2

Middlesboro, KY Homes for Rent

Section Image
  • /7

    $1,400 Per Month

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • Townhouse for Rent

    801 Winchester Ave, Middlesboro, KY 40965

    Property Id: 2527594Welcome to your new home at 801 Winchester Ave in Middlesboro, KY! This charming 2 bed, 1 bath townhouse boasts modern amenities such as a dishwasher, washer/dryer in unit, and central heat pump. Enjoy the convenience of designated parking and a lush lawn, perfect for pets. Don't miss out on this cozy retreat near parks for only $1400/month. No smoking allowed. Contact

    (606) 752-0147

    801 Winchester Ave, Middlesboro, KY 40965
  • /13

    $1,275 Per Month

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    1027 Chichester Ave Unit 1027 B, Middlesboro, KY 40965

    Property Id: 25754562 bed / 1 bath pet friendly. Large yard. Minutes from LMU campuses. Credit check, background check, eviction check required. Pet considered on individual basis with non refundable pet deposit. Tenant pays utilities, electricity, water (and garbage), internet. Landlord will take care of yard. $375 nonrefundable pet deposit per pet (pet must be approved

    (423) 801-5698

    1027 Chichester Ave Unit 1027 B, Middlesboro, KY 40965

Why Live in Middlesboro

Middlesboro, Kentucky, is a small city located in a meteor crater just west of the historic Cumberland Gap. This unique location provides residents with access to a variety of recreational and historic sites, including the Cumberland Gap National Historical Park. The park offers miles of trails leading to caves, creeks, scenic viewpoints, and Civil War landmarks, making it a prime spot for those seeking things to do outdoors. Middlesboro also features several city parks and the historic Middlesboro Country Club, the oldest continuously operating golf course in America. The city is home to a mix of Craftsman-style and midcentury ranch homes, with some properties dating back to the 1910s. While new construction has been limited since the 1990s, there are communities for manufactured homes available. Community events like the Cumberland Mountain Fall Festival and activities at Binghamtown Baptist Church and the Middlesboro-Bell County Public Library foster a strong sense of community. The main street area along Cumberland Avenue hosts local coffee shops, pizza parlors, and other eateries, while 12th Street offers chain restaurants and big box retailers. However, residents should be aware of potential flooding due to the city's topography and heavy traffic around the Cumberland Gap Tunnel during peak hours. Middlesboro Independent Schools have average ratings, and the city is also home to the Middlesboro Campus for Southeast Kentucky Community & Technical College.

How to Rent a Home