Middlesboro, KY Real Estate & Homes For Sale
57 homes
- NEW - 2 DAYS AGO0.25 ACRESTurn Key Realty
- 0.33 ACRESCentury 21 Virginia Wilder Real Estate
- FOR SALE BY OWNER
- 0.63 ACRESBlack Diamond Realty, Imagine MLS
- 0.25 ACRESKeller Williams Legacy Group, Imagine MLS
- Coldwell Banker Bisceglia Real
- Coldwell Banker Bisceglia Realty & Auction Co, Imagine MLS
- Black Diamond Realty, Imagine MLS
- Coldwell Banker Bisceglia Realty & Auction Co, Imagine MLS
- Coldwell Banker Bisceglia Realty & Auction Co, Imagine MLS
- Coldwell Banker Bisceglia Realty & Auction Co, Imagine MLS
- Coldwell Banker Bisceglia Realty & Auction Co, Imagine MLS
- Century 21 Virginia Wilder Real Estate, Imagine MLS
- Black Diamond Realty, Imagine MLS
- Turn Key Realty, Imagine MLS
- Turn Key Realty, Imagine MLS
- Turn Key Realty, Imagine MLS
- Black Diamond Realty, Imagine MLS
- Black Diamond Realty, Imagine MLS
- Black Diamond Realty, Imagine MLS
- Coldwell Banker Bisceglia Realty & Auction Co, Imagine MLS
- ListWithFreedom.com, Imagine MLS
- Century 21 Virginia Wilder Real Estate
Middlesboro, KY Real Estate Trends
Learn about the Middlesboro, KY housing market through trends and averages.Affordability of Living in Middlesboro, KY
| Month | Median home value |
|---|---|
| May 2025 | $122k |
| June 2025 | $122k |
| July 2025 | $121k |
| August 2025 | $119k |
| September 2025 | $116k |
| October 2025 | $114k |
| November 2025 | $113k |
| December 2025 | $112k |
| January 2026 | $112k |
| February 2026 | $113k |
| March 2026 | $115k |
| April 2026 | $115k |
Trends and affordability stats are provided by third party data sources.
Average Home Value in Middlesboro, KY, by Home Size
Currently, there are 3 new listings in Middlesboro, KY and 57 homes for sale.
| Home Size | Home Value* |
|---|---|
| 2 bedrooms (10 homes) | $91,683 |
| 3 bedrooms (21 homes) | $153,381 |
| 4 bedrooms (6 homes) | $222,419 |
What Locals Say about Middlesboro

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 presented by local MLS brokerage: Zillow, Inc., local broker - Eric Young - (865) 378-5282.
Listing Information presented by local MLS brokerage: Zillow, Inc., local broker - Eric Young - (865) 378-5282.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of NKMLS. Real estate listings held by IDX Brokerage firms other than Zillow, Inc. are marked with the Internet Data Exchange logo or the Internet Data Exchange thumbnail logo and detailed information about them includes the name of the listing Brokers.
Listing information is deemed reliable, but not guaranteed.
Copyright 2026 Northern Kentucky Multiple Listing Service, Inc. All rights reserved.
Listing information is deemed reliable, but not guaranteed.
Copyright 2026 Northern Kentucky Multiple Listing Service, Inc. All rights reserved.

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.