Middlesborough, KY homes for sale & real estate

55 homes

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Recommended

$75,000

2 beds1 bath1,456 sq ft

1720 Exeter Ave, Middlesboro, KY 40965

Fenced in corner lot • Outdoor space • 0.4 acre lot

(423) 626-6353

ABOUT THIS HOME
Middlesborough, KY Homes for Sale
50 Davidson Lane, Miracle, KY | 2 Bed • 1 Bath • Chalet • Approximately 2.13 Acres (per seller; sits on two parcels). Chalet-style home with rustic charm 2 bedrooms, 1 bathroom Situated on 2.13 acres (per seller) Well and septic system Kitchen appliances, washer, and dryer convey Large outbuilding for storage/workshop Quiet, private setting Across from Boone's Ridge Wildlife Refuge Abundant wildlife: bear, turkey, bobcat, elk & more Perfect for those seeking a weekend retreat, investment, or permanent residence in a serene natural setting. Buyer to verify all pertinent information.

$165,000

2 beds1 bath676 sq ft

50 Davidson Ln, Miracle, KY 40856

Abundant wildlife • 2.13 acre lot • Built 2005

ABOUT THIS HOME
Middlesborough, KY Homes for Sale
NO RESTRICTIONS! Right outside city limits (with city amenities but no taxes) and close to trailheads you'll find this newly renovated, VERY NICE, single wide with 3 bedrooms and 2 baths, 3 porches, nice level land with a firepit and the mountains in your back yard! Perfect for a rental property or air bnb or your own place to call home!

$108,000

3 beds2 baths924 sq ft

234 S 46th St, Middlesboro, KY 40965

Firepit • Close to trailheads • Level land

(423) 626-6353

ABOUT THIS HOME
Middlesborough, KY Homes for Sale
Don't miss this opportunity to own a historic home on Cumberland Avenue with a rare corner lot. This 3,800 sq ft turn of the century home, that has been completely updated, boasts 4 bedrooms, 2 full baths and 1 half bath. On the primary level you'll find a covered front porch, sun room, large living room, and oversized dedicated dining area. Off of the dining room, you'll find a massive kitchen with a huge island and bar stools ready to host dinner parties. Also on the primary level you will find the primary suite with attached full bathroom. Off of the kitchen there is also a half bath for guests. On the second level of the home, you'll find 3 more great sized bedrooms and a full bathroom

$398,500

4 beds2.5 baths3,885 sq ft

2702 Cumberland Ave, Middlesboro, KY 40965

Covered front porch • Sun room • Large living room

ABOUT THIS HOME
Middlesborough, KY Homes for Sale
BEAUTIFUL MOVE IN READY HOME IN AMBLESIDE. Discover your next home in Ambleside, a tranquil subdivision in the heart of Middlesboro outside the city limits. With the beautiful landscaped yard that offers a warm, inviting atmosphere. Enjoy the peaceful suburban setting with the convenience of nearby amenities including shopping, dining, parks and entertainment. This home has 3 bedrooms with the primary bedroom having a walk-in closet and full bath. There is a finished bonus room upstairs for a family room or office. The utility room is on the main floor next to the garage. The kitchen has plenty of storage space with oak custom cabinets and includes the refrigerator, stove with an above micr

$269,500

3 beds2.5 baths1,692 sq ft

220 Windermere Dr, Middlesboro, KY 40965

Utility room • Finished bonus room • Flat lot

Property at 850 Big Buck Ln, Middlesboro, KY 40965, 5 beds, 4 baths

$599,000

5 beds4 baths4,331 sq ft

850 Big Buck Ln, Middlesboro, KY 40965

(276) 861-2023

Property at 101 Earle Ln, Middlesboro, KY 40965, 3 beds, 2 baths

$98,000

3 beds2 baths1,104 sq ft

101 Earle Ln, Middlesboro, KY 40965

(423) 869-3000

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

$188,000

3 beds1.5 baths1,800 sq ft

3008 State Highway 441, Middlesboro, KY 40965

(423) 869-5111

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

$249,900

4 beds2.5 baths2,456 sq ft

1203 Winchester Ave, Middlesboro, KY 40965

(606) 248-4932

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

$105,000

2 beds1 bath910 sq ft

310 Barkley Dr, Middlesboro, KY 40965

(423) 869-3000

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

$299,900

3 beds2 baths2,270 sq ft

900 Twin Fawn Trl, Middlesboro, KY 40965

(423) 626-6353

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

$299,900

3 beds2.5 baths2,512 sq ft

440 Sams Mtn, Middlesboro, KY 40965

(423) 869-3000

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

$199,000

3 beds2 baths1,312 sq ft

708 Ilchester Ave, Middlesboro, KY 40965

(423) 869-3000

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

$100,000

6 beds4 baths2,520 sq ft

416 Winchester Ave, Middlesboro, KY 40965

Property at 63 Old Pineville Pike, Middlesboro, KY 40965, 3 beds, 2 baths

$199,900

3 beds2 baths1,560 sq ft

63 Old Pineville Pike, Middlesboro, KY 40965

(276) 861-2023

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 209 Dalewood Rd, Middlesboro, KY 40965, 4 beds, 2 baths

$115,000

4 beds2 baths1,568 sq ft

209 Dalewood Rd, Middlesboro, KY 40965

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

$230,000

3 beds2 baths1,900 sq ft

4921 W Cumberland Ave, Middlesboro, KY 40965

(423) 869-3000

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 5 Abbey Ln, Middlesboro, KY 40965, 3 beds, 2 baths

$249,900

3 beds2 baths1,221 sq ft

5 Abbey Ln, Middlesboro, KY 40965

(606) 248-4932

Property at 119 Wagon Hollow Rd, Middlesboro, KY 40965

$300,000

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

$249,900

4 beds2.5 baths2,020 sq ft

825 S 28th St, Middlesboro, KY 40965

(606) 248-4932

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

$184,999

3 beds1 bath996 sq ft

105 Mudlick Rd, Middlesboro, KY 40965

(423) 869-3121

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 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 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 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 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 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 4163 441, Middlesboro, KY 40965

$10,500

— beds— baths— sq ft

4163 441, Middlesboro, KY 40965

Property at 1107 Winchester Ave, Middlesboro, KY 40965

$49,900

— beds— baths— sq ft

1107 Winchester Ave, Middlesboro, KY 40965

(606) 248-4932

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 Wells Camp Rd, Middlesboro, KY 40965

$7,500

— beds— baths— sq ft

0 Wells Camp Rd, Middlesboro, KY 40965

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Average home prices near Middlesborough, KY

Cities

Zip Codes

40965 homes for sale
$204,900
40977 homes for sale
$180,000

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)

$247,500

+90.5% YoY | Aug 2025

1 year
3 year
5 year

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

Location

Data

Aug 2025

Growth

% YoY

Middlesborough, KY

$247,500

+90.5%

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