20$199,000
3 bd · 1 ba · 1,480 sqft
1102 W Chester Ave, Middlesboro, KY
Kevin J Bisceglia · Coldwell Banker Bisceglia Real
Homes Under $500K in Middlesboro, KY
Hide MapHomes Under $500K in Middlesboro, KY
21 of 44 Listings
20$199,000
3 bd · 1 ba · 1,480 sqft
1102 W Chester Ave, Middlesboro, KY
Kevin J Bisceglia · Coldwell Banker Bisceglia Real
New11$99,900
3 bd · 3 ba · 2,800 sqft
141 Lick Fork Road, Middlesboro, KY
Derek Eisenberg · Continental Real Estate Group
New4$175,000
4 bd · 2 ba · 1,590 sqft
808 N 28th St, Middlesboro, KY
Misti McGrath · Realty Group
16$119,900
3 bd · 2 ba · 1,260 sqft
706 Ilchester Ave, Middlesboro, KY
Virginia Wilder · Century 21 Virginia Wilder Real Estate
Price Reduced18$110,000
3 bd · 2 ba · 1,963 sqft
901 Exeter Avenue, Middlesboro, KY
Russell Tribell · Fathom Realty KY LLC
15$105,900
3 bd · 2 ba · 1,966 sqft
412 N 24th Street, Middlesboro, KY
Dawn Risner · Turn Key Realty
47$180,000
3 bd · 2 ba · 1,168 sqft
8 Castleford Way, Middlesboro, KY
Victoria Allen · Century 21 Virginia Wilder Real Estate
33$475,000
5 bd · 3 ba · 2,542 sqft
2004 Twin Fawn Tr, Middlesboro, KY
Virginia Wilder · Century 21 Virginia Wilder Real Estate
25$169,000
3 bd · 2 ba · 1,592 sqft
810 1/2 Rochester Ave, Middlesboro, KY
Brad Cawood · Backwoods Realty & Development
13$60,000
3 bd · 2 ba · 1,490 sqft
834 S 31st Street, Middlesboro, KY
Joann Baker · Joann Baker & Associates
17$129,000
3 bd · 1 ba · 1,404 sqft
708 W Chester Ave, Middlesboro, KY
Mike Hensley · REMAX PROFESSIONAL'S
22$229,000
4 bd · 2 ba · 1,544 sqft
812 Worchester Ave, Middlesboro, KY
Misti McGrath · Realty Group
28$235,000
3 bd · 2 ba · 1,400 sqft
800 S 28th St, Middlesboro, KY
Mike Hensley · REMAX PROFESSIONAL'S
15$59,000
2 bd · 1 ba · 920 sqft
518 S 43rd St, Middlesboro, KY
Mike Hensley · REMAX PROFESSIONAL'S
Price Reduced29$264,900
5 bd · 3 ba · 3,068 sqft
207 Arthur Heights, Middlesboro, KY
Sheila Durham · Coldwell Banker Bisceglia Realty & Auction Co
12$215,000
3 bd · 2 ba · 1,352 sqft
209 S 19th Street, Middlesboro, KY
Megan Stanaford · Black Diamond Realty
3$17,000
2 bd · 1 ba · 936 sqft
110 Danbury Ave, Middlesboro, KY
Misti McGrath · Realty Group
1$279,000
3 bd · 3 ba · 2,210 sqft
515 Englewood Road, Middlesboro, KY
Kevin Carroll · Backwoods Realty & Development
Price Reduced49$299,900
5 bd · 2 ba · 2,664 sqft
926 Doncaster Avenue, Middlesboro, KY
Kevin Bisceglia · Coldwell Banker Bisceglia Realty & Auction Co
45$279,000
4 bd · 2 ba · 2,032 sqft
400 Gloucester Ave, Middlesboro, KY
Sheila Durham · Coldwell Banker Bisceglia Real
16$60,000
3 bd · 1 ba · 768 sqft
712 Balmoral Road, Middlesboro, KY
Megan Stanaford · Black Diamond Realty
East Tennessee REALTORS MLS (Knoxville)Imagine MLS (Bluegrass REALTORS)Source: HJN community data
August 2026 · This period is still settling