Middlesboro, KY Homes for Sale

45 listings

Homes for Sale in Middlesboro, KY

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23 of 45 Listings

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Homes for Sale in Middlesboro, KY

23 of 45 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

22

Active

$285,000

3 bd · 2 ba · 2,400 sqft

406 N 25th St, Middlesboro, KY

Misti McGrath · Realty Group

24Active

$239,900

3 bd · 3 ba · 1,710 sqft

616 Balmoral Rd, Middlesboro, KY

Kevin Carroll · Backwoods Realty & Development

3Active

$175,500

3 bd · 1 ba · 1,066 sqft

114 E Rochester Avenue, Middlesboro, KY

Melanie Mullins · Backwoods Realty & Development

60Active

$625,000

4 bd · 5 ba · 5,426 sqft

2247 State Highway 188, Middlesboro, KY

Mike Hensley · REMAX PROFESSIONAL'S

18Active

$135,000

2 bd · 1 ba · 1,008 sqft

413 S 26th St, Middlesboro, KY

Brad Cawood · Backwoods Realty & Development

Price Reduced37Active

$227,000

5 bd · 4 ba · 3,195 sqft

717 S 27th Street, Middlesboro, KY

Barry Turner · RE/MAX LakeTime Realty London

32Active

$340,000

5 bd · 3 ba · 3,000 sqft

103 Sherwood Rd, Middlesboro, KY

Misti McGrath · Realty Group

19Active

$235,000

3 bd · 2 ba · 1,600 sqft

88 Tracy Ridge Rd, Middlesboro, KY

Mike Hensley · REMAX PROFESSIONAL'S

23Active

$315,000

4 bd · 3 ba · 2,488 sqft

1015 Old Wilson Lane, Middlesboro, KY

Misti McGrath · Realty Group

15Active

$145,900

3 bd · 2 ba · 1,386 sqft

810 W Rochester Ave, Middlesboro, KY

Nichole Goins · Heartland Real Estate, LLC

30Active

$175,000

2 bd · 1 ba · 700 sqft

1801 & 1801 1/2 Exeter Avenue, Middlesboro, KY

Victoria Allen · Century 21 Virginia Wilder Real Estate

17Active

$150,000

2 bd · 1 ba · 876 sqft

305 N 15th St, Middlesboro, KY

Mike Hensley · REMAX PROFESSIONAL'S

20Active

$199,000

3 bd · 1 ba · 1,480 sqft

1102 W Chester Ave, Middlesboro, KY

Kevin J Bisceglia · Coldwell Banker Bisceglia Real

16Active

$119,900

3 bd · 2 ba · 1,260 sqft

706 Ilchester Ave, Middlesboro, KY

Virginia Wilder · Century 21 Virginia Wilder Real Estate

15Active

$105,900

3 bd · 2 ba · 1,966 sqft

412 N 24th Street, Middlesboro, KY

Dawn Risner · Turn Key Realty

59Active

$575,000

3 bd · 2 ba · 2,016 sqft

2010 Twin Fawn Trail, Middlesboro, KY

Lisa Stacy-Gibbs · Backwoods Realty & Development

33Active

$475,000

5 bd · 3 ba · 2,542 sqft

2004 Twin Fawn Tr, Middlesboro, KY

Virginia Wilder · Century 21 Virginia Wilder Real Estate

Price Reduced47Active

$175,000

3 bd · 2 ba · 1,168 sqft

8 Castleford Way, Middlesboro, KY

Victoria Allen · Century 21 Virginia Wilder Real Estate

17Active

$129,000

3 bd · 1 ba · 1,404 sqft

708 W Chester Ave, Middlesboro, KY

Mike Hensley · REMAX PROFESSIONAL'S

22Active

$219,000

4 bd · 2 ba · 1,544 sqft

812 Worchester Ave, Middlesboro, KY

Misti McGrath · Realty Group

28Active

$229,000

3 bd · 2 ba · 1,400 sqft

800 S 28th St, Middlesboro, KY

Mike Hensley · REMAX PROFESSIONAL'S

15Active

$51,000

2 bd · 1 ba · 920 sqft

518 S 43rd St, Middlesboro, KY

Mike Hensley · REMAX PROFESSIONAL'S

Price Reduced35Active

$264,900

5 bd · 3 ba · 3,068 sqft

207 Arthur Heights, Middlesboro, KY

Sheila Durham · Coldwell Banker Bisceglia Realty & Auction Co

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: 2026-10-21 15:29:52 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

September 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 1, 2026

Median home size: 1,186 sq. ft.

Middlesboro, KY community profile

Area: 73.6 sq. mi.

Source: HJN community data

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Harlan (4)

Flat Lick (3)

Fourmile (3)

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: 2026-10-21 15:29:52 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

September 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 1, 2026

Median home size: 1,186 sq. ft.