Courtesy: Action Realty
606-248-7653
This three-bedroom, two-bath home at 908 Manchester has been thoughtfully updated with a brand new metal roof, fresh HVAC system, and energy-efficient windows. At fourteen hundred square feet on a nice lot, it's move-in ready and priced to sell. It's in a quiet neighborhood, super close to schools, and offers great value in the Middlesboro market. Perfect for families or anyone wanting low-maintenance living with modern comforts.
Courtesy: Black Diamond Realty
606-552-0879
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!
Courtesy: RE/MAX LakeTime Realty London
606-862-0555
This open floor plan home is waiting for your large family. This home features 5 bedrooms and 4 full baths, cathedral ceilings, a rock fireplace in the living room, and a full, unfinished basement just waiting for you to make more living space. Located in downtown with an out-of-town feel, get in to see this home now. *Buyer to verify acreage and septic.
Courtesy: Century 21 Virginia Wilder Real Estate
276-861-2023
This home is turnkey and ready to move right in; it has been well maintained over the years. This home has 4 Bedrooms, 2 Full Baths, Dining Room and a Kitchen that comes with Range, Refrigerator, Dishwasher and Microwave plus the laundry room has a washer and dryer set that will stay with home. Step out the back door and just a few steps up the hill is a wonderful workshop and a storage shed. Home has a country setting with a private drive in the front and a right of way to the property from the back. Public water and septic system, internet is available, great views and close to Wal-Mart, hospital, churches and much more!
Courtesy: Realty Group
423-626-6353
Super cute starter home with 2 beds and 1 full bath. Recently remodeled with excellent updates. The backyard is an oasis with additional building with electricity. Starter home, income producing property, downsizing or whatever fits your needs, this home has it!
Courtesy: Century 21 Virginia Wilder Real Estate
276-861-2023
This brick ranch style home has 3 bedrooms, 1.5 bathrooms, living room, eat-in kitchen that extends to dining area, range, refrigerator, new dishwasher, washer and dryer stay with home; double pane windows; 1 car attached garage with pull down ladder to access attic partially floored for storage; yard is partially fenced with chain link fence for pets, nice yard; the septic system was replaced and upgraded in 2015; new metal roof in 2015, heat pump and air unit replaced in 2017, outside unit of heat pump unit was replaced in 2023 with warranty, in 2017 hot water heater was upgraded from 30 gallon to a 50 gallon water heater. In 2026 seller completely had home remodeled and spent $30,000 by installing waterproof laminate, new ceiling fans, new dishwasher, freshly painted, replaced all interior doors and baseboard, and front storm door, bathroom sinks, and commodes were replaced, kitchen cabinets were painted white, kitchen and bathroom faucets were replaced, added new garage door with garage door opener, replaced wooden attic stairs with new HD metal stairs, dozed front and side top soil, additional gravel was added for additional parking beside of concrete driveway. This home is close to downtown Middlesboro and hospital, city water, high speed internet.
Courtesy: Turn Key Realty
423-869-5111
This beautiful 2 bed 1 bath with beautiful hardwood floors, sits only minutes away from downtown Middlesboro and the Cumberland Gap National Park. This home has had some great improvements such as a new roof and new windows installed. don't miss your opportunity to call this your own.
Courtesy: Black Diamond Realty
606-552-0879
Courtesy: Keller Williams Legacy Group
859-544-6175
Opportunities are built on the right properties and this could be the one! The potential of this home is limitless. a home with instant equity to put your finishing touches on!
Courtesy: Coldwell Banker Bisceglia Real
606-248-4932
Exceptional 3 bedrooms, 1 bath home in the heart of Middlesboro. Located just off Cumberland Ave on 30th St, this home's location is what you have been looking for--within walking distance of downtown, schools, and the hospital. Just down the street from the T-ball field and the city pool. With hardwood floors throughout and beautiful wood trim, this house is waiting for a family to make it a home! Don't wait---make an appointment to tour this home-it is a must-see!
Courtesy: REMAX PROFESSIONAL'S
423-869-3000
This home is older home well maintained, 2 bd 1 full bath with an efficiency apartment behind the house great for the mother-in-law. The apartment is open space with 1 bdrm and a full bath. Metal roof, vinyl siding and windows, hardwood, laminate & tile floors. Privacy and a chain link fenced in back yard, 2 storage buildings, level back yard. Great student home and rental!!
Courtesy: Turn Key Realty
423-869-5111
Welcome to Historic Middlesboro KY - Beautifully Renovated Home with Stunning Mountain Views! Situated on an easy-to-maintain 0.29-acre lot, this charming home in the heart of Middlesboro KY JUST MINUTES FROM ONE OF THE OLDEST GOLF COURSES--This House blends historic charm with modern updates. Enjoy breathtaking views of the Cumberland Mountains, Cumberland Gap National Park, and the iconic Pinnacle. Steps away from hiking trails, local shops, cafes, and restaurants. Featuring 2 spacious bedrooms, 1 renovated full baths, new flooring, a modern kitchen. Ideal for a permanent home, vacation retreat, or short-term rental. Conveniently close to LMU campuses, Cumberland College, Knoxville, and Gatlinburg. Experience peaceful living with natural beauty. THIS HOUSE IS A MUST SEE!!
Courtesy: Mountain Realty
865-345-5050
Large Price Reduction!! Charming 2 bedroom, 1.5 bath home situated on a beautiful, quiet lot with plenty of potential and possibilities! This property features an extra-large carport, storage shed, and inviting front porch perfect for enjoying peaceful mornings or evenings outdoors. The large backyard offers plenty of space for entertaining, gardening, or relaxing, while the enclosed back mudroom/workshop provides excellent extra storage, hobby space, or room for projects. Inside, you'll find additional flexible living space upstairs that could easily serve as a third bedroom, home office, playroom, or bonus living area to fit your needs. Conveniently located just minutes from Lincoln Memorial University, shopping, and local amenities, this home combines privacy with convenience. Whether you're looking for a starter home, investment property, or rental opportunity, this property offers endless potential. The home could benefit from some updates, making it a fantastic opportunity to add your own style and value. Don't miss this affordable home with room to grow in a desirable location! *All information contained herein is deemed reliable but not guaranteed. Buyers to verify all information independently, but not limited to square footage, acreage, taxes, etc..
Courtesy: REMAX PROFESSIONAL'S
423-869-3000
Old home needs work with an attached older home that needs to be torn down. Great Location on Cumberland Ave behind Food City
Courtesy: Coldwell Banker Bisceglia Realty & Auction Co
606-248-4932
CHARMING VICTORIA HOME. Experience the timeless allure of this late-1800s Victorian masterpiece, where historic character meets expansive modern living. Boasting over 2,404 finished square feet—plus a versatile 600-square-foot finished attic space—this impressive residence offers a total of five spacious bedrooms, providing ample room for family, guests, or a dedicated home office. The primary bedroom is currently under renovation, offering the rare opportunity to add your final personal touch to the suite. While the primary bedroom bath has been completely remodeled with a walk in shower, bluetooth speakers, Step into your personal sanctuary with this top-of-the-line intelligent toilet. A seamless one-piece, skirted design, this smart fixture features a motion-activated lid that opens upon approach and an automatic, high-efficiency flush for ultimate sanitation. The integrated bidet offers customizable warm water cleaning, heated seating for year-round comfort, and an automatic air purifier to keep the atmosphere fresh and serene. The heart of the home flows through classic spaces designed for both grand entertaining and quiet retreats. Enjoy the traditional elegance of the parlor, a formal dining room for holiday gatherings, and a comfortable living room. Outside, the large wrap-around porch serves as the perfect vantage point for beautiful neighborhood views, while the screened-in porch and fenced in courtyard beautiful elegance to the home.
Courtesy: Coldwell Banker Bisceglia Realty & Auction Co
606-248-4932
CHARMING 2 BEDROOM/ONE BATH HOME! This charming 2 bedroom, 1 bath home offers a perfect blend of comfort and convenience, completely outside of the flood zone. Enjoy leisurely mornings on the large covered front porch or entertain guest on the back deck overlooking your private fully fenced in yard - perfect for pets or gardening. This move in ready property also features a detached 2 -car carport, providing ample shaded parking and storage. Don't miss this gem, conveniently located close to all the local amenities. Plus only a 10 minutes drive to LMU main campus.
Courtesy: Coldwell Banker Bisceglia Realty & Auction Co
606-248-4932
Super nice four bedroom, two and 1/2 bath, 2488 sq ft with hardwood floors on a level lot in Middlesboro. Welcome to a home designed for the way you live. This stunning split level residence offers the perfect architectural solution for those seeking distinct spaces without sacrificing an open feel. This home offers privacy and distinct zones for living, working and relaxing.
Courtesy: Coldwell Banker Bisceglia Realty & Auction Co
606-248-4932
This charming property offers the perfect blend of cozy indoor living and expansive outdoor space. Nestled in the heart of Middlesboro this home is situated on 1.5 acres. This brick ranch home with a basement has 1344 square feet, and features 3 bedrooms and 2 baths on the main floor along with the washer and dryer. The home provides plenty of room for family and guests. The heart of the home is designed for comfort and gatherings highlighting the fireplace in the dining area to create a warm inviting atmosphere. This home has built in shelving and natural wood cabinets in the kitchen along with an island. The potential is endless with an additional 634 square feet of living finished living space in the basement with a fireplace. The basement has a finished bathroom and additional 624 square feet unfinished that can be used as a workshop or other workspace. Walk out of the basement onto a large patio area. There is a short walk to the fenced in area and barn that can house many animal options. This home is near all the amenities including groceries, entertainment, shopping and restaurants. This is a rare gem in the heart of Middlesboro. Call for an appointment today!
Courtesy: Fathom Realty TN LLC
888-455-6040
This home is located in the city of Middlesboro minutes away from the hospital, close to downtown. Walmart, LMU are minutes away. It's located in a very safe neighborhood. The home includes a 364' single care garage.
Courtesy: Century 21 Virginia Wilder Real Estate
276-861-2023
Welcome to the stunning 713 Exeter Ave located in the lovely town of Middlesboro KY, less than 5 minutes to downtown Middlesboro, 15 minutes from LMU, & super close to Norris Lake. This home makes a perfect residence for anyone looking in the area and would make a great rental property as well! This home offers ample space with 4 bedrooms on the main level and tons of potential for a loft or 2 bedrooms upstairs! This home also includes a formal dining area, fully fenced backyard, and carport space! Don't miss out on this opportunity!
Courtesy: Black Diamond Realty
606-552-0879
Charming Home for Sale in Middlesboro, KY - 1200 W Chester Ave Welcome to this inviting home located in the heart of Middlesboro! Situated on a spacious corner lot at 1200 W Chester Avenue, this property offers comfort, convenience, and small-town charm—all in one. Comfortable living spaces with plenty of natural light. Functional kitchen with ample cabinet storage Generous yard—perfect for outdoor gatherings, gardening, or relaxing evenings. Convenient access and parking. Close to local schools, parks, and shopping This home is ideal for anyone looking to enjoy living with easy access to town amenities. Whether you're relaxing indoors or enjoying the outdoor space, this property offers plenty of potential to make it your own. Located in a friendly neighborhood just minutes from downtown Middlesboro, you'll love the blend of quiet surroundings and nearby conveniences. Don't miss out on this opportunity! Schedule your showing today and see what makes this home special. 3 bedrooms, 1.5 bathrooms and so much more!
Courtesy: Black Diamond Realty
606-552-0879
Beautiful 5-Bedroom Home on 1.165 Acres - Middlesboro, KY Welcome to 717 Highway 441, a stunning custom manufactured home offering space, comfort, and modern charm—all set on a generous 1.165-acre lot. This gorgeous home features 5 spacious bedrooms and 3 full bathrooms, perfect for families of all sizes. Step inside to find large, open rooms, ample closet space, and beautifully designed bathrooms throughout. The heart of the home is a large, well-appointed kitchen, ideal for cooking, gathering, and entertaining. You'll also appreciate the oversized laundry room, adding convenience and extra storage. Enjoy outdoor living with a nice back deck, perfect for relaxing or hosting guests. A front deck is currently being completed, adding even more curb appeal and outdoor space. Additional features include: City water and sewer. Expansive lot with room to roam. This property combines comfort, space, and value in a peaceful setting. Call today to schedule your private showing—this one won't last long!
Courtesy: Black Diamond Realty
606-552-0879
3 bed, 1 bath fixer-upper in Middlesboro, KY! Great investment opportunity—flip, rent, or make it your own. City water/sewer (per public record). Priced for potential—bring your ideas!
Courtesy: Black Diamond Realty
606-552-0879
Great investment opportunity with this one. Built in 2000 per appraisal, this property offers a total of 1,664 square feet and is currently occupied by reliable, long-term tenants. Each unit features 2 bedrooms and 1 bathroom, providing comfortable living space for residents. The address, listed as 102 A&B Redwood Road, originates from a previous appraisal. The property is confirmed per the appraisal as NOT in the flood zone, adding peace of mind for investors. This is a versatile opportunity—ideal for investors seeking steady rental income or for owner-occupants who wish to live in one unit while renting the other to offset expenses. Additionally, the neighboring properties at 103 and 105 Nutwood Road are also available for purchase for separate price. These homes are currently used as rental properties, with one already occupied, offering further investment potential. Showings are available upon request. Please do not disturb the tenants.
Courtesy: Black Diamond Realty
606-552-0879
Welcome home to this spacious and inviting 3-bedroom, 1.5-bath property that offers both comfort and versatility! In addition to the three bedrooms, you'll find a bonus room that can easily serve as a 4th bedroom, home office, or flex space to fit your needs. This home features both a cozy living room and a separate den, providing plenty of space for relaxing or entertaining. The den is highlighted by a charming fireplace—perfect for gathering on cooler evenings. The eat-in kitchen offers a warm and functional space for everyday meals. Step outside to enjoy a large backyard complete with a swimming pool, an expansive deck, and a screened-in area attached to the deck—perfect for relaxing without worrying about pests while still enjoying the outdoors. Whether you're hosting guests or unwinding after a long day, this outdoor space has it all. With its flexible layout, multiple living spaces, and great indoor and outdoor amenities, this home has something for everyone. Don't miss your chance to make it yours!
 |
| Real Estate listings held by other brokerage firms are marked with the name of the listing broker. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Copyright 2026 Knoxville Area Association of Realtors. All rights reserved. |
Middlesboro is located in Kentucky. Middlesboro 40965 is less family-centric than the surrounding county with 25.04% of the households containing married families with children. The county average for households married with children is 26.4%.
