Middlesborough, KY - single-family homes for sale

42 of 42 results displayed

New
$240,000Active
3 beds 2 baths2,154 sq. ft.
116 Edgewood Road, Middlesboro, KY 40965
MLS# 26013326Listed by: BLACK DIAMOND REALTY
New
$350,000Active
5 beds 4 baths3,195 sq. ft.
717 S 27th Street, Middlesboro, KY 40965
MLS# 26013256Listed by: RE/MAX LAKETIME REALTY LONDON
New

$175,000Active
4 beds 2 baths1,440 sq. ft.
64 Dunlap Hollow Rd, Middlesboro, KY 40965
MLS# 1343957Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
New
$150,000Active
2 beds 1 baths840 sq. ft.
422 Wilderness Rd, Middlesboro, KY 40965
MLS# 1343837Listed by: REALTY GROUP
New
$175,000Active
2 beds 1 baths792 sq. ft.
815 Dorchester Ave, Middlesboro, KY 40965
MLS# 1343066Listed by: TURN KEY REALTY
$155,000Active
3 beds 1 baths1,104 sq. ft.
1807 Winchester Ave, Middlesboro, KY 40965
MLS# 1342793Listed by: REMAX PROFESSIONAL'S
$140,000Active
2 beds 1 baths1,008 sq. ft.
413 S 26th St, Middlesboro, KY 40965
MLS# 1342457Listed by: TURN KEY REALTY
$134,000Active
5 beds 4 baths2,844 sq. ft.
215 S 21st Street, Middlesboro, KY 40965
MLS# 26011288Listed by: BLACK DIAMOND REALTY
$219,999Active
3 beds 2 baths3,948 sq. ft.
2621 W Cumberland Avenue, Middlesboro, KY 40965
MLS# 26011050Listed by: KELLER WILLIAMS LEGACY GROUP
$220,000Active
3 beds 1 baths1,652 sq. ft.
116 N Petersborough Ave, Middlesboro, KY 40965
MLS# 1341032Listed by: COLDWELL BANKER BISCEGLIA REAL
$225,000Active
3 beds 2 baths1,400 sq. ft.
908 Chester Ave, Middlesboro, KY 40965
MLS# 1340728Listed by: REMAX PROFESSIONAL'S
$110,000Active
2 beds 2 baths1,426 sq. ft.
123 Cawood Lane, Middlesboro, KY 40965
MLS# 1340557Listed by: MOUNTAIN REALTY
$299,000Active
5 beds 3 baths3,068 sq. ft.
207 Arthur Heights, Middlesboro, KY 40965
MLS# 26010558Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$125,000Pending
4 beds 2 baths2,592 sq. ft.
316 Exeter Ave, Middlesboro, KY 40965
MLS# 1340116Listed by: REMAX PROFESSIONAL'S
$70,000Active
2 beds 1 baths792 sq. ft.
918 E Cumberland Ave, Middlesboro, KY 40965
MLS# 1340131Listed by: REMAX PROFESSIONAL'S
$135,000Active
2 beds 1 baths1,120 sq. ft.
2002 Winchester Avenue, Middlesboro, KY 40965
MLS# 26010030Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$325,000Active
4 beds 3 baths2,488 sq. ft.
1015 Old Wilson Lane, Middlesboro, KY 40965
MLS# 26009828Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$279,900Active
3 beds 2 baths2,016 sq. ft.
127 Alpine #127, Middlesboro, KY 40965
MLS# 26007901Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$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
$179,900Active
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
$30,000Pending
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
$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: BACKWOODS REALTY & DEVELOPMENT
$135,000Active
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
$259,000Pending
4 beds 3 baths1,832 sq. ft.
206 Summit Drive, Middlesboro, KY 40965
MLS# 1327623Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$94,900Active
2 beds 2 baths1,240 sq. ft.
816 W Chester Avenue, Middlesboro, KY 40965
MLS# 26001413Listed by: CENTURY 21 PINNACLE
$139,900Active
4 beds 2 baths1,908 sq. ft.
405 S 37th St, Middlesboro, KY 40965
MLS# 1326276Listed by: COLDWELL BANKER BISCEGLIA REAL
$40,000Active
3 beds 2 baths1,230 sq. ft.
406 Rochester Avenue, Middlesboro, KY 40965
MLS# 26000523Listed by: BLACK DIAMOND REALTY
$79,000Pending
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
$240,000Pending
3 beds 3 baths1,856 sq. ft.
129 Lower Gibson Lane, Middlesboro, KY 40965
MLS# 1316259Listed by: REMAX PROFESSIONAL'S
$85,000Active
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
$270,000Active
3 beds 3 baths3,174 sq. ft.
113 Hollywood Drive, Middlesboro, KY 40965
MLS# 1277166Listed by: COLDWELL BANKER BISCEGLIA REAL
$99,999Active
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 Advantage Realty, CENTURY 21 Legacy

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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.