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 Ave 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: -0.89% Traditional cash on cash: 1.14% Airbnb Rental Income: $1375 Traditional Rental Income: $2767 Airbnb ROI: -0.89% Traditional ROI: 1.14%
725 N 19th St 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: -0.3% Traditional cash on cash: 0.83% Airbnb Rental Income: $1375 Traditional Rental Income: $1858 Airbnb ROI: -0.3% Traditional ROI: 0.83%
Other Investment Properties for Sale in Middlesboro
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.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.41% Airbnb Rental Income: $null Traditional Rental Income: $2549 Airbnb ROI: N/A Traditional ROI: 3.41%
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.	$148,000	Airbnb cash on cash: 4.25% Traditional cash on cash: 9.37% Airbnb Rental Income: $1375 Traditional Rental Income: $1682 Airbnb ROI: 4.25% Traditional ROI: 9.37%
1200 W Chester Ave Middlesboro , KY Charming Home for Sale in Middlesboro, KY - 1200 W Chester Ave Welcome to this inviting ho...	3 beds \| 1 baths \| 1,028 sq.ft.	$179,900	Airbnb cash on cash: 3.15% Traditional cash on cash: 9.49% Airbnb Rental Income: $1231 Traditional Rental Income: $1922 Airbnb ROI: 3.15% 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.	$170,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 10.16% Airbnb Rental Income: $1231 Traditional Rental Income: $1917 Airbnb ROI: 3.5% Traditional ROI: 10.16%
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 \| 3 baths \| 1,856 sq.ft.	$240,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 7.2% Airbnb Rental Income: $1231 Traditional Rental Income: $2003 Airbnb ROI: 2.06% Traditional ROI: 7.2%
123 Upper Gibson Lane Middlesboro , KY Schedule to see this cozy home that has 2 traditional bedrooms with closets and one room t...	2 beds \| 1 baths \| 1,088 sq.ft.	$155,000	Airbnb cash on cash: 4.66% Traditional cash on cash: 11.64% Airbnb Rental Income: $1375 Traditional Rental Income: $1991 Airbnb ROI: 4.66% Traditional ROI: 11.64%
918 E Cumberland Ave Middlesboro , KY This home rest on a lot that goes from city street to ally. This home has 3 bedrooms and o...	2 beds \| 1 baths \| 792 sq.ft.	$75,000	Airbnb cash on cash: 5.1% Traditional cash on cash: 11.88% Airbnb Rental Income: $1231 Traditional Rental Income: $1621 Airbnb ROI: 5.1% Traditional ROI: 11.88%
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: 2.96% Traditional cash on cash: 6.97% Airbnb Rental Income: $1375 Traditional Rental Income: $1678 Airbnb ROI: 2.96% Traditional ROI: 6.97%
11 Castleford Way Middlesboro , KY Price Improvement + Seller offering $5,000 toward buyer's closing cost with an acceptable ...	3 beds \| 1 baths \| 1,100 sq.ft.	$189,500	Airbnb cash on cash: 2.28% Traditional cash on cash: 7.06% Airbnb Rental Income: $1231 Traditional Rental Income: $1698 Airbnb ROI: 2.28% Traditional ROI: 7.06%
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: 1.07% Traditional cash on cash: 8.18% Airbnb Rental Income: $1231 Traditional Rental Income: $2648 Airbnb ROI: 1.07% Traditional ROI: 8.18%
923 Winchester Ave Middlesboro , KY 923 Winchester Ave, Middlesboro, KY 40965 \| Single Family Residential	1 beds \| 1 baths \| 800 sq.ft.	$85,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.11% Airbnb Rental Income: $null Traditional Rental Income: $1006 Airbnb ROI: N/A Traditional ROI: 9.11%
63 Old Pineville Pike Middlesboro , KY 63 Old Pineville Pike, Middlesboro, KY 40965 \| Single Family Residential	3 beds \| 2 baths \| 1,560 sq.ft.	$159,000	Airbnb cash on cash: 3.05% Traditional cash on cash: 10.38% Airbnb Rental Income: $1231 Traditional Rental Income: $1950 Airbnb ROI: 3.05% Traditional ROI: 10.38%
140 Wellington Dr Middlesboro , KY Nice 3-bedroom 2 bath home just for the picking. Priced is right with the possibility of a...	4 beds \| 2 baths \| 1,612 sq.ft.	$219,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.28% Airbnb Rental Income: $null Traditional Rental Income: $1970 Airbnb ROI: N/A Traditional ROI: 7.28%
259 Watson Ln Middlesboro , KY 259 Watson Ln, Middlesboro, KY 40965 \| Single Family Residential	3 beds \| 1 baths \| 1,976 sq.ft.	$2,500,000	Airbnb cash on cash: -1.53% Traditional cash on cash: -0.98% Airbnb Rental Income: $1231 Traditional Rental Income: $2121 Airbnb ROI: -1.53% Traditional ROI: -0.98%

Your search for investment property begins and ends here

Condos for Sale in Middlesboro, KY

508 & 512 Winchester Ave

Middlesboro, KY

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

$960,000

Airbnb cash on cash: -0.89%

Traditional cash on cash: 1.14%

Airbnb Rental Income: $1375

Traditional Rental Income: $2767

Airbnb ROI: -0.89%

Traditional ROI: 1.14%

725 N 19th St

Middlesboro, KY

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

$855,000

Airbnb cash on cash: -0.3%

Traditional cash on cash: 0.83%

Airbnb Rental Income: $1375

Traditional Rental Income: $1858

Airbnb ROI: -0.3%

Traditional ROI: 0.83%

Other Investment Properties for Sale in Middlesboro

Middlesboro , KY

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

$499,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.41%

Airbnb Rental Income: $null

Traditional Rental Income: $2549

Airbnb ROI: N/A

Traditional ROI: 3.41%

Middlesboro , KY

2 beds | 1 baths | 952 sq.ft.

$148,000

Airbnb cash on cash: 4.25%

Traditional cash on cash: 9.37%

Airbnb Rental Income: $1375

Traditional Rental Income: $1682

Airbnb ROI: 4.25%

Traditional ROI: 9.37%

Middlesboro , KY

3 beds | 1 baths | 1,028 sq.ft.

$179,900

Airbnb cash on cash: 3.15%

Traditional cash on cash: 9.49%

Airbnb Rental Income: $1231

Traditional Rental Income: $1922

Airbnb ROI: 3.15%

Traditional ROI: 9.49%

Middlesboro , KY

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%

Middlesboro , KY

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

$170,000

Airbnb cash on cash: 3.5%

Traditional cash on cash: 10.16%

Airbnb Rental Income: $1231

Traditional Rental Income: $1917

Airbnb ROI: 3.5%

Traditional ROI: 10.16%

Middlesboro , KY

3 beds | 3 baths | 1,856 sq.ft.

$240,000

Airbnb cash on cash: 2.06%

Traditional cash on cash: 7.2%

Airbnb Rental Income: $1231

Traditional Rental Income: $2003

Airbnb ROI: 2.06%

Traditional ROI: 7.2%

Middlesboro , KY

2 beds | 1 baths | 1,088 sq.ft.

$155,000

Airbnb cash on cash: 4.66%