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.

Golden Highlands Investment Property for Sale in Middlesboro, KY

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

Showing 25 Golden Highlands Investment Property 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
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 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: 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%
409 Meadow Lane Middlesboro, KY This 4 bedroom home is located just minutes away from Downtown Middlesboro KY. This home f...	4 beds \| 2 baths \| 1,120 sq.ft.	$168,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.13% Airbnb Rental Income: $null Traditional Rental Income: $2021 Airbnb ROI: N/A Traditional ROI: 10.13%
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 Avenue Middlesboro, KY This home rest on a lot that goes from city street to ally. This home has 3 bedrooms and o...	3 beds \| 1 baths \| 792 sq.ft.	$120,000	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%
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: 2.48% Traditional cash on cash: 7.73% Airbnb Rental Income: $1231 Traditional Rental Income: $1798 Airbnb ROI: 2.48% 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: 1.36% Traditional cash on cash: 7.05% Airbnb Rental Income: $1231 Traditional Rental Income: $2155 Airbnb ROI: 1.36% Traditional ROI: 7.05%
105, 103, 120 Nutwood Road unit: A & B Middlesboro, KY 2 homes (103 and 105 Nutwood) and a duplex (120 Redwood) currently used as rental properti...	3 beds \| 1 baths \| 728 sq.ft.	$210,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 5.69% Airbnb Rental Income: $1231 Traditional Rental Income: $1596 Airbnb ROI: 1.88% Traditional ROI: 5.69%
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: 0.41% Traditional cash on cash: 5.3% Airbnb Rental Income: $1231 Traditional Rental Income: $2444 Airbnb ROI: 0.41% 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: 3.08% Traditional cash on cash: 9.32% Airbnb Rental Income: $1375 Traditional Rental Income: $2038 Airbnb ROI: 3.08% 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: -0.89% 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 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: -0.3% Traditional cash on cash: 0.83% Airbnb Rental Income: $1375 Traditional Rental Income: $1858 Airbnb ROI: -0.3% 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: 1.6% Traditional cash on cash: 6.93% Airbnb Rental Income: $1231 Traditional Rental Income: $2096 Airbnb ROI: 1.6% 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: 1.71% Traditional cash on cash: 6.83% Airbnb Rental Income: $1231 Traditional Rental Income: $2045 Airbnb ROI: 1.71% 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: 3.23% Traditional cash on cash: 10.11% Airbnb Rental Income: $1231 Traditional Rental Income: $1951 Airbnb ROI: 3.23% 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: 0.97% Traditional cash on cash: 7.27% Airbnb Rental Income: $1231 Traditional Rental Income: $2501 Airbnb ROI: 0.97% 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: 5.93% Traditional cash on cash: 10.28% Airbnb Rental Income: $1375 Traditional Rental Income: $1440 Airbnb ROI: 5.93% Traditional ROI: 10.28%

Your search for investment property begins and ends here

Golden Highlands Investment Property for Sale in Middlesboro, KY

359 Beans Fork Rd

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%

1200 W Chester Avenue

Middlesboro, KY

3 beds | 2 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

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: 3.5%

Traditional cash on cash: 10.16%

Airbnb Rental Income: $1231

Traditional Rental Income: $1917

Airbnb ROI: 3.5%

Traditional ROI: 10.16%

409 Meadow Lane

Middlesboro, KY

4 beds | 2 baths | 1,120 sq.ft.

$168,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.13%

Airbnb Rental Income: $null

Traditional Rental Income: $2021

Airbnb ROI: N/A

Traditional ROI: 10.13%

129 Lower Gibson Lane

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%

123 Upper Gibson Lane

Middlesboro, KY

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 Avenue

Middlesboro, KY

3 beds | 1 baths | 792 sq.ft.

$120,000

Airbnb cash on cash: 5.1%

Traditional cash on cash: 11.88%

Airbnb Rental Income: $1231

Traditional Rental Income: $1621

Airbnb ROI: 5.1%