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 | 3 baths | 3,544 sq.ft. |
$310,000 |
Airbnb cash on cash: N/A
|
603 Chester AveMiddlesboro, KYCharming 3-bedroom, 2-bath home with a bonus room and ample storage, conveniently located ... |
3 beds | 2 baths | 1,670 sq.ft. |
$184,500 |
Airbnb cash on cash: N/A
|
908 Chester AveMiddlesboro, KYVery well maintained 3 bedroom, 2 bath home located on Chester Avenue in Middlesboro. Mai... |
3 beds | 2 baths | 1,400 sq.ft. |
$197,000 |
Airbnb cash on cash: N/A
|
3800 West Cumberland AvenueMiddlesboro, KYPRIME LOCATION. This beautiful brick ranch style home three bedrooms and one and a half b... |
3 beds | 2 baths | 1,624 sq.ft. |
$189,900 |
Airbnb cash on cash: N/A
|
1002 Chester AveMiddlesboro, KY4 Bedroom 1 bath brick, one and a half story home on a large level lot. 4 year old roof, ... |
4 beds | 1 baths | 2,073 sq.ft. |
$190,000 |
Airbnb cash on cash: N/A
|
23 Ennismore DriveMiddlesboro, KYNestled in the highly sought-after Ambleside community, this stunning 6,000-square-foot es... |
4 beds | 6 baths | 6,000 sq.ft. |
$595,000 |
Airbnb cash on cash: N/A
|
230 Windermere DriveMiddlesboro, KYThree bedroom, two bath well maintained home in beautiful Ambleside Subdivision. Living r... |
3 beds | 2 baths | 2,099 sq.ft. |
$270,000 |
Airbnb cash on cash: N/A
|
3201 W Cumberland AveMiddlesboro, KYAbsolutely gorgeous home with 3 suites, all 3 bedrooms have their own FULL bath! Additiona... |
3 beds | 4 baths | 2,272 sq.ft. |
$325,000 |
Airbnb cash on cash: N/A
|
2103 Winchester AvenueMiddlesboro, KYTwo for 1! The main house at 2103 Winchester Ave has 2100 sf, one bath and four bedrooms. ... |
4 beds | 1 baths | 2,100 sq.ft. |
$285,000 |
Airbnb cash on cash: N/A
|
811 Gloucester AveMiddlesboro, KYThis 3 bedroom, 1 bath brick home is located on a quiet dead-end street in the heart of hi... |
3 beds | 1 baths | 1,661 sq.ft. |
$202,500 |
Airbnb cash on cash: N/A
|
123 Twin Acres RdMiddlesboro, KYYou'll have it all in this beautiful ranch style home on Twin Acres Rd. Living room, dinin... |
4 beds | 2 baths | 3,338 sq.ft. |
$329,900 |
Airbnb cash on cash: N/A
|
114 East Rochester AvenueMiddlesboro, KYBack on the Market, no fault of the home. USDA approved and has been taking out of the flo... |
3 beds | 1 baths | 1,066 sq.ft. |
$129,900 |
Airbnb cash on cash: N/A
|
1015 Old Wilson LaneMiddlesboro, KYFIRST TIME ON THE MARKET! This wonderful split foyer is in the city limits and has additi... |
4 beds | 3 baths | 2,488 sq.ft. |
$550,000 |
Airbnb cash on cash: N/A
|
104 Hollywood Drive DriveMiddlesboro, KYThis beautiful, spacious, well-kept home sitting on a gorgeous corner lot, in a great loca... |
3 beds | 2 baths | 1,500 sq.ft. |
$199,900 |
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. |
$289,900 |
Airbnb cash on cash: N/A
|
101 Kim LaneMiddlesboro, KYDon't miss out on this hidden gem in the city limits of Middlesboro. This house has it all... |
5 beds | 4 baths | 3,874 sq.ft. |
$440,000 |
Airbnb cash on cash: N/A
|
515 Worchester AveMiddlesboro, KYCharming and Spacious Family Home in Historical Middlesboro Welcome to this beautifully... |
4 beds | 4 baths | 4,300 sq.ft. |
$489,000 |
Airbnb cash on cash: N/A
|
114 George Ann DriveMiddlesboro, KY3 bedroom 2 bath in an excellent neighborhood! PRIME location right next door to the hospi... |
4 beds | 2 baths | 1,796 sq.ft. |
$299,000 |
Airbnb cash on cash: N/A
|
4921 West Cumberland AvenueMiddlesboro, KYThis beautiful home conveniently located close to all amenities of downtown Middlesboro is... |
3 beds | 2 baths | 1,900 sq.ft. |
$289,900 |
Airbnb cash on cash: N/A
|
2410 Cumberland AvenueMiddlesboro, KYRemarkable Folk Victorian Historical Home. This home was built in 1908, redesigned for to... |
5 beds | 4 baths | 3,000 sq.ft. |
$325,000 |
Airbnb cash on cash: N/A
|
1009 Rochester AveMiddlesboro, KYNeed space? I got you! 3 oversized bedrooms with BONUS ROOMS (more than one) Formal dini... |
3 beds | 2 baths | 2,206 sq.ft. |
$230,000 |
Airbnb cash on cash: N/A
|
46 Evans LaneMiddlesboro, KYNeed extra space? How about a 70ft garage with 3 additional buildings (with electricity) a... |
4 beds | 2 baths | 2,500 sq.ft. |
$299,000 |
Airbnb cash on cash: N/A
|
211 Gum Spring RdMiddlesboro, KYLocated in Middlesboro, KY, this charming 3-bedroom, 2-bathroom home is waiting for you to... |
3 beds | 2 baths | 960 sq.ft. |
$167,000 |
Airbnb cash on cash: N/A
|
164 Lake Hill RoadMiddlesboro, KYIf you love a home with great craftmanship and structural authenticity, then you need only... |
3 beds | 1 baths | 3,136 sq.ft. |
$238,900 |
Airbnb cash on cash: N/A
|
124 Beans Fork RoadMiddlesboro, KYThis recently updated 3 bed- 2 bath property is situated on a generous 2.78 acre lot with ... |
3 beds | 2 baths | 1,316 sq.ft. |
$154,900 |
Airbnb cash on cash: N/A
|
626 S 22nd StMiddlesboro, KYWonderfully maintained home sitting on approximately 4+/- acres, beautiful flat, and clear... |
3 beds | 2 baths | 1,456 sq.ft. |
$220,000 |
Airbnb cash on cash: N/A
|
164 Lake Hill Rd RdMiddlesboro, KYIf you love a home with great craftmanship and structural authenticity, then you need only... |
3 beds | 1 baths | 3,136 sq.ft. |
$238,900 |
Airbnb cash on cash: N/A
|
225 N 10th StMiddlesboro, KYHow cute is this?! Newly renovated with gorgeous views of Middlesboro and within walking d... |
3 beds | 2 baths | 1,014 sq.ft. |
$170,000 |
Airbnb cash on cash: N/A
|
512 N 25th StMiddlesboro, KYThis charming home in a residential area downtown Middlesboro. Relax on the perfect porch ... |
2 beds | 1 baths | 2,031 sq.ft. |
$235,000 |
Airbnb cash on cash: N/A
|
100 Ellenwood RdMiddlesboro, KYNewly Remodeled 3 bedroom 2 bath with fenced yard located seconds away from downtown Middl... |
3 beds | 2 baths | 1,120 sq.ft. |
$145,000 |
Airbnb cash on cash: N/A
|
409 Shillilah VillageMiddlesboro, KYDo you hear the mountains calling you? This cute little chalet nestled in mother nature's... |
1 beds | 1 baths | 676 sq.ft. |
$108,900 |
Airbnb cash on cash: N/A
|
359 Beans Fork RdMiddlesboro, KYCharming fully renovated 2-bedroom, 1-bathroom home featuring ample storage and a detached... |
2 beds | 1 baths | 952 sq.ft. |
$137,000 |
Airbnb cash on cash: N/A
|
2105 Winchester AvenueMiddlesboro, KYTwo properties for 1 price! This 1,040,sf house is included with the sale of 2103 Winchest... |
2 beds | 1 baths | 1,040 sq.ft. |
$285,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Middlesboro, KY
There are 33 properties for sale in the city of Middlesboro . The median list price in Middlesboro is $199,900 and the average price per square foot is $99. In November 2024, the average monthly cash on cash return in Middlesboro is 10.00%. The average monthly rental income in Middlesboro is $2,265.