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 |
|---|---|---|---|
140 Hickory LaneMiddlesboro, KY3-bedroom, 2-bath home situated on a spacious 0.66-acre lot, offering the perfect blend of... |
3 beds | 2 baths | 1,209 sq.ft. |
$164,900 |
Airbnb cash on cash: 3.42%
|
807 Exeter AveMiddlesboro, KYNew 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%
|
4921 W CUMBERLAND AveMiddlesboro, KYCharming 3-Bedroom Home in a Prime Location! Discover comfort and convenience in this beau... |
3 beds | 2 baths | 1,900 sq.ft. |
$232,500 |
Airbnb cash on cash: 1.78%
|
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. |
$324,900 |
Airbnb cash on cash: N/A
|
359 Beans Fork RdMiddlesboro, KYI 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: 4.51%
|
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. |
$455,000 |
Airbnb cash on cash: N/A
|
180 Stevenson Branch RdMiddlesboro, KYCharming 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: 3.05%
|
129 Lower Gibson LaneMiddlesboro, KYThe 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%
|
123 Upper Gibson LaneMiddlesboro, KYSchedule 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: 3.6%
|
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. |
$130,000 |
Airbnb cash on cash: 3.39%
|
1208 KY-217Middlesboro, KYHere 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%
|
11 Castleford WayMiddlesboro, KYThis one checks the boxes and close to Major Regional Colleges! Renovated, truly move in r... |
3 beds | 1 baths | 1,100 sq.ft. |
$195,000 |
Airbnb cash on cash: 1.33%
|
409 Fairview RoadMiddlesboro, KYThis 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
|
Real Estate investment in Middlesboro, KY
There are 25 properties for sale in the city of Middlesboro . The median list price in Middlesboro is $196,750 and the average price per square foot is $118. In March 2026, the average monthly cash on cash return in Middlesboro is 9.00%. The average monthly rental income in Middlesboro is $1,939.