- 2 bds
- 2 ba
- 6,696 sqft
TURN KEY REALTY. Listing provided by Imagine MLS
Generous lot sizes
Middlesboro KY Luxury Homes
61 results
- 508 & 512 E Winchester Ave, Middlesboro, KY 40965
- 725 N 19th St, Middlesboro, KY 40965
- 2 bds
- 2 ba
- 15,119 sqft
TURN KEY REALTY. Listing provided by Imagine MLSSingle-story property
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- 142 Edgewood Rd, Middlesboro, KY 40965
- 7 bds
- 5 ba
- 6,276 sqft
BACKWOODS REALTY & DEVELOPMENTWalkout basement
- Price cut: $15,000 (8/9)
- 523 N 30th St, Middlesboro, KY 40965
- 5 bds
- 4 ba
- 3,146 sqft
BACKWOODS REALTY & DEVELOPMENT. Listing provided by Imagine MLSAttached guest quarters
- 103 Kingsbury Woods Rd, Middlesboro, KY 40965
- 3 bds
- 3 ba
- 3,397 sqft
LISTWITHFREEDOM.COM. Listing provided by Imagine MLSPrice cut: $30,000 (7/28)
- 2909 W Cumberland Ave, Middlesboro, KY 40965
- 3 bds
- 2 ba
- 2,000 sqft
BACKWOODS REALTY & DEVELOPMENTSpacious and playful backyard
- Open: Sat 10am-2pm (9/12)
- 1015 Old Wilson Ln, Middlesboro, KY 40965
- 4 bds
- 3 ba
- 2,488 sqft
COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO. Listing provided by Imagine MLSPrice cut: $10,000 (8/17)
- 926 Doncaster Ave, Middlesboro, KY 40965
- 5 bds
- 2 ba
- 2,664 sqft
COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO. Listing provided by Imagine MLSPrice cut: $10,000 (8/24)
- 400 Gloucester Ave, Middlesboro, KY 40965
- 4 bds
- 2 ba
- 2,032 sqft
COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO. Listing provided by Imagine MLSUpdated kitchen
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- 312 W Chester Ave, Middlesboro, KY 40965
- 6 bds
- 4 ba
- 3,594 sqft
COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO. Listing provided by Imagine MLS6 days on Zillow
- 717 Highway 441, Middlesboro, KY 40965
- 5 bds
- 3 ba
- 2,100 sqft
BLACK DIAMOND REALTY. Listing provided by Imagine MLSNice back deck
- 515 Englewood Rd, Middlesboro, KY 40965
- 3 bds
- 3 ba
- 2,210 sqft
BACKWOODS REALTY & DEVELOPMENT. Listing provided by Imagine MLSWalk-out finished basement
- 321 E Chester Ave, Middlesboro, KY 40965
- 1.69 acres lot
COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO. Listing provided by Imagine MLSFlat acres
- 113 Hollywood Dr, Middlesboro, KY 40965
- 3 bds
- 3 ba
- 3,174 sqft
COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO. Listing provided by Imagine MLSTraditional brick ranch
- 717 S 27th St, Middlesboro, KY 40965
- 5 bds
- 4 ba
- 3,195 sqft
RE/MAX LAKETIME REALTY LONDON. Listing provided by Imagine MLSPrice cut: $30,000 (8/7)
- 119 Wagon Hollow Rd, Middlesboro, KY 40965
- -- bds
- -- ba
- 1,500 sqft
BLACK DIAMOND REALTYSeveral outbuildings
- 119 S 20th St, Middlesboro, KY 40965
- 2 bds
- 2 ba
- 1,750 sqft
KENTUCKY HOMES AND LAND LLCPrice cut: $19,000 (8/18)
- 156 Wellington Dr, Middlesboro, KY 40965
- 3 bds
- 2 ba
- 1,320 sqft
BLACK DIAMOND REALTY. Listing provided by Imagine MLSSwimming pool
- 623 N 20th St, Middlesboro, KY 40965
- 6 bds
- 6 ba
- 2,700 sqft
CONTINENTAL REAL ESTATE GROUP. Listing provided by Imagine MLSNewer appliances
- 301 Does Xing, Middlesboro, KY 40965
- 3 bds
- 3 ba
- 2,016 sqft
CENTURY 21 VIRGINIA WILDER REAL ESTATEBalcony upstairs
- Beautiful kitchen
- 209 S 19th St, Middlesboro, KY 40965
- 3 bds
- 2 ba
- 1,352 sqft
BLACK DIAMOND REALTY. Listing provided by Imagine MLSPrivate setting
- 116 Edgewood Rd, Middlesboro, KY 40965
- 3 bds
- 2 ba
- 2,154 sqft
BLACK DIAMOND REALTY. Listing provided by Imagine MLSPrice cut: $9,900 (8/12)
- Price cut: $100 (8/25)
- 1102 W Chester Ave, Middlesboro, KY 40965
- 3 bds
- 1 ba
- 1,480 sqft
COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO. Listing provided by Imagine MLSThree bedrooms
- 414 24th St, Middlesboro, KY 40965
- 2 bds
- 2 ba
- 1,608 sqft
TURN KEY REALTY. Listing provided by Imagine MLSSpacious layout
- 815 Dorchester Ave, Middlesboro, KY 40965
- 2 bds
- 1 ba
- 792 sqft
BACKWOODS REALTY & DEVELOPMENTPrice cut: $5,000 (8/16)
- 64 Dunlap Hollow Rd, Middlesboro, KY 40965
- 4 bds
- 2 ba
- 1,440 sqft
CENTURY 21 VIRGINIA WILDER REAL ESTATECountry setting
- 4607 W Cumberland Ave, Middlesboro, KY 40965
- -- bds
- -- ba
- -- sqft
CENTURY 21 VIRGINIA WILDER REAL ESTATEPrice cut: $5,100 (8/20)
- 908 Manchester Ave, Middlesboro, KY 40965
- 3 bds
- 2 ba
- 1,100 sqft
ACTION REALTY. Listing provided by Imagine MLSPrice cut: $5,400 (8/7)
- 56 days on Zillow
- New windows
- Large eat in kitchen
- 2002 Winchester Ave, Middlesboro, KY 40965
- 2 bds
- 1 ba
- 1,120 sqft
COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO. Listing provided by Imagine MLSLarge covered front porch
- 405 S 37th St, Middlesboro, KY 40965
- 4 bds
- 2 ba
- 1,908 sqft
COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO. Listing provided by Imagine MLSFenced in yard
- 215 S 21st St, Middlesboro, KY 40965
- 5 bds
- 4 ba
- 2,844 sqft
BLACK DIAMOND REALTY. Listing provided by Imagine MLS99 days on Zillow
- 901 Exeter Ave, Middlesboro, KY 40965
- 3 bds
- 2 ba
- 1,963 sqft
FATHOM REALTY KY LLC. Listing provided by Imagine MLSWelcoming front porch
- 1720 Exeter Ave, Middlesboro, KY 40965
- 2 bds
- 1 ba
- 1,456 sqft
CENTURY 21 VIRGINIA WILDER REAL ESTATE. Listing provided by Imagine MLSPrice cut: $10,000 (8/24)
- Freshly painted exterior
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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Listing Information presented by local MLS brokerage: Zillow, Inc., local broker - Eric Young - (865) 378-5282.
The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of NKMLS. Real estate listings held by IDX Brokerage firms other than Zillow, Inc. are marked with the Internet Data Exchange logo or the Internet Data Exchange thumbnail logo and detailed information about them includes the name of the listing Brokers. Listing information is deemed reliable, but not guaranteed. Copyright 2026 Northern Kentucky Multiple Listing Service, Inc. All rights reserved.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
