Real Estate Investment Properties for Sale in Middlesboro, KY

Looking for investment property in Middlesboro, KY with high ROI ?

Explore a variety of short-term homes & houses in Middlesboro, KY. Invest wisely with VRBO & Middlesboro, KY Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Middlesboro, KY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
915 Lothbury Ave Middlesboro, KY Charming & Spacious Home with Poolside Living in Historic Middlesboro! This 3-bedroom, 4-b...	3 beds \| 4 baths \| 2,349 sq.ft.	$299,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 7.5% Airbnb Rental Income: $1188 Traditional Rental Income: $2642 Airbnb ROI: 0.96% Traditional ROI: 7.5%
515 Englewood Rd Middlesboro, KY Explore this charming home offering a blend of tranquility and convenience! Nestled in tow...	3 beds \| 3 baths \| 2,210 sq.ft.	$279,900	Airbnb cash on cash: 1.23% Traditional cash on cash: 8.77% Airbnb Rental Income: $1188 Traditional Rental Income: $2788 Airbnb ROI: 1.23% Traditional ROI: 8.77%
805 Worchester Ave Middlesboro, KY This home has been brought back beyond its Glory!! Completely remodeled from the sub floor...	5 beds \| 3 baths \| 2,250 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.08% Airbnb Rental Income: $null Traditional Rental Income: $2865 Airbnb ROI: N/A Traditional ROI: 7.08%
515 N 25th St Middlesboro, KY Cute as I'll get out! And no, I don't mean cute as in little either. This one packs a big ...	3 beds \| 1 baths \| 2,000 sq.ft.	$185,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 9.6% Airbnb Rental Income: $1188 Traditional Rental Income: $1986 Airbnb ROI: 2.86% Traditional ROI: 9.6%
505 S 38th St Middlesboro, KY Located in Middlesboro, KY, this property is conveniently close to the hospital, schools, ...	2 beds \| 2 baths \| 1,144 sq.ft.	$198,500	Airbnb cash on cash: 3.66% Traditional cash on cash: 7.99% Airbnb Rental Income: $1434 Traditional Rental Income: $1821 Airbnb ROI: 3.66% Traditional ROI: 7.99%
523 N 30th St Middlesboro, KY Spacious All-Brick Home with Attached Guest Quarters - Prime Location! This beautifully ma...	5 beds \| 4 baths \| 3,146 sq.ft.	$458,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.79% Airbnb Rental Income: $null Traditional Rental Income: $3607 Airbnb ROI: N/A Traditional ROI: 6.79%
409 Meadow Lane Middlesboro, KY This 4 bedroom home is located just minutes away from Downtown Middlesboro KY. With upgrad...	4 beds \| 2 baths \| 1,120 sq.ft.	$184,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.14% Airbnb Rental Income: $null Traditional Rental Income: $2021 Airbnb ROI: N/A Traditional ROI: 9.14%
708 Ilchester Ave Middlesboro, KY Newly renovated 3 bedroom, 2 bath house located in a great neighborhood in Middlesboro, Ky...	3 beds \| 2 baths \| 1,312 sq.ft.	$180,000	Airbnb cash on cash: 2.79% Traditional cash on cash: 10% Airbnb Rental Income: $1188 Traditional Rental Income: $2036 Airbnb ROI: 2.79% Traditional ROI: 10%
114 Rochester Ave Middlesboro, KY Charming Fully Remodeled Brick Ranch - Move-In Ready! Welcome home to this beautifully upd...	3 beds \| 2 baths \| 1,008 sq.ft.	$164,900	Airbnb cash on cash: 2.9% Traditional cash on cash: 9.64% Airbnb Rental Income: $1188 Traditional Rental Income: $1860 Airbnb ROI: 2.9% Traditional ROI: 9.64%
220 Windermere Drive Middlesboro, KY BEAUTIFUL MOVE IN READY HOME IN AMBLESIDE. Discover your next home in Ambleside, a tranqui...	3 beds \| 2 baths \| 1,692 sq.ft.	$269,500	Airbnb cash on cash: 1.43% Traditional cash on cash: 7.42% Airbnb Rental Income: $1188 Traditional Rental Income: $2322 Airbnb ROI: 1.43% Traditional ROI: 7.42%
2702 Cumberland Avenue Middlesboro, KY Don't miss this opportunity to own a historic home on Cumberland Avenue with a rare corner...	4 beds \| N/A baths \| 3,885 sq.ft.	$369,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.41% Airbnb Rental Income: $null Traditional Rental Income: $3308 Airbnb ROI: N/A Traditional ROI: 7.41%
129 Lower Gibson Lane Middlesboro, KY The Chateau on the Creek - Home for Sale in Middlesboro, KY (Bell County) Welcome to The C...	3 beds \| 2 baths \| 1,856 sq.ft.	$245,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 7.04% Airbnb Rental Income: $1188 Traditional Rental Income: $2003 Airbnb ROI: 1.85% Traditional ROI: 7.04%
6 Hampton Court Middlesboro, KY Beautiful split foyer home in Ambleside. The view from the front window is amazing. This w...	4 beds \| 3 baths \| 1,966 sq.ft.	$249,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.8% Airbnb Rental Income: $null Traditional Rental Income: $2696 Airbnb ROI: N/A Traditional ROI: 9.8%
918 E Cumberland Avenue Middlesboro, KY This home rest on a lot that goes from city street to ally. This home has 3 bedrooms and o...	3 beds \| 1 baths \| 792 sq.ft.	$180,000	Airbnb cash on cash: 2.92% Traditional cash on cash: 7.7% Airbnb Rental Income: $1188 Traditional Rental Income: $1621 Airbnb ROI: 2.92% Traditional ROI: 7.7%
45 Fourmile Run Road Middlesboro, KY Newly Remodeled, move-in ready home. This home is nestled in the heart of Middlesboro on a...	3 beds \| 2 baths \| 934 sq.ft.	$172,000	Airbnb cash on cash: 2.97% Traditional cash on cash: 8.86% Airbnb Rental Income: $1188 Traditional Rental Income: $1767 Airbnb ROI: 2.97% Traditional ROI: 8.86%
1308 Gloucester Ave Middlesboro, KY This beautiful 5 bedroom 3.5 bath home located in Middlesboro, Kentucky comes complete wit...	5 beds \| 4 baths \| 4,829 sq.ft.	$539,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.02% Airbnb Rental Income: $null Traditional Rental Income: $3917 Airbnb ROI: N/A Traditional ROI: 6.02%
1208 KY-217 Middlesboro, KY Here is your opportunity to own a home in a desirable community. Approximately 11 acres in...	2 beds \| 2 baths \| 960 sq.ft.	$189,000	Airbnb cash on cash: 3.23% Traditional cash on cash: 6.97% Airbnb Rental Income: $1434 Traditional Rental Income: $1678 Airbnb ROI: 3.23% Traditional ROI: 6.97%

Real Estate investment in Middlesboro, KY

There are 17 properties for sale in the city of Middlesboro . The median list price in Middlesboro is $184,950 and the average price per square foot is $103. In December 2025, the average monthly cash on cash return in Middlesboro is 9.00%. The average monthly rental income in Middlesboro is $2,012.

Middlesboro, KY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 17 investment properties available for sale in Middlesboro.

In 2025, the best neighborhood to buy investment property is Middlesboro.

The ROI for Long-Term is higher than the Short-Term in Middlesboro with average rental income of $2,012.

Your search for investment property begins and ends here

Investment Property for Sale in Middlesboro, KY

915 Lothbury Ave

Middlesboro, KY

3 beds | 4 baths | 2,349 sq.ft.

$299,000

Airbnb cash on cash: 0.96%

Traditional cash on cash: 7.5%

Airbnb Rental Income: $1188

Traditional Rental Income: $2642

Airbnb ROI: 0.96%

Traditional ROI: 7.5%

515 Englewood Rd

Middlesboro, KY

3 beds | 3 baths | 2,210 sq.ft.

$279,900

Airbnb cash on cash: 1.23%

Traditional cash on cash: 8.77%

Airbnb Rental Income: $1188

Traditional Rental Income: $2788

Airbnb ROI: 1.23%

Traditional ROI: 8.77%

805 Worchester Ave

Middlesboro, KY

5 beds | 3 baths | 2,250 sq.ft.

$349,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.08%

Airbnb Rental Income: $null

Traditional Rental Income: $2865

Airbnb ROI: N/A

Traditional ROI: 7.08%

515 N 25th St

Middlesboro, KY

3 beds | 1 baths | 2,000 sq.ft.

$185,000

Airbnb cash on cash: 2.86%

Traditional cash on cash: 9.6%

Airbnb Rental Income: $1188

Traditional Rental Income: $1986

Airbnb ROI: 2.86%

Traditional ROI: 9.6%

505 S 38th St

Middlesboro, KY

2 beds | 2 baths | 1,144 sq.ft.

$198,500

Airbnb cash on cash: 3.66%

Traditional cash on cash: 7.99%

Airbnb Rental Income: $1434

Traditional Rental Income: $1821

Airbnb ROI: 3.66%

Traditional ROI: 7.99%

523 N 30th St

Middlesboro, KY

5 beds | 4 baths | 3,146 sq.ft.

$458,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.79%

Airbnb Rental Income: $null

Traditional Rental Income: $3607

Airbnb ROI: N/A

Traditional ROI: 6.79%

409 Meadow Lane

Middlesboro, KY

4 beds | 2 baths | 1,120 sq.ft.

$184,900

Airbnb cash on cash: N/A

Traditional cash on cash: 9.14%

Airbnb Rental Income: $null

Traditional Rental Income: $2021

Airbnb ROI: N/A

Traditional ROI: 9.14%

708 Ilchester Ave

Middlesboro, KY

3 beds | 2 baths | 1,312 sq.ft.

$180,000

Airbnb cash on cash: 2.79%

Traditional cash on cash: 10%

Airbnb Rental Income: $1188

Traditional Rental Income: $2036

Airbnb ROI: 2.79%