Middlesborough, KY - single-family homes for sale

33 of 33 results displayed

New
$115,000Active
2 beds 1 baths850 sq. ft.
1009 E Cumberland Ave, Middlesboro, KY 40965
MLS# 1337921Listed by: REMAX PROFESSIONAL'S
New
$279,900Active
3 beds 2 baths2,016 sq. ft.
127 Alpine #127, Middlesboro, KY 40965
MLS# 26007901Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$169,900Pending
3 beds 2 baths1,184 sq. ft.
707 Gloucester Ave, Middlesboro, KY 40965
MLS# 1336660Listed by: TURN KEY REALTY
$249,900Active
3 beds 2 baths1,346 sq. ft.
913 Doncaster St, Middlesboro, KY 40965
MLS# 1336350Listed by: FATHOM REALTY TN LLC
$180,000Active
4 beds 1 baths2,430 sq. ft.
713 Exeter Avenue, Middlesboro, KY 40965
MLS# 26007393Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$187,000Active
3 beds 2 baths1,028 sq. ft.
1200 W Chester Avenue, Middlesboro, KY 40965
MLS# 26007323Listed by: BLACK DIAMOND REALTY
$349,900Pending
3 beds 2 baths2,126 sq. ft.
3306 W Cumberland Avenue, Middlesboro, KY 40965
MLS# 26006987Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$295,000Active
5 beds 3 baths2,100 sq. ft.
717 Highway 441, Middlesboro, KY 40965
MLS# 26006775Listed by: BLACK DIAMOND REALTY
$30,000Active
2 beds 1 baths1,244 sq. ft.
103 Nutwood Road, Middlesboro, KY 40965
MLS# 26005898Listed by: BLACK DIAMOND REALTY
$50,000Active
3 beds 1 baths728 sq. ft.
105 Nutwood Road, Middlesboro, KY 40965
MLS# 26005884Listed by: BLACK DIAMOND REALTY
$229,000Pending
3 beds 3 baths2,000 sq. ft.
810 Worchester Ave, Middlesboro, KY 40965
MLS# 1333149Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$239,900Pending
4 beds 3 baths2,455 sq. ft.
1203 Winchester Avenue, Middlesboro, KY 40965
MLS# 26004238Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$399,000Active
3 beds 3 baths3,397 sq. ft.
103 Kingsbury Woods, Middlesboro, KY 40965
MLS# 26003950Listed by: LISTWITHFREEDOM.COM
$455,000Active
5 beds 4 baths3,146 sq. ft.
523 N 30th St, Middlesboro, KY 40965
MLS# 1330109Listed by: TURN KEY REALTY
$168,000Pending
4 beds 2 baths1,120 sq. ft.
409 Meadow Lane, Middlesboro, KY 40965
MLS# 1329538Listed by: TURN KEY REALTY
$142,000Active
3 beds 1 baths1,404 sq. ft.
708 W Chester Ave, Middlesboro, KY 40965
MLS# 1328773Listed by: REMAX PROFESSIONAL'S
$140,000Pending
4 beds 2 baths995 sq. ft.
172 Beans Fork Road, Middlesboro, KY 40965
MLS# 26001939Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$259,000Active
4 beds 3 baths1,832 sq. ft.
206 Summit Drive, Middlesboro, KY 40965
MLS# 1327623Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$109,900Active
2 beds 2 baths1,240 sq. ft.
816 W Chester Avenue, Middlesboro, KY 40965
MLS# 26001413Listed by: CENTURY 21 PINNACLE
$159,900Active
4 beds 2 baths1,908 sq. ft.
405 S 37th Street, Middlesboro, KY 40965
MLS# 26000834Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$85,000Active
1 beds 1 baths800 sq. ft.
923 Winchester Ave, Middlesboro, KY 40965
MLS# 1324643Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$24,900Pending
3 beds 2 baths960 sq. ft.
13 Duncan Lane, Middlesboro, KY 40965
MLS# 1323130Listed by: TURN KEY REALTY
$120,000Active
3 beds 1 baths792 sq. ft.
918 E Cumberland Avenue, Middlesboro, KY 40965
MLS# 25504336Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$155,000Pending
2 beds 1 baths1,088 sq. ft.
123 Upper Gibson Lane, Middlesboro, KY 40965
MLS# 25502716Listed by: BLACK DIAMOND REALTY
$240,000Pending
3 beds 3 baths1,856 sq. ft.
129 Lower Gibson Lane, Middlesboro, KY 40965
MLS# 1316259Listed by: REMAX PROFESSIONAL'S
$165,000Pending
3 beds 2 baths1,056 sq. ft.
4605 W Cumberland Ave, Middlesboro, KY 40965
MLS# 1315630Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$68,000Pending
2 beds 1 baths1,456 sq. ft.
1720 Exeter Ave, Middlesboro, KY 40965
MLS# 1315173Listed by: REALTY GROUP
$319,900Pending
6 beds 4 baths4,033 sq. ft.
832 N 25th Street, Middlesboro, KY 40965
MLS# 25011376Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$100,000Active
2 beds 1 baths910 sq. ft.
310 Barkley Drive, Middlesboro, KY 40965
MLS# 1311219Listed by: REMAX PROFESSIONAL'S
$2,500,000Active
3 beds 2 baths1,976 sq. ft.
259 Watson Lane, Middlesboro, KY 40965
MLS# 1306495Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$490,000Pending
7 beds 5 baths6,276 sq. ft.
142 Edgewood Rd, Middlesboro, KY 40965
MLS# 1290184Listed by: TURN KEY REALTY
$299,000Active
3 beds 3 baths3,174 sq. ft.
113 Hollywood Drive, Middlesboro, KY 40965
MLS# 1277166Listed by: COLDWELL BANKER BISCEGLIA REAL
$109,000Active
3 beds 2 baths1,296 sq. ft.
252 Chasteen Drive, Middlesboro, KY 40965
MLS# 1316842Listed by: REALTY NETWORK, INC

Local realty services provided by:CENTURY 21 Legacy, CENTURY 21 Virginia Wilder Real Estate

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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.

Terms of use Accessibility DMCA notice Fraud alert Privacy policy Fair housing Do not sell info NY reasonable accommodation Submit agent or broker complaint

Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.

©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.