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Middlesboro, KY Homes for Sale — Page 2 | Realty.com

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Homes for Sale in Middlesboro, KY

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18 of 45 Listings

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18 of 45 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

12Active
$215,000
3 bd · 2 ba · 1,352 sqft
209 S 19th Street, Middlesboro, KY
Megan Stanaford · Black Diamond Realty
23Active
$199,000
3 bd · 1 ba · 1,480 sqft
1102 W Chester Avenue, Middlesboro, KY
David Gambrell · Coldwell Banker Bisceglia Realty & Auction Co
1Active
$595,000
7 bd · 5 ba · 6,276 sqft
142 Edgewood Rd, Middlesboro, KY
Lisa Stacy-Gibbs · Backwoods Realty & Development

1Active
$279,000
3 bd · 3 ba · 2,210 sqft
515 Englewood Road, Middlesboro, KY
Kevin Carroll · Backwoods Realty & Development
45Active
$279,000
4 bd · 2 ba · 2,032 sqft
400 Gloucester Ave, Middlesboro, KY
Sheila Durham · Coldwell Banker Bisceglia Real
26Active
$199,900
4 bd · 2 ba · 1,612 sqft
140 Wellington Drive, Middlesboro, KY
Janice Pratt · Fathom Realty TN LLC
34Active
$359,500
3 bd · 2 ba · 2,000 sqft
2909 W Cumberland Ave, Middlesboro, KY
Lisa Stacy-Gibbs · Backwoods Realty & Development
19Active
$135,000
2 bd · 2 ba · 1,400 sqft
125 Cawood Lane, Middlesboro, KY
Misti McGrath · Realty Group
Price Reduced30Active
$200,000
3 bd · 2 ba · 2,154 sqft
116 Edgewood Road, Middlesboro, KY
Megan Stanaford · Black Diamond Realty
34Active
$149,000
4 bd · 2 ba · 1,440 sqft
64 Dunlap Hollow Rd, Middlesboro, KY
Virginia Wilder · Century 21 Virginia Wilder Real Estate
Price Reduced41Active
$120,000
5 bd · 4 ba · 2,844 sqft
215 S 21st Street, Middlesboro, KY
Megan Stanaford · Black Diamond Realty
40Active
$229,500
3 bd · 3 ba · 2,016 sqft
301 Doe's Crossing, Middlesboro, KY
Virginia Wilder · Century 21 Virginia Wilder Real Estate
26Active
$135,000
2 bd · 1 ba · 1,120 sqft
2002 Winchester Avenue, Middlesboro, KY
Sheila Durham · Coldwell Banker Bisceglia Realty & Auction Co
Price Reduced16Active
$295,000
5 bd · 3 ba · 2,100 sqft
717 Highway 441, Middlesboro, KY
Megan Stanaford · Black Diamond Realty
Price Reduced17Active
$230,000
3 bd · 2 ba · 1,320 sqft
156 Wellington Drive, 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
Price Reduced17Active
$100,000
4 bd · 2 ba · 1,908 sqft
405 S 37th Street, Middlesboro, KY
Kevin Bisceglia · Coldwell Banker Bisceglia Realty & Auction Co
22Active
$97,000
3 bd · 2 ba · 1,296 sqft
252 Chasteen Drive, Middlesboro, KY
Aaron Rose · Realty Network, Inc

1 2

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: 2026-10-01 14:56:41 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

Nearby areas

ZIP codes

40965 (44)
40701 (42)
40906 (31)
40977 (23)
40769 (7)
40734 (6)
40873 (5)
40940 (5)

Cities

Corbin (42)
Barbourville (31)
Pineville (23)
Williamsburg (7)
Frakes (5)
Harlan (4)
Flat Lick (3)
Fourmile (3)

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.

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: 2026-10-01 14:56:41 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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Nearby areas

ZIP codes

40965 (44)
40701 (42)
40906 (31)
40977 (23)
40769 (7)
40734 (6)
40873 (5)
40940 (5)

Cities

Corbin (42)
Barbourville (31)
Pineville (23)
Williamsburg (7)
Frakes (5)
Harlan (4)
Flat Lick (3)
Fourmile (3)

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.