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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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.	$199,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 9.49% Airbnb Rental Income: $1188 Traditional Rental Income: $2212 Airbnb ROI: 2.02% Traditional ROI: 9.49%
140 Chasteen Drive Middlesboro, KY If you have been looking for a home to call your own, don't miss out on this lovely home w...	3 beds \| 2 baths \| 1,800 sq.ft.	$195,000	Airbnb cash on cash: 2.78% Traditional cash on cash: 11.79% Airbnb Rental Income: $1188 Traditional Rental Income: $2470 Airbnb ROI: 2.78% Traditional ROI: 11.79%
103 Leafwood Rd Middlesboro, KY Classic two-story home built in 1923, thoughtfully renovated to blend modern upgrades with...	2 beds \| 2 baths \| 1,326 sq.ft.	$165,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 9.18% Airbnb Rental Income: $1434 Traditional Rental Income: $1829 Airbnb ROI: 3.95% Traditional ROI: 9.18%
314 Picadilly Court Middlesboro, KY Spacious home located in Ambleside subdivision. This home has 4 bedrooms and 2 1/2 bathroo...	4 beds \| 2 baths \| 2,576 sq.ft.	$293,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.49% Airbnb Rental Income: $null Traditional Rental Income: $2106 Airbnb ROI: N/A Traditional ROI: 5.49%
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.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.15% Airbnb Rental Income: $null Traditional Rental Income: $2549 Airbnb ROI: N/A Traditional ROI: 3.15%
807 Exeter Ave Middlesboro, KY New custom built home in the heart of Middlesboro. This home features three (3) bedrooms a...	3 beds \| 2 baths \| 1,200 sq.ft.	$249,900	Airbnb cash on cash: 1.95% Traditional cash on cash: 5.9% Airbnb Rental Income: $1188 Traditional Rental Income: $1734 Airbnb ROI: 1.95% Traditional ROI: 5.9%
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.	$279,900	Airbnb cash on cash: 1.23% Traditional cash on cash: 8.77% Airbnb Rental Income: $1188 Traditional Rental Income: $2788 Airbnb ROI: 1.23% Traditional ROI: 8.77%
4921 W CUMBERLAND Ave Middlesboro, KY Charming 3-Bedroom Home in a Prime Location! Discover comfort and convenience in this beau...	3 beds \| 2 baths \| 1,900 sq.ft.	$235,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 9.04% Airbnb Rental Income: $1188 Traditional Rental Income: $2416 Airbnb ROI: 1.78% Traditional ROI: 9.04%
805 Worchester Ave Middlesboro, KY This home has been brought back beyond its Glory!! Completely remodeled from the sub floor...	5 beds \| 3 baths \| 2,250 sq.ft.	$339,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.31% Airbnb Rental Income: $null Traditional Rental Income: $2865 Airbnb ROI: N/A Traditional ROI: 7.31%
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.	$150,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 9.22% Airbnb Rental Income: $1434 Traditional Rental Income: $1682 Airbnb ROI: 4.51% Traditional ROI: 9.22%
505 S 38th St Middlesboro, KY Located in Middlesboro, KY, this property is conveniently close to the hospital, schools, ...	2 beds \| 2 baths \| 1,144 sq.ft.	$198,500	Airbnb cash on cash: 3.66% Traditional cash on cash: 7.99% Airbnb Rental Income: $1434 Traditional Rental Income: $1821 Airbnb ROI: 3.66% Traditional ROI: 7.99%
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.	$458,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.79% Airbnb Rental Income: $null Traditional Rental Income: $3607 Airbnb ROI: N/A Traditional ROI: 6.79%
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.	$179,900	Airbnb cash on cash: 3.05% Traditional cash on cash: 9.57% Airbnb Rental Income: $1188 Traditional Rental Income: $1917 Airbnb ROI: 3.05% Traditional ROI: 9.57%
409 Meadow Lane Middlesboro, KY This 4 bedroom home is located just minutes away from Downtown Middlesboro KY. With upgrad...	4 beds \| 2 baths \| 1,120 sq.ft.	$184,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.14% Airbnb Rental Income: $null Traditional Rental Income: $2021 Airbnb ROI: N/A Traditional ROI: 9.14%
220 Windermere Drive Middlesboro, KY BEAUTIFUL MOVE IN READY HOME IN AMBLESIDE. Discover your next home in Ambleside, a tranqui...	3 beds \| 2 baths \| 1,692 sq.ft.	$269,500	Airbnb cash on cash: 1.43% Traditional cash on cash: 7.42% Airbnb Rental Income: $1188 Traditional Rental Income: $2322 Airbnb ROI: 1.43% Traditional ROI: 7.42%
2702 Cumberland Avenue Middlesboro, KY Don't miss this opportunity to own a historic home on Cumberland Avenue with a rare corner...	4 beds \| 2 baths \| 3,885 sq.ft.	$359,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.69% Airbnb Rental Income: $null Traditional Rental Income: $3308 Airbnb ROI: N/A Traditional ROI: 7.69%
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 \| 2 baths \| 1,856 sq.ft.	$240,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 7.2% Airbnb Rental Income: $1188 Traditional Rental Income: $2003 Airbnb ROI: 1.91% Traditional ROI: 7.2%
123 Upper Gibson Lane Middlesboro, KY Cozy 3 bedroom, 1 bathroom home sitting on a surveyed acre with detached 1 car garage that...	3 beds \| 2 baths \| 1,088 sq.ft.	$155,000	Airbnb cash on cash: 3.6% Traditional cash on cash: 11.64% Airbnb Rental Income: $1188 Traditional Rental Income: $1991 Airbnb ROI: 3.6% Traditional ROI: 11.64%
6 Hampton Court Middlesboro, KY Beautiful split foyer home in Ambleside. The view from the front window is amazing. This w...	4 beds \| 3 baths \| 1,966 sq.ft.	$249,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.8% Airbnb Rental Income: $null Traditional Rental Income: $2696 Airbnb ROI: N/A Traditional ROI: 9.8%
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.	$160,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 8.76% Airbnb Rental Income: $1188 Traditional Rental Income: $1621 Airbnb ROI: 3.39% Traditional ROI: 8.76%
45 Fourmile Run Road Middlesboro, KY Newly Remodeled, move-in ready home. This home is nestled in the heart of Middlesboro on a...	3 beds \| 2 baths \| 934 sq.ft.	$172,000	Airbnb cash on cash: 2.97% Traditional cash on cash: 8.86% Airbnb Rental Income: $1188 Traditional Rental Income: $1767 Airbnb ROI: 2.97% Traditional ROI: 8.86%
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: 3.23% Traditional cash on cash: 6.97% Airbnb Rental Income: $1434 Traditional Rental Income: $1678 Airbnb ROI: 3.23% Traditional ROI: 6.97%
11 Castleford Way Middlesboro, KY Renovated and truly move in ready! Proudly owned by just one owner, this home shows except...	3 beds \| 1 baths \| 1,100 sq.ft.	$235,200	Airbnb cash on cash: 1.33% Traditional cash on cash: 5.36% Airbnb Rental Income: $1188 Traditional Rental Income: $1698 Airbnb ROI: 1.33% Traditional ROI: 5.36%
409 Fairview Road Middlesboro, KY This 4 bedroom 3 1/2 bath ranch is siting on 2.17 acres minutes from downtown. With a view...	4 beds \| 4 baths \| 2,684 sq.ft.	$369,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.96% Airbnb Rental Income: $null Traditional Rental Income: $3499 Airbnb ROI: N/A Traditional ROI: 7.96%
1908 W Chester Middlesboro, KY This fully renovated, 100% occupied multi-family complex is an exceptional investment oppo...	N/A beds \| N/A baths \| 4,000 sq.ft.	$799,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.23% Airbnb Rental Income: $null Traditional Rental Income: $1646 Airbnb ROI: N/A Traditional ROI: 0.23%
832 N 25th St Middlesboro, KY	6 beds \| 3 baths \| 4,033 sq.ft.	$319,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.48% Airbnb Rental Income: $null Traditional Rental Income: $3202 Airbnb ROI: N/A Traditional ROI: 8.48%
164 Walker Lane Middlesboro, KY Charming 3 Bedroom, 2 Bath Home - Fully Updated and Move-In Ready! Renovations and upgrade...	3 beds \| 2 baths \| 1,040 sq.ft.	$174,500	Airbnb cash on cash: 2.41% Traditional cash on cash: 8.3% Airbnb Rental Income: $1188 Traditional Rental Income: $1780 Airbnb ROI: 2.41% Traditional ROI: 8.3%
113 Hollywood Dr Middlesboro, KY 113 Hollywood Dr, Middlesboro, KY 40965 \| Single Family Residential	3 beds \| 2 baths \| 3,174 sq.ft.	$299,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 7.22% Airbnb Rental Income: $1188 Traditional Rental Income: $2648 Airbnb ROI: 0.66% Traditional ROI: 7.22%
923 Winchester Ave Middlesboro, KY 923 Winchester Ave, Middlesboro, KY 40965 \| Single Family Residential	1 beds \| 1 baths \| 800 sq.ft.	$99,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.63% Airbnb Rental Income: $null Traditional Rental Income: $1006 Airbnb ROI: N/A Traditional ROI: 7.63%
63 Old Pineville Pike Middlesboro, KY 63 Old Pineville Pike, Middlesboro, KY 40965 \| Single Family Residential	3 beds \| 2 baths \| 1,560 sq.ft.	$185,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 8.7% Airbnb Rental Income: $1188 Traditional Rental Income: $1950 Airbnb ROI: 2.17% Traditional ROI: 8.7%
140 Wellington Dr Middlesboro, KY 140 Wellington Dr, Middlesboro, KY 40965 \| Single Family Residential	3 beds \| 2 baths \| 1,612 sq.ft.	$249,900	Airbnb cash on cash: 1.15% Traditional cash on cash: 6.1% Airbnb Rental Income: $1188 Traditional Rental Income: $1970 Airbnb ROI: 1.15% Traditional ROI: 6.1%
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: -1.55% Traditional cash on cash: -0.98% Airbnb Rental Income: $1188 Traditional Rental Income: $2121 Airbnb ROI: -1.55% Traditional ROI: -0.98%
280 Parker Lane Middlesboro, KY Beautiful and practically brand new! This 3 bedroom 2 bath home is perfect for a sweet fam...	3 beds \| 2 baths \| 1,375 sq.ft.	$210,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 7.96% Airbnb Rental Income: $1188 Traditional Rental Income: $2047 Airbnb ROI: 1.7% Traditional ROI: 7.96%
4607 W Cumberland Ave Middlesboro, KY 4607 W Cumberland Ave, Middlesboro, KY 40965 \| Multi Family	N/A beds \| N/A baths \| 0 sq.ft.	$189,000	Airbnb cash on cash: 2.09% Traditional cash on cash: 3.81% Airbnb Rental Income: $1188 Traditional Rental Income: $1110 Airbnb ROI: 2.09% Traditional ROI: 3.81%
321 Chester Ave Middlesboro, KY 321 Chester Ave, Middlesboro, KY 40965 \| Other	N/A beds \| N/A baths \| N/A	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.39% Airbnb Rental Income: $null Traditional Rental Income: $831 Airbnb ROI: N/A Traditional ROI: 0.39%
00 00-us 25e Pineville Hwy Middlesboro, KY 00 00-us 25e Pineville Hwy, Middlesboro, KY 40965 \| Other	N/A beds \| N/A baths \| N/A	$600,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.54% Airbnb Rental Income: $null Traditional Rental Income: $831 Airbnb ROI: N/A Traditional ROI: -0.54%
312 Blakely Ln Middlesboro, KY 312 Blakely Ln, Middlesboro, KY 40965 \| Other	N/A beds \| N/A baths \| N/A	$139,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.68% Airbnb Rental Income: $null Traditional Rental Income: $831 Airbnb ROI: N/A Traditional ROI: 3.68%
119 Wagon Hollow Rd Middlesboro, KY 119 Wagon Hollow Rd, Middlesboro, KY 40965 \| Multi Family	N/A beds \| N/A baths \| 1,500 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.81% Airbnb Rental Income: $null Traditional Rental Income: $1194 Airbnb ROI: N/A Traditional ROI: 2.81%
206 Summit Dr Middlesboro, KY 206 Summit Dr, Middlesboro, KY 40965 \| Single Family Residential	4 beds \| 2 baths \| 1,832 sq.ft.	$279,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.08% Airbnb Rental Income: $null Traditional Rental Income: $2179 Airbnb ROI: N/A Traditional ROI: 6.08%

Real Estate investment in Middlesboro, KY

There are 39 properties for sale in the city of Middlesboro . The median list price in Middlesboro is $189,000 and the average price per square foot is $115. In January 2026, the average monthly cash on cash return in Middlesboro is 9.00%. The average monthly rental income in Middlesboro is $1,867.

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 Long-Term is higher than the Short-Term in Middlesboro with average rental income of $1,867.

Your search for investment property begins and ends here

Investment Property for Sale in Middlesboro, KY

908 Chester Ave

Middlesboro, KY

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

$199,000

Airbnb cash on cash: 2.02%

Traditional cash on cash: 9.49%

Airbnb Rental Income: $1188

Traditional Rental Income: $2212

Airbnb ROI: 2.02%

Traditional ROI: 9.49%

140 Chasteen Drive

Middlesboro, KY

3 beds | 2 baths | 1,800 sq.ft.

$195,000

Airbnb cash on cash: 2.78%

Traditional cash on cash: 11.79%

Airbnb Rental Income: $1188

Traditional Rental Income: $2470

Airbnb ROI: 2.78%

Traditional ROI: 11.79%

103 Leafwood Rd

Middlesboro, KY

2 beds | 2 baths | 1,326 sq.ft.

$165,000

Airbnb cash on cash: 3.95%

Traditional cash on cash: 9.18%

Airbnb Rental Income: $1434

Traditional Rental Income: $1829

Airbnb ROI: 3.95%

Traditional ROI: 9.18%

314 Picadilly Court

Middlesboro, KY

4 beds | 2 baths | 2,576 sq.ft.

$293,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.49%

Airbnb Rental Income: $null

Traditional Rental Income: $2106

Airbnb ROI: N/A

Traditional ROI: 5.49%

2004 Twin Fawn Trl

Middlesboro, KY

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

$525,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.15%

Airbnb Rental Income: $null

Traditional Rental Income: $2549

Airbnb ROI: N/A

Traditional ROI: 3.15%

807 Exeter Ave

Middlesboro, KY

3 beds | 2 baths | 1,200 sq.ft.

$249,900

Airbnb cash on cash: 1.95%

Traditional cash on cash: 5.9%

Airbnb Rental Income: $1188

Traditional Rental Income: $1734

Airbnb ROI: 1.95%

Traditional ROI: 5.9%

515 Englewood Rd

Middlesboro, KY

3 beds | 3 baths | 2,210 sq.ft.

$279,900

Airbnb cash on cash: 1.23%

Traditional cash on cash: 8.77%

Airbnb Rental Income: $1188

Traditional Rental Income: $2788

Airbnb ROI: 1.23%

Traditional ROI: 8.77%

4921 W CUMBERLAND Ave

Middlesboro, KY

3 beds | 2 baths | 1,900 sq.ft.

$235,000

Airbnb cash on cash: 1.78%

Traditional cash on cash: 9.04%

Airbnb Rental Income: $1188

Traditional Rental Income: $2416

Airbnb ROI: 1.78%