Movoto Real Estate

Middlesboro, KY Homes for Sale & Real Estate

74 Homes
 
225 Sherwood Rd, Middlesboro, KY 40965
  • $469,900
  • 3Bd
  • 3Ba
  • 3,258 Sq Ft
New 31 Hours
230 Windermere Dr, Middlesboro, KY 40965
  • $274,000
  • 3Bd
  • 2Ba
  • 2,099 Sq Ft
New 34 Hours
508 Worchester Ave, Middlesboro, KY 40965
  • $234,900
  • 3Bd
  • 2Ba
  • 2,191 Sq Ft
New 4 Days
0 Bowling Rd, Middlesboro, KY 40965
  • $25,000
  • 0.9 Acre
616 Balmoral Rd, Middlesboro, KY 40965
  • $239,900
  • 3Bd
  • 3Ba
  • 1,710 Sq Ft
2247 State Highway 188, Middlesboro, KY 40965
  • $625,000
  • 4Bd
  • 5Ba
  • 5,426 Sq Ft
406 N 25th St, Middlesboro, KY 40965
  • $285,000
  • 3Bd
  • 2Ba
  • 2,400 Sq Ft
114 E Rochester Ave, Middlesboro, KY 40965
  • $175,500
  • 3Bd
  • 1Ba
  • 1,066 Sq Ft
717 S 27th St, Middlesboro, KY 40965
  • $227,000
  • 5Bd
  • 4Ba
  • 3,195 Sq Ft
$40.5K
103 Sherwood Rd, Middlesboro, KY 40965
  • $320,000
  • 5Bd
  • 3Ba
  • 3,000 Sq Ft
$20K
88 Tracy Ridge Rd, Middlesboro, KY 40965
  • $235,000
  • 3Bd
  • 2Ba
  • 1,600 Sq Ft
1015 Old Wilson Ln, Middlesboro, KY 40965
  • $299,000
  • 4Bd
  • 3Ba
  • 2,488 Sq Ft
$16K
810 W Rochester Ave, Middlesboro, KY 40965
  • $145,900
  • 3Bd
  • 2Ba
  • 1,386 Sq Ft
1801 1801 12 Exeter Ave, Middlesboro, KY 40965
  • $175,000
  • 2Bd
  • 1Ba
  • 700 Sq Ft
113 N 18th St, Middlesboro, KY 40965
  • $1,750,000
  • 0.5 Acre
305 N 15th St, Middlesboro, KY 40965
  • $150,000
  • 2Bd
  • 1Ba
  • 876 Sq Ft
$8K
312 Blakely Ln, Middlesboro, KY 40965
  • $139,000
  • 5.33 Acre
1102 W Chester Ave, Middlesboro, KY 40965
  • $199,000
  • 3Bd
  • 1Ba
  • 1,480 Sq Ft
2004 Twin Fawn Tr, Middlesboro, KY 40965
  • $475,000
  • 5Bd
  • 3Ba
  • 2,542 Sq Ft
8 Castleford Way, Middlesboro, KY 40965
  • $160,000
  • 3Bd
  • 2Ba
  • 1,168 Sq Ft
$15K
412 N 24th St, Middlesboro, KY 40965
  • $105,900
  • 3Bd
  • 2Ba
  • 1,966 Sq Ft
2010 Twin Fawn Trl, Middlesboro, KY 40965
  • $575,000
  • 3Bd
  • 2Ba
  • 2,016 Sq Ft
708 W Chester Ave, Middlesboro, KY 40965
  • $129,000
  • 3Bd
  • 1Ba
  • 1,404 Sq Ft
706 Ilchester Ave, Middlesboro, KY 40965
  • $119,900
  • 3Bd
  • 2Ba
  • 1,260 Sq Ft
207 Arthur Hts, Middlesboro, KY 40965
  • $264,900
  • 5Bd
  • 3Ba
  • 3,068 Sq Ft
$14.1K
209 S 19th St, Middlesboro, KY 40965
  • $215,000
  • 3Bd
  • 2Ba
  • 1,352 Sq Ft
812 Worchester Ave, Middlesboro, KY 40965
  • $219,000
  • 4Bd
  • 2Ba
  • 1,544 Sq Ft
$10K
312 W Chester Ave, Middlesboro, KY 40965
  • $299,000
  • 6Bd
  • 4Ba
  • 3,594 Sq Ft
515 Englewood Rd, Middlesboro, KY 40965
  • $279,000
  • 3Bd
  • 3Ba
  • 2,210 Sq Ft
400 Gloucester Ave, Middlesboro, KY 40965
  • $279,000
  • 4Bd
  • 2Ba
  • 2,032 Sq Ft
$20K
140 Wellington Dr, Middlesboro, KY 40965
  • $199,900
  • 4Bd
  • 2Ba
  • 1,612 Sq Ft
$100
2909 W Cumberland Ave, Middlesboro, KY 40965
  • $359,500
  • 3Bd
  • 2Ba
  • 2,000 Sq Ft
125 Cawood Ln, Middlesboro, KY 40965
  • $135,000
  • 2Bd
  • 2Ba
  • 1,400 Sq Ft
$7.5K
518 S 43rd St, Middlesboro, KY 40965
  • $51,000
  • 2Bd
  • 1Ba
  • 920 Sq Ft
$8K
623 N 20th St, Middlesboro, KY 40965
  • $229,500
  • 6Bd
  • 6Ba
  • 2,700 Sq Ft
116 Edgewood Rd, Middlesboro, KY 40965
  • $200,000
  • 3Bd
  • 2Ba
  • 2,154 Sq Ft
$9.9K
64 Dunlap Hollow Rd, Middlesboro, KY 40965
  • $149,000
  • 4Bd
  • 2Ba
  • 1,440 Sq Ft
$10K
413 S 26th St, Middlesboro, KY 40965
  • $125,000
  • 2Bd
  • 1Ba
  • 1,008 Sq Ft
$10K
215 S 21st St, Middlesboro, KY 40965
  • $120,000
  • 5Bd
  • 4Ba
  • 2,844 Sq Ft
$13K
2002 Winchester Ave, Middlesboro, KY 40965
  • $135,000
  • 2Bd
  • 1Ba
  • 1,120 Sq Ft
109 Bloomsbury Ave, Middlesboro, KY 40965
  • $21,000
  • 0.17 Acre
$1K
2107 Winchester Ave, Middlesboro, KY 40965
  • $29,000
  • 0.34 Acre
$6K
717 Highway 441, Middlesboro, KY 40965
  • $295,000
  • 5Bd
  • 3Ba
  • 2,100 Sq Ft
$15K
0000 Edgewood Rd, Middlesboro, KY 40965
  • $50,000
  • 0.38 Acre
205 Exeter Ave, Middlesboro, KY 40965
  • $15,000
  • 0.13 Acre
$2K
156 Wellington Dr, Middlesboro, KY 40965
  • $230,000
  • 3Bd
  • 2Ba
  • 1,320 Sq Ft
$15K
523 N 30th St, Middlesboro, KY 40965
  • $455,000
  • 5Bd
  • 4Ba
  • 3,146 Sq Ft
lot S 12 13 Sams Mountain Rd, Middlesboro, KY 40965
  • $30,000
  • 1.26 Acre
301 Does Xing, Middlesboro, KY 40965
  • $229,500
  • 3Bd
  • 3Ba
  • 2,016 Sq Ft
$3K
119 Wagon Hollow Rd, Middlesboro, KY 40965
  • $250,000
  • —Bd
  • —Ba
  • 1,500 Sq Ft
1 - 50 of 74 Homes for sale in Middlesboro, KY
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Middlesboro, KY real estate market trends

Statistics as of October 2026
$175K
Avg. list price
$102/Sqft
Avg. price/sqft
66
Homes for sale
1,581 Sqft
Avg. home size
109 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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