Courtesy: REMAX PROFESSIONAL'S
423-869-3000
Charming 2 bedroom home located in historic Middlesboro, KY. Great location, close to shopping and the Cumberland Gap. Home has so much potential with the right vision and a little effort. Don't miss out on this one!
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
2 homes (103 and 105 Nutwood) and a duplex (120 Redwood) currently used as rental properties, priced to sell. Call to schedule a showing.
Courtesy: Black Diamond Realty
606-552-0879
Great investment opportunity. 2 bedroom 1 bathroom home, city utilities. Call for showings.
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!
Courtesy: Turn Key Realty
423-869-5111
Located in the desirable Ambleside subdivision, this beautifully decorated and well-maintained two-story home features soft, relaxing paint colors throughout and gorgeous luxury vinyl flooring that creates a warm and inviting atmosphere. This charming home offers 3 spacious bedrooms and 1.5 bathrooms. The main level includes a comfortable living room, formal dining room, kitchen, and a large laundry room, along with an attached garage. A storage shed provides additional space for tools and equipment. Step outside to the back patio, perfect for relaxing or entertaining guests while enjoying a peaceful outdoor setting. Conveniently located just minutes from Downtown Middlesboro, where you'll find dining, shopping, and small-town charm, along with community gatherings, live music, and events at the Levitt AMP Middlesboro Music Series Pavilion. Outdoor lovers will appreciate being just minutes from Cumberland Gap National Historical Park, offering hiking, history, and endless outdoor adventure. Situated in Bell County on the border of Kentucky, Tennessee, and Virginia, this location provides easy access to all three states while enjoying the beauty and history of the Cumberland Gap region. Thoughtfully maintained and full of charm, this home offers the perfect blend of cozy living space and functionality, making it easy to settle in and feel right at home. Come see this super cute home in a great location and all it has to offer! Seller incentives available! Offering $2,500 toward buyer's closing costs plus a 1-year home warranty with an acceptable offer.
Courtesy: ListWithFreedom.com
855-456-4945
Rare opportunity to own a premier golf course property on Hole #2 at the Middlesboro Golf Course—one of only four homes situated directly on the course. Perfectly positioned on a generous 0.67-acre lot, this spacious residence offers a grand total living space, including a finished basement, providing plenty of room to live, entertain, and relax. With three bedrooms and three full baths, the home offers both comfort and functionality, while the finished basement creates flexible space ideal for a media room, home office, guest suite, or recreation area. Outdoor living is just as impressive, featuring a 290-square-foot back deck and a 252-square-foot patio that overlook the beautifully maintained fairway. Whether you're enjoying calm mornings with coffee, taking in the peaceful golf course views, or hosting gatherings, the setting delivers a lifestyle that is both scenic and private. A 504-square-foot garage adds convenience and storage, completing this exceptional property. Homes in this location rarely become available.
Courtesy: Turn Key Realty
423-869-5111
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!
Courtesy: REMAX PROFESSIONAL'S
423-869-3000
Great little 3 bedroom house in a wonderful neighborhood in historic Middlesboro, Ky. Very convenient to downtown and Lincoln Memorial university. Fenced in back yard and large eat in kitchen make this a good option for just about anyone. Would also make a great opportunity for someone wanting to purchase a rental property.
Courtesy: Century 21 Virginia Wilder Real Estate
276-861-2023
This 2-story gorgeous home sits in the mountains of Kentucky and is located in the desired subdivision of Vista Venado! This home sits on 0.944 acre. The main floor offers an open floor plan with a large living room with gas log fireplace. The living room extends to the formal dining area. The spacious kitchen has room for a breakfast table. The kitchen appliances stay with home and includes a dishwasher, a new refrigerator, a new cook stove and a new built in microwave. There are lots of cabinets and a pantry. The main floor also has a half bathroom. The upstairs has 3 bedrooms and 2 full bathrooms, laundry room and a computer/study room that leads out to the balcony. This home has central gas heat and central air. Lots of windows to enjoy the amazing mountain views. There is a wonderful view overlooking the city of Middlesboro. The new laminate flooring throughout this home is waterproof. City water, the driveway was paved November 2024, this home is move in ready with possession at closing, there is a balcony upstairs and a wrapped deck on the main level with a natural gas connection for your gas grill, never worry about running out of gas in those propane tanks again! Internet available. This home is located in the county yet less than 5 minutes to downtown Middlesboro.
Courtesy: Century 21 Virginia Wilder Real Estate
276-861-2023
Beautiful move-in ready renovated Property. Home features four bedrooms 2 1/2 baths. kitchen features soft closed custom cabinets, kitchen island and stainless steel appliances. Laminated floors throughout the home. Enjoy your coffee on screened in back porch. Storage building for your tools, lawnmower etc..Property is located within minutes from Lmu main campus, Shopping, restaurants, and hospital. No flood insurance needed!!
Courtesy: Century 21 Pinnacle
859-623-1900
Ranch-style home built in 1950 offering over 1,200 square feet with 2 bedrooms and 2 full bathrooms. Features include a covered patio, a fireplace in the living room, and additional space suitable for a den or workspace. The home sits on an approximate 0.38-acre lot.
Courtesy: Coldwell Banker Bisceglia Real
606-248-4932
Looking for a home to raise your family? Don't let this one go by! Spacious 4 bedrooms, 2 bath home with a fenced in yard, this one is just the right size for a growing family. Just minutes from the hospital and schools, yet tucked away on a side street with little traffic. Let us show you your new home today! Schedule a showing before it's gone.
Courtesy: Century 21 Virginia Wilder Real Estate
276-861-2023
This cozy apartment with 1 bedroom and 1 bathroom has an office attached and storage room with garage door, city water, public sewer, paved driveway, corner level lot, natural gas available and high speed internet available, close to hospital.
Courtesy: Fathom Realty TN LLC
888-455-6040
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!
Courtesy: Century 21 Virginia Wilder Real Estate
276-861-2023
This gorgeous cape cod home sits on 4.4 acres with deer visiting often. This home has 5 bedrooms, 2.5 bathrooms, formal living room with fireplace, family room (could be used as formal dining room) a second fireplace in the sunroom, amazing kitchen with island, the kitchen counter tops are granite, the stainless-steel appliances stay, which include double wall ovens, gas range with gas oven (natural gas), side by side refrigerator and dishwasher. Island has a breakfast bar. The kitchen extends into the dining area. The master suite is on the main level with tray ceiling. There is a half bathroom on the main floor for guests. The beautiful staircase leads to 4 bedrooms and one full bathroom upstairs. The laundry room also has a mop sink and is off from the 2-car heated garage. There is a laundry chute in this home, main floor heating is natural gas/heat pump/air, the upstairs has electric heat pump/air, high quality bamboo flooring, crown molding, double pane windows, natural gas, public water, internet available, lots of storage, 2-50 gallon water heaters, new shingle roof installed October 2025, home comes with extra-large storage shed, awesome views from this property. The 12 X 32 detached garage/storage shed has a roll up door for easy access. This home is conveniently located in Middlesboro in the beautiful Vista Venado Subdivision, one mile to shopping and dining, and to hospital.
Courtesy: Turn Key Realty
423-869-5111
This property is now under auction terms. All Bids must be submitted during the auction via the property service listing page at www.servicelinkauction.com. This sale is subject to a 5% or $2,500 minimum buyer s premium pursuant to the auction Terms & Conditions. All bids will be subject to seller approval (minimums may apply).
Courtesy: Coldwell Banker Bisceglia Realty & Auction Co
606-248-4932
This home rest on a lot that goes from city street to ally. This home has 3 bedrooms and one bath with a large kitchen and large living room. This home needs some attention but has a lot of potential. The downstairs could be used as apartment or extra living space. There is another home on the property and might be possible to repair.
Courtesy: Realty Network, Inc
423-869-3121
Welcome to this versatile 3-bedroom, 2-bathroom home offering 1,296 sq. ft. of living space in a convenient Middlesboro location. With a new roof and a freshly painted exterior, this property is move-in ready and full of potential. Step inside to find a layout that offers both comfort and flexibility. The home features multiple kitchens and laundry areas, creating the unique opportunity to easily convert the property into two rental units or maintain it as a single-family residence with extra convenience. The outside is just as impressive, with a spacious fenced backyard, perfect for gatherings, pets, or a garden. You'll also appreciate ample off-street parking, seasonal mountain views, and plenty of storage space throughout. Located close to schools, shopping, and town amenities, this property combines practicality with investment potential. Whether you're looking for a family home or an income-producing opportunity, 252 Chasteen Drive is a must-see!
 |
| 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%.
