Middlesborough, KY homes for sale & real estate

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915 Lothbury Ave, Middlesboro, KY 40965
915 Lothbury Ave, Middlesboro, KY 40965
915 Lothbury Ave, Middlesboro, KY 40965
ABOUT THIS HOME
Middlesborough, KY Homes for Sale
Charming & Spacious Home with Poolside Living in Historic Middlesboro! This 3-bedroom, 4-bath home offers an abundance of space, comfort, and entertainment features for the whole family. Step outside to your own private retreat featuring a inground pool, a dedicated pool room with its own shower, and a convenient outdoor bathroom—ideal for summer gatherings. Unwind on the screened-in porch with a custom daybed swing, or fire up the natural gas grill in the outdoor cooking area designed for effortless entertaining. Inside, you'll find rich hardwood flooring throughout and a warm, inviting layout. The primary suite is a true escape, complete with an ensuite bathroom and a relaxin

$299,000

3 beds4 baths2,349 sq ft

915 Lothbury Ave, Middlesboro, KY 40965

0.32 acre lot • Garage • Pool

(423) 869-5111

5 Abbey Ln, Middlesboro, KY 40965
5 Abbey Ln, Middlesboro, KY 40965
5 Abbey Ln, Middlesboro, KY 40965
ABOUT THIS HOME
Middlesborough, KY Homes for Sale
Tired of living in a house where you don't know your neighbors and feel like you can't enjoy your neighborhood? You can change all that with this 3 bedroom, 2 bath HOME in Ambleside subdivision. Have a problem with stairs? Not anymore. Two of the bedrooms and one bath are on the 2nd floor, but one bedroom and bath are on the first level. Nice open concept living room/dining room. You can enjoy your neighborhood sitting on your covered front porch or sitting on your covered patio in your fenced-in back yard. Make an appointment today. We'll be glad to welcome you home.

$249,900

3 beds2 baths1,221 sq ft

5 Abbey Ln, Middlesboro, KY 40965

0.6 acre lot • Garage • Covered front porch

(606) 248-4932

515 Englewood Rd, Middlesboro, KY 40965
515 Englewood Rd, Middlesboro, KY 40965
515 Englewood Rd, Middlesboro, KY 40965
ABOUT THIS HOME
Middlesborough, KY Homes for Sale
Explore this charming home offering a blend of tranquility and convenience! Nestled in town yet surrounded by nature, this rare gem features a spacious walk-out finished basement and an open kitchen/living room with stainless steel appliances. Loft bedroom. Enjoy panoramic views from the expansive glass windows overlooking the . 75-acre yard, perfect for daily wildlife sightings from your living room or balcony. Recently updated, the home boasts beautiful hardwood floors, custom cabinetry, a lifetime warranty metal roof, and a smart HVAC system. Inside, a vaulted wooden ceiling and a striking wooden spiral staircase enhance the home's unique character. The main level includes a generous own

$289,900

3 beds3 baths2,210 sq ft

515 Englewood Rd, Middlesboro, KY 40965

0.75 acre lot • Panoramic views • Hardwood floors

(423) 869-5111

510 Chester Ave, Middlesboro, KY 40965
510 Chester Ave, Middlesboro, KY 40965
510 Chester Ave, Middlesboro, KY 40965
ABOUT THIS HOME
Middlesborough, KY Homes for Sale
Excellent location on this fixer upper in Middlesboro. 3 bed 1 bath, oversized kitchen with a nice level yard. Buyer/buyers agent to verify all information

$55,000

3 beds1 bath1,344 sq ft

510 Chester Ave, Middlesboro, KY 40965

0.3 acre lot • Level yard • Oversized kitchen

(423) 626-6353

119 Wagon Hollow Rd, Middlesboro, KY 40965
119 Wagon Hollow Rd, Middlesboro, KY 40965
119 Wagon Hollow Rd, Middlesboro, KY 40965
ABOUT THIS HOME
Middlesborough, KY Homes for Sale
Welcome to the best of all worlds! One home and an operational store that fronts Highway 217. Several outbuildings and just over 20 acres makes this the perfect property for homesteading as seller had livestock on the property at one time. The land is gently rolling to level, Pineville city water in place, spectrum internet and you're off the beaten path but just a 15 minute drive back into town. (119 Wagon Hollow Rd) has a wrap around porch, large kitchen, dining and living room areas, oversized bathroom with garden tub and stand up shower. Pretty flooring throughout. Kitchen appliances convey with the property. The store (4080 hwy 217) is an adorable cabin style design with wrap around p

$425,000

— beds— baths1,500 sq ft

119 Wagon Hollow Rd, Middlesboro, KY 40965

Wrap around porch • Pineville city water • Large kitchen

(865) 567-5188

Property at 428 Wilderness Rd, Middlesboro, KY 40965, 3 beds, 1 bath

$159,000

3 beds1 bath1,320 sq ft

428 Wilderness Rd, Middlesboro, KY 40965

(423) 869-5111

Property at 416 Winchester Ave, Middlesboro, KY 40965, 6 beds, 4 baths

$105,000

6 beds4 baths2,520 sq ft

416 Winchester Ave, Middlesboro, KY 40965

Property at 440 Sams Mtn, Middlesboro, KY 40965, 3 beds, 2.5 baths

$325,000

3 beds2.5 baths2,512 sq ft

440 Sams Mtn, Middlesboro, KY 40965

(423) 869-3000

Property at 259 Watson Ln, Middlesboro, KY 40965, 3 beds, 1.5 baths

$2,500,000

3 beds1.5 baths1,976 sq ft

259 Watson Ln, Middlesboro, KY 40965

(276) 861-2023

Property at 114 Rochester Ave, Middlesboro, KY 40965, 3 beds, 1.5 baths

$125,000

3 beds1.5 baths1,008 sq ft

114 Rochester Ave, Middlesboro, KY 40965

Property at 10 Thaxted Ln, Middlesboro, KY 40965, 3 beds, 2 baths

$289,900

3 beds2 baths2,096 sq ft

10 Thaxted Ln, Middlesboro, KY 40965

(606) 248-4932

Property at 708 Ilchester Ave, Middlesboro, KY 40965, 3 beds, 2 baths

$210,000

3 beds2 baths1,312 sq ft

708 Ilchester Ave, Middlesboro, KY 40965

(423) 869-3000

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

$209,900

3 beds2 baths1,684 sq ft

1315 Winchester Ave, Middlesboro, KY 40965

(423) 489-9744

Property at 409 Meadow Ln, Middlesboro, KY 40965, 4 beds, 1.5 baths

$189,000

4 beds1.5 baths1,120 sq ft

409 Meadow Ln, Middlesboro, KY 40965

(423) 869-5111

Property at 626 S 22nd St, Middlesboro, KY 40965, 3 beds, 2 baths

$190,000

3 beds2 baths1,456 sq ft

626 S 22nd St, Middlesboro, KY 40965

(423) 626-6353

Property at 832 North 25th St, Middlesboro, KY 40965, 6 beds, 3.5 baths

$329,900

6 beds3.5 baths4,033 sq ft

832 North 25th St, Middlesboro, KY 40965

Property at 921 Winchester Ave, Middlesboro, KY 40965, 3 beds, 2 baths

$115,000

3 beds2 baths1,344 sq ft

921 Winchester Ave, Middlesboro, KY 40965

(276) 861-2023

Property at 105 Mudlick Rd, Middlesboro, KY 40965, 3 beds, 1 bath

$190,000

3 beds1 bath996 sq ft

105 Mudlick Rd, Middlesboro, KY 40965

(423) 869-3121

Property at 4921 W Cumberland Ave, Middlesboro, KY 40965, 3 beds, 2 baths

$256,000

3 beds2 baths1,900 sq ft

4921 W Cumberland Ave, Middlesboro, KY 40965

(423) 869-3000

Property at 180 Stevenson Branch Rd, Middlesboro, KY 40965, 3 beds, 1 bath

$182,050

3 beds1 bath1,200 sq ft

180 Stevenson Branch Rd, Middlesboro, KY 40965

(423) 869-5111

Property at 138 Robinson Ln, Middlesboro, KY 40965, 3 beds, 2 baths

$150,000

3 beds2 baths648 sq ft

138 Robinson Ln, Middlesboro, KY 40965

(423) 869-5111

Property at 164 Walker Ln, Middlesboro, KY 40965, 3 beds, 1.5 baths

$179,900

3 beds1.5 baths1,040 sq ft

164 Walker Ln, Middlesboro, KY 40965

(423) 869-3000

Property at 900 Twin Fawn Trl, Middlesboro, KY 40965, 3 beds, 2 baths

$320,000

3 beds2 baths2,270 sq ft

900 Twin Fawn Trl, Middlesboro, KY 40965

(423) 626-6353

Property at 523 N 30th St, Middlesboro, KY 40965, 5 beds, 4 baths

$458,000

5 beds4 baths3,146 sq ft

523 N 30th St, Middlesboro, KY 40965

(423) 869-5111

Property at 825 S 28th St, Middlesboro, KY 40965, 4 beds, 2.5 baths

$260,000

4 beds2.5 baths2,020 sq ft

825 S 28th St, Middlesboro, KY 40965

(606) 248-4932

Property at 515 N 25th St, Middlesboro, KY 40965, 3 beds, 1 bath

$195,000

3 beds1 bath2,000 sq ft

515 N 25th St, Middlesboro, KY 40965

(423) 626-6353

Property at 112 Exeter Ave, Middlesboro, KY 40965, 2 beds, 1 bath

$109,900

2 beds1 bath1,236 sq ft

112 Exeter Ave, Middlesboro, KY 40965

Property at 4922 W Cumberland Ave, Middlesboro, KY 40965, 3 beds, 2 baths

$249,900

3 beds2 baths1,989 sq ft

4922 W Cumberland Ave, Middlesboro, KY 40965

(606) 248-4932

Property at 516 S 34th St, Middlesboro, KY 40965, 2 beds, 1 bath

$650,000

2 beds1 bath776 sq ft

516 S 34th St, Middlesboro, KY 40965

(423) 869-3000

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

$192,900

3 beds2 baths1,408 sq ft

106 S 38th St, Middlesboro, KY 40965

(606) 248-4932

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

$259,900

3 beds2.5 baths2,016 sq ft

301 Doe's Xing, Middlesboro, KY 40965

(276) 861-2023

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

$157,000

3 beds1 bath1,110 sq ft

1005 Hollywood Dr, Middlesboro, KY 40965

(423) 869-0075

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

$297,500

5 beds3.5 baths3,000 sq ft

2410 Cumberland Ave, Middlesboro, KY 40965

(606) 248-4932

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

$119,000

3 beds2 baths1,296 sq ft

252 Chasteen Dr, Middlesboro, KY 40965

(276) 861-2023

Property at 0 Home Run Rd, Middlesboro, KY 40965

$18,500

— beds— baths— sq ft

0 Home Run Rd, Middlesboro, KY 40965

(276) 861-2023

Property at Hwy 217, Middlesboro, KY 40965

$139,900

— beds— baths— sq ft

Hwy 217, Middlesboro, KY 40965

(423) 489-9744

Property at 321 Chester Ave, Middlesboro, KY 40965

$349,900

— beds— baths— sq ft

321 Chester Ave, Middlesboro, KY 40965

(606) 248-4932

Property at 0 Wells Camp Rd, Middlesboro, KY 40965

$7,500

— beds— baths— sq ft

0 Wells Camp Rd, Middlesboro, KY 40965

Property at 0 Highway 217, Middlesboro, KY 40965

$29,900

— beds— baths— sq ft

0 Highway 217, Middlesboro, KY 40965

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Average home prices near Middlesborough, KY

Cities

Zip Codes

40965 homes for sale
$197,000
40977 homes for sale
$219,900

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)

$272,700

+21.3% YoY | Jun 2025

1 year
3 year
5 year

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

Location

Data

Jun 2025

Growth

% YoY

Middlesborough, KY

$272,700

+21.3%

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