- 2 bds
- 1 ba
- 768 sqft
CENTURY 21 VIRGINIA WILDER REAL ESTATE. Listing provided by Imagine MLS
5 hours ago
Middlesboro KY Real Estate & Homes For Sale
56 results
- 2354 Highway 441, Middlesboro, KY 40965
- Updated interior
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- 215 S 21st St, Middlesboro, KY 40965
- 5 bds
- 4 ba
- 2,844 sqft
BLACK DIAMOND REALTY. Listing provided by Imagine MLS172 days on Zillow
- 412 N 24th St, Middlesboro, KY 40965
- 3 bds
- 2 ba
- 1,966 sqft
TURN KEY REALTY. Listing provided by Imagine MLS53 days on Zillow
- Open floor plan
- 816 W Chester Ave, Middlesboro, KY 40965
- 2 bds
- 2 ba
- 1,240 sqft
CENTURY 21 PINNACLE. Listing provided by Imagine MLSCovered patio
- 8 Castleford Way, Middlesboro, KY 40965
- 3 bds
- 2 ba
- 1,168 sqft
CENTURY 21 VIRGINIA WILDER REAL ESTATE. Listing provided by Imagine MLSPrice cut: $15,000 (10/26)
- Large storage shed
- 116 Edgewood Rd, Middlesboro, KY 40965
- 3 bds
- 2 ba
- 2,154 sqft
BLACK DIAMOND REALTY. Listing provided by Imagine MLSDetached garage
- 64 Dunlap Hollow Rd, Middlesboro, KY 40965
- 4 bds
- 2 ba
- 1,440 sqft
CENTURY 21 VIRGINIA WILDER REAL ESTATECountry setting
- 129 days on Zillow
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- 207 Arthur Hts, Middlesboro, KY 40965
- 5 bds
- 3 ba
- 3,068 sqft
COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO. Listing provided by Imagine MLSBluetooth speakers
- Swimming pool
- 405 S 37th St, Middlesboro, KY 40965
- 4 bds
- 2 ba
- 1,908 sqft
COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO. Listing provided by Imagine MLSPrice cut: $29,900 (10/12)
- 2004 Twin Fawn Trl, Middlesboro, KY 40965
- 5 bds
- 3 ba
- 2,542 sqft
CENTURY 21 VIRGINIA WILDER REAL ESTATEFamily room
- Walkout basement
- Huge back deck
- Price cut: $20,000 (10/27)
- Start survey
Help others discover what makes this area unique.
Fill out a short survey to help others know what it's like to live here. - Cozy move-in ready home
- Beautiful kitchen
- Price cut: $5,000 (11/3)
- Freshly painted exterior
- Price cut: $10,000 (10/26)
- Spacious and playful backyard
- 706 Ilchester Ave, Middlesboro, KY 40965
- 3 bds
- 2 ba
- 1,260 sqft
CENTURY 21 VIRGINIA WILDER REAL ESTATEPrice cut: $30,000 (11/7)
- Price cut: $8,000 (10/19)
- Modern updates
- Balcony upstairs
- 225 Sherwood Rd, Middlesboro, KY 40965
- 3 bds
- 3 ba
- 3,258 sqft
MOUNTAIN REALTY GROUP LLC. Listing provided by Imagine MLSTwo additional spacious bedrooms
- 114 E Rochester Ave, Middlesboro, KY 40965
- 3 bds
- 1 ba
- 1,066 sqft
BACKWOODS REALTY & DEVELOPMENT. Listing provided by Imagine MLSNew heat pump
- Storage building
- 156 Wellington Dr, Middlesboro, KY 40965
- 3 bds
- 2 ba
- 1,320 sqft
BLACK DIAMOND REALTY. Listing provided by Imagine MLSSwimming pool
- 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
- Price cut: $16,000 (10/27)
- 508 Worchester Ave, Middlesboro, KY 40965
- 3 bds
- 2 ba
- 2,191 sqft
MOUNTAIN REALTY GROUP LLC. Listing provided by Imagine MLSPrivate outdoor space
- Attached guest quarters
- Large eat in kitchen
- 623 N 20th St, Middlesboro, KY 40965
- 6 bds
- 6 ba
- 2,700 sqft
CONTINENTAL REAL ESTATE GROUP. Listing provided by Imagine MLSNewer appliances
- 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
- 312 W Chester Ave, Middlesboro, KY 40965
- 6 bds
- 4 ba
- 3,594 sqft
COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO. Listing provided by Imagine MLS79 days on Zillow
- 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
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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.
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.
Buying a Home in Middlesboro KY: Frequently Asked Questions
How much do homes cost in Middlesboro KY?
Home values in Middlesboro, KY, as measured by the Zillow Home Value Index, came to $119,592 as of September 2026. That figure covers all homes in the area, not only those on the market. The median list price of homes for sale is $163,500, which is higher than the index value.
Are home values going up or down in Middlesboro KY?
Home values in Middlesboro, KY decreased 1.7% over the past year as of September 2026. The Zillow Home Value Index now stands at $119,592.
Is Middlesboro KY a buyer's or seller's market?
Middlesboro, KY is currently rated a strong seller's market by Zillow Market Temperature. That label generally means homes sell faster and buyers face more competition. Among current listings, 14.8% have had a price cut.
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