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

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3 beds New construction With a pool

Homes for Sale in Middlesboro, KY

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13 of 38 Listings

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13 of 38 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

15Active
$159,900
2 bd · 1 ba · 792 sqft
815 Dorchester Ave, Middlesboro, KY
Lisa Stacy-Gibbs · Backwoods Realty & Development
18Active
$135,000
2 bd · 1 ba · 1,008 sqft
413 S 26th St, Middlesboro, KY
Brad Cawood · Backwoods Realty & Development
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
18Active
$70,000
2 bd · 2 ba · 1,426 sqft
123 Cawood Lane, Middlesboro, KY
Dustin Clay Daniels · Mountain Realty
13Active
$35,000
2 bd · 1 ba · 792 sqft
918 E Cumberland Ave, Middlesboro, KY
Steve Mason · REMAX PROFESSIONAL'S
18Active
$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
Price Reduced20Active
$369,000
3 bd · 3 ba · 3,397 sqft
103 Kingsbury Woods, Middlesboro, KY
Tony Giglio · ListWithFreedom.com
13Active
$455,000
5 bd · 4 ba · 3,146 sqft
523 N 30th St, Middlesboro, KY
Kevin Carroll · Backwoods Realty & Development
Price Reduced17Active
$129,900
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: 2026-08-31 16:07:38 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

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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: 2026-08-31 16:07:38 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

By feature

New construction
With a pool

Nearby areas

ZIP codes

40701 (51)
40965 (39)
40977 (28)
40906 (27)
40734 (8)
40769 (6)
40759 (5)
40806 (4)

Cities

Corbin (51)
Pineville (28)
Barbourville (27)
Gray (8)
Williamsburg (6)
Rockholds (5)
Baxter (4)
Flat Lick (4)

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

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.

Nearby areas

ZIP codes

40701 (51)
40965 (39)
40977 (28)
40906 (27)
40734 (8)
40769 (6)
40759 (5)
40806 (4)

Cities

Corbin (51)
Pineville (28)
Barbourville (27)
Gray (8)
Williamsburg (6)
Rockholds (5)
Baxter (4)
Flat Lick (4)