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
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%
615 S 22nd Street Middlesboro, KY NOT FOR RENT. Come check out this beautifully renovated 2 bedroom, 2.5 bath home, metal ro...	2 beds \| 3 baths \| 960 sq.ft.	$200,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 5.31% Airbnb Rental Income: $1388 Traditional Rental Income: $1452 Airbnb ROI: 2.76% Traditional ROI: 5.31%
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.	$164,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.66% Airbnb Rental Income: $null Traditional Rental Income: $800 Airbnb ROI: N/A Traditional ROI: 2.66%
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%
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: 4.32% Traditional cash on cash: 9.37% Airbnb Rental Income: $1388 Traditional Rental Income: $1682 Airbnb ROI: 4.32% Traditional ROI: 9.37%
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: 2.94% Traditional cash on cash: 9.49% Airbnb Rental Income: $1189 Traditional Rental Income: $1922 Airbnb ROI: 2.94% 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: 3.28% Traditional cash on cash: 10.16% Airbnb Rental Income: $1189 Traditional Rental Income: $1917 Airbnb ROI: 3.28% 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: 1.91% Traditional cash on cash: 7.2% Airbnb Rental Income: $1189 Traditional Rental Income: $2003 Airbnb ROI: 1.91% Traditional ROI: 7.2%
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: 3.02% Traditional cash on cash: 6.97% Airbnb Rental Income: $1388 Traditional Rental Income: $1678 Airbnb ROI: 3.02% 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: 2.08% Traditional cash on cash: 7.06% Airbnb Rental Income: $1189 Traditional Rental Income: $1698 Airbnb ROI: 2.08% Traditional ROI: 7.06%
140 Wellington Drive 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%
23 Castleford Way Middlesboro, KY Located in the desirable Ambleside subdivision, this beautifully decorated and well-mainta...	3 beds \| 2 baths \| 1,080 sq.ft.	$192,500	Airbnb cash on cash: 2.29% Traditional cash on cash: 7.73% Airbnb Rental Income: $1189 Traditional Rental Income: $1798 Airbnb ROI: 2.29% Traditional ROI: 7.73%
156 Wellington Drive Middlesboro, KY Welcome home to this spacious and inviting 3-bedroom, 1.5-bath property that offers both c...	3 beds \| 2 baths \| 1,320 sq.ft.	$245,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 7.05% Airbnb Rental Income: $1189 Traditional Rental Income: $2155 Airbnb ROI: 1.21% Traditional ROI: 7.05%
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%
3306 W Cumberland Avenue Middlesboro, KY Newly remodeled home on Cumberland Ave, right next to Middlesboro Elementary School. Sitti...	3 beds \| 2 baths \| 2,126 sq.ft.	$349,900	Airbnb cash on cash: 0.3% Traditional cash on cash: 5.3% Airbnb Rental Income: $1189 Traditional Rental Income: $2444 Airbnb ROI: 0.3% Traditional ROI: 5.3%
414 S 24th Street 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: 3.14% Traditional cash on cash: 9.32% Airbnb Rental Income: $1388 Traditional Rental Income: $2038 Airbnb ROI: 3.14% Traditional ROI: 9.32%
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: -0.88% Traditional cash on cash: 1.14% Airbnb Rental Income: $1388 Traditional Rental Income: $2767 Airbnb ROI: -0.88% 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: -0.29% Traditional cash on cash: 0.83% Airbnb Rental Income: $1388 Traditional Rental Income: $1858 Airbnb ROI: -0.29% Traditional ROI: 0.83%
713 Exeter Avenue 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.	$180,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.37% Airbnb Rental Income: $null Traditional Rental Income: $1947 Airbnb ROI: N/A Traditional ROI: 9.37%
907 Doncaster Ave Middlesboro, KY 907 DONCASTER MIDDLESBORO KY 40965 This home is located in the city of Middlesboro minutes...	3 beds \| 2 baths \| 1,398 sq.ft.	$249,900	Airbnb cash on cash: 1.45% Traditional cash on cash: 6.93% Airbnb Rental Income: $1189 Traditional Rental Income: $2096 Airbnb ROI: 1.45% Traditional ROI: 6.93%
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: 1.56% Traditional cash on cash: 6.83% Airbnb Rental Income: $1189 Traditional Rental Income: $2045 Airbnb ROI: 1.56% Traditional ROI: 6.83%
707 Gloucester Ave Middlesboro, KY Located in Middlesboro, Kentucky, this charming home offers a fantastic location just minu...	3 beds \| 2 baths \| 1,184 sq.ft.	$169,900	Airbnb cash on cash: 3.02% Traditional cash on cash: 10.11% Airbnb Rental Income: $1189 Traditional Rental Income: $1951 Airbnb ROI: 3.02% Traditional ROI: 10.11%
127 Alpine #127 Middlesboro, KY This charming property offers the perfect blend of cozy indoor living and expansive outdoo...	3 beds \| 2 baths \| 2,016 sq.ft.	$279,900	Airbnb cash on cash: 0.83% Traditional cash on cash: 7.27% Airbnb Rental Income: $1189 Traditional Rental Income: $2501 Airbnb ROI: 0.83% Traditional ROI: 7.27%
1009 E Cumberland Ave Middlesboro, KY Charming 2 bedroom home located in historic Middlesboro, KY. Great location, close to shop...	2 beds \| 1 baths \| 850 sq.ft.	$115,000	Airbnb cash on cash: 6.03% Traditional cash on cash: 10.28% Airbnb Rental Income: $1388 Traditional Rental Income: $1440 Airbnb ROI: 6.03% Traditional ROI: 10.28%
2002 Winchester Avenue 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: 4.89% Traditional cash on cash: 11.25% Airbnb Rental Income: $1388 Traditional Rental Income: $1792 Airbnb ROI: 4.89% Traditional ROI: 11.25%

Real Estate investment in Middlesboro, KY

There are 26 properties for sale in the city of Middlesboro . The median list price in Middlesboro is $182,000 and the average price per square foot is $88. In May 2026, the average monthly cash on cash return in Middlesboro is 9.00%. The average monthly rental income in Middlesboro is $1,951.

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

There are 26 investment properties available for sale in Middlesboro.

In 2026, the best neighborhood to buy investment property is Middlesboro.

The ROI for Long-Term is higher than the Short-Term in Middlesboro with average rental income of $1,951.

Your search for investment property begins and ends here

Investment Property for Sale in Middlesboro, KY

207 Arthur Heights

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%

615 S 22nd Street

Middlesboro, KY

2 beds | 3 baths | 960 sq.ft.

$200,000

Airbnb cash on cash: 2.76%

Traditional cash on cash: 5.31%

Airbnb Rental Income: $1388

Traditional Rental Income: $1452

Airbnb ROI: 2.76%

Traditional ROI: 5.31%

1801 Exeter Ave

Middlesboro, KY

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

$164,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.66%

Airbnb Rental Income: $null

Traditional Rental Income: $800

Airbnb ROI: N/A

Traditional ROI: 2.66%

1015 Old Wilson Lane

Middlesboro, KY

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%

359 Beans Fork Rd

Middlesboro, KY

2 beds | 1 baths | 952 sq.ft.

$148,000

Airbnb cash on cash: 4.32%

Traditional cash on cash: 9.37%

Airbnb Rental Income: $1388

Traditional Rental Income: $1682

Airbnb ROI: 4.32%

Traditional ROI: 9.37%

1200 W Chester Avenue

Middlesboro, KY

3 beds | 2 baths | 1,028 sq.ft.

$179,900

Airbnb cash on cash: 2.94%

Traditional cash on cash: 9.49%

Airbnb Rental Income: $1189

Traditional Rental Income: $1922

Airbnb ROI: 2.94%

Traditional ROI: 9.49%

523 N 30th St

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%

180 Stevenson Branch Rd

Middlesboro, KY

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

$170,000

Airbnb cash on cash: 3.28%

Traditional cash on cash: 10.16%

Airbnb Rental Income: $1189

Traditional Rental Income: $1917

Airbnb ROI: 3.28%