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.

Multi Family for Sale in Middlesboro, KY

Search for Multi Family for Sale in Middlesboro, Kentucky. Browse all of Mashvisor’s Multi Family listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 2 Multi Family listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
4607 W Cumberland Ave Middlesboro, KY 4607 W Cumberland Ave, Middlesboro, KY 40965 \| Multi Family	N/A beds \| N/A baths \| 0 sq.ft.	$189,000	Airbnb cash on cash: 2.09% Traditional cash on cash: 3.81% Airbnb Rental Income: $1188 Traditional Rental Income: $1110 Airbnb ROI: 2.09% Traditional ROI: 3.81%
119 Wagon Hollow Rd Middlesboro, KY 119 Wagon Hollow Rd, Middlesboro, KY 40965 \| Multi Family	N/A beds \| N/A baths \| 1,500 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.81% Airbnb Rental Income: $null Traditional Rental Income: $1194 Airbnb ROI: N/A Traditional ROI: 2.81%
Other Investment Properties for Sale in Middlesboro
908 Chester Ave Middlesboro , KY This home is older home well maintained, 2 bd 1 full bath with an efficiency apartment beh...	3 beds \| 2 baths \| 1,400 sq.ft.	$199,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 9.49% Airbnb Rental Income: $1188 Traditional Rental Income: $2212 Airbnb ROI: 2.02% Traditional ROI: 9.49%
140 Chasteen Drive Middlesboro , KY If you have been looking for a home to call your own, don't miss out on this lovely home w...	3 beds \| 2 baths \| 1,800 sq.ft.	$195,000	Airbnb cash on cash: 2.78% Traditional cash on cash: 11.79% Airbnb Rental Income: $1188 Traditional Rental Income: $2470 Airbnb ROI: 2.78% Traditional ROI: 11.79%
103 Leafwood Rd Middlesboro , KY Classic two-story home built in 1923, thoughtfully renovated to blend modern upgrades with...	2 beds \| 2 baths \| 1,326 sq.ft.	$165,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 9.18% Airbnb Rental Income: $1434 Traditional Rental Income: $1829 Airbnb ROI: 3.95% Traditional ROI: 9.18%
314 Picadilly Court Middlesboro , KY Spacious home located in Ambleside subdivision. This home has 4 bedrooms and 2 1/2 bathroo...	4 beds \| 2 baths \| 2,576 sq.ft.	$293,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.49% Airbnb Rental Income: $null Traditional Rental Income: $2106 Airbnb ROI: N/A Traditional ROI: 5.49%
2004 Twin Fawn Trl Middlesboro , KY BEAUTIFUL LUXURY HOME! This grand 1 and 1/2 story home is located right outside the city ...	5 beds \| 2 baths \| 2,542 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.15% Airbnb Rental Income: $null Traditional Rental Income: $2549 Airbnb ROI: N/A Traditional ROI: 3.15%
807 Exeter Ave Middlesboro , KY New custom built home in the heart of Middlesboro. This home features three (3) bedrooms a...	3 beds \| 2 baths \| 1,200 sq.ft.	$249,900	Airbnb cash on cash: 1.95% Traditional cash on cash: 5.9% Airbnb Rental Income: $1188 Traditional Rental Income: $1734 Airbnb ROI: 1.95% Traditional ROI: 5.9%
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%
4921 W CUMBERLAND Ave Middlesboro , KY Charming 3-Bedroom Home in a Prime Location! Discover comfort and convenience in this beau...	3 beds \| 2 baths \| 1,900 sq.ft.	$235,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 9.04% Airbnb Rental Income: $1188 Traditional Rental Income: $2416 Airbnb ROI: 1.78% Traditional ROI: 9.04%
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.	$339,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.31% Airbnb Rental Income: $null Traditional Rental Income: $2865 Airbnb ROI: N/A Traditional ROI: 7.31%
359 Beans Fork Rd Middlesboro , KY I love a good sunroom, don't you? Recently updated 2-bedroom 1 bath home is move in ready!...	2 beds \| 1 baths \| 952 sq.ft.	$150,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 9.22% Airbnb Rental Income: $1434 Traditional Rental Income: $1682 Airbnb ROI: 4.51% Traditional ROI: 9.22%
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%
180 Stevenson Branch Rd Middlesboro , KY Charming Rustic Cabin with Modern Comforts on 2 Acres Welcome to 180 Stevenson Branch Rd i...	3 beds \| 1 baths \| 1,200 sq.ft.	$179,900	Airbnb cash on cash: 3.05% Traditional cash on cash: 9.57% Airbnb Rental Income: $1188 Traditional Rental Income: $1917 Airbnb ROI: 3.05% Traditional ROI: 9.57%
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%
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%

Your search for investment property begins and ends here

Multi Family for Sale in Middlesboro, KY

4607 W Cumberland Ave

Middlesboro, KY

N/A beds | N/A baths | 0 sq.ft.

$189,000

Airbnb cash on cash: 2.09%

Traditional cash on cash: 3.81%

Airbnb Rental Income: $1188

Traditional Rental Income: $1110

Airbnb ROI: 2.09%

Traditional ROI: 3.81%

119 Wagon Hollow Rd

Middlesboro, KY

N/A beds | N/A baths | 1,500 sq.ft.

$250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.81%

Airbnb Rental Income: $null

Traditional Rental Income: $1194

Airbnb ROI: N/A

Traditional ROI: 2.81%

Other Investment Properties for Sale in Middlesboro

Middlesboro , KY

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

$199,000

Airbnb cash on cash: 2.02%

Traditional cash on cash: 9.49%

Airbnb Rental Income: $1188

Traditional Rental Income: $2212

Airbnb ROI: 2.02%

Traditional ROI: 9.49%

Middlesboro , KY

3 beds | 2 baths | 1,800 sq.ft.

$195,000

Airbnb cash on cash: 2.78%

Traditional cash on cash: 11.79%

Airbnb Rental Income: $1188

Traditional Rental Income: $2470

Airbnb ROI: 2.78%

Traditional ROI: 11.79%

Middlesboro , KY

2 beds | 2 baths | 1,326 sq.ft.

$165,000

Airbnb cash on cash: 3.95%

Traditional cash on cash: 9.18%

Airbnb Rental Income: $1434

Traditional Rental Income: $1829

Airbnb ROI: 3.95%

Traditional ROI: 9.18%

Middlesboro , KY

4 beds | 2 baths | 2,576 sq.ft.

$293,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.49%

Airbnb Rental Income: $null

Traditional Rental Income: $2106

Airbnb ROI: N/A

Traditional ROI: 5.49%

Middlesboro , KY

5 beds | 2 baths | 2,542 sq.ft.

$525,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.15%

Airbnb Rental Income: $null

Traditional Rental Income: $2549

Airbnb ROI: N/A

Traditional ROI: 3.15%

Middlesboro , KY

3 beds | 2 baths | 1,200 sq.ft.

$249,900

Airbnb cash on cash: 1.95%

Traditional cash on cash: 5.9%

Airbnb Rental Income: $1188

Traditional Rental Income: $1734

Airbnb ROI: 1.95%

Traditional ROI: 5.9%

Middlesboro , KY

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

$279,900

Airbnb cash on cash: 1.23%