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
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: 0.01% Traditional cash on cash: 4.28% Airbnb Rental Income: $1011 Traditional Rental Income: $1938 Airbnb ROI: 0.01% Traditional ROI: 4.28%
207 Arthur Hts Middlesboro, KY CHARMING VICTORIA HOME. Experience the timeless allure of this late-1800s Victorian master...	5 beds \| 2 baths \| 3,068 sq.ft.	$279,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.55% Airbnb Rental Income: $null Traditional Rental Income: $3259 Airbnb ROI: N/A Traditional ROI: 10.55%
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%
125 Cawood Ln Middlesboro, KY Cute as a button! This adorable cottage style home would make an excellent choice for a fi...	2 beds \| 2 baths \| 1,400 sq.ft.	$142,500	Airbnb cash on cash: 5.24% Traditional cash on cash: 10.43% Airbnb Rental Income: $1445 Traditional Rental Income: $1724 Airbnb ROI: 5.24% Traditional ROI: 10.43%
1015 Old Wilson Ln Middlesboro, KY Super nice four bedroom, two and 1/2 bath, 2488 sq ft with hardwood floors on a level lot ...	4 beds \| 2 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%
2802 W Cumberland Ave Middlesboro, KY Exceptional and holy smokes what style! 3-bedroom 1.5 bath home on a Cumberland Avenue cor...	3 beds \| 1 baths \| 1,304 sq.ft.	$260,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 6.26% Airbnb Rental Income: $1011 Traditional Rental Income: $2084 Airbnb ROI: 0.43% Traditional ROI: 6.26%
116 Edgewood Rd Middlesboro, KY Mountain Views, Privacy & Endless Possibilities! Discover the perfect blend of privacy, sp...	3 beds \| 1 baths \| 2,154 sq.ft.	$209,900	Airbnb cash on cash: 1.21% Traditional cash on cash: 9.7% Airbnb Rental Income: $1011 Traditional Rental Income: $2343 Airbnb ROI: 1.21% Traditional ROI: 9.7%
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: 3.28% Traditional cash on cash: 6.97% Airbnb Rental Income: $1445 Traditional Rental Income: $1678 Airbnb ROI: 3.28% Traditional ROI: 6.97%
717 S 27th St 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.	$267,500	Airbnb cash on cash: N/A Traditional cash on cash: 9.23% Airbnb Rental Income: $null Traditional Rental Income: $3198 Airbnb ROI: N/A Traditional ROI: 9.23%
156 Wellington Dr Middlesboro, KY Welcome home to this spacious and inviting 3-bedroom, 1.5-bath property that offers both c...	3 beds \| 1 baths \| 1,320 sq.ft.	$230,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 7.62% Airbnb Rental Income: $1011 Traditional Rental Income: $2155 Airbnb ROI: 0.72% Traditional ROI: 7.62%
717 Highway 441 Middlesboro, KY Beautiful 5-Bedroom Home on 1.165 Acres - Middlesboro, KY Welcome to 717 Highway 441, a st...	5 beds \| 3 baths \| 2,100 sq.ft.	$295,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.79% Airbnb Rental Income: $null Traditional Rental Income: $2770 Airbnb ROI: N/A Traditional ROI: 7.79%
414 S 24th St Middlesboro, KY Prime commercial opportunity at 414 S 24th Street in Middlesboro, KY! This versatile prope...	2 beds \| 2 baths \| 1,608 sq.ft.	$182,000	Airbnb cash on cash: 3.41% Traditional cash on cash: 9.32% Airbnb Rental Income: $1445 Traditional Rental Income: $2038 Airbnb ROI: 3.41% Traditional ROI: 9.32%
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: -0.82% Traditional cash on cash: 1.14% Airbnb Rental Income: $1445 Traditional Rental Income: $2767 Airbnb ROI: -0.82% 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: -0.23% Traditional cash on cash: 0.83% Airbnb Rental Income: $1445 Traditional Rental Income: $1858 Airbnb ROI: -0.23% Traditional ROI: 0.83%
713 Exeter Ave Middlesboro, KY Welcome to the stunning 713 Exeter Ave located in the lovely town of Middlesboro KY, less ...	4 beds \| 1 baths \| 2,430 sq.ft.	$165,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.29% Airbnb Rental Income: $null Traditional Rental Income: $1947 Airbnb ROI: N/A Traditional ROI: 10.29%
913 Doncaster St Middlesboro, KY This home is located in the city of Middlesboro minutes away from the hospital, close to d...	3 beds \| 2 baths \| 1,346 sq.ft.	$249,900	Airbnb cash on cash: 0.93% Traditional cash on cash: 6.83% Airbnb Rental Income: $1011 Traditional Rental Income: $2045 Airbnb ROI: 0.93% Traditional ROI: 6.83%
127 Alpine Rd Middlesboro, KY This charming property offers the perfect blend of cozy indoor living and expansive outdoo...	3 beds \| 2 baths \| 2,016 sq.ft.	$264,900	Airbnb cash on cash: 0.35% Traditional cash on cash: 7.61% Airbnb Rental Income: $1011 Traditional Rental Income: $2501 Airbnb ROI: 0.35% Traditional ROI: 7.61%
2002 Winchester Ave Middlesboro, KY CHARMING 2 BEDROOM/ONE BATH HOME! This charming 2 bedroom, 1 bath home offers a perfect bl...	2 beds \| 1 baths \| 1,120 sq.ft.	$135,000	Airbnb cash on cash: 5.26% Traditional cash on cash: 11.25% Airbnb Rental Income: $1445 Traditional Rental Income: $1792 Airbnb ROI: 5.26% Traditional ROI: 11.25%
2621 W Cumberland Avenue Middlesboro, KY Opportunities are built on the right properties and this could be the one! The potential o...	3 beds \| 2 baths \| 3,948 sq.ft.	$214,999	Airbnb cash on cash: 0.72% Traditional cash on cash: 9.2% Airbnb Rental Income: $1011 Traditional Rental Income: $2380 Airbnb ROI: 0.72% Traditional ROI: 9.2%
1807 Winchester Ave Middlesboro, KY Three-bedroom traditional brick ranch home. Located on a level lot convenient to the local...	3 beds \| 1 baths \| 1,104 sq.ft.	$155,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 9.88% Airbnb Rental Income: $1011 Traditional Rental Income: $1831 Airbnb ROI: 1.93% Traditional ROI: 9.88%
908 Manchester Ave Middlesboro, KY MOTIVATED SELLER This three-bedroom, two-bath home at 908 Manchester has been thoughtfully...	3 beds \| 2 baths \| 1,100 sq.ft.	$142,500	Airbnb cash on cash: 1.93% Traditional cash on cash: 10.17% Airbnb Rental Income: $1011 Traditional Rental Income: $1873 Airbnb ROI: 1.93% Traditional ROI: 10.17%
1010 W Chester Middlesboro, KY Charming Renovated Ranch in the Heart of Middlesboro! Welcome home to 1010 W Chester Avenu...	2 beds \| 1 baths \| 1,275 sq.ft.	$149,999	Airbnb cash on cash: 4.76% Traditional cash on cash: 10% Airbnb Rental Income: $1445 Traditional Rental Income: $1766 Airbnb ROI: 4.76% Traditional ROI: 10%
371 Eagle Ln Middlesboro, KY Looking for a nice home that is USDA, FHA, or VA approved? We have just what you have been...	2 beds \| 1 baths \| 853 sq.ft.	$159,900	Airbnb cash on cash: 4.83% Traditional cash on cash: 8.2% Airbnb Rental Income: $1445 Traditional Rental Income: $1530 Airbnb ROI: 4.83% Traditional ROI: 8.2%

Real Estate investment in Middlesboro, KY

There are 39 properties for sale in the city of Middlesboro . The median list price in Middlesboro is $159,450 and the average price per square foot is $72. In August 2026, the average monthly cash on cash return in Middlesboro is 10.00%. The average monthly rental income in Middlesboro is $1,987.

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

There are 39 investment properties available for sale in Middlesboro.

In 2026, 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 $1,445.

Your search for investment property begins and ends here

Investment Property for Sale in Middlesboro, KY

210 Claiborne Circle

Middlesboro, KY

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

$319,900

Airbnb cash on cash: 0.01%

Traditional cash on cash: 4.28%

Airbnb Rental Income: $1011

Traditional Rental Income: $1938

Airbnb ROI: 0.01%

Traditional ROI: 4.28%

207 Arthur Hts

Middlesboro, KY

5 beds | 2 baths | 3,068 sq.ft.

$279,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.55%

Airbnb Rental Income: $null

Traditional Rental Income: $3259

Airbnb ROI: N/A

Traditional ROI: 10.55%

1801 Exeter Ave

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%

125 Cawood Ln

Middlesboro, KY

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

$142,500

Airbnb cash on cash: 5.24%

Traditional cash on cash: 10.43%

Airbnb Rental Income: $1445

Traditional Rental Income: $1724

Airbnb ROI: 5.24%

Traditional ROI: 10.43%

1015 Old Wilson Ln

Middlesboro, KY

4 beds | 2 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%

2802 W Cumberland Ave

Middlesboro, KY

3 beds | 1 baths | 1,304 sq.ft.

$260,000

Airbnb cash on cash: 0.43%

Traditional cash on cash: 6.26%

Airbnb Rental Income: $1011

Traditional Rental Income: $2084

Airbnb ROI: 0.43%

Traditional ROI: 6.26%

116 Edgewood Rd

Middlesboro, KY

3 beds | 1 baths | 2,154 sq.ft.

$209,900

Airbnb cash on cash: 1.21%

Traditional cash on cash: 9.7%

Airbnb Rental Income: $1011

Traditional Rental Income: $2343

Airbnb ROI: 1.21%

Traditional ROI: 9.7%

1208 KY-217

Middlesboro, KY

2 beds | 2 baths | 960 sq.ft.

$189,000

Airbnb cash on cash: 3.28%

Traditional cash on cash: 6.97%

Airbnb Rental Income: $1445

Traditional Rental Income: $1678

Airbnb ROI: 3.28%