Courtesy: Coldwell Banker Bisceglia Real
606-248-4932
Looking for a HOME and not just another house? This is it! With 5 bedrooms, 2 baths, and even a bonus room to use as a den or rec room, this home was built with 'family living' in mind. The kitchen is equipped with a new island/breakfast bar that seats six and blends seamlessly with the dining area. With lots of room inside plus a pool with nice deck and patio in the back, you have a great blend of inside and outside living. Put this one on your must-see list--it may be the last one you have to look at to find your perfect home.
Courtesy: Backwoods Realty & Development
423-419-5742
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: Coldwell Banker Bisceglia Real
606-248-4932
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!
Courtesy: Black Diamond Realty
606-552-0879
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.
Courtesy: Century 21 Pinnacle
859-623-1900
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.
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: Kentucky Homes and Land LLC
Tina Eades
423-215-0943
New on the market, this multipurpose commercial historical property could be your own personal residential space. With 1,750 square feet total, completely refinished, new water lines, sewer lines from the house to the street, new floors, new steel tubs, exhaust fans, new plumbing and water heater, new deck, LED lighting, real tile backsplashes over the kitchen counters and tubs. Two bedrooms upstairs with one bathroom, and another bathroom downstairs with an open flat. This could be your space for a office, a salon, additional rental income space, or make it all a residential home, personal use. All this in the heart of Middlesboro, Kentucky. Make this your own. You will not regret.
Courtesy: Backwoods Realty & Development
423-419-5742
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.!!!
Courtesy: Realty Group
423-626-6353
Cute as a button! This adorable cottage style home would make an excellent choice for a first home! Come see today!
Courtesy: Fathom Realty KY LLC
304-645-7700
Charming Renovated Ranch in the Heart of Middlesboro! Welcome home to 1010 W Chester Avenue, a cozy and beautifully updated 2-bedroom, 1-bath brick ranch right in the heart of Middlesboro, KY. If you've been looking for that perfect blend of classic hometown charm and worry-free modern living, this is the one you've been waiting for. Step inside this solid traditional brick home and you'll immediately notice the inviting vibe. The entire house has been refreshed with updated paint throughout, creating a bright and airy atmosphere that lets the natural light pour in. Underfoot, you'll love the beautifully restored original hardwood floors paired with updated flooring that ties the whole home together perfectly. The heart of the home features a spacious eat-in kitchen complete with updated cabinets and a brand-new refrigerator added in 2024. For ultimate convenience, a brand-new dedicated laundry room has been added right off the kitchen. Around the corner, the living room serves up the ultimate cozy Appalachian factor with its classic brick, wood-burning fireplace—perfect for those crisp mountain evenings. Key Updates & Features: Brand New Roof (2024): Complete with durable 25-year shingles for total peace of mind. Modernized Kitchen & Bath: Features updated cabinetry, flooring, and a 2024 refrigerator. Convenient Layout: 1,275 sq. ft. of comfortable, main-level living space with an added laundry room and a convenient 1-car attached carport. Level Lot: A nice 50x140 level yard that's easy to maintain and perfect for relaxing. Tucked away on a great level lot near the West End, this property puts you just minutes from local schools, shopping, and all the dining downtown Middlesboro has to offer. Whether you're buying your very first home, downsizing, or looking for a solid investment in Bell County, this move-in-ready gem is ready for its next chapter. Don't wait on this one—call today to schedule your personal tour and let's go take a look!
Courtesy: REMAX PROFESSIONAL'S
423-869-3000
Two bedroom, 1 bath home located in a great neighborhood. Large bedrooms, living room, and kitchen. Don't miss the opportunity to make this home your own.
Courtesy: Century 21 Virginia Wilder Real Estate
276-861-2023
Welcome to 1720 Exeter Avenue, this adorable fixer has tons of potential with 2 living areas, a detached garage, brand new metal roof, and a fully fenced yard! Less than 5 minutes to schools and hospital, and only 15 minutes from LMU Harrogate main campus. Offered at a great price! Call or text today to schedule a showing!
Courtesy: Fathom Realty KY LLC
304-645-7700
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!
Courtesy: Action Realty
606-248-7653
MOTIVATED SELLER 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: Backwoods Realty & Development
423-419-5742
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
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.
Courtesy: Backwoods Realty & Development
423-419-5742
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
Major 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.
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| 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. |
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The data relating to real estate for sale on this web site comes in part from the Broker ReciprocitySM Program of the Northern Kentucky Multiple Listing Service, Inc. Real estate listings held by brokerage firms other than the owner of this site are marked with the Broker ReciprocitySM logo or the Broker ReciprocitySM thumbnail logo (a little black house) and detailed information about them includes the name of the listing brokers. The broker providing the data believes the data to be correct, but advises interested parties to confirm the data before relying on it in a purchase decision. Copyright 2026 Northern Kentucky Multiple Listing Service, Inc. All rights reserved. |
Middlesboro is located in Kentucky.
