Middlesboro, KY homes for sale & real estate

5 days on Rocket

$2,957 Closing Credit¹

$249,000

3 beds • 2.5 baths • 1,900 sqft

286 Tiwani Ridge Rd, Middlesboro, KY 40965

#1296060, Listing Office: Realty Group

0 Wells Camp Rd, Middlesboro KY, 40965 land for sale

5 days on Rocket

$7,500

Land • 0.20 Acres

0 Wells Camp Rd, Middlesboro, KY 40965

#25006635, Listing Office: Black Diamond Realty

Save big

You could save thousands when you partner with Rocket Homes℠ and Rocket Mortgage®

7 days on Rocket

$1,424 Closing Credit¹

$119,900

2 beds • 1 bath

112 Exeter Ave, Middlesboro, KY 40965

#25006450, Listing Office: Action Realty

7 days on Rocket

$3,561 Closing Credit¹

$299,900

4 beds • 2 baths • 3,338 sqft

123 Twin Acres Rd, Middlesboro, KY 40965

#1295631, Listing Office: Action Realty

$3,443 Closing Credit¹

$289,900

3 beds • 2 baths

4922 W Cumberland Ave, Middlesboro, KY 40965

#25006370, Listing Office: Coldwell Banker Bisceglia Realty & Auction Co

$3,443 Closing Credit¹

$289,900

3 beds • 2 baths • 1,989 sqft

4922 W Cumberland Ave, Middlesboro, KY 40965

#1295519, Listing Office: Coldwell Banker Bisceglia Real

$1,366 Closing Credit¹

$115,000

3 beds • 2 baths • 1,344 sqft

921 Winchester Ave, Middlesboro, KY 40965

#1293786, Listing Office: Century 21 Virginia Wilder Real Estate

Room to negotiate?

Median Sold Price

$145.7K

Avg. Sale Time

93 Days

Based on our March 2025 Market Report.

$7,719 Closing Credit¹

$650,000

2 beds • 1 bath • 776 sqft

516 S 34th St, Middlesboro, KY 40965

#1293374

$2,369 Closing Credit¹

$199,500

2 beds • 2 baths

806 Manchester Ave, Middlesboro, KY 40965

#25004825, Listing Office: Coldwell Banker Bisceglia Realty & Auction Co

$2,369 Closing Credit¹

$199,500

2 beds • 2 baths • 1,899 sqft

806 Manchester Ave, Middlesboro, KY 40965

#1293064

$1,899 Closing Credit¹

$159,900

2 beds • 2 baths

109 N 30th St, Middlesboro, KY 40965

#25004465, Listing Office: Sallie Davidson, Realtors

$1,068 Closing Credit¹

$89,900

2 beds • 1 bath

1809 Exeter Ave, Middlesboro, KY 40965

#25004051, Listing Office: Shawn Rogers Realty, Inc

$2,552 Closing Credit¹

$214,900

3 beds • 2 baths • 1,408 sqft

106 S 38th St, Middlesboro, KY 40965

#1292147, Listing Office: Coldwell Banker Bisceglia Real

$3,324 Closing Credit¹

$279,900

3 beds • 2.5 baths • 1,974 sqft

9 Ennismore Dr, Middlesboro, KY 40965

#1291613, Listing Office: Turn Key Realty

$2,552 Closing Credit¹

$214,900

3 beds • 2 baths

106 S 38th St, Middlesboro, KY 40965

#25003238, Listing Office: Coldwell Banker Bisceglia Realty & Auction Co

$2,078 Closing Credit¹

$175,000

2 beds • 1 bath • 1,008 sqft

413 S 26th St, Middlesboro, KY 40965

#1290233, Listing Office: Turn Key Realty

$3,194 Closing Credit¹

$269,000

3 beds • 2.5 baths • 2,016 sqft

301 Does Xing, Middlesboro, KY 40965

#1288966, Listing Office: Century 21 Virginia Wilder Real Estate

$3,741 Closing Credit¹

$315,000

3 beds • 4 baths • 2,349 sqft

915 Lothbury Ave, Middlesboro, KY 40965

#1287518, Listing Office: Turn Key Realty

407 Exeter Ave, Middlesboro KY, 40965 land for sale

$29,900

Land • 0.26 Acres

407 Exeter Ave, Middlesboro, KY 40965

#1286317

$1,663 Closing Credit¹

$140,000

3 beds • 2 baths

112 Parker Ln, Middlesboro, KY 40965

#24026218, Listing Office: Coldwell Banker Bisceglia Realty & Auction Co

$2,672 Closing Credit¹

$225,000

2 beds • 2 baths • 1,144 sqft

505 S S 38th St, Middlesboro, KY 40965

#1284881, Listing Office: Turn Key Realty

$1,068 Closing Credit¹

$89,900

3 beds • 1 bath • 1,492 sqft

549 S S 43rd St, Middlesboro, KY 40965

#1283670, Listing Office: Turn Key Realty

$1,953 Closing Credit¹

$164,500

3 beds • 1 bath • 1,110 sqft

1005 Hollywood Dr, Middlesboro, KY 40965

#1283319, Listing Office: Heartland Real Estate, LLC

$2,730 Closing Credit¹

$229,900

3 beds • 2 baths • 1,684 sqft

1315 Winchester Ave, Middlesboro, KY 40965

#1282005, Listing Office: AAA Realty, Inc.

Backup offers

$3,551 Closing Credit¹

$299,000

3 beds • 2.5 baths

109 Hollywood Dr, Middlesboro, KY 40965

#24022848, Listing Office: Coldwell Banker Bisceglia Realty & Auction Co

$3,324 Closing Credit¹

$279,900

3 beds • 2 baths

4921 W Cumberland Ave, Middlesboro, KY 40965

#24022719, Listing Office: Action Realty

$24,000

Land • 1.46 Acres

LOT13 Venado Dr, Middlesboro, KY 40965

#1280147, Listing Office: Century 21 Virginia Wilder Real Estate

$831 Closing Credit¹

$70,000

3 beds • 1.5 baths • 1,430 sqft

210 Welch Ln, Middlesboro, KY 40965

#1280087, Listing Office: REMAX PROFESSIONAL'S

$2,791 Closing Credit¹

$235,000

2 beds • 1 bath • 2,031 sqft

512 N 25th St, Middlesboro, KY 40965

#1278575

$45,000

Land • 3.16 Acres

19 Venado Dr, Middlesboro, KY 40965

#24020807, Listing Office: Coldwell Banker Bisceglia Realty & Auction Co

$3,551 Closing Credit¹

$299,000

3 beds • 2.5 baths • 3,174 sqft

113 Hollywood Dr, Middlesboro, KY 40965

#1277166, Listing Office: Coldwell Banker Bisceglia Real

0 Home Run Rd, Middlesboro KY, 40965 land for sale

$19,500

Land • 1.14 Acres

0 Home Run Rd, Middlesboro, KY 40965

#24018475, Listing Office: Century 21 Virginia Wilder Real Estate

$3,622 Closing Credit¹

$305,000

5 beds • 3.5 baths

2410 Cumberland Ave, Middlesboro, KY 40965

#24018171, Listing Office: Coldwell Banker Bisceglia Realty & Auction Co

$3,622 Closing Credit¹

$305,000

5 beds • 3.5 baths • 3,000 sqft

2410 Cumberland Ave, Middlesboro, KY 40965

#1274726, Listing Office: Coldwell Banker Bisceglia Real

$4,511 Closing Credit¹

$379,900

5 beds • 4 baths • 2,943 sqft

717 S 27th St, Middlesboro, KY 40965

#1271628, Listing Office: REMAX PROFESSIONAL'S

$2,374 Closing Credit¹

$199,900

3 beds • 1 bath • 1,661 sqft

811 Gloucester Ave, Middlesboro, KY 40965

#1270976, Listing Office: REMAX PROFESSIONAL'S

$1,651 Closing Credit¹

$139,000

4 beds • 1 bath • 1,560 sqft

63 Old Pineville Pike, Middlesboro, KY 40965

#1267675, Listing Office: Century 21 Virginia Wilder Real Estate

$3,443 Closing Credit¹

$289,900

3 beds • 3 baths • 2,210 sqft

515 Englewood Rd, Middlesboro, KY 40965

#1262597, Listing Office: Turn Key Realty

$5,225 Closing Credit¹

$440,000

5 beds • 4 baths

101 Kim Ln, Middlesboro, KY 40965

#24008758, Listing Office: Coldwell Banker Bisceglia Realty & Auction Co

$5,225 Closing Credit¹

$440,000

5 beds • 4 baths • 3,874 sqft

101 Kim Ln, Middlesboro, KY 40965

#1261697, Listing Office: Coldwell Banker Bisceglia Real

Middlesboro, KY Real Estate Market Overview

Browse 44 homes for sale in Middlesboro, KY. View properties, photos, nearby real estate with school and housing market information. The number of listings in Middlesboro, KY decreased by 2% between February 2025 and March 2025. While the average time on the market in March 2025 was 93 days, the median list price was $145,750. Over 0 listings were sold over their listed price in March 2025 in Middlesboro, KY. In the same period over 4 listings were sold below the listed price and 0 listings were sold for the listed price.

From Rocket Homes Real Estate and based on county public records data

Schools near Middlesboro, KY

Elementary Schools

Middlesboro Elementary School
3400 Cumberland Ave
Public District PK-4
Ellen Myers Primary School
275 Nettleton Rd
Public District PK-4

Middle Schools

Middlesboro Middle School
4400 W Cumberland Ave
Public District 5-8
Yellow Creek School Center
4840 W Cumberland Ave
Public District PK-8

High Schools

Middlesboro High School
4404 W Cumberland Ave
Public District 9-12

Data provided by Great Schools

Homes for sale in Middlesboro, KY

Middlesboro, KY Real Estate Market Overview

What is it like to live in Middlesboro, KY

Overview

Housing types

Advantages

Convenience

Transportation

Schools near Middlesboro, KY

Housing market reports in Bell County

Homes for sale near Middlesboro, KY

Top real estate cities in Kentucky