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
109 Hollywood Drive Middlesboro, KY This 3,544 sf home built approximately in 1965 was completely remodeled and updated in 202...	3 beds \| 3 baths \| 3,544 sq.ft.	$299,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 7.42% Airbnb Rental Income: $1635 Traditional Rental Income: $2633 Airbnb ROI: 2.23% Traditional ROI: 7.42%
428 Wilderness Rd Middlesboro, KY Beautiful house located in Middlesboro Kentucky minutes away from Lincoln Memorial Univers...	3 beds \| 1 baths \| 1,320 sq.ft.	$154,900	Airbnb cash on cash: 5.44% Traditional cash on cash: 4.42% Airbnb Rental Income: $1635 Traditional Rental Income: $1023 Airbnb ROI: 5.44% Traditional ROI: 4.42%
915 Lothbury Ave Middlesboro, KY Charming & Spacious Home with Poolside Living in Historic Middlesboro! This 3-bedroom, 4-...	3 beds \| 4 baths \| 2,349 sq.ft.	$299,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 7.5% Airbnb Rental Income: $1635 Traditional Rental Income: $2642 Airbnb ROI: 2.28% 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: 2.65% Traditional cash on cash: 8.77% Airbnb Rental Income: $1635 Traditional Rental Income: $2788 Airbnb ROI: 2.65% Traditional ROI: 8.77%
4921 W Cumberland Ave Middlesboro, KY Nice Ranch style home with an oversized 1 car garage with a 2-car carport attached, 3 bd, ...	3 beds \| 2 baths \| 1,900 sq.ft.	$230,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 9.32% Airbnb Rental Income: $1635 Traditional Rental Income: $2416 Airbnb ROI: 3.61% Traditional ROI: 9.32%
626 S 22nd St Middlesboro, KY Wonderfully maintained home sitting on 12 beautiful flat, and cleared lots at the dead end...	3 beds \| 2 baths \| 1,456 sq.ft.	$190,000	Airbnb cash on cash: 4.91% Traditional cash on cash: 9.61% Airbnb Rental Income: $1635 Traditional Rental Income: $2022 Airbnb ROI: 4.91% Traditional ROI: 9.61%
1005 Hollywood Drive Middlesboro, KY Located in Middlesboro KY, you will find this 3 bedroom 1 bath ranch style home with a ful...	3 beds \| 1 baths \| 1,110 sq.ft.	$157,000	Airbnb cash on cash: 5.7% Traditional cash on cash: 9.85% Airbnb Rental Income: $1635 Traditional Rental Income: $1796 Airbnb ROI: 5.7% Traditional ROI: 9.85%
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: 4.98% Traditional cash on cash: 9.6% Airbnb Rental Income: $1635 Traditional Rental Income: $1986 Airbnb ROI: 4.98% Traditional ROI: 9.6%
505 S South 38th St St Middlesboro, KY Located in Middlesboro, KY, this property is conveniently close to the hospital, schools, ...	2 beds \| 2 baths \| 1,144 sq.ft.	$225,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 6.95% Airbnb Rental Income: $1173 Traditional Rental Income: $1821 Airbnb ROI: 2.1% Traditional ROI: 6.95%
106 S 38th Street Middlesboro, KY Well-kept Brick Ranch Home. This home is conveniently located in the heart of the city li...	3 beds \| 2 baths \| 1,404 sq.ft.	$187,900	Airbnb cash on cash: 4.74% Traditional cash on cash: 9.79% Airbnb Rental Income: $1635 Traditional Rental Income: $2075 Airbnb ROI: 4.74% Traditional ROI: 9.79%
516 S 34th St Middlesboro, KY Unbelievable find in the city limits of Middlesboro. 13.7 acres inside the city limits wi...	2 beds \| 1 baths \| 776 sq.ft.	$650,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 0.32% Airbnb Rental Income: $1173 Traditional Rental Income: $1413 Airbnb ROI: -0.71% Traditional ROI: 0.32%
825 S 28th Street Middlesboro, KY Beautiful, split foyer home with 4 bedrooms and 2 Â½ bathrooms. The upstairs features a k...	4 beds \| 3 baths \| 2,020 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.44% Airbnb Rental Income: $null Traditional Rental Income: $2477 Airbnb ROI: N/A Traditional ROI: 8.44%
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%
900 Twin Fawn Trail Middlesboro, KY In the beautiful hills of Vista Venado lies the gorgeous 3 bedroom and 2 bath 900 Twin Faw...	3 beds \| 2 baths \| 2,270 sq.ft.	$299,900	Airbnb cash on cash: 1.9% Traditional cash on cash: 6.32% Airbnb Rental Income: $1635 Traditional Rental Income: $2423 Airbnb ROI: 1.9% Traditional ROI: 6.32%
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.	$189,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.93% Airbnb Rental Income: $null Traditional Rental Income: $2021 Airbnb ROI: N/A Traditional ROI: 8.93%
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.	$199,000	Airbnb cash on cash: 4.41% Traditional cash on cash: 8.98% Airbnb Rental Income: $1635 Traditional Rental Income: $2036 Airbnb ROI: 4.41% Traditional ROI: 8.98%
5 Abbey Lane Middlesboro, KY Tired of living in a house where you don't know your neighbors and feel like you can't enj...	3 beds \| 2 baths \| 1,221 sq.ft.	$249,900	Airbnb cash on cash: 3.01% Traditional cash on cash: 7.45% Airbnb Rental Income: $1635 Traditional Rental Income: $2223 Airbnb ROI: 3.01% Traditional ROI: 7.45%
3008 State Highway 441 Middlesboro, KY This Newly Remodeled home is located just minutes away from downtown Middlesboro and the ...	3 beds \| 2 baths \| 1,800 sq.ft.	$198,000	Airbnb cash on cash: 4.5% Traditional cash on cash: 10.47% Airbnb Rental Income: $1635 Traditional Rental Income: $2294 Airbnb ROI: 4.5% Traditional ROI: 10.47%
102 Stone Creek Drive Middlesboro, KY 2-bedroom 1 bath on corner lot with 1 year old roof! Fenced in level yard and then some, s...	2 beds \| 1 baths \| 952 sq.ft.	$169,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 7.78% Airbnb Rental Income: $1173 Traditional Rental Income: $1564 Airbnb ROI: 2.96% Traditional ROI: 7.78%
1203 Winchester Avenue Middlesboro, KY Beautiful home in the heart of Middlesboro. Make a grand entrance to the spacious formal ...	4 beds \| 3 baths \| 2,455 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 11.51% Airbnb Rental Income: $null Traditional Rental Income: $3144 Airbnb ROI: N/A Traditional ROI: 11.51%
220 Windermere Drive Middlesboro, KY BEAUTIFUL MOVE IN READY HOME IN AMBLESIDE. Discover your next home in Ambleside, a tranqu...	3 beds \| 3 baths \| 1,692 sq.ft.	$269,500	Airbnb cash on cash: 2.9% Traditional cash on cash: 7.42% Airbnb Rental Income: $1635 Traditional Rental Income: $2322 Airbnb ROI: 2.9% Traditional ROI: 7.42%

Real Estate investment in Middlesboro, KY

There are 21 properties for sale in the city of Middlesboro . The median list price in Middlesboro is $190,000 and the average price per square foot is $112. In September 2025, the average monthly cash on cash return in Middlesboro is 9.00%. The average monthly rental income in Middlesboro is $2,075.

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

There are 21 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 $2,075.

Your search for investment property begins and ends here

Investment Property for Sale in Middlesboro, KY

109 Hollywood Drive

Middlesboro, KY

3 beds | 3 baths | 3,544 sq.ft.

$299,000

Airbnb cash on cash: 2.23%

Traditional cash on cash: 7.42%

Airbnb Rental Income: $1635

Traditional Rental Income: $2633

Airbnb ROI: 2.23%

Traditional ROI: 7.42%

428 Wilderness Rd

Middlesboro, KY

3 beds | 1 baths | 1,320 sq.ft.

$154,900

Airbnb cash on cash: 5.44%

Traditional cash on cash: 4.42%

Airbnb Rental Income: $1635

Traditional Rental Income: $1023

Airbnb ROI: 5.44%

Traditional ROI: 4.42%

915 Lothbury Ave

Middlesboro, KY

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

$299,000

Airbnb cash on cash: 2.28%

Traditional cash on cash: 7.5%

Airbnb Rental Income: $1635

Traditional Rental Income: $2642

Airbnb ROI: 2.28%

Traditional ROI: 7.5%

515 Englewood Rd

Middlesboro, KY

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

$279,900

Airbnb cash on cash: 2.65%

Traditional cash on cash: 8.77%

Airbnb Rental Income: $1635

Traditional Rental Income: $2788

Airbnb ROI: 2.65%

Traditional ROI: 8.77%

4921 W Cumberland Ave

Middlesboro, KY

3 beds | 2 baths | 1,900 sq.ft.

$230,000

Airbnb cash on cash: 3.61%

Traditional cash on cash: 9.32%

Airbnb Rental Income: $1635

Traditional Rental Income: $2416

Airbnb ROI: 3.61%

Traditional ROI: 9.32%

626 S 22nd St

Middlesboro, KY

3 beds | 2 baths | 1,456 sq.ft.

$190,000

Airbnb cash on cash: 4.91%

Traditional cash on cash: 9.61%

Airbnb Rental Income: $1635

Traditional Rental Income: $2022

Airbnb ROI: 4.91%

Traditional ROI: 9.61%

1005 Hollywood Drive

Middlesboro, KY

3 beds | 1 baths | 1,110 sq.ft.

$157,000

Airbnb cash on cash: 5.7%

Traditional cash on cash: 9.85%

Airbnb Rental Income: $1635

Traditional Rental Income: $1796

Airbnb ROI: 5.7%

Traditional ROI: 9.85%

515 N 25th St

Middlesboro, KY

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

$185,000

Airbnb cash on cash: 4.98%

Traditional cash on cash: 9.6%

Airbnb Rental Income: $1635

Traditional Rental Income: $1986

Airbnb ROI: 4.98%