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$50,000
26006363 MLS
Lot on Edgewood road, can be purchased with 205 N 20th Street Middlesboro KY; former duplex was removed and now vacant land. City utilities available.

0000 Edgewood Rd, Middlesboro

Listing courtesy of Megan Stanaford of Black Diamond Realty.

$264,900
5 Beds ⋅ 3 Baths ⋅ 26010558 MLS
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.

207 Arthur Hts, Middlesboro

Listing courtesy of Sheila Durham of Coldwell Banker Bisceglia Realty & Auction Co.

$229,500
6 Beds ⋅ 6 Baths ⋅ 26013646 MLS
Excellent investment opportunity with a strong ~9% cap rate at asking price! This unique 4-unit property offers incredible versatility-perfect as a pure cash-flowing asset or an ideal opportunity to live in one unit while renting out the other three. The property consists of four fully occupied units: a main multi-family building featuring one 2-bedroom unit and two 1-bedroom units, plus a detached, standalone 2-bedroom, 2-bathroom manufactured home. All units have been historically well-maintained, feature newer appliances, and have received numerous updates and improvements over the years. Currently rented at stable, conservative rates, this property offers an immediate return on investment with substantial upside potential to increase rents to market value. A formidable long term opportunity.

623 N 20th St, Middlesboro

Listing courtesy of Derek Eisenberg of Continental Real Estate Group.

$230,000
3 Beds ⋅ 2 Baths ⋅ 26005639 MLS
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!

156 Wellington Dr, Middlesboro

Listing courtesy of Megan Stanaford of Black Diamond Realty.

$275,000
25012296 MLS
1.695 flat acres in the city of Middlesboro. Zoned B3 (Central Business District). Some uses permitted are: Wholesale & Retail Trade, Sporting Goods, Banks, Theater, Auto Repair, Pharmacy, Hotel-Motel, Bed & Breakfast, and Multi Family

321 Chester Ave, Middlesboro

Listing courtesy of Kevin Bisceglia of Coldwell Banker Bisceglia Realty & Auction Co.

$135,000
2 Beds ⋅ 1 Baths ⋅ 26010030 MLS
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.

2002 Winchester Ave, Middlesboro

Listing courtesy of Sheila Durham of Coldwell Banker Bisceglia Realty & Auction Co.

$29,000
26009102 MLS
PRIME LOCATION, NO FLOOD ZONE! Discover the ultimate blank canvas within the city limits. This fully cleared, level, and build ready lot offers an exceptional opportunity to build your dream home, or next investment project. Situated entirely outside the FEMA flood zone, this lot offers peace of mind and reduced insurance costs. All city utilities are ready for connection. This lot would always be suitable for a double-wide manufactured home. Don't miss this opportunity to build in a premier location.

2107 Winchester Ave, Middlesboro

Listing courtesy of Sheila Durham of Coldwell Banker Bisceglia Realty & Auction Co.

$22,500
25008692 MLS
Lot available within the city limits of Middlesboro KY; The Bell County Ky online PVA site shows approximately 0.355 of an acre more or less. City utilities are available. There was a home on the property but was demoed April 2025. Buyer to verify all pertinent information; sold as is where is.

526 Balmoral Rd, Middlesboro

Listing courtesy of Megan Stanaford of Black Diamond Realty.

$39,900
26006342 MLS
Opportunity awaits on this 4.24-acre tract offering a peaceful setting with endless potential. The property was previously improved with a home that has recently been lost to fire, presenting a unique chance to start fresh and bring your vision to life. With utilities previously in place (buyer to verify), this parcel may offer a head start for rebuilding, whether you're considering a custom home, manufactured home, or investment project. The land provides ample space for privacy, gardening, recreation, or additional improvements. Conveniently located with easy access to nearby amenities while still offering a quiet, rural feel, this property combines location, acreage, and opportunity. Property is being sold as-is. Buyer and buyer's agent to verify all information including utilities, zoning, and land use.

1197 Beans Fork Rd, Middlesboro

Listing courtesy of Sarah Richards of RE/MAX Preferred Group.

$15,000
26006275 MLS
Great lot, city utilities available.

205 Exeter Ave, Middlesboro

Listing courtesy of Megan Stanaford of Black Diamond Realty.

$375,000
26012603 MLS
3,200 sf building in the city limits of Middlesboro. Built in 1998, this building is located on a high-visibility street behind the Middlesboro Mall. With lots of parking, this building would be an excellent opportunity to own your own business. This building would be great for retail, commercial or a restaurant.

601 N 15th St, Middlesboro

Listing courtesy of Kevin Bisceglia of Coldwell Banker Bisceglia Realty & Auction Co.

$129,900
4 Beds ⋅ 2 Baths ⋅ 26000834 MLS
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.

405 S 37th St, Middlesboro

Listing courtesy of Kevin Bisceglia of Coldwell Banker Bisceglia Realty & Auction Co.

$21,000
26009366 MLS
50x150 lot; used to have a home on premises but that has been removed. City utilities available, buyer to verify all aspects of the property.

109 Bloomsbury Ave, Middlesboro

Listing courtesy of Megan Stanaford of Black Diamond Realty.

$295,000
5 Beds ⋅ 3 Baths ⋅ 26006775 MLS
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!

717 Hwy 441, Middlesboro

Listing courtesy of Megan Stanaford of Black Diamond Realty.

$142,500
2 Beds ⋅ 2 Baths ⋅ 1346436 MLS
Cute as a button! This adorable cottage style home would make an excellent choice for a first home! Come see today!

125 Cawood Lane, Middlesboro

Listing courtesy of Misti McGrath of Realty Group.

$59,000
2 Beds ⋅ 1 Baths ⋅ 1345724 MLS
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.

518 S 43rd St, Middlesboro

Listing courtesy of Mike Hensley of REMAX PROFESSIONAL'S.

$29,000
1344123 MLS
0.9 Acres Partially cleared with wooded area in back for privacy. City limits. All utilities available. Perfect location for a home or two right next to the mountains!

Bowling Rd, Middlesboro

Listing courtesy of Misti McGrath of Realty Group.

$149,000
4 Beds ⋅ 2 Baths ⋅ 1343957 MLS
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!

64 Dunlap Hollow Rd, Middlesboro

Listing courtesy of Virginia Wilder of Century 21 Virginia Wilder Real Estate.

$155,000
2 Beds ⋅ 1 Baths ⋅ 1343066 MLS
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!!

815 Dorchester Ave, Middlesboro

Listing courtesy of Lisa Stacy-Gibbs of Backwoods Realty & Development.

$135,000
2 Beds ⋅ 1 Baths ⋅ 1342457 MLS
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.

413 S 26th St, Middlesboro

Listing courtesy of Brad Cawood of Backwoods Realty & Development.

$70,000
2 Beds ⋅ 2 Baths ⋅ 1340557 MLS
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..

123 Cawood Lane, Middlesboro

Listing courtesy of Dustin Clay Daniels of Mountain Realty.

$35,000
2 Beds ⋅ 1 Baths ⋅ 1340131 MLS
Old home needs work with an attached older home that needs to be torn down. Great Location on Cumberland Ave behind Food City

918 E Cumberland Ave, Middlesboro

Listing courtesy of Steve Mason of REMAX PROFESSIONAL'S.

$455,000
5 Beds ⋅ 4 Baths ⋅ 1330109 MLS
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!

523 N 30th St, Middlesboro

Listing courtesy of Kevin Carroll of Backwoods Realty & Development.

$279,000
3 Beds ⋅ 3 Baths ⋅ 1329448 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

Listing courtesy of Kevin Carroll of Backwoods Realty & Development.

$30,000
1328410 MLS
LOCATION!! LOCATION!! Ready to build your dream home. Property is located minutes from Middlesboro. Wooded lot with electric and water available. Close to shopping, restaurants and hospitals. Minutes from LMU main campus. Buyer to verify acres!

LOTS 12 & 13 Sams Mountain RD., Middlesboro

Listing courtesy of Sharon K Teaney of Century 21 Virginia Wilder Real Estate.

$229,500
3 Beds ⋅ 3 Baths ⋅ 1328317 MLS
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.

301 Doe's Crossing, Middlesboro

Listing courtesy of Virginia Wilder of Century 21 Virginia Wilder Real Estate.

$250,000
1327234 MLS
Welcome to the best of all worlds! One home and an operational store that fronts Highway 217. Several outbuildings and just over 20 acres make this the perfect property for homesteading as seller had livestock on the property at one time. The land is gently rolling to level, Pineville city water in place, spectrum internet and you're off the beaten path but just a 15 minute drive back into town. (119 Wagon Hollow Rd) has a wrap around porch, large kitchen, dining and living room areas, oversized bathroom with garden tub and stand up shower. Pretty flooring throughout. Kitchen appliances convey with the property. The store (4080 hwy 217) is an adorable cabin style design with wrap around porch and swing. Inside theres a bathroom and plenty space for more shelving if you'd like to expand. Call for an appointment to tour all that Wagon Hollow Road has to offer.

119 Wagon Hollow Rd, Middlesboro

Listing courtesy of Megan Stanaford of Black Diamond Realty.

$129,900
4 Beds ⋅ 2 Baths ⋅ 1326276 MLS
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.

405 S 37th St, Middlesboro

Listing courtesy of Kevin J Bisceglia of Coldwell Banker Bisceglia Real.

$97,000
3 Beds ⋅ 2 Baths ⋅ 1316842 MLS
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!

252 Chasteen Drive, Middlesboro

Listing courtesy of Aaron Rose of Realty Network, Inc.

$15,000
1315958 MLS
Unrestricted lot in a good location in Middlesboro. Has old home on the property that does not hold any value and would need to be disposed of.

118 Polly Hollow Right Fork Rd, Middlesboro

Listing courtesy of Mike Hensley of REMAX PROFESSIONAL'S.

Listings courtesy of Spartanburg Association of Realtors as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.