Middlesboro, KY - single-family homes for sale

42 of 42 results displayed

New
$310,000Active
5 beds 3 baths2,100 sq. ft.
717 Highway 441, Middlesboro, KY 40965
MLS# 26006775Listed by: BLACK DIAMOND REALTY
New
$30,000Active
2 beds 1 baths1,244 sq. ft.
103 Nutwood Road, Middlesboro, KY 40965
MLS# 26005898Listed by: BLACK DIAMOND REALTY
New
$50,000Active
3 beds 1 baths728 sq. ft.
105 Nutwood Road, Middlesboro, KY 40965
MLS# 26005884Listed by: BLACK DIAMOND REALTY
$245,000Active
3 beds 2 baths1,320 sq. ft.
156 Wellington Drive, Middlesboro, KY 40965
MLS# 26005639Listed 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
$239,900Active
4 beds 3 baths2,455 sq. ft.
1203 Winchester Avenue, Middlesboro, KY 40965
MLS# 26004238Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$202,500Active
3 beds 2 baths1,080 sq. ft.
23 Castleford Way, Middlesboro, KY 40965
MLS# 1331558Listed by: TURN KEY REALTY
$575,000Pending
4 beds 4 baths3,480 sq. ft.
2794 Us Hwy 25 E, Middlesboro, KY 40965
MLS# 1331334Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$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
$105,000Pending
3 beds 2 baths1,056 sq. ft.
925 Winchester Ave, Middlesboro, KY 40965
MLS# 1329979Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$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
$249,000Active
3 beds 3 baths2,016 sq. ft.
301 Doe's Crossing, Middlesboro, KY 40965
MLS# 1328317Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$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
$148,000Pending
2 beds 1 baths952 sq. ft.
359 Beans Fork Rd, Middlesboro, KY 40965
MLS# 1327412Listed by: REALTY GROUP
$115,000Active
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
$44,000Pending
3 beds 2 baths1,230 sq. ft.
406 Rochester Avenue, Middlesboro, KY 40965
MLS# 26000523Listed by: BLACK DIAMOND REALTY
$99,000Active
1 beds 1 baths800 sq. ft.
923 Winchester Ave, Middlesboro, KY 40965
MLS# 1324643Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$195,000Active
3 beds 1 baths1,100 sq. ft.
11 Castleford Way, Middlesboro, KY 40965
MLS# 25508059Listed by: KENTUCKY LAND AND HOME
$249,900Active
3 beds 2 baths1,612 sq. ft.
140 Wellington Drive, Middlesboro, KY 40965
MLS# 1323746Listed by: FATHOM REALTY TN LLC
$499,000Active
5 beds 3 baths2,542 sq. ft.
2004 Twin Fawn Tr, Middlesboro, KY 40965
MLS# 1323538Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$189,000Pending
2 beds 2 baths960 sq. ft.
1208 Ky-217, Middlesboro, KY 40965
MLS# 25507211Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$24,900Pending
3 beds 2 baths960 sq. ft.
13 Duncan Lane, Middlesboro, KY 40965
MLS# 1323130Listed by: TURN KEY REALTY
$130,000Active
3 beds 1 baths792 sq. ft.
918 E Cumberland Avenue, Middlesboro, KY 40965
MLS# 25504336Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$79,900Pending
3 beds 2 baths1,848 sq. ft.
72 Happy Hollow Hill Road, Middlesboro, KY 40965
MLS# 25504175Listed 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
$324,900Pending
5 beds 3 baths2,250 sq. ft.
805 Worchester Ave, Middlesboro, KY 40965
MLS# 1315952Listed 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
$175,000Active
3 beds 2 baths1,560 sq. ft.
63 Old Pineville Pike, Middlesboro, KY 40965
MLS# 1310085Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$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
$170,000Active
3 beds 1 baths1,200 sq. ft.
180 Stevenson Branch Rd, Middlesboro, KY 40965
MLS# 1301528Listed by: TURN KEY REALTY
$115,000Pending
3 beds 2 baths1,344 sq. ft.
921 Winchester Ave, Middlesboro, KY 40965
MLS# 1293786Listed 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 Simpson & Associates, 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.