Middlesborough, KY homes for sale & real estate

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ABOUT THIS HOME
Middlesborough, KY Homes for Sale
Charming 3-Bedroom Home in a Prime Location! Discover comfort and convenience in this beautifully maintained 3-bedroom, 2-bathroom home located close to shopping, restaurants, schools, and parks — everything you need is just minutes away! Inside, you'll find a warm and inviting layout featuring hardwood and vinyl flooring, offering both style and durability. The spacious living areas are perfect for relaxing or entertaining family and friends. Step outside to enjoy a generous yard with two outdoor storage sheds, providing plenty of room for tools, hobbies, or extra storage. Whether you're a first-time buyer, growing family, or possibly downsizing, this home has something for eve

$235,000

3 beds2 baths1,900 sq ft

4921 W Cumberland Ave, Middlesboro, KY 40965

Generous yard • 0.36 acre lot • 2 garage spots

(865) 345-5050

ABOUT THIS HOME
Middlesborough, KY Homes for Sale
Newly Remodeled, move-in ready home. This home is nestled in the heart of Middlesboro on a . 489 acre lot. This home has 3 bedrooms and 2 newly renovated bathrooms. The washer and dryer will stay with home. This quiet cozy home has a log cabin look with a large covered front porch. I also has a carport or breezeway to get to the garage. This home also has a fenced in chicken coop. All the amenities are easily accessible.

$172,000

3 beds2 baths934 sq ft

45 Fourmile Run Rd, Middlesboro, KY 40965

Move in ready • Newly remodeled • 0.49 acre lot

ABOUT THIS HOME
Middlesborough, KY Homes for Sale
This home rest on a lot that goes from city street to ally. This home has 3 bedrooms and one bath with a large kitchen and large living room. This home needs some attention but has a lot of potential. The downstairs could be used as apartment or extra living space. There is another home on the property and might be possible to repair.

$180,000

3 beds1 bath792 sq ft

918 E Cumberland Ave, Middlesboro, KY 40965

3,750 sq ft lot • Built 1991 • Listed 35 days

ABOUT THIS HOME
Middlesborough, KY Homes for Sale
If you have been looking for a home to call your own, don't miss out on this lovely home with a white picket fence. A spacious 1,800 sf home with 3 bedrooms and 2 bathrooms on a large lot with a fenced-in back yard. You will love the kitchen with granite countertops and the laminate and tile flooring throughout. Don't let this one get away. We'll be happy to show you how this home can be your home.

$205,000

3 beds2 baths1,800 sq ft

140 Chasteen Dr, Middlesboro, KY 40965

Fenced-in back yard • Granite countertops • 0.3 acre lot

(606) 248-4932

ABOUT THIS HOME
Middlesborough, KY Homes for Sale
First Time on The Market this gorgeous contemporary home was custom built in 2022 with approximately 4,331 SF including the 2 car attached garage. This home has 3 'En Suites' plus 2 more bedrooms for a total of 5 bedrooms and 4 full bathrooms. The unique ceilings were designed just for this home! You will find the large living room to be relaxing with a built-in electric fireplace. The custom kitchen has lots of cabinets and countertops and an island plus a walk-in pantry making this kitchen a dream! The dining room extends from the kitchen with lots of windows! The laundry room has a large sink and leads to the attached 2 car garage. The main 'En Suite' is on the main floor and extends

$569,999

5 beds4 baths4,331 sq ft

850 Big Buck Ln, Middlesboro, KY 40965

Unique ceilings • Covered front porch • Custom built

(276) 861-2023

Property at 280 Parker Ln, Middlesboro, KY 40965, 3 beds, 2 baths

$235,000

3 beds2 baths1,375 sq ft

280 Parker Ln, Middlesboro, KY 40965

(423) 626-6353

Property at 3008 State Highway 441, Middlesboro, KY 40965, 3 beds, 1.5 baths

$169,000

3 beds1.5 baths1,800 sq ft

3008 State Highway 441, Middlesboro, KY 40965

(423) 869-5111

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

$329,900

6 beds3.5 baths4,033 sq ft

832 N 25th St, Middlesboro, KY 40965

Property at 6 Hampton Ct, Middlesboro, KY 40965, 4 beds, 3 baths

$249,000

4 beds3 baths1,966 sq ft

6 Hampton Ct, Middlesboro, KY 40965

Property at 1720 Exeter Ave, Middlesboro, KY 40965, 2 beds, 1 bath

$75,000

2 beds1 bath1,456 sq ft

1720 Exeter Ave, Middlesboro, KY 40965

(423) 626-6353

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

$115,000

3 beds2 baths1,296 sq ft

252 Chasteen Dr, Middlesboro, KY 40965

(423) 869-3121

Property at 1203 Winchester Ave, Middlesboro, KY 40965, 4 beds, 2.5 baths

$229,900

4 beds2.5 baths2,456 sq ft

1203 Winchester Ave, Middlesboro, KY 40965

(606) 248-4932

Property at 903 Ilchester Ave, Middlesboro, KY 40965, 2 beds, 1 bath

$112,000

2 beds1 bath1,056 sq ft

903 Ilchester Ave, Middlesboro, KY 40965

Property at 2702 Cumberland Ave, Middlesboro, KY 40965, 4 beds, 2.5 baths

$369,900

4 beds2.5 baths3,885 sq ft

2702 Cumberland Ave, Middlesboro, KY 40965

Property at 805 Worchester Ave, Middlesboro, KY 40965, 5 beds, 3 baths

$349,900

5 beds3 baths2,250 sq ft

805 Worchester Ave, Middlesboro, KY 40965

(423) 869-3000

Property at 807 Exeter Ave, Middlesboro, KY 40965, 3 beds, 2 baths

$249,900

3 beds2 baths1,200 sq ft

807 Exeter Ave, Middlesboro, KY 40965

(423) 489-9744

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

$279,900

3 beds3 baths2,210 sq ft

515 Englewood Rd, Middlesboro, KY 40965

(423) 869-5111

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

$179,900

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

$145,000

3 beds2 baths648 sq ft

138 Robinson Ln, Middlesboro, KY 40965

(423) 869-5111

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

$184,900

4 beds1.5 baths1,120 sq ft

409 Meadow Ln, Middlesboro, KY 40965

(423) 869-5111

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

$198,500

2 beds2 baths1,144 sq ft

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

(423) 869-5111

Property at 129 Lower Gibson Ln, Middlesboro, KY 40965, 3 beds, 2.5 baths

$245,000

3 beds2.5 baths1,856 sq ft

129 Lower Gibson Ln, Middlesboro, KY 40965

(423) 869-3000

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

$180,000

3 beds2 baths1,312 sq ft

708 Ilchester Ave, Middlesboro, KY 40965

(423) 869-3000

Property at 220 Windermere Dr, Middlesboro, KY 40965, 3 beds, 2.5 baths

$269,500

3 beds2.5 baths1,692 sq ft

220 Windermere Dr, Middlesboro, KY 40965

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

$175,000

3 beds1 bath996 sq ft

105 Mudlick Rd, Middlesboro, KY 40965

(423) 869-3121

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

$299,000

3 beds4 baths2,349 sq ft

915 Lothbury Ave, 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 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 63 Old Pineville Pike, Middlesboro, KY 40965, 3 beds, 2 baths

$185,000

3 beds2 baths1,560 sq ft

63 Old Pineville Pike, Middlesboro, KY 40965

(276) 861-2023

Property at 310 Barkley Dr, Middlesboro, KY 40965, 2 beds, 1 bath

$100,000

2 beds1 bath910 sq ft

310 Barkley Dr, Middlesboro, KY 40965

(423) 869-3000

Property at 119 Wagon Hollow Rd, Middlesboro, KY 40965

$250,000

— beds— baths1,500 sq ft

119 Wagon Hollow Rd, Middlesboro, KY 40965

(865) 567-5188

Property at 00 Highway 217 & 1344 Tract 2, Middlesboro, KY 40965

$285,000

0 beds— baths— sq ft

00 Highway 217 & 1344 Tract 2, Middlesboro, KY 40965

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

$110,000

2 beds1 bath1,008 sq ft

413 S 26th 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 118 Polly Hollow Right Fork Rd, Middlesboro, KY 40965

$17,500

— beds— baths— sq ft

118 Polly Hollow Right Fork Rd, Middlesboro, KY 40965

(423) 869-3000

Property at LOT 9 Brush Mountain Cir, Middlesboro, KY 40856

$29,900

— beds— baths— sq ft

LOT 9 Brush Mountain Cir, Middlesboro, KY 40856

Property at 0 Home Run Rd, Middlesboro, KY 40965

$17,000

— beds— baths— sq ft

0 Home Run Rd, Middlesboro, KY 40965

(276) 861-2023

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Average home prices near Middlesborough, KY

Cities

Zip Codes

40965 homes for sale
$198,500
40977 homes for sale
$224,900

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)

$180,000

-5.0% YoY | Oct 2025

1 year
3 year
5 year

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

Location

Data

Oct 2025

Growth

% YoY

Middlesborough, KY

$180,000

-5.0%

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