Homes Under $300K in Middlesboro, KY

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3 beds New construction With a pool

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21 of 41 Listings

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Homes Under $300K in Middlesboro, KY

21 of 41 Listings

20

41 listings

Homes Under $300K in Middlesboro, KY

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21 of 41 Listings

Map

Homes Under $300K in Middlesboro, KY

21 of 41 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

20

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Active

$199,000

3 bd · 1 ba · 1,480 sqft

1102 W Chester Ave, Middlesboro, KY

Kevin J Bisceglia · Coldwell Banker Bisceglia Real

New11Active

$99,900

3 bd · 3 ba · 2,800 sqft

141 Lick Fork Road, Middlesboro, KY

Derek Eisenberg · Continental Real Estate Group

New4Active

$175,000

4 bd · 2 ba · 1,590 sqft

808 N 28th St, Middlesboro, KY

Misti McGrath · Realty Group

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

16Active

$119,900

3 bd · 2 ba · 1,260 sqft

706 Ilchester Ave, Middlesboro, KY

Virginia Wilder · Century 21 Virginia Wilder Real Estate

Price Reduced18Active

$110,000

3 bd · 2 ba · 1,963 sqft

901 Exeter Avenue, Middlesboro, KY

Russell Tribell · Fathom Realty KY LLC

15Active

$105,900

3 bd · 2 ba · 1,966 sqft

412 N 24th Street, Middlesboro, KY

Dawn Risner · Turn Key Realty

47Active

$180,000

3 bd · 2 ba · 1,168 sqft

8 Castleford Way, Middlesboro, KY

Victoria Allen · Century 21 Virginia Wilder Real Estate

25Active

$169,000

3 bd · 2 ba · 1,592 sqft

810 1/2 Rochester Ave, Middlesboro, KY

Brad Cawood · Backwoods Realty & Development

13Active

$60,000

3 bd · 2 ba · 1,490 sqft

834 S 31st Street, Middlesboro, KY

Joann Baker · Joann Baker & Associates

17Active

$129,000

3 bd · 1 ba · 1,404 sqft

708 W Chester Ave, Middlesboro, KY

Mike Hensley · REMAX PROFESSIONAL'S

22Active

$229,000

4 bd · 2 ba · 1,544 sqft

812 Worchester Ave, Middlesboro, KY

Misti McGrath · Realty Group

28Active

$235,000

3 bd · 2 ba · 1,400 sqft

800 S 28th St, Middlesboro, KY

Mike Hensley · REMAX PROFESSIONAL'S

15Active

$59,000

2 bd · 1 ba · 920 sqft

518 S 43rd St, Middlesboro, KY

Mike Hensley · REMAX PROFESSIONAL'S

Price Reduced35Active

$264,900

5 bd · 3 ba · 3,068 sqft

207 Arthur Heights, Middlesboro, KY

Sheila Durham · Coldwell Banker Bisceglia Realty & Auction Co

12Active

$215,000

3 bd · 2 ba · 1,352 sqft

209 S 19th Street, Middlesboro, KY

Megan Stanaford · Black Diamond Realty

3Active

$17,000

2 bd · 1 ba · 936 sqft

110 Danbury Ave, Middlesboro, KY

Misti McGrath · Realty Group

1Active

$279,000

3 bd · 3 ba · 2,210 sqft

515 Englewood Road, Middlesboro, KY

Kevin Carroll · Backwoods Realty & Development

Price Reduced49Active

$299,900

5 bd · 2 ba · 2,664 sqft

926 Doncaster Avenue, Middlesboro, KY

Kevin Bisceglia · Coldwell Banker Bisceglia Realty & Auction Co

45Active

$279,000

4 bd · 2 ba · 2,032 sqft

400 Gloucester Ave, Middlesboro, KY

Sheila Durham · Coldwell Banker Bisceglia Real

16Active

$60,000

3 bd · 1 ba · 768 sqft

712 Balmoral Road, Middlesboro, KY

Megan Stanaford · Black Diamond Realty

26Active

$199,900

4 bd · 2 ba · 1,612 sqft

140 Wellington Drive, Middlesboro, KY

Janice Pratt · Fathom Realty TN LLC

Listing data & MLS disclosures

East Tennessee REALTORS MLS (Knoxville): 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 ©2026 Knoxville Area AOR, Inc®. All Rights Reserved. Last Updated: 2026-09-17 16:25:40 UTC
Imagine MLS (Bluegrass REALTORS): The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) Program of Bluegrass REALTORS®. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Real estate listings held by IDX brokerage firms other than Realty.com, are marked with the IDX logo or the IDX thumbnail logo and detailed information about them includes the name of the listing IDX brokers. Information deemed reliable but not guaranteed. Copyright © 2026 Bluegrass REALTORS®. All Rights Reserved.

Middlesboro housing market

August 2026 · This period is still settling

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,186 sq. ft.

Middlesboro, KY community profile

Area: 73.6 sq. mi.

Source: HJN community data

Explore Middlesboro homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Listing data & MLS disclosures

East Tennessee REALTORS MLS (Knoxville): 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 ©2026 Knoxville Area AOR, Inc®. All Rights Reserved. Last Updated: 2026-09-17 16:25:40 UTC
Imagine MLS (Bluegrass REALTORS): The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) Program of Bluegrass REALTORS®. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Real estate listings held by IDX brokerage firms other than Realty.com, are marked with the IDX logo or the IDX thumbnail logo and detailed information about them includes the name of the listing IDX brokers. Information deemed reliable but not guaranteed. Copyright © 2026 Bluegrass REALTORS®. All Rights Reserved.

Middlesboro, KY community profile

Area: 73.6 sq. mi.

Source: HJN community data

Middlesboro housing market

August 2026 · This period is still settling

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,186 sq. ft.

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Middlesboro housing market

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Middlesboro, KY community profile

Explore Middlesboro homes

Your local brokerage

Listing data & MLS disclosures

Middlesboro, KY community profile

Middlesboro housing market

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026