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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
109 Hollywood DriveMiddlesboro, KYThis 3,544 sf home built approximately in 1965 was completely remodeled and updated in 202... |
3 beds | N/A baths | 3,544 sq.ft. |
$299,000 |
Airbnb cash on cash: 1.31%
|
192 Owens LaneMiddlesboro, KYThree-bedroom, 2 bath home on 4 private acres overlooking historic Middlesboro, Ky. Partia... |
3 beds | 1 baths | 2,600 sq.ft. |
$165,000 |
Airbnb cash on cash: 3.8%
|
140 Chasteen DriveMiddlesboro, KYIf 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. |
$215,000 |
Airbnb cash on cash: 2.99%
|
915 Lothbury AveMiddlesboro, KYCharming & Spacious Home with Poolside Living in Historic Middlesboro! This 3-bedroom, 4-b... |
3 beds | 4 baths | 2,349 sq.ft. |
$299,000 |
Airbnb cash on cash: 1.36%
|
515 Englewood RdMiddlesboro, KYExplore 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: 1.66%
|
626 S 22nd StMiddlesboro, KYWonderfully maintained home sitting on 12 beautiful flat, and cleared lots at the dead end... |
3 beds | 2 baths | 1,456 sq.ft. |
$190,000 |
Airbnb cash on cash: 3.47%
|
805 Worchester AveMiddlesboro, KYThis home has been brought back beyond its Glory!! Completely remodeled from the sub floor... |
5 beds | 3 baths | 2,250 sq.ft. |
$349,900 |
Airbnb cash on cash: N/A
|
1005 Hollywood DriveMiddlesboro, KYLocated in Middlesboro KY, you will find this 3 bedroom 1 bath ranch style home with a ful... |
3 beds | 1 baths | 1,110 sq.ft. |
$157,000 |
Airbnb cash on cash: 3.97%
|
515 N 25th StMiddlesboro, KYCute as I'll get out! And no, I don't mean cute as in little either. This one packs a big ... |
3 beds | 1 baths | 2,000 sq.ft. |
$185,000 |
Airbnb cash on cash: 3.51%
|
505 S 38th StMiddlesboro, KYLocated in Middlesboro, KY, this property is conveniently close to the hospital, schools, ... |
2 beds | 2 baths | 1,144 sq.ft. |
$225,000 |
Airbnb cash on cash: 3.3%
|
516 S 34th StMiddlesboro, KYUnbelievable find in the city limits of Middlesboro. 13.7 acres inside the city limits wit... |
2 beds | 1 baths | 776 sq.ft. |
$650,000 |
Airbnb cash on cash: -0.29%
|
523 N 30th StMiddlesboro, KYSpacious 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
|
900 Twin Fawn TrailMiddlesboro, KYIn the beautiful hills of Vista Venado lies the gorgeous 3 bedroom and 2 bath 900 Twin Faw... |
3 beds | 2 baths | 2,270 sq.ft. |
$299,900 |
Airbnb cash on cash: 0.98%
|
409 Meadow LaneMiddlesboro, KYThis 4 bedroom home is located just minutes away from Downtown Middlesboro KY. With upgrad... |
4 beds | N/A baths | 1,120 sq.ft. |
$184,900 |
Airbnb cash on cash: N/A
|
708 Ilchester AveMiddlesboro, KYNewly renovated 3 bedroom, 2 bath house located in a great neighborhood in Middlesboro, Ky... |
3 beds | 2 baths | 1,312 sq.ft. |
$180,000 |
Airbnb cash on cash: 3.46%
|
5 Abbey LaneMiddlesboro, KYTired of living in a house where you don't know your neighbors and feel like you can't enj... |
3 beds | 2 baths | 1,221 sq.ft. |
$249,900 |
Airbnb cash on cash: 1.91%
|
3008 State Highway 441Middlesboro, KYThis Newly Remodeled home is located just minutes away from downtown Middlesboro and the H... |
3 beds | N/A baths | 1,800 sq.ft. |
$174,000 |
Airbnb cash on cash: 3.68%
|
1203 Winchester AvenueMiddlesboro, KYBeautiful home in the heart of Middlesboro. Make a grand entrance to the spacious formal l... |
4 beds | N/A baths | 2,455 sq.ft. |
$249,900 |
Airbnb cash on cash: N/A
|
220 Windermere DriveMiddlesboro, KYBEAUTIFUL MOVE IN READY HOME IN AMBLESIDE. Discover your next home in Ambleside, a tranqui... |
3 beds | N/A baths | 1,692 sq.ft. |
$269,500 |
Airbnb cash on cash: 1.88%
|
2702 Cumberland AvenueMiddlesboro, KYDon't miss this opportunity to own a historic home on Cumberland Avenue with a rare corner... |
4 beds | N/A baths | 3,885 sq.ft. |
$369,900 |
Airbnb cash on cash: N/A
|
115 George Ann DriveMiddlesboro, KYThis Beautiful 3 bedroom 2 bath brick home sits in the beautiful city of Middlesboro. With... |
3 beds | 2 baths | 2,008 sq.ft. |
$275,000 |
Airbnb cash on cash: 1.79%
|
129 Lower Gibson LaneMiddlesboro, KYThe Chateau on the Creek - Home for Sale in Middlesboro, KY (Bell County) Welcome to The C... |
3 beds | N/A baths | 1,856 sq.ft. |
$245,000 |
Airbnb cash on cash: 2.34%
|
6 Hampton CourtMiddlesboro, KYBeautiful 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
|
918 E Cumberland AvenueMiddlesboro, KYThis 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. |
$200,000 |
Airbnb cash on cash: 3.13%
|
Real Estate investment in Middlesboro, KY
There are 24 properties for sale in the city of Middlesboro . The median list price in Middlesboro is $207,500 and the average price per square foot is $116. In November 2025, the average monthly cash on cash return in Middlesboro is 10.00%. The average monthly rental income in Middlesboro is $2,029.