Middlesborough, KY homes for sale & real estate

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921 Winchester Ave, Middlesboro, KY 40965
921 Winchester Ave, Middlesboro, KY 40965
921 Winchester Ave, Middlesboro, KY 40965
ABOUT THIS HOME
Middlesborough, KY Homes for Sale
This country style home has 2 bedrooms with optional 3rd bedroom, 2 bathrooms, living room, dining room, kitchen, and large laundry room, central heat and air is about 6 years old, insulated windows are about 10 years old, seller is installing new cook stove and refrigerator, home has city water and city sewer, high speed internet available, concrete driveway, storage shed stays with home. Level yard, covered front porch.

$115,000

3 beds2 baths1,344 sq ft

921 Winchester Ave, Middlesboro, KY 40965

8,712 sq ft lot • Car-dependent

(276) 861-2023

$650,000

2 beds1 bath776 sq ft

516 S 34th St, Middlesboro, KY 40965

13.73 acre lot • Car-dependent

(423) 869-3000

806 Manchester Ave, Middlesboro, KY 40965
806 Manchester Ave, Middlesboro, KY 40965
806 Manchester Ave, Middlesboro, KY 40965
ABOUT THIS HOME
Middlesborough, KY Homes for Sale
Beautiful 2 bedrooms, 2 bathrooms (master bath is extra large) home in great neighborhood. Home offers a large bonus/sun room, beautiful cream-colored kitchen cabinets, tile and hardwood flooring. Don't let this one get away! Is super clean and in move-in condition. (Age is estimated and square footage to be verified)

$199,500

2 beds2 baths1,899 sq ft

806 Manchester Ave, Middlesboro, KY 40965

7,405 sq ft lot • Car-dependent

(606) 248-4932

$159,900

2 beds2 baths1,040 sq ft

109 North 30th St, Middlesboro, KY 40965

7,492 sq ft lot • Car-dependent

$150,000

3 beds2 baths1,272 sq ft

2817 KY 441, Middlesboro, KY 40965

0.69 acre lot • Car-dependent

Property at 1809 Exeter Ave, Middlesboro, KY 40965, 2 beds, 1 bath

$89,900

2 beds1 bath1,064 sq ft

1809 Exeter Ave, Middlesboro, KY 40965

Property at 106 S 38th St, Middlesboro, KY 40965, 3 beds, 2 baths

$214,900

3 beds2 baths1,408 sq ft

106 S 38th St, Middlesboro, KY 40965

(606) 248-4932

Property at 9 Ennismore Dr, Middlesboro, KY 40965, 3 beds, 2.5 baths

$279,900

3 beds2.5 baths1,974 sq ft

9 Ennismore Dr, Middlesboro, KY 40965

(423) 869-5111

Property at 413 S 26th St, Middlesboro, KY 40965, 2 beds, 1 bath

$175,000

2 beds1 bath1,008 sq ft

413 S 26th St, Middlesboro, KY 40965

(423) 869-5111

Property at 904 E Cumberland Ave, Middlesboro, KY 40965, 4 beds, 2 baths

$285,000

4 beds2 baths2,300 sq ft

904 E Cumberland Ave, Middlesboro, KY 40965

(423) 626-6353

Property at 301 Doe's Xing, Middlesboro, KY 40965, 3 beds, 2.5 baths

$269,000

3 beds2.5 baths2,016 sq ft

301 Doe's Xing, Middlesboro, KY 40965

(276) 861-2023

Property at 3575 Highway 441, Middlesboro, KY 40965, 2 beds, 1 bath

$110,000

2 beds1 bath1,204 sq ft

3575 Highway 441, Middlesboro, KY 40965

(606) 248-4932

Property at 915 Lothbury Ave, Middlesboro, KY 40965, 3 beds, 4 baths

$315,000

3 beds4 baths2,349 sq ft

915 Lothbury Ave, Middlesboro, KY 40965

(423) 869-5111

Property at 112 Parker Ln, Middlesboro, KY 40965, 3 beds, 2 baths

$140,000

3 beds2 baths1,439 sq ft

112 Parker Ln, Middlesboro, KY 40965

Property at 505 S South 38th St St, Middlesboro, KY 40965, 2 beds, 2 baths

$225,000

2 beds2 baths1,144 sq ft

505 S South 38th St St, Middlesboro, KY 40965

(423) 869-5111

Property at 1005 Hollywood Dr, Middlesboro, KY 40965, 3 beds, 1 bath

$164,500

3 beds1 bath1,110 sq ft

1005 Hollywood Dr, Middlesboro, KY 40965

(423) 869-0075

Property at 549 S S 43rd St, Middlesboro, KY 40965, 3 beds, 1 bath

$89,900

3 beds1 bath1,492 sq ft

549 S S 43rd St, Middlesboro, KY 40965

(423) 869-5111

Property at 109 Hollywood Dr, Middlesboro, KY 40965, 3 beds, 2.5 baths

$299,000

3 beds2.5 baths3,544 sq ft

109 Hollywood Dr, Middlesboro, KY 40965

(606) 248-4932

Property at 1315 Winchester Ave, Middlesboro, KY 40965, 3 beds, 2 baths

$229,900

3 beds2 baths1,684 sq ft

1315 Winchester Ave, Middlesboro, KY 40965

(423) 489-9744

Property at 210 Welch Ln, Middlesboro, KY 40965, 3 beds, 1.5 baths

$70,000

3 beds1.5 baths1,430 sq ft

210 Welch Ln, Middlesboro, KY 40965

(423) 869-3000

Property at 512 N 25th St, Middlesboro, KY 40965, 2 beds, 1 bath

$235,000

2 beds1 bath2,031 sq ft

512 N 25th St, Middlesboro, KY 40965

(423) 869-5111

Property at 113 Hollywood Dr, Middlesboro, KY 40965, 3 beds, 2.5 baths

$299,000

3 beds2.5 baths3,174 sq ft

113 Hollywood Dr, Middlesboro, KY 40965

(606) 248-4932

Property at 1002 Chester Ave, Middlesboro, KY 40965, 4 beds, 1 bath

$170,000

4 beds1 bath2,073 sq ft

1002 Chester Ave, Middlesboro, KY 40965

(423) 626-6353

Property at 2410 Cumberland Ave, Middlesboro, KY 40965, 5 beds, 3.5 baths

$305,000

5 beds3.5 baths3,000 sq ft

2410 Cumberland Ave, Middlesboro, KY 40965

(606) 248-4932

Property at 127 Cawood Ln, Middlesboro, KY 40965, 4 beds, 2 baths

$185,000

4 beds2 baths2,163 sq ft

127 Cawood Ln, Middlesboro, KY 40965

(423) 869-3121

Property at 717 S 27th St, Middlesboro, KY 40965, 5 beds, 4 baths

$379,900

5 beds4 baths2,943 sq ft

717 S 27th St, Middlesboro, KY 40965

(423) 869-3000

Property at 811 Gloucester Ave, Middlesboro, KY 40965, 3 beds, 1 bath

$199,900

3 beds1 bath1,661 sq ft

811 Gloucester Ave, Middlesboro, KY 40965

(423) 869-3000

Property at 63 Old Pineville Pike, Middlesboro, KY 40965, 4 beds, 1 bath

$139,000

4 beds1 bath1,560 sq ft

63 Old Pineville Pike, Middlesboro, KY 40965

(276) 861-2023

Property at 515 Englewood Rd, Middlesboro, KY 40965, 3 beds, 3 baths

$289,900

3 beds3 baths2,210 sq ft

515 Englewood Rd, Middlesboro, KY 40965

(423) 869-5111

Property at 101 Kim Ln, Middlesboro, KY 40965, 5 beds, 4 baths

$440,000

5 beds4 baths3,874 sq ft

101 Kim Ln, Middlesboro, KY 40965

(606) 248-4932

Property at 1015 Old Wilson Ln, Middlesboro, KY 40965, 4 beds, 2.5 baths

$550,000

4 beds2.5 baths2,488 sq ft

1015 Old Wilson Ln, Middlesboro, KY 40965

Property at 501 North 25th St, Middlesboro, KY 40965, 4 beds, 2 baths

$169,900

4 beds2 baths1,689 sq ft

501 North 25th St, Middlesboro, KY 40965

Property at 252 Chasteen Dr, Middlesboro, KY 40965, 3 beds, 2 baths

$105,000

3 beds2 baths1,296 sq ft

252 Chasteen Dr, Middlesboro, KY 40965

(276) 861-2023

Property at 0 Highway 217, Middlesboro, KY 40965

$29,900

— beds— baths— sq ft

0 Highway 217, Middlesboro, KY 40965

Property at 00 Ky Hwy 217, Middlesboro, KY 40965

$300,000

— beds— baths— sq ft

00 Ky Hwy 217, Middlesboro, KY 40965

Property at 407 Exeter Ave, Middlesboro, KY 40965

$29,900

— beds— baths— sq ft

407 Exeter Ave, Middlesboro, KY 40965

(423) 869-5111

Property at KY Hwy 217 Ave, Middlesboro, KY 40965

$149,900

— beds— baths— sq ft

KY Hwy 217 Ave, Middlesboro, KY 40965

(423) 489-9744

Property at Lot 13 Venado Dr, Middlesboro, KY 40965

$24,000

— beds— baths— sq ft

Lot 13 Venado Dr, Middlesboro, KY 40965

(276) 861-2023

Property at 19 Venado Dr, Middlesboro, KY 40965

$45,000

— beds— baths— sq ft

19 Venado Dr, Middlesboro, KY 40965

Property at 0 Home Run Rd, Middlesboro, KY 40965

$19,500

— beds— baths— sq ft

0 Home Run Rd, Middlesboro, KY 40965

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Average home prices near Middlesborough, KY

Cities

Zip Codes

40965 homes for sale
$199,500
40977 homes for sale
$221,400

Middlesborough, KY real estate trends

All Home Types trends in Middlesborough, KY

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$116,250

+111.4% YoY | Feb 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Feb 2025

Growth

% YoY

Middlesborough, KY

$116,250

+111.4%

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