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.

Condos for Sale in Middlesboro, KY

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

Showing 2 Condo 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
508 & 512 Winchester Avenue Middlesboro, KY Prime Multi-Family Investment Opportunity - 508 & 512 Winchester Avenue, Middlesboro, KY T...	2 beds \| 2 baths \| 6,696 sq.ft.	$960,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 1.14% Airbnb Rental Income: $1421 Traditional Rental Income: $2767 Airbnb ROI: -0.84% Traditional ROI: 1.14%
725 N 19th Street Middlesboro, KY Prime Multifamily Investment Opportunity Presenting a well-established commercial apartmen...	2 beds \| 2 baths \| 15,119 sq.ft.	$855,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 0.83% Airbnb Rental Income: $1421 Traditional Rental Income: $1858 Airbnb ROI: -0.25% Traditional ROI: 0.83%
Other Investment Properties for Sale in Middlesboro
210 Claiborne Circle Middlesboro , KY Like-new one-owner home built in 2018 by Overholt Construction. Features open floor plan a...	3 beds \| 2 baths \| 1,585 sq.ft.	$319,900	Airbnb cash on cash: 1.19% Traditional cash on cash: 4.28% Airbnb Rental Income: $1435 Traditional Rental Income: $1938 Airbnb ROI: 1.19% Traditional ROI: 4.28%
413 S 26th St Middlesboro , KY This beautiful 2 bed 1 bath with beautiful hardwood floors, sits only minutes away from do...	2 beds \| 1 baths \| 1,008 sq.ft.	$140,000	Airbnb cash on cash: 5.17% Traditional cash on cash: 9.62% Airbnb Rental Income: $1421 Traditional Rental Income: $1593 Airbnb ROI: 5.17% Traditional ROI: 9.62%
207 Arthur Heights Middlesboro , KY CHARMING VICTORIA HOME. Experience the timeless allure of this late-1800s Victorian master...	5 beds \| 3 baths \| 3,068 sq.ft.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.79% Airbnb Rental Income: $null Traditional Rental Income: $3259 Airbnb ROI: N/A Traditional ROI: 9.79%
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.	$225,000	Airbnb cash on cash: 2.65% Traditional cash on cash: 8.31% Airbnb Rental Income: $1435 Traditional Rental Income: $2212 Airbnb ROI: 2.65% Traditional ROI: 8.31%
422 Wilderness Rd Middlesboro , KY Super cute starter home with 2 beds and 1 full bath. Recently remodeled with excellent upd...	2 beds \| 1 baths \| 840 sq.ft.	$150,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 3.99% Airbnb Rental Income: $1421 Traditional Rental Income: $932 Airbnb ROI: 4.43% Traditional ROI: 3.99%
1801 Exeter Ave Middlesboro , KY 2 HOMES with one FULLY remodeled home in back 2 bedroom 1 bath Cute as a button! Home on c...	N/A beds \| N/A baths \| 700 sq.ft.	$159,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.8% Airbnb Rental Income: $null Traditional Rental Income: $800 Airbnb ROI: N/A Traditional ROI: 2.8%
1015 Old Wilson Lane Middlesboro , KY Super nice four bedroom, two and 1/2 bath, 2488 sq ft with hardwood floors on a level lot ...	4 beds \| 3 baths \| 2,488 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.38% Airbnb Rental Income: $null Traditional Rental Income: $2915 Airbnb ROI: N/A Traditional ROI: 7.38%
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.	$279,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 8.8% Airbnb Rental Income: $1435 Traditional Rental Income: $2788 Airbnb ROI: 2.02% Traditional ROI: 8.8%
116 Edgewood Road Middlesboro , KY Mountain Views, Privacy & Endless Possibilities! Discover the perfect blend of privacy, sp...	3 beds \| 2 baths \| 2,154 sq.ft.	$240,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 8.38% Airbnb Rental Income: $1435 Traditional Rental Income: $2343 Airbnb ROI: 2.49% Traditional ROI: 8.38%
1200 W Chester Avenue Middlesboro , KY Charming Home for Sale in Middlesboro, KY - 1200 W Chester Ave Welcome to this inviting ho...	3 beds \| 2 baths \| 1,028 sq.ft.	$179,900	Airbnb cash on cash: 4.14% Traditional cash on cash: 9.49% Airbnb Rental Income: $1435 Traditional Rental Income: $1922 Airbnb ROI: 4.14% Traditional ROI: 9.49%
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.	$455,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.84% Airbnb Rental Income: $null Traditional Rental Income: $3607 Airbnb ROI: N/A Traditional ROI: 6.84%
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.	$160,000	Airbnb cash on cash: 4.88% Traditional cash on cash: 10.84% Airbnb Rental Income: $1435 Traditional Rental Income: $1917 Airbnb ROI: 4.88% Traditional ROI: 10.84%
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: 3.17% Traditional cash on cash: 6.97% Airbnb Rental Income: $1421 Traditional Rental Income: $1678 Airbnb ROI: 3.17% Traditional ROI: 6.97%
717 S 27th Street Middlesboro , KY This open floor plan home is waiting for your large family. This home features 5 bedrooms ...	5 beds \| 4 baths \| 3,195 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.59% Airbnb Rental Income: $null Traditional Rental Income: $3198 Airbnb ROI: N/A Traditional ROI: 7.59%
113 Hollywood Dr Middlesboro , KY 113 Hollywood Dr, Middlesboro, KY 40965 \| Single Family Residential	3 beds \| 2 baths \| 3,174 sq.ft.	$270,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 8.18% Airbnb Rental Income: $1435 Traditional Rental Income: $2648 Airbnb ROI: 1.73% Traditional ROI: 8.18%

Your search for investment property begins and ends here

Condos for Sale in Middlesboro, KY

508 & 512 Winchester Avenue

Middlesboro, KY

2 beds | 2 baths | 6,696 sq.ft.

$960,000

Airbnb cash on cash: -0.84%

Traditional cash on cash: 1.14%

Airbnb Rental Income: $1421

Traditional Rental Income: $2767

Airbnb ROI: -0.84%

Traditional ROI: 1.14%

725 N 19th Street

Middlesboro, KY

2 beds | 2 baths | 15,119 sq.ft.

$855,000

Airbnb cash on cash: -0.25%

Traditional cash on cash: 0.83%

Airbnb Rental Income: $1421

Traditional Rental Income: $1858

Airbnb ROI: -0.25%

Traditional ROI: 0.83%

Other Investment Properties for Sale in Middlesboro

Middlesboro , KY

3 beds | 2 baths | 1,585 sq.ft.

$319,900

Airbnb cash on cash: 1.19%

Traditional cash on cash: 4.28%

Airbnb Rental Income: $1435

Traditional Rental Income: $1938

Airbnb ROI: 1.19%

Traditional ROI: 4.28%

Middlesboro , KY

2 beds | 1 baths | 1,008 sq.ft.

$140,000

Airbnb cash on cash: 5.17%

Traditional cash on cash: 9.62%

Airbnb Rental Income: $1421

Traditional Rental Income: $1593

Airbnb ROI: 5.17%

Traditional ROI: 9.62%

Middlesboro , KY

5 beds | 3 baths | 3,068 sq.ft.

$299,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.79%

Airbnb Rental Income: $null

Traditional Rental Income: $3259

Airbnb ROI: N/A

Traditional ROI: 9.79%

Middlesboro , KY

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

$225,000

Airbnb cash on cash: 2.65%

Traditional cash on cash: 8.31%

Airbnb Rental Income: $1435

Traditional Rental Income: $2212

Airbnb ROI: 2.65%

Traditional ROI: 8.31%

Middlesboro , KY

2 beds | 1 baths | 840 sq.ft.

$150,000

Airbnb cash on cash: 4.43%

Traditional cash on cash: 3.99%

Airbnb Rental Income: $1421

Traditional Rental Income: $932

Airbnb ROI: 4.43%

Traditional ROI: 3.99%

Middlesboro , KY

N/A beds | N/A baths | 700 sq.ft.

$159,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.8%

Airbnb Rental Income: $null

Traditional Rental Income: $800

Airbnb ROI: N/A

Traditional ROI: 2.8%

Middlesboro , KY

4 beds | 3 baths | 2,488 sq.ft.

$325,000

Airbnb cash on cash: N/A