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 |
|---|---|---|---|
210 Claiborne CircleMiddlesboro, KYLike-new one-owner home built in 2018 by Overholt Construction. Features open floor plan a... |
3 beds | 2 baths | 1,585 sq.ft. |
$319,900 |
Airbnb cash on cash: 1.19%
|
413 S 26th StMiddlesboro, KYThis beautiful 2 bed 1 bath with beautiful hardwood floors, sits only minutes away from do... |
2 beds | 1 baths | 1,008 sq.ft. |
$140,000 |
Airbnb cash on cash: 5.17%
|
207 Arthur HeightsMiddlesboro, KYCHARMING 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
|
908 Chester AveMiddlesboro, KYThis home is older home well maintained, 2 bd 1 full bath with an efficiency apartment beh... |
3 beds | 2 baths | 1,400 sq.ft. |
$225,000 |
Airbnb cash on cash: 2.65%
|
422 Wilderness RdMiddlesboro, KYSuper cute starter home with 2 beds and 1 full bath. Recently remodeled with excellent upd... |
2 beds | 1 baths | 840 sq.ft. |
$150,000 |
Airbnb cash on cash: 4.43%
|
1801 Exeter AveMiddlesboro, KY2 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. |
$159,000 |
Airbnb cash on cash: N/A
|
1015 Old Wilson LaneMiddlesboro, KYSuper 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
|
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. |
$279,000 |
Airbnb cash on cash: 2.02%
|
116 Edgewood RoadMiddlesboro, KYMountain Views, Privacy & Endless Possibilities! Discover the perfect blend of privacy, sp... |
3 beds | 2 baths | 2,154 sq.ft. |
$240,000 |
Airbnb cash on cash: 2.49%
|
1200 W Chester AvenueMiddlesboro, KYCharming 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: 4.14%
|
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. |
$160,000 |
Airbnb cash on cash: 4.88%
|
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: 3.17%
|
717 S 27th StreetMiddlesboro, KYThis open floor plan home is waiting for your large family. This home features 5 bedrooms ... |
5 beds | 4 baths | 3,195 sq.ft. |
$350,000 |
Airbnb cash on cash: N/A
|
113 Hollywood DrMiddlesboro, KY113 Hollywood Dr, Middlesboro, KY 40965 | Single Family Residential |
3 beds | 2 baths | 3,174 sq.ft. |
$270,000 |
Airbnb cash on cash: 1.73%
|
63 Old Pineville PikeMiddlesboro, KY63 Old Pineville Pike, Middlesboro, KY 40965 | Single Family Residential |
3 beds | 2 baths | 1,560 sq.ft. |
$159,000 |
Airbnb cash on cash: 4.17%
|
140 Wellington DriveMiddlesboro, KYNice 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
|
259 Watson LnMiddlesboro, KY259 Watson Ln, Middlesboro, KY 40965 | Single Family Residential |
3 beds | 1 baths | 1,976 sq.ft. |
$2,500,000 |
Airbnb cash on cash: -1.46%
|
4607 W Cumberland AveMiddlesboro, KY4607 W Cumberland Ave, Middlesboro, KY 40965 | Multi Family |
N/A beds | N/A baths | 0 sq.ft. |
$165,000 |
Airbnb cash on cash: 3.96%
|
321 Chester AveMiddlesboro, KY321 Chester Ave, Middlesboro, KY 40965 | Other |
N/A beds | N/A baths | N/A |
$275,000 |
Airbnb cash on cash: N/A
|
312 Blakely LnMiddlesboro, KY312 Blakely Ln, Middlesboro, KY 40965 | Other |
N/A beds | N/A baths | N/A |
$139,000 |
Airbnb cash on cash: N/A
|
119 Wagon Hollow RdMiddlesboro, KY119 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
|
301 Doe's XingMiddlesboro, KY301 Doe's Xing, Middlesboro, KY 40965 | Single Family Residential |
3 beds | 2 baths | 2,016 sq.ft. |
$232,500 |
Airbnb cash on cash: 2.2%
|
103 Kingsbury WoodsMiddlesboro, KY103 Kingsbury Woods, Middlesboro, KY 40965 | Single Family Residential |
3 beds | 3 baths | 3,397 sq.ft. |
$399,000 |
Airbnb cash on cash: 0.59%
|
156 Wellington DriveMiddlesboro, KYWelcome home to this spacious and inviting 3-bedroom, 1.5-bath property that offers both c... |
3 beds | 2 baths | 1,320 sq.ft. |
$230,000 |
Airbnb cash on cash: 2.35%
|
717 Highway 441Middlesboro, KYBeautiful 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
|
414 S 24th StreetMiddlesboro, KYPrime 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: 3.3%
|
508 & 512 Winchester AvenueMiddlesboro, KYPrime 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: -0.84%
|
725 N 19th StreetMiddlesboro, KYPrime Multifamily Investment Opportunity Presenting a well-established commercial apartmen... |
2 beds | 2 baths | 15,119 sq.ft. |
$855,000 |
Airbnb cash on cash: -0.25%
|
713 Exeter AvenueMiddlesboro, KYWelcome to the stunning 713 Exeter Ave located in the lovely town of Middlesboro KY, less ... |
4 beds | 1 baths | 2,430 sq.ft. |
$175,000 |
Airbnb cash on cash: N/A
|
913 Doncaster StMiddlesboro, KYThis 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: 2.43%
|
127 Alpine #127Middlesboro, KYThis 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: 1.61%
|
2002 Winchester AvenueMiddlesboro, KYCHARMING 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: 5.11%
|
2621 W Cumberland AvenueMiddlesboro, KYOpportunities are built on the right properties and this could be the one! The potential o... |
3 beds | 2 baths | 3,948 sq.ft. |
$214,999 |
Airbnb cash on cash: 2.45%
|
116 N Petersborough AveMiddlesboro, KY116 N Petersborough Ave, Middlesboro, KY 40965 | Single Family Residential |
3 beds | 1 baths | 1,652 sq.ft. |
$215,000 |
Airbnb cash on cash: 2.63%
|
1425 Highway 441Middlesboro, KY1425 Highway 441, Middlesboro, KY 40965 | Single Family Residential |
3 beds | 1 baths | 1,242 sq.ft. |
$165,000 |
Airbnb cash on cash: 3.96%
|
1807 Winchester AveMiddlesboro, KYThree-bedroom traditional brick ranch home. Located on a level lot convenient to the local... |
3 beds | 1 baths | 1,104 sq.ft. |
$155,000 |
Airbnb cash on cash: 4.32%
|
815 Dorchester AveMiddlesboro, KYWelcome to Historic Middlesboro KY - Beautifully Renovated Home with Stunning Mountain Vie... |
2 beds | 1 baths | 792 sq.ft. |
$169,000 |
Airbnb cash on cash: 4.03%
|
908 Manchester AvenueMiddlesboro, KYThis three-bedroom, two-bath home at 908 Manchester has been thoughtfully updated with a b... |
3 beds | 2 baths | 1,100 sq.ft. |
$159,900 |
Airbnb cash on cash: 4.13%
|
64 Dunlap Hollow RdMiddlesboro, KY64 Dunlap Hollow Rd, Middlesboro, KY 40965 | Manufactured Home |
4 beds | 2 baths | 1,440 sq.ft. |
$175,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Middlesboro, KY
There are 40 properties for sale in the city of Middlesboro . The median list price in Middlesboro is $159,950 and the average price per square foot is $77. In June 2026, the average monthly cash on cash return in Middlesboro is 10.00%. The average monthly rental income in Middlesboro is $1,927.