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Middlesboro, KY Homes for Rent

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    $1,800 per month

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • House for Rent

    814 W Chester Ave, Middlesboro, KY 40965

    Property Id: 2081700Welcome to your new home at 814 W.Chester Ave in Middlesboro! This charming 3 bedroom, 2 bathroom single-family unit is available for rent starting August 1st, 2025. Enjoy modern amenities such as a dishwasher, washer/dryer, freezer, and more. Pets allowed for cats and small dogs. Don't miss out on this cozy and convenient property!

    814 W Chester Ave, Middlesboro, KY 40965
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    $1,200 per month

    • 2 Beds
    • 1.5 Baths
    • 720 Sq Ft
    • Townhouse for Rent

    1908 W Chester Ave, Middlesboro, KY 40965

    Property Id: 1676478Welcome to your new home at 1908 West Chester Ave in Middlesboro, KY! This charming 2 bed, 1.5 bath townhouse features modern amenities including a dishwasher, central air, and washer/dryer hookups. Pets allowed for cats and small dogs. Available 12/02/2024 for $1400/month. Don't miss out on this gem!

    1908 W Chester Ave, 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.

Frequently Asked Questions

What are the most popular zip codes in Middlesboro, KY for renters?
The most popular zip codes in Middlesboro, KY for renters is 37879.
How to Rent a Home