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.	$310,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.12% Airbnb Rental Income: $null Traditional Rental Income: $2633 Airbnb ROI: N/A Traditional ROI: 7.12%
603 Chester Ave Middlesboro, KY Charming 3-bedroom, 2-bath home with a bonus room and ample storage, conveniently located ...	3 beds \| 2 baths \| 1,670 sq.ft.	$184,500	Airbnb cash on cash: N/A Traditional cash on cash: 11.61% Airbnb Rental Income: $null Traditional Rental Income: $2400 Airbnb ROI: N/A Traditional ROI: 11.61%
908 Chester Ave Middlesboro, KY Very well maintained 3 bedroom, 2 bath home located on Chester Avenue in Middlesboro. Mai...	3 beds \| 2 baths \| 1,400 sq.ft.	$197,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.48% Airbnb Rental Income: $null Traditional Rental Income: $2212 Airbnb ROI: N/A Traditional ROI: 9.48%
1002 Chester Ave Middlesboro, KY 4 Bedroom 1 bath brick, one and a half story home on a large level lot. 4 year old roof, ...	4 beds \| 1 baths \| 2,073 sq.ft.	$180,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.62% Airbnb Rental Income: $null Traditional Rental Income: $2333 Airbnb ROI: N/A Traditional ROI: 11.62%
23 Ennismore Drive Middlesboro, KY Nestled in the highly sought-after Ambleside community, this stunning 6,000-square-foot es...	4 beds \| 6 baths \| 6,000 sq.ft.	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.74% Airbnb Rental Income: $null Traditional Rental Income: $5978 Airbnb ROI: N/A Traditional ROI: 8.74%
230 Windermere Drive Middlesboro, KY Three bedroom, two bath well maintained home in beautiful Ambleside Subdivision. Living r...	3 beds \| 2 baths \| 2,099 sq.ft.	$270,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.69% Airbnb Rental Income: $null Traditional Rental Income: $2439 Airbnb ROI: N/A Traditional ROI: 7.69%
2103 Winchester Avenue Middlesboro, KY Two for 1! The main house at 2103 Winchester Ave has 2100 sf, one bath and four bedrooms. ...	3 beds \| 1 baths \| 2,100 sq.ft.	$240,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.61% Airbnb Rental Income: $null Traditional Rental Income: $2466 Airbnb ROI: N/A Traditional ROI: 8.61%
811 Gloucester Ave Middlesboro, KY This 3 bedroom, 1 bath brick home is located on a quiet dead-end street in the heart of hi...	3 beds \| 1 baths \| 1,661 sq.ft.	$202,500	Airbnb cash on cash: N/A Traditional cash on cash: 8.89% Airbnb Rental Income: $null Traditional Rental Income: $2156 Airbnb ROI: N/A Traditional ROI: 8.89%
123 Twin Acres Road Middlesboro, KY You'll have it all in this lovely brick ranch style home. Living room, dining room, kitch...	4 beds \| 2 baths \| 3,338 sq.ft.	$309,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.15% Airbnb Rental Income: $null Traditional Rental Income: $2607 Airbnb ROI: N/A Traditional ROI: 7.15%
1015 Old Wilson Lane Middlesboro, KY FIRST TIME ON THE MARKET! This wonderful split foyer is in the city limits and has additi...	4 beds \| 3 baths \| 2,488 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.64% Airbnb Rental Income: $null Traditional Rental Income: $2915 Airbnb ROI: N/A Traditional ROI: 3.64%
104 Hollywood Drive Drive Middlesboro, KY This beautiful, spacious, well-kept home sitting on a gorgeous corner lot, in a great loca...	3 beds \| 2 baths \| 1,500 sq.ft.	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.29% Airbnb Rental Income: $null Traditional Rental Income: $2265 Airbnb ROI: N/A Traditional ROI: 10.29%
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.	$289,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.43% Airbnb Rental Income: $null Traditional Rental Income: $2788 Airbnb ROI: N/A Traditional ROI: 8.43%
101 Kim Lane Middlesboro, KY Don't miss out on this hidden gem in the city limits of Middlesboro. This house has it all...	5 beds \| 4 baths \| 3,874 sq.ft.	$440,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.58% Airbnb Rental Income: $null Traditional Rental Income: $3765 Airbnb ROI: N/A Traditional ROI: 7.58%
4921 West Cumberland Avenue Middlesboro, KY This beautiful home conveniently located close to all amenities of downtown Middlesboro is...	3 beds \| 2 baths \| 1,900 sq.ft.	$283,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.4% Airbnb Rental Income: $null Traditional Rental Income: $2416 Airbnb ROI: N/A Traditional ROI: 7.4%
2410 Cumberland Avenue Middlesboro, KY Remarkable Folk Victorian Historical Home. This home was built in 1908, redesigned for to...	5 beds \| 4 baths \| 3,000 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.5% Airbnb Rental Income: $null Traditional Rental Income: $4055 Airbnb ROI: N/A Traditional ROI: 11.5%
164 Lake Hill Road Middlesboro, KY If you love a home with great craftmanship and structural authenticity, then you need only...	3 beds \| 1 baths \| 3,136 sq.ft.	$238,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.51% Airbnb Rental Income: $null Traditional Rental Income: $2207 Airbnb ROI: N/A Traditional ROI: 7.51%
164 Lake Hill Rd Rd Middlesboro, KY If you love a home with great craftmanship and structural authenticity, then you need only...	3 beds \| 1 baths \| 3,136 sq.ft.	$238,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.92% Airbnb Rental Income: $null Traditional Rental Income: $2188 Airbnb ROI: N/A Traditional ROI: 7.92%
225 N 10th St Middlesboro, KY How cute is this?! Newly renovated with gorgeous views of Middlesboro and within walking d...	3 beds \| 2 baths \| 1,014 sq.ft.	$160,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.31% Airbnb Rental Income: $null Traditional Rental Income: $2024 Airbnb ROI: N/A Traditional ROI: 11.31%
512 N 25th St Middlesboro, KY This charming home in a residential area downtown Middlesboro. Relax on the perfect porch ...	2 beds \| 1 baths \| 2,031 sq.ft.	$235,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.18% Airbnb Rental Income: $null Traditional Rental Income: $2025 Airbnb ROI: N/A Traditional ROI: 7.18%
409 Shillilah Village Middlesboro, KY Do you hear the mountains calling you? This cute little chalet nestled in mother nature's...	1 beds \| 1 baths \| 676 sq.ft.	$108,900	Airbnb cash on cash: N/A Traditional cash on cash: 11.57% Airbnb Rental Income: $null Traditional Rental Income: $1486 Airbnb ROI: N/A Traditional ROI: 11.57%
359 Beans Fork Rd Middlesboro, KY Charming fully renovated 2-bedroom, 1-bathroom home featuring ample storage and a detached...	2 beds \| 1 baths \| 952 sq.ft.	$137,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.24% Airbnb Rental Income: $null Traditional Rental Income: $1682 Airbnb ROI: N/A Traditional ROI: 10.24%
2105 Winchester Avenue Middlesboro, KY Two properties for 1 price! This 1,040,sf house is included with the sale of 2103 Winchest...	2 beds \| 1 baths \| 1,040 sq.ft.	$240,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.07% Airbnb Rental Income: $null Traditional Rental Income: $1664 Airbnb ROI: N/A Traditional ROI: 5.07%
205 Oakwood Rd Middlesboro, KY This is an adorable 2 bedroom, 1 and a half bath home located in a quiet neighborhood in H...	2 beds \| 2 baths \| 1,020 sq.ft.	$135,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.69% Airbnb Rental Income: $null Traditional Rental Income: $1792 Airbnb ROI: N/A Traditional ROI: 11.69%
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.	$164,500	Airbnb cash on cash: N/A Traditional cash on cash: 9.37% Airbnb Rental Income: $null Traditional Rental Income: $1796 Airbnb ROI: N/A Traditional ROI: 9.37%
515 North 25th Street Middlesboro, KY Location! Location! Location! Move In Ready & Fully Furnished!! Prime Real Estate withi...	3 beds \| 1 baths \| 1,700 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.9% Airbnb Rental Income: $null Traditional Rental Income: $1986 Airbnb ROI: N/A Traditional ROI: 6.9%
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: N/A Traditional cash on cash: 6.95% Airbnb Rental Income: $null Traditional Rental Income: $1821 Airbnb ROI: N/A Traditional ROI: 6.95%

Real Estate investment in Middlesboro, KY

There are 26 properties for sale in the city of Middlesboro . The median list price in Middlesboro is $190,750 and the average price per square foot is $100. In January 2025, the average monthly cash on cash return in Middlesboro is 10.00%. The average monthly rental income in Middlesboro is $2,184.

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

There are 26 investment properties available for sale in Middlesboro.

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

The ROI for Short-Term is higher than the Long-Term in Middlesboro with average rental income of $N/A.

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.

$310,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.12%

Airbnb Rental Income: $null

Traditional Rental Income: $2633

Airbnb ROI: N/A

Traditional ROI: 7.12%

603 Chester Ave

Middlesboro, KY

3 beds | 2 baths | 1,670 sq.ft.

$184,500

Airbnb cash on cash: N/A

Traditional cash on cash: 11.61%

Airbnb Rental Income: $null

Traditional Rental Income: $2400

Airbnb ROI: N/A

Traditional ROI: 11.61%

908 Chester Ave

Middlesboro, KY

3 beds | 2 baths | 1,400 sq.ft.

$197,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.48%

Airbnb Rental Income: $null

Traditional Rental Income: $2212

Airbnb ROI: N/A

Traditional ROI: 9.48%

1002 Chester Ave

Middlesboro, KY

4 beds | 1 baths | 2,073 sq.ft.

$180,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.62%

Airbnb Rental Income: $null

Traditional Rental Income: $2333

Airbnb ROI: N/A

Traditional ROI: 11.62%

23 Ennismore Drive

Middlesboro, KY

4 beds | 6 baths | 6,000 sq.ft.

$595,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.74%

Airbnb Rental Income: $null

Traditional Rental Income: $5978

Airbnb ROI: N/A

Traditional ROI: 8.74%

230 Windermere Drive

Middlesboro, KY

3 beds | 2 baths | 2,099 sq.ft.

$270,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.69%

Airbnb Rental Income: $null

Traditional Rental Income: $2439

Airbnb ROI: N/A

Traditional ROI: 7.69%

2103 Winchester Avenue

Middlesboro, KY

3 beds | 1 baths | 2,100 sq.ft.

$240,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.61%

Airbnb Rental Income: $null

Traditional Rental Income: $2466

Airbnb ROI: N/A

Traditional ROI: 8.61%

811 Gloucester Ave

Middlesboro, KY

3 beds | 1 baths | 1,661 sq.ft.

$202,500

Airbnb cash on cash: N/A

Traditional cash on cash: 8.89%

Airbnb Rental Income: $null

Traditional Rental Income: $2156

Airbnb ROI: N/A