Middlesboro Homes for Sale

Middlesboro Homes for Sale

Welcome to Middlesboro, Kentucky – a hidden gem nestled in the heart of Bell County! This charming city is surrounded by the stunning Appalachian Mountains, offering breathtaking views and a rich tapestry of natural beauty. Known for its unique history as the only city in the world built within a meteorite crater, Middlesboro boasts a vibrant community and a welcoming atmosphere that makes it a perfect place to call home.

Middlesboro is not just about scenic landscapes; it also offers a variety of amenities that cater to all lifestyles. From quaint local shops and delightful eateries to recreational parks and outdoor activities, there’s something for everyone. Whether you’re an outdoor enthusiast eager to explore the nearby Daniel Boone National Forest or someone who enjoys a leisurely stroll through the historic downtown area, Middlesboro has it all.

For those considering a move to this delightful city, you’ll be pleased to know that there are a variety of homes for sale in Middlesboro. From charming single-family residences to modern townhouses, the real estate market here offers options that cater to diverse tastes and budgets. Many homes feature spacious yards, inviting interiors, and easy access to local amenities, making them perfect for families, retirees, or anyone looking to enjoy a peaceful lifestyle.

With a strong sense of community and a wealth of outdoor adventures at your doorstep, Middlesboro is more than just a place to live – it’s a place to thrive. Explore the homes for sale today and discover the perfect property that suits your needs in this enchanting Kentucky city!

Newest Middlesboro Homes for Sale

225 Sherwood Rd, Middlesboro
$469,900
3 Beds ⋅ 3 Baths ⋅ 26029553 MLS
Welcome home to an exceptional single-family residence that perfectly blends spacious living, thoughtful design, and breathtaking views in a peaceful Middlesboro neighborhood. This beautifully maintained 1994 brick home offers nearly 3,810 square feet of comfortable living space on a professionally landscaped 0.92-acre lot, creating an inviting setting where every day feels a little more relaxed. Step inside to an expansive open floor plan that flows effortlessly between the living, dining, and kitchen areas. Vaulted ceilings in the living room lend a grand, airy feel, while the chef's kitchen—seamlessly integrated into the heart of the home—makes entertaining as easy as everyday family meals. A generous walk-in pantry and expansive laundry room add practical elegance to the layout. The luxurious primary suite serves as a true private retreat, featuring a spa-like bath with a walk-in shower, soothing soaker tub, and a large walk-in closet. Two additional spacious bedrooms and a versatile bonus room provide flexibility for a home office, guest suite, playroom, or hobby space, while 2 full baths plus a half bath keep everything convenient. Energy-efficient geothermal heating and cooling deliver year-round comfort with lower utility costs. Outside, the elegant brick exterior and meticulously landscaped grounds create instant curb appeal. Multiple garage spaces—including an attached 2-car garage, an additional 1-car garage, and a 2½-car detached garage—offer abundant room for vehicles, tools, and recreational equipment. Nestled in a serene setting with panoramic views, this one-of-a-kind home combines classic charm, modern functionality, and an unbeatable location. Whether you're seeking a peaceful primary residence or a place to enjoy Middlesboro's mountain surroundings, 225 Sherwood Rd is ready to welcome you.

225 Sherwood Rd, Middlesboro
508 Worchester Ave, Middlesboro
$234,900
3 Beds ⋅ 2 Baths ⋅ 26029407 MLS
Welcome to this cozy and beautiful home nestled in Middlesboro Kentucky. Enjoy the appeal of a private outdoor space enhanced by a brand-new fence, perfect for relaxing or entertaining. Situated close to Lincoln Memorial University and within easy reach of all the everyday amenities Middlesboro has to offer, this charming property combines comfort with exceptional convenience. Schedule a showing today and experience the warmth and practicality of this inviting residence.

508 Worchester Ave, Middlesboro
114 E Rochester Ave, Middlesboro
$175,500
3 Beds ⋅ 1 Baths ⋅ 26028237 MLS
Welcome to this charming 3-bedroom, 1-bath home tucked away as the last house on a quiet dead-end street--offering extra privacy and minimal traffic. Enjoy peace of mind with major updates already completed: a new heat pump, a new water heater, and a durable metal roof only 2 years old. Thoughtful extras include lights installed in both the attic and crawl space for easy access and maintenance. This property is not located in a flood zone and is served by public water and sewer--no well or septic worries. Solid, move-in ready home in a convenient Middlesboro location. Don't miss this opportunity!

114 E Rochester Ave, Middlesboro
1801 & 1801 1/2 Exeter Ave, Middlesboro
$175,000
2 Beds ⋅ 1 Baths ⋅ 26026368 MLS
TWO HOMES FOR THE PRICE OF ONE!!! live in the recently remodeled 2 bed /1 bath homes while you renovate the other home on this parcel that has already been gutted for the new owner to start working on it! This is a great opportunity for real estate investors or those looking to get into rental properties! LMU (Main Campus) being just 15 minutes brings a huge demand for rental properties just like this! Less than 5 minutes to a hospital and downtown Middlesboro, also minutes away from National & State Parks! Don't miss out on this opportunity! Schedule your showing today!

1801 & 1801 1/2 Exeter Ave, Middlesboro
8 Castleford Way, Middlesboro
$160,000
3 Beds ⋅ 2 Baths ⋅ 26025315 MLS
Welcome to 8 Castleford Way located in the beautiful subdivision Ambleside. This home is also conveniently located near National & state parks. This home includes a screened back porch and fenced backyard. Master Bed / Bath on main level of the home including the living room, kitchen, and laundry! Call or text today to schedule your showing!

8 Castleford Way, Middlesboro
412 N 24th St, Middlesboro
$105,900
3 Beds ⋅ 2 Baths ⋅ 26025309 MLS

412 N 24th St, Middlesboro
209 S 19th St, Middlesboro
$215,000
3 Beds ⋅ 2 Baths ⋅ 26022968 MLS
209 S. 19th Street, Middlesboro, KY 40965 Beautiful 2022 manufactured home offering approximately 1,352 sq. ft. of comfortable living space with 3 bedrooms and 2 bathrooms. The home is situated in a private setting while still conveniently located within town. Features include city utilities and a concrete block foundation. The PVA reflects approximately 0.50 acre; buyer to verify acreage and all property information. A great opportunity for buyers looking for a newer home with convenient in-town access and a private feel. Schedule your showing today

209 S 19th St, Middlesboro
1102 W Chester Ave, Middlesboro
$199,000
3 Beds ⋅ 1 Baths ⋅ 26022803 MLS
Just listed 1480 sq ft historical spilt level home at 1102 W Chester Ave Middlesboro Ky. This home is in walking distance from downtown. It has three bedrooms and one bath and a large den with a beautiful fireplace. The eat in kitchen is right off the den area. There is a covered screened in porch just off the dinning area.

1102 W Chester Ave, Middlesboro
515 Englewood Rd, Middlesboro
$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
400 Gloucester Ave, Middlesboro
$279,000
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
215 S 21st St, Middlesboro
$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
116 Edgewood Rd, Middlesboro
$200,000
3 Beds ⋅ 2 Baths ⋅ 26013326 MLS
Mountain Views, Privacy & Endless Possibilities! Discover the perfect blend of privacy, space, and convenience at 116 Edgewood Road in Middlesboro. This spacious 2,154-square-foot home offers 3 bedrooms and 2 full bathrooms, nestled on approximately 0.75 acres while remaining within walking distance of downtown amenities. Step inside to find a versatile floor plan with multiple living areas and flexible spaces that can easily accommodate additional bedrooms, home offices, recreation rooms, or multi-generational living. The home's unique layout even presents the potential for conversion into separate living quarters, making it an attractive opportunity for homeowners and investors alike. Enjoy beautiful mountain, city, and park views from your property while experiencing the peace and privacy of a wooded setting where local wildlife is often seen. The home features central heating and cooling, a detached garage, ample parking, durable metal roofing, and city utilities. Recent improvements have already been completed, providing a solid foundation for the next owner to personalize and make their own. Whether you're searching for a spacious family home, an investment opportunity, or a property with room to grow, this unique Middlesboro residence offers exceptional value. Property Highlights 3 Bedrooms | 2 Bathrooms 2,154 Sq. Ft. of Living Space Approximately 0.75 Acres Detached Garage & Additional Parking Mountain, City & Park Views Central Heating & Air Conditioning Flexible Layout with Multi-Use Spaces Potential for Multi-Family or Income-Producing Use Convenient Access to Downtown Middlesboro Don't miss this rare opportunity to own a spacious home with privacy, views, and unlimited potential in the heart of Middlesboro. Schedule your private showing today!

116 Edgewood Rd, Middlesboro
Start Your Search

How much is your home worth?

Get instant property value now!