Hot
$320,000
Views: 11
Bedrooms: 5Bds
Bathrooms: 3Ba
Area: 3,000sqft
Single family home for sale
Realty Group, Listing provided by East Tennessee Realtors® Mls
Skip to Main Content 
Hot103 Sherwood Rd, Middlesboro, KY 40965 
Price Drop: $6K
800 S 28th Street, Middlesboro, KY 40965
31 & 29 E 10th Lothbury St, Middlesboro, KY 40965Price Drop: $70.5K
717 S 27th Street, Middlesboro, KY 40965 
1015 Old Wilson Ln, Middlesboro, KY 40965Price Drop: $10K
413 S 26th Street, Middlesboro, KY 40965 
518 S 43rd Street, Middlesboro, KY 40965Price Drop: $13.5K
123 Cawood Ln, Middlesboro, KY 40965 
406 N 25th Street, Middlesboro, KY 40965
405 S 37th Street, Middlesboro, KY 40965
305 N 15th Street, Middlesboro, KY 40965
125 Cawood Ln, Middlesboro, KY 40965Price Drop: $15.1K
926 Doncaster Ave, Middlesboro, KY 40965 
810 W Rochester Ave, Middlesboro, KY 40965
808 N 28th Street, Middlesboro, KY 40965
812 Worchester Ave, Middlesboro, KY 40965
207 Arthur Hts, Middlesboro, KY 40965
1102 W Chester Ave, Middlesboro, KY 40965
2002 Winchester Ave, Middlesboro, KY 40965
412 N 24th Street, Middlesboro, KY 40965
64 Dunlap Holw Rd, Middlesboro, KY 40965
708 W Chester Ave, Middlesboro, KY 40965
113 Hollywood Dr, Middlesboro, KY 40965
2909 W Cumberland Ave, Middlesboro, KY 40965
116 Edgewood Rd, Middlesboro, KY 40965
252 Chasteen Dr, Middlesboro, KY 40965
215 S 21st Street, Middlesboro, KY 40965
406 Rochester Ave, Middlesboro, KY 40965
105, 103 120 Nutwood Rd #A & B, Middlesboro, KY 40965
903 Ilchester Ave, Middlesboro, KY 40965
Do Real Estate on the Go!
Country Homes for Sale in Middlesborough, KY
30 Homes for Sale
Sort by:
HotPrice Drop: $6K$229,000
Views: 9
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,400sqft
Sale Pending
Remax Professional'S, Listing provided by East Tennessee Realtors® Mls
$180,000
Views: 1
Bedrooms: 5Bds
Bathrooms: 3Ba
Area: 3,000sqft
Sale Pending
Century 21 Virginia Wilder Real Estate, Listing provided by East Tennessee Realtors® Mls
Price Drop: $70.5K$227,000
Views: 14
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 3,195sqft
Sale Pending
Re/Max Laketime Realty London
$299,000
Views: 6
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,488sqft
Single family home for sale
Realty Group, Listing provided by East Tennessee Realtors® Mls
Price Drop: $10K$125,000
Views: 8
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 1,008sqft
Single family home for sale
Backwoods Realty & Development, Listing provided by East Tennessee Realtors® Mls
$51,000
Views: 11
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 920sqft
Single family home for sale
Remax Professional'S, Listing provided by East Tennessee Realtors® Mls
Price Drop: $13.5K$70,000
Views: 11
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,426sqft
Sale Pending
Mountain Realty, Listing provided by East Tennessee Realtors® Mls
$285,000
Views: 7
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 2,400sqft
Single family home for sale
Realty Group, Listing provided by East Tennessee Realtors® Mls
$100,000
Views: 10
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 1,908sqft
Single family home for sale
Coldwell Banker Bisceglia Realty & Auction Co
$150,000
Views: 10
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 876sqft
Single family home for sale
Remax Professional'S, Listing provided by East Tennessee Realtors® Mls
$135,000
Views: 31
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,400sqft
Single family home for sale
Realty Group, Listing provided by East Tennessee Realtors® Mls
Price Drop: $15.1K$299,900
Views: 15
Bedrooms: 5Bds
Bathrooms: 2Ba
Area: 2,664sqft
Sale Pending
Coldwell Banker Bisceglia Realty & Auction Co
$145,900
Views: 5
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,386sqft
Single family home for sale
Heartland Real Estate, Llc, Listing provided by East Tennessee Realtors® Mls
$175,000
Views: 12
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 1,590sqft
Sale Pending
Realty Group, Listing provided by East Tennessee Realtors® Mls
$219,000
Views: 13
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 1,544sqft
Single family home for sale
Realty Group, Listing provided by East Tennessee Realtors® Mls
$264,900
Views: 17
Bedrooms: 5Bds
Bathrooms: 3Ba
Area: 3,068sqft
Single family home for sale
Coldwell Banker Bisceglia Realty & Auction Co
$199,000
Views: 6
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,480sqft
Single family home for sale
Coldwell Banker Bisceglia Real, Listing provided by East Tennessee Realtors® Mls
$135,000
Views: 14
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 1,120sqft
Single family home for sale
Coldwell Banker Bisceglia Realty & Auction Co
$105,900
Views: 22
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,966sqft
Single family home for sale
Turn Key Realty
$149,000
Views: 16
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 1,440sqft
Single family home for sale
Century 21 Virginia Wilder Real Estate, Listing provided by East Tennessee Realtors® Mls
$129,000
Views: 10
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,404sqft
Single family home for sale
Remax Professional'S, Listing provided by East Tennessee Realtors® Mls
$270,000
Views: 10
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 3,174sqft
Sale Pending
Coldwell Banker Bisceglia Realty & Auction Co
$359,500
Views: 12
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 2,000sqft
Single family home for sale
Backwoods Realty & Development, Listing provided by East Tennessee Realtors® Mls
$200,000
Views: 23
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 2,154sqft
Single family home for sale
Black Diamond Realty
$97,000
Views: 8
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,296sqft
Single family home for sale
Realty Network, Inc, Listing provided by East Tennessee Realtors® Mls
$120,000
Views: 7
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 2,844sqft
Single family home for sale
Black Diamond Realty
$40,000
Views: 15
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,230sqft
Single family home for sale
Black Diamond Realty
$210,000
Views: 7
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 728sqft
Townhouse for sale
Black Diamond Realty
$112,000
Views: 5
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 1,056sqft
Single family home for sale
Century 21 Virginia Wilder Real Estate
Don't miss out on new listings — and get instant email alerts!
- Real Estate
- Homes For Sale
- Kentucky
- Middlesborough
- Country Homes
Do Real Estate on the Go!
Find your dream home, receive real-time updates, and many more!
No. of Homes
No. of Homes
Based on information from the Knoxville Area Association of REALTORS MLS through Oct 31, 2026, 5:00 PM. Information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. This website may not include listings or property addresses of sellers who have directed their listing brokers to withhold their listing or their property address from display on the Internet. © 2026 Knoxville Area Association of REALTORS® MLS. All Rights Reserved. Angela Fowler Real Estate, LLC | 423.320.4620 | afowler@catt.com Mailing Address: 452 Kailors Cove Cir, Ringgold, GA 30736
Based on information from the IMAGINE MLS® through Oct 31, 2026, 5:00 PM. Copyrighted by the Imagine MLS®. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data on this website is deemed reliable but is not guaranteed accurate by the MLS. © 2026 IMAGINE MLS®. All Rights Reserved.
Click to see all homes
30
Homes Available
$ NaN
Median List Price
- Days
Avg on Market