Middlesboro, KY Homes For Sale
36 listings. Live MLS data, refreshed nightly. Middlesboro market overview
Middlesboro, KY
Get alerts on new listings
We'll email you when new homes match these filters. No spam, unsubscribe anytime.
Loading map…
Listings
$359,500
2909 W Cumberland Ave, Middlesboro, KY 40965
Middlesboro, 40965
3 bd·2 ba
46 days on market
Listed by Lisa Stacy-Gibbs, Backwoods Realty & Development
$135,000
125 Cawood Lane, Middlesboro, KY 40965
Middlesboro, 40965
2 bd·2 ba
94 days on market
Listed by Misti McGrath, Realty Group
No photo
$279,000
515 Englewood Rd, Middlesboro, KY 40965
Middlesboro, 40965
3 bd·3 ba
694 days on market
Listed by Kevin Carroll, Backwoods Realty & Development
$149,000
64 Dunlap Hollow Rd, Middlesboro, KY 40965
Middlesboro, 40965
4 bd·2 ba
95 days on market
Listed by Virginia Wilder, Century 21 Virginia Wilder Real Estate
No photo
$229,500
301 Doe's Crossing, Middlesboro, KY 40965
Middlesboro, 40965
3 bd·2.5 ba
193 days on market
Listed by Virginia Wilder, Century 21 Virginia Wilder Real Estate
No photo
$455,000
523 N 30th St, Middlesboro, KY 40965
Middlesboro, 40965
5 bd·4 ba
453 days on market
Listed by Kevin Carroll, Backwoods Realty & Development
No photo
$30,000
LOTS 12 & 13 Sams Mountain RD., Middlesboro, KY 40965
Middlesboro, 40965
199 days on market
Listed by Sharon K Teaney, Century 21 Virginia Wilder Real Estate
No photo
$250,000
119 Wagon Hollow Rd, Middlesboro, KY 40965
Middlesboro, 40965
382 days on market
Listed by Megan Stanaford, Black Diamond Realty
$100,000
405 S 37th St, Middlesboro, KY 40965
Middlesboro, 40965
4 bd·2 ba
274 days on market
Listed by Kevin J Bisceglia, Coldwell Banker Bisceglia Real
$97,000
252 Chasteen Drive, Middlesboro, KY 40965
Middlesboro, 40965
3 bd·2 ba
362 days on market
Listed by Aaron Rose, Realty Network, Inc
No photo
$15,000
118 Polly Hollow Right Fork Rd, Middlesboro, KY 40965
Middlesboro, 40965
336 days on market
Listed by Mike Hensley, REMAX PROFESSIONAL'S
No photo
$275,000
321 Chester Ave, Middlesboro, KY 40965
Middlesboro, 40965
437 days on market
Listed by Kevin J Bisceglia, Coldwell Banker Bisceglia Real
Listing data provided by East Tennessee REALTORS® MLS via Trestle/CoreLogic. Last sample-row update: August 24, 2026. Information herein deemed reliable but not guaranteed. Equal Housing Opportunity.