Middlesboro Real Estate

Welcome to Middlesboro, Kentucky – a charming city nestled in the heart of Bell County, where the beauty of the Appalachian Mountains meets a rich tapestry of history and community spirit. Founded in 1888, Middlesboro is uniquely situated within a meteorite crater, giving it a distinctive topography that adds to its allure. This vibrant city boasts a friendly atmosphere, making it an ideal place for families, retirees, and outdoor enthusiasts alike.

Middlesboro is known for its lush landscapes and outdoor recreational opportunities. With the nearby Cumberland Gap National Historical Park, residents and visitors can immerse themselves in nature, exploring miles of scenic trails, picturesque views, and diverse wildlife. The city also offers a wealth of local parks, perfect for picnics, sports, and family gatherings.

The downtown area is a delightful blend of historic architecture and modern amenities. Here, you’ll find unique shops, cozy cafes, and local restaurants serving up delicious Southern cuisine. The community is tight-knit, with numerous events and festivals throughout the year that celebrate the city's heritage and foster a sense of belonging.

Education is a priority in Middlesboro, with access to quality schools and higher education institutions, ensuring that residents have ample opportunities for growth and learning.

Whether you’re seeking a peaceful retreat or an active lifestyle, Middlesboro welcomes you with open arms. Come discover the charm and warmth of this hidden gem in Kentucky – where every day feels like home.

Newest Listings in Middlesboro

$455,000

5 Beds ⋅ 4 Baths ⋅ 26020660 MLS

Spacious All-Brick Home with Attached Guest Quarters - Prime Location! This beautifully maintained, all-brick home offers exceptional flexibility and space, featuring a main residence with 3 bedrooms, 2 bathrooms, a bonus room perfect for a home office, rec room, or additional sleeping area, and two laundry rooms for added convenience. In addition, the property includes a fully separate, attached living space—ideal for extended family or rental income. The guest quarters offer 2 bedrooms, 2 bathrooms, a full kitchen, living room, laundry area, and private entry—essentially two homes in one! Located just minutes from two local colleges and close to shopping and dining, this move-in-ready property is a rare opportunity for multi-generational living or income potential. With numerous upgrades throughout, this spacious home could be the dream property you've been waiting for!

523 N 30th St, Middlesboro

Listing courtesy of Kevin Carroll of Backwoods Realty & Development.

$279,000

3 Beds ⋅ 3 Baths ⋅ 26020657 MLS

Discover the perfect blend of peaceful living and everyday convenience in this unique, nature-surrounded home located right in town. Set on approximately 0.75 acres, this property offers privacy, scenic surroundings, and abundant natural light through dramatic floor-to-ceiling windows overlooking the wooded landscape and spacious yard. Inside, the home showcases warm character with vaulted wood ceilings, exposed beams, hardwood floors, and a striking custom spiral staircase that creates a true centerpiece. The open kitchen and living area feature custom cabinetry, stainless steel appliances, and seamless flow, ideal for both daily living and entertaining. The main level includes a spacious owner's suite with a luxury bath featuring a jacuzzi tub, walk-in shower, and private balcony access, perfect for enjoying peaceful mountain and nature views. A second bedroom, full guest bath, and access to the rear deck and fenced yard complete the main floor. Upstairs, the loft bedroom provides flexible space for sleeping, office, or retreat. The walk-out finished basement offers additional living space with a full bath, laundry area, and multiple possibilities including recreation, guest quarters, or home office. A heated and cooled converted garage with built-in shelving provides excellent storage or workspace. Recent updates include beautiful hardwood flooring, smart HVAC system, and a lifetime warranty metal roof. Outdoor features include a large storage shed and expansive yard ideal for enjoying wildlife, relaxing, or entertaining. This rare property combines charm, space, and setting—schedule your private showing today to experience it for yourself.

515 Englewood Rd, Middlesboro

Listing courtesy of Kevin Carroll of Backwoods Realty & Development.

$299,000

4 Beds ⋅ 2 Baths ⋅ 1350232 MLS

Nestled in the heart of downtown Middlesboro, this beautifully maintained 1930 home offers over 2,000 square feet of comfortable living space with 4 bedrooms and 2 full baths. The updated kitchen is designed for both style and functionality, featuring custom soft-close cabinetry, under-cabinet lighting, a double oven, and a French-door refrigerator with double freezer drawers. This kitchen also has a fill-pot feature next to the stove. The kitchen's backdown is where you will , find a covered deck--perfect for entertaining family and friends. Situated on a quiet dead-end street, this property combines the convenience of downtown living with the privacy and tranquility you've been looking for. The home offers a flexible floor plan with two bedrooms on the main level with cedar lined closets and two bedrooms upstairs. The foyer entryway offers a closet and space for coats and shoes to conveniently stored. A spacious living room with a fireplace creates a warm gathering space, while the formal dining room and vented sunroom provide additional areas for relaxation and entertaining. The basement includes a two-car garage, workshop, and ample storage space, offering plenty of room for hobbies and organization. Schedule an appointment TODAY!

400 Gloucester Ave, Middlesboro

Listing courtesy of Sheila Durham of Coldwell Banker Bisceglia Real.

$299,000

4 Beds ⋅ 2 Baths ⋅ 26020497 MLS

Nestled in the heart of downtown Middlesboro, this beautifully maintained 1930 home offers over 2,000 square feet of comfortable living space with 4 bedrooms and 2 full baths. The updated kitchen is designed for both style and functionality, featuring custom soft-close cabinetry, under-cabinet lighting, a double oven, and a French-door refrigerator with double freezer drawers. This kitchen also has a fill-pot feature next to the stove. The kitchen's backdown is where you will , find a covered deck—perfect for entertaining family and friends. Situated on a quiet dead-end street, this property combines the convenience of downtown living with the privacy and tranquility you've been looking for. The home offers a flexible floor plan with two bedrooms on the main level with cedar lined closets and two bedrooms upstairs. The foyer entryway offers a closet and space for coats and shoes to conveniently stored. A spacious living room with a fireplace creates a warm gathering space, while the formal dining room and vented sunroom provide additional areas for relaxation and entertaining. The basement includes a two-car garage, workshop, and ample storage space, offering plenty of room for hobbies and organization. Schedule an appointment TODAY!

400 Gloucester Ave, Middlesboro

Listing courtesy of Sheila Durham of Coldwell Banker Bisceglia Realty & Auction Co.

$60,000

3 Beds ⋅ 1 Baths ⋅ 26019521 MLS

Investment opportunity with this 3 bedroom 1 bathroom home. Owner is relocating for work and must sell. The home is in progress of being renovated. Call for more info.

712 Balmoral Rd, Middlesboro

Listing courtesy of Megan Stanaford of Black Diamond Realty.

$19,900

3 Beds ⋅ 2 Baths ⋅ 26019353 MLS

Manufactured home with 3 bedrooms and 2 bathrooms. Situated on a 0.36 acre lot built in 2000. Please be advised that any offers on this property require a minimum Earnest Money Deposit of 1% of the Purchase Price or $1,000, whichever is greater. Purchasers may use any lender they choose to finance the purchase of a property. However, the seller requires that all non-cash offers must be pre-qualified by Caliber Home Loans, Inc. prior to offer acceptance. Property is NOT vacant; do not disturb occupants.

13 Duncan Ln, Middlesboro

Listing courtesy of James Martin of Century 21 Pinnacle.

$200,000

4 Beds ⋅ 2 Baths ⋅ 1348714 MLS

Nice 3-bedroom 2 bath home just for the picking. Priced is right with the possibility of a 4th bedroom. The kitchen, dining room, living room, 3 bedrooms and 1 bath are on the main level. The bonus room (optional 4th bedroom), full bath with laundry facilities downstairs. This home has a back deck, patio and storage building. Don't let this one get away!

140 Wellington Drive, Middlesboro

Listing courtesy of Janice Pratt of Fathom Realty TN LLC.

$359,500

3 Beds ⋅ 2 Baths ⋅ 1348099 MLS

This beautiful brick has touches of class to enjoy for a lifetime. With all the beauty of her old style from big rooms, original cherry doors 9 1/2 foot ceilings and original hardwood floors. A fabulous front porch, a 2 car garage with a spacious and playful backyard. On the inside you will enjoy a kitchen that sparkles white with stainless steel appliances and a grand island for cooking and entertaining. The owner's suite hosts a 5-piece bathroom with a double vanity. Move in ready!!!! This house is a once in a lifetime purchase.!!!

2909 W Cumberland Ave, Middlesboro

Listing courtesy of Lisa Stacy-Gibbs of Backwoods Realty & Development.

$110,000

3 Beds ⋅ 2 Baths ⋅ 26014433 MLS

Hey Neighbors! If you've been looking for a solid property with room to build some serious sweat equity, you'll want to take a look at this one. Sitting on a spacious corner lot inside the Middlesboro city limits, this 1.5-story brick veneer home offers a massive 1,963 square feet of living space and sits on over half an acre 0.539 acres per (Bell County PVA). With a potential of 4 bedrooms, 2 baths, hardwood floors, and a sturdy metal roof, the foundational pieces are right here waiting for your vision. The home is being sold AS-IS, making it the perfect blank canvas for a dedicated house flipper, an investor looking to grow their rental portfolio, or a handy homeowner wanting to customize their dream space from top to bottom. Several of the rooms are currently unfinished and need to be updated, giving you the unique opportunity to choose your own finishes, layouts, and style without paying for someone else's recent choices. Sit back and sip some sweet tea on the welcoming front porch and plan some landscaping around the spacious yard. Opportunities at this price point with this much square footage don't come around every day in our neck of the woods. So bring your toolbelt, your imagination, and let's go take a peek at this properties potential!

901 Exeter Ave, Middlesboro

Listing courtesy of Russell Tribell of Fathom Realty KY LLC.

$855,000

2 Beds ⋅ 2 Baths ⋅ 26007225 MLS

Prime Multifamily Investment Opportunity Presenting a well-established commercial apartment building in the heart of Middlesboro, Kentucky. Built in 1990, this single-story property offers approximately 15,225 square feet of space ideally suited for residential rental units, providing stable cash flow in a convenient location. Strategically positioned on N 19th Street, the building benefits from easy access to local amenities, employment centers, and essential services in Bell County. Solid 1990 construction with a functional single-story design for easy maintenance and accessibility. This property represents an excellent value-add or turnkey investment for investors seeking entry into Kentucky's multifamily sector. Whether you're looking to maintain current operations or implement updates for higher rents, 725 N 19th Street delivers a solid foundation in a community with long-term housing needs.

725 N 19th St, Middlesboro

Listing courtesy of Beth Combs of Turn Key Realty.

$182,000

2 Beds ⋅ 2 Baths ⋅ 26007215 MLS

Prime commercial opportunity at 414 S 24th Street in Middlesboro, KY! This versatile property offers excellent visibility and accessibility in a well-established area, just minutes from historic downtown Middlesboro and major routes. Ideal for office space, retail, professional services, or an investment property with strong potential in Bell County. Spacious layout, solid construction, and convenient location make it a turnkey solution for your business needs. Don't miss this chance to own a piece of Middlesboro's growing commercial market.

414 S 24th St, Middlesboro

Listing courtesy of Beth Combs of Turn Key Realty.

$120,000

5 Beds ⋅ 4 Baths ⋅ 26011288 MLS

Investment Opportunity - Fire-Damaged Home at 215 S. 21st Street, Middlesboro, KY Investor Special! This property at 215 S. 21st Street, Middlesboro, KY has sustained significant fire damage and is being offered as-is. This is an excellent opportunity for experienced investors, contractors, or buyers looking for a major renovation or potential rebuild project. Situated in an established neighborhood, the property offers convenient access to schools, shopping, restaurants, and other local amenities. Property Highlights: * Heavily damaged by fire * Sold as-is * Ideal for investors, contractors, or rehab specialists * Potential renovation or redevelopment opportunity * Convenient Middlesboro location Buyers are encouraged to conduct their own inspections and due diligence to determine the best use of the property. If you're looking for your next project, this could be the opportunity you've been waiting for.

215 S 21st St, Middlesboro

Listing courtesy of Megan Stanaford of Black Diamond Realty.

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Listings courtesy of Spartanburg Association of Realtors as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.