Recently Sold Homes in Middlesborough, KY

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SOLD NOV 3, 2025

ABOUT THIS HOME
Recently Sold Home in Middlesborough, KY:
This 3,544 sf home built approximately in 1965 was completely remodeled and updated in 2022. The list of upgrades is extensive! In addition to all updated electrical wiring with new switches, new receptacles (including GFI outlets), and new LED lighting, a new roof, TWO new HVAC units, new crown molding, new baseboards, and new paint, the kitchen cabinets were refinished with all new hardware, new countertops were installed, a new sink and faucet were installed, and a new tile floor was installed. The library has recessed lighting an French doors. Both the entertainment room and the den had new recessed lighting, new carpet and new paint. The dining room and formal living room both got new

$275,000 Last sold price

3 beds2.5 baths3,544 sq ft

109 Hollywood Dr, Middlesboro, KY 40965

(606) 248-4932

SOLD OCT 10, 2025

ABOUT THIS HOME
Recently Sold Home in Middlesborough, KY:
2-bedroom 1 bath on corner lot with 1 year old roof! Fenced in level yard and then some, so don't let the fence size throw you off. This beauty has a cathedral ceiling, with open floor plan. extremely well-maintained home perfect for a first-time home buyer! COME SEE!

$152,500 Last sold price

2 beds1 bath952 sq ft

102 Stone Creek Dr, Middlesboro, KY 40965

(423) 626-6353

SOLD NOV 19, 20253D WALKTHROUGH

ABOUT THIS HOME
Recently Sold Home in Middlesborough, KY:
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.

$239,500 Last sold price

3 beds2 baths1,221 sq ft

5 Abbey Ln, Middlesboro, KY 40965

(606) 248-4932

SOLD SEP 15, 2025

ABOUT THIS HOME
Recently Sold Home in Middlesborough, KY:
Looking for a home and an investment opportunity? This property offers two separate living spaces under one roof�each featuring 2 bedrooms and 1 bath. Ideal for multi-generational living or rental income. Enjoy a spacious backyard and a convenient location just minutes from downtown Middlesboro, KY.

$167,000 Last sold price

4 beds2 baths2,024 sq ft

919 Rochester Ave, Middlesboro, KY 40965

(423) 869-5111

SOLD NOV 19, 2025

ABOUT THIS HOME
Recently Sold Home in Middlesborough, KY:
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!

$90,000 Last sold price

3 beds2 baths924 sq ft

234 S 46th St, Middlesboro, KY 40965

(423) 626-6353

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

$180,000 Last sold price

3 beds2 baths1,408 sq ft

106 S 38th St, Middlesboro, KY 40965

(606) 248-4932

Property at 115 George Ann Dr, Middlesboro, KY 40965, 3 beds, 2 baths

$271,500 Last sold price

3 beds2 baths2,008 sq ft

115 George Ann Dr, Middlesboro, KY 40965

(423) 869-5111

Property at 414 SE North 24th St, Middlesboro, KY 40965, 4 beds, 2 baths

$167,000 Last sold price

4 beds2 baths1,600 sq ft

414 SE North 24th St, Middlesboro, KY 40965

(423) 869-5111

Property at 515 Winchester Ave, Middlesboro, KY 40965, 3 beds, 1 bath

$60,000 Last sold price

3 beds1 bath1,100 sq ft

515 Winchester Ave, Middlesboro, KY 40965

(423) 626-6353

Property at 101 Shillalah Spur, Miracle, KY 40856, 3 beds, 2 baths

$180,000 Last sold price

3 beds2 baths1,036 sq ft

101 Shillalah Spur, Miracle, KY 40856

Property at 50 Davidson Ln, Miracle, KY 40856, 2 beds, 1 bath

$130,000 Last sold price

2 beds1 bath676 sq ft

50 Davidson Ln, Miracle, KY 40856

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

$231,000 Last sold price

4 beds2.5 baths2,020 sq ft

825 S 28th St, Middlesboro, KY 40965

(606) 248-4932

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

$290,000 Last sold price

3 beds2 baths2,270 sq ft

900 Twin Fawn Trl, Middlesboro, KY 40965

(423) 626-6353

Property at 305 N 15th St, Middlesboro, KY 40965, 2 beds, 1 bath

$50,000 Last sold price

2 beds1 bath876 sq ft

305 N 15th St, Middlesboro, KY 40965

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

$147,000 Last sold price

3 beds1 bath1,320 sq ft

428 Wilderness Rd, Middlesboro, KY 40965

(423) 869-5111

Property at 192 Owens Ln, Middlesboro, KY 40965, 3 beds, 1 bath

$145,000 Last sold price

3 beds1 bath2,600 sq ft

192 Owens Ln, Middlesboro, KY 40965

(423) 869-3000

Property at 4163 441, Middlesboro, KY 40965

$8,000 Last sold price

— beds— baths— sq ft

4163 441, Middlesboro, KY 40965

Property at 423 N 10th St, Middlesboro, KY 40965

$1,250,000 Last sold price

— beds— baths— sq ft

423 N 10th St, Middlesboro, KY 40965

(606) 248-4932

Property at Lot #2 Bellwood, Middlesboro, KY 40965

$22,500 Last sold price

— beds— baths— sq ft

Lot #2 Bellwood, Middlesboro, KY 40965

Property at Lot #6 Bellwood Rd, Middlesboro, KY 40965

$13,000 Last sold price

— beds— baths— sq ft

Lot #6 Bellwood Rd, Middlesboro, KY 40965

Property at Lot #1 Bellwood, Middlesboro, KY 40965

$10,000 Last sold price

— beds— baths— sq ft

Lot #1 Bellwood, Middlesboro, KY 40965

Property at Arie Turner Ln, Middlesboro, KY 40965

$26,000 Last sold price

— beds— baths— sq ft

Arie Turner Ln, Middlesboro, KY 40965

(276) 861-2023

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Recently Sold Homes in Middlesborough

There are currently 22 recently sold homes for sale in Middlesborough at a median listing price of $188K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Middlesborough stay on the market for 116 days. This map is refreshed with the newest listings in Middlesborough every 15 minutes.

In the past month, 5 homes have been sold in Middlesborough. In addition to houses in Middlesborough, there was also 1 condo, 0 townhouses, and 0 multi-family units for sale in Middlesborough last month. Find your dream home in Middlesborough using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Middlesborough are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Middlesborough. Our Middlesborough real estate stats and trends will give you more information about home buying and selling trends in Middlesborough. If you're looking to sell your home in the Middlesborough area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Middlesborough with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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