Courtesy: Coldwell Banker Bisceglia Real
606-248-4932
Newly remodeled home on Cumberland Ave, right next to Middlesboro Elementary School. Sitting on a half acre lot, this spacious home has been updated in every way in the past year. The plumbing and electrical have both been updated. The fireplace has been inspected for safety and a new damper installed. The HVAC system and the water heater are both new. In addition, this home has all new appliances, new flooring, new ceiling fans, and a brand new roof installed in March of 2026. Don't wait on this one--it won't last long!
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 Septic system 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: Coldwell Banker Bisceglia Real
606-248-4932
Beautiful home in the heart of Middlesboro. Make a grand entrance to the spacious formal living room with hardwood floors and a gas fireplace. The dining area is right off the galley kitchen, which has a door leading onto the carpeted porch-perfect for entertaining or cooking outside. There is easy access from the carport right into the large open den/family room. Also on the main level there is a bonus room with a 1/2 bath that could be used as a home office, 2 bedrooms, and 1 full bath. The upstairs has 2 bedrooms and a full bath. The home sits on a nice level lot, combining with the lot next door for a total of 1/2 acre
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!
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: Kentucky Land and Home
859-619-9970
This one checks the boxes and close to Major Regional Colleges! Renovated, truly move in ready, county taxed (not city!), and not in a flood zone, this home is an ideal match for first time buyers, downsizers, or anyone wanting low maintenance living. It also sits in a prime location just minutes from major regional colleges like Southeast Kentucky Community & Technical College (5-10 minutes) and Lincoln Memorial University in Harrogate, TN (about 15 minutes) including the LMU Vet School and LMU DCOM. Union College and the University of the Cumberlands are also within an easy commute. Proudly owned by just one owner, the care shows the moment you step inside. Fresh paint, new luxury vinyl and laminate flooring, and thoughtful updates throughout create that clean feeling. The kitchen shines with new granite countertops, an updated sink and faucet, and finishes that pair beautifully with the existing cabinetry. Down the hall, the bathroom has been tastefully updated as well. Major components offer peace of mind: the HVAC is only 5 years old with 5 years of warranty remaining, the water heater is new, and the roof was replaced in 2013. Gutter guards add easy maintenance, and even the backyard shed features brand new interior wood. With the washer and dryer included, you can move right in and get to living.
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!
Courtesy: Fathom Realty TN LLC
888-455-6040
New custom built home in the heart of Middlesboro. This home features three (3) bedrooms and two (2) bathrooms. Walking up to the home you are immediately greeted with a covered front porch constructed using composite decking and adorned with large columns. As you enter this home you are met with a spacious living room/kitchen/dinning room designed in an open concept style. Kitchen is complete with custom cabinets and granite countertops. As you continue down the hall way you will find two (2) bedrooms and a full bathroom along with a utility room with washer/dryer hook up. The Master Suite is at he end of the hallway and is complete with a large walk-in closet and a walk-in shower. Bathrooms complete with built-in blue tooth speakers. LED lighting throughout the home. In the fenced-in back yard there is a 16' x 20' storage shed on a concrete slab. This home is minutes from downtown Middlesboro, hospital, Walmart and LMU.
Courtesy: Coldwell Banker Bisceglia Realty & Auction Co
606-248-4932
UNIQUE OPPORTUNITY PROPERTY. This property offers plenty of potential. Formerly Shillelagh garage and swimming hole, this property has above the ground fuel tanks that could provide ATV's, Side-by-side, farm equipment fuel for work or entertainment. There are Off-road trails for ATV enthusiasts to enjoy the endless trails. These 9.613 surveyed acres can be used for residential, commercial or farmland. The garage has electricity and plumbing for a restroom. There are 2 small cabins that were used as changing areas for the local swimmers in the community. With no restrictions these 9 acres could be converted to a camp site with tents or for camper parking for vacationers to enjoy the nature. The 2 ponds could be used for livestock, swimming or stock them with fish to build your own favor fishing hole. The property is boarded by a stream. This property is only minutes from Boone's Ridge Wildlife Preserve. This property has also had an environmental Assessment done on the property. For additional information of the study, contact information will be provided to the buyer by the seller. This diamond in the rough could be the gem you have been searching for
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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%.
