Middlesborough, KY - homes for sale

45 of 45 results displayed

New
$239,900Active
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
$25,000Active
0.3 Acres
2503 Exeter Ave, Middlesboro, KY 40965
MLS# 1330573Listed by: REALTY GROUP
$210,000Active
2 beds 3 baths960 sq. ft.
615 S 22nd Street, Middlesboro, KY 40965
MLS# 26003147Listed by: BLACK DIAMOND REALTY
$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
$168,000Active
4 beds 2 baths1,120 sq. ft.
409 Meadow Lane, Middlesboro, KY 40965
MLS# 1329538Listed by: TURN KEY REALTY
$279,000Active
3 beds 3 baths2,210 sq. ft.
515 Englewood Rd, Middlesboro, KY 40965
MLS# 1329448Listed by: TURN KEY REALTY
$139,900Pending
3 beds 2 baths1,680 sq. ft.
2523 Exeter Avenue, Middlesboro, KY 40965
MLS# 26002575Listed by: THRESHOLD REAL ESTATE SERVICES
$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
$197,000Active
3 beds 2 baths1,238 sq. ft.
1200 W Chester Ave, Middlesboro, KY 40965
MLS# 1327952Listed by: COLDWELL BANKER BISCEGLIA REAL
$259,000Active
4 beds 3 baths1,832 sq. ft.
206 Summit Drive, Middlesboro, KY 40965
MLS# 1327623Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$139,000Active
5.33 Acres
312 Blakely Lane, Middlesboro, KY 40965
MLS# 26001499Listed by: ACTION REALTY
$115,000Pending
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
$199,000Active
3 beds 2 baths1,400 sq. ft.
908 Chester Ave, Middlesboro, KY 40965
MLS# 1325838Listed by: REMAX PROFESSIONAL'S
$79,900Active
-- beds -- baths2,256 sq. ft.
417-A&B Avondale Ave, Middlesboro, KY 40965
MLS# 1324983Listed by: MOUNTAIN REALTY
$99,000Active
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
$159,900Pending
3 beds 2 baths934 sq. ft.
45 Fourmile Run Road, Middlesboro, KY 40965
MLS# 25506029Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$232,500Pending
3 beds 2 baths1,900 sq. ft.
4921 W Cumberland Ave, Middlesboro, KY 40965
MLS# 1319805Listed by: MOUNTAIN REALTY
$194,500Active
3 beds 2 baths1,375 sq. ft.
280 Parker Lane, Middlesboro, KY 40965
MLS# 1319571Listed by: REALTY GROUP
$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
$249,900Active
3 beds 2 baths1,200 sq. ft.
807 Exeter Ave, Middlesboro, KY 40965
MLS# 1316511Listed by: FATHOM REALTY TN LLC
$240,000Active
3 beds 3 baths1,856 sq. ft.
129 Lower Gibson Lane, Middlesboro, KY 40965
MLS# 1316259Listed by: REMAX PROFESSIONAL'S
$15,000Active
0.13 Acres
118 Polly Hollow Right Fork Rd, Middlesboro, KY 40965
MLS# 1315958Listed 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
$189,000Active
-- beds -- baths
4607 W Cumberland Ave, Middlesboro, KY 40965
MLS# 1315760Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$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
$1,250,000Pending
64.84 Acres
423 N 10th Street, Middlesboro, KY 40965
MLS# 23023309Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$22,500Active
0.36 Acres
526 Balmoral Road, Middlesboro, KY 40965
MLS# 25008692Listed by: BLACK DIAMOND REALTY
$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
$17,000Pending
1.14 Acres
0 Home Run Rd, Middlesboro, KY 40965
MLS# 1306547Listed 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
$349,900Active
1.69 Acres
321 Chester Avenue, Middlesboro, KY 40965
MLS# 25012296Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$115,000Active
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 Virginia Wilder Real Estate, CENTURY 21 Legacy

Neighborhoods near Middlesborough, KY

Zip codes near Middlesborough, KY

Popular searches near Middlesborough, KY

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.

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.