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Middlesboro housing market

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

Middlesboro, KY community profile

Explore Middlesboro homes

Your local brokerage

Listing data & MLS disclosures

Middlesboro, KY community profile

Middlesboro housing market

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