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Homes Recently Sold in Middlesboro, KY | Page 2

223 Homes
 
314 Picadilly Ct, Middlesboro, KY 40965
  • $293,000
  • 4Bd
  • 3Ba
  • 2,576 Sq Ft
SOLD
220 Windermere Dr, Middlesboro, KY 40965
  • $240,000
  • 3Bd
  • 3Ba
  • 1,692 Sq Ft
SOLD
3008 State Highway 441, Middlesboro, KY 40965
  • $168,700
  • 3Bd
  • 2Ba
  • 1,800 Sq Ft
SOLD
850 Big Buck Ln, Middlesboro, KY 40965
  • $555,000
  • 5Bd
  • 4Ba
  • 4,331 Sq Ft
SOLD
101 Earle Ln, Middlesboro, KY 40965
  • $87,000
  • 3Bd
  • 2Ba
  • 1,104 Sq Ft
SOLD
708 Ilchester Ave, Middlesboro, KY 40965
  • $175,000
  • 3Bd
  • 2Ba
  • 1,312 Sq Ft
SOLD
1308 Gloucester Ave, Middlesboro, KY 40965
  • $539,000
  • 5Bd
  • 4Ba
  • 4,829 Sq Ft
SOLD
114 Rochester Ave, Middlesboro, KY 40965
  • $175,000
  • 3Bd
  • 2Ba
  • 1,008 Sq Ft
SOLD
Arie Turner Lane, Middlesboro, KY 40965
  • $26,000
  • 2 Acre
SOLD
515 N 25th St, Middlesboro, KY 40965
  • $196,000
  • 3Bd
  • 1Ba
  • 2,000 Sq Ft
SOLD
192 Owens Ln, Middlesboro, KY 40965
  • $145,000
  • 3Bd
  • 1Ba
  • 2,600 Sq Ft
SOLD
234 S 46th St, Middlesboro, KY 40965
  • $90,000
  • 3Bd
  • 2Ba
  • 924 Sq Ft
SOLD
5 Abbey Ln, Middlesboro, KY 40965
  • $239,500
  • 3Bd
  • 2Ba
  • 1,221 Sq Ft
SOLD
4163 441, Middlesboro, KY 40965
  • $8,000
  • 0.4 Acre
SOLD
900 Twin Fawn Trl, Middlesboro, KY 40965
  • $290,000
  • 3Bd
  • 2Ba
  • 2,270 Sq Ft
SOLD
109 Hollywood Dr, Middlesboro, KY 40965
  • $275,000
  • 3Bd
  • 3Ba
  • 3,544 Sq Ft
SOLD
428 Wilderness Rd, Middlesboro, KY 40965
  • $147,000
  • 3Bd
  • 1Ba
  • 1,320 Sq Ft
SOLD
825 S 28th St, Middlesboro, KY 40965
  • $231,000
  • 4Bd
  • 3Ba
  • 2,020 Sq Ft
SOLD
106 S 38th St, Middlesboro, KY 40965
  • $180,000
  • 3Bd
  • 2Ba
  • 1,404 Sq Ft
SOLD
lot Apt 2 Bellwood, Middlesboro, KY 40965
  • $22,500
  • 0.28 Acre
SOLD
lot Apt 1 Bellwood, Middlesboro, KY 40965
  • $10,000
  • 0.28 Acre
SOLD
102 Stone Creek Dr, Middlesboro, KY 40965
  • $152,500
  • 2Bd
  • 1Ba
  • 952 Sq Ft
SOLD
115 George Ann Dr, Middlesboro, KY 40965
  • $271,500
  • 3Bd
  • 2Ba
  • 2,008 Sq Ft
SOLD
lot Apt 6 Bellwood Rd, Middlesboro, KY 40965
  • $13,000
  • 0.41 Acre
SOLD
414 SE North 24th St, Middlesboro, KY 40965
  • $167,000
  • 4Bd
  • 2Ba
  • 1,600 Sq Ft
SOLD
919 Rochester Ave, Middlesboro, KY 40965
  • $167,000
  • 4Bd
  • 2Ba
  • 2,024 Sq Ft
SOLD
423 N 10th St, Middlesboro, KY 40965
  • $1,250,000
  • —Bd
  • —Ba
SOLD
515 Winchester Ave, Middlesboro, KY 40965
  • $60,000
  • 3Bd
  • 1Ba
  • 1,100 Sq Ft
SOLD
10 Thaxted Ln, Middlesboro, KY 40965
  • $280,000
  • 3Bd
  • 2Ba
  • 2,096 Sq Ft
SOLD
4922 W Cumberland Ave, Middlesboro, KY 40965
  • $220,000
  • 3Bd
  • 2Ba
  • 1,989 Sq Ft
SOLD
2824 W Cumberland Ave, Middlesboro, KY 40965
  • $390,000
  • 4Bd
  • 3Ba
  • 2,500 Sq Ft
SOLD
206 Nottingham Dr, Middlesboro, KY 40965
  • $190,000
  • 2Bd
  • 2Ba
  • 1,059 Sq Ft
SOLD
Photos coming soon
  • $70,000
  • 4Bd
  • 2Ba
  • 1,200 Sq Ft
SOLD
709 Balmoral Rd, Middlesboro, KY 40965
  • $275,000
  • 4Bd
  • 2Ba
  • 1,950 Sq Ft
SOLD
218 Windermere Dr, Middlesboro, KY 40965
  • $225,000
  • 3Bd
  • 2Ba
  • 1,296 Sq Ft
SOLD
238 Windermere Dr, Middlesboro, KY 40965
  • $265,000
  • 3Bd
  • 2Ba
  • 1,603 Sq Ft
SOLD
3202 W Cumberland Ave, Middlesboro, KY 40965
  • $107,500
  • 3Bd
  • 2Ba
  • 2,044 Sq Ft
SOLD
1809 Exeter Ave, Middlesboro, KY 40965
  • $40,000
  • 3Bd
  • 1Ba
  • 1,064 Sq Ft
SOLD
1813 Winchester Ave, Middlesboro, KY 40965
  • $65,000
  • 2Bd
  • 1Ba
  • 1,008 Sq Ft
SOLD
422 Wilderness Rd, Middlesboro, KY 40965
  • $134,500
  • 2Bd
  • 1Ba
  • 850 Sq Ft
SOLD
3575 Highway 441, Middlesboro, KY 40965
  • $60,000
  • 2Bd
  • 1Ba
  • 1,204 Sq Ft
SOLD
112 Parker Ln, Middlesboro, KY 40965
  • $148,400
  • 3Bd
  • 2Ba
  • 1,439 Sq Ft
SOLD
600 S 38th St, Middlesboro, KY 40965
  • $90,000
  • 2Bd
  • 1Ba
  • 1,040 Sq Ft
SOLD
810 S 28th St, Middlesboro, KY 40965
  • $160,000
  • 3Bd
  • 2Ba
  • 1,040 Sq Ft
SOLD
524 E Lothbury Ave, Middlesboro, KY 40965
  • $160,000
  • 2Bd
  • 1Ba
  • 800 Sq Ft
SOLD
9 Ennismore Dr, Middlesboro, KY 40965
  • $270,800
  • 3Bd
  • 3Ba
  • 1,974 Sq Ft
SOLD
2817 Ky 441, Middlesboro, KY 40965
  • $135,000
  • 3Bd
  • 2Ba
  • 1,272 Sq Ft
SOLD
135 Highpoint Rd, Middlesboro, KY 40965
  • $290,000
  • 3Bd
  • 1Ba
  • 1,200 Sq Ft
SOLD
123 Twin Acres Rd, Middlesboro, KY 40965
  • $272,700
  • 4Bd
  • 2Ba
  • 3,338 Sq Ft
SOLD
101 Kim Ln, Middlesboro, KY 40965
  • $400,000
  • 5Bd
  • 4Ba
  • 3,874 Sq Ft
SOLD
51 - 100 of 223 Homes in Middlesboro, KY
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Middlesboro, KY real estate market trends

Statistics as of September 2026
$184K
Avg. list price
$98/Sqft
Avg. price/sqft
62
Homes for sale
1,707 Sqft
Avg. home size
107 Days
Avg. days on market
Movoto makes it easy to track market trends in Middlesboro, KY. Whether you’re entering the market or planning your next move, understanding these key metrics can guide smart decisions. Looking for more detailed housing market stats in Middlesboro, KY?
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