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3133 Us Highway 25e, Middlesboro
$1,790,000
25008431 MLS
Opportunity Alert! Whatever your business idea, this property has the potential to make it a reality. From location to actual usable space and even more property to expand, there is no shortage of boxes that this commercial property will check mark. Offering three separate buildings with large open spaces, office area, worship space plus a large apartment that could be rented or used by the new owner. These buildings are red steel buildings and have stood strong over the years with many years of life ahead of them. With all of the items mentioned above, this property could be used for a storage facility, boat and RV storage, turn it into a medical or health clinic, auto repair, even a possible church! Let your mind dream a little and then set up a showing to see how this listing can make it happen.

3133 Us Highway 25e, Middlesboro

Listing courtesy of G Daniel Carmack of Sallie Davidson, Realtors.

113 N 18th St, Middlesboro
$1,750,000
1356342 MLS
Established turnkey towing and auto repair business ready for you to take on. Building has 2 offices, waiting room, 2 half baths, with a 10k sq foot garage featuring 4 lifts, 8 bays, tire machine, air compressor, new roof and mini split system, new gas heat (one unit not installed). Paint booth included in the back of the building with new separate electric ready to go. Paint booth comes with everything you need to get started brand new never used Vinyl wrap, cutter and laminator. Everything goes with the exception of personal tools and one air compressor. Including but not limited to, 8 trucks different sizes and ages 3 rollbacks, one medium duty wrecker, 2 smaller wreckers and the only rotator tow truck within a 60 mile radius. Please call for more information.

113 N 18th St, Middlesboro

Listing courtesy of Misti McGrath of Realty Group.

2247 State Highway 188, Middlesboro
$625,000
4 Beds ⋅ 5 Baths ⋅ 1358708 MLS
Discover exceptional space, privacy, and distinctive character in this impressive 4-bedroom, 4.5-bath home offering 5,426 square feet of living space on a beautiful 0.67-acre lot. Hardwood and tile flooring throughout, along with four fireplaces, add warmth and timeless appeal. The spacious cook's kitchen features a gas cooking range, double ovens, and ample room for preparing meals and gathering with family and friends. A formal dining area provides the perfect setting for entertaining, while a dedicated home office offers a convenient space for working from home. Each bedroom features its own attached bathroom, providing comfort and privacy for family members and guests. The primary suite offers a relaxing retreat, complete with a large copper soaking tub. Outside, enjoy the inviting entertaining area and swimming pool, or unwind in the peaceful backyard overlooking the beautiful creek that borders the property. The private setting offers a serene escape while remaining conveniently located to Middlesboro and Harrogate. Additional features include an oversized two-car garage and overbuilt 2x6 exterior wall construction. With generous living spaces, unique details, and a beautiful creekside setting, this exceptional property combines comfort, functionality, and privacy in a truly inviting home.

2247 State Highway 188, Middlesboro

Listing courtesy of Mike Hensley of REMAX PROFESSIONAL'S.

142 Edgewood Rd, Middlesboro
$595,000
7 Beds ⋅ 5 Baths ⋅ 1290184 MLS
A One-of-a-Kind Dream Home with Spectacular Views! This stunning home offers breathtaking views from every window and boasts 7 spacious bedrooms, 3 full bathrooms, and 2 half bathrooms—plenty of room for the entire family! Step inside and be captivated by the grand staircase and an incredible private library, perfect for quiet moments or working from home. The walkout basement is ready to be finished to your specifications, allowing you to create the ultimate entertainment space, home gym, or guest suite. As an added bonus, the price includes an extra buildable lot, giving you even more possibilities for expansion or investment. Don't miss out on this rare opportunity to own a truly unique home. Schedule your showing today!

142 Edgewood Rd, Middlesboro

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

2004 Twin Fawn Tr, Middlesboro
$475,000
5 Beds ⋅ 3 Baths ⋅ 1355491 MLS
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.

2004 Twin Fawn Tr, Middlesboro

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

225 Sherwood Rd, Middlesboro
$469,900
3 Beds ⋅ 3 Baths ⋅ 26029553 MLS
Welcome home to an exceptional single-family residence that perfectly blends spacious living, thoughtful design, and breathtaking views in a peaceful Middlesboro neighborhood. This beautifully maintained 1994 brick home offers nearly 3,810 square feet of comfortable living space on a professionally landscaped 0.92-acre lot, creating an inviting setting where every day feels a little more relaxed. Step inside to an expansive open floor plan that flows effortlessly between the living, dining, and kitchen areas. Vaulted ceilings in the living room lend a grand, airy feel, while the chef's kitchen—seamlessly integrated into the heart of the home—makes entertaining as easy as everyday family meals. A generous walk-in pantry and expansive laundry room add practical elegance to the layout. The luxurious primary suite serves as a true private retreat, featuring a spa-like bath with a walk-in shower, soothing soaker tub, and a large walk-in closet. Two additional spacious bedrooms and a versatile bonus room provide flexibility for a home office, guest suite, playroom, or hobby space, while 2 full baths plus a half bath keep everything convenient. Energy-efficient geothermal heating and cooling deliver year-round comfort with lower utility costs. Outside, the elegant brick exterior and meticulously landscaped grounds create instant curb appeal. Multiple garage spaces—including an attached 2-car garage, an additional 1-car garage, and a 2½-car detached garage—offer abundant room for vehicles, tools, and recreational equipment. Nestled in a serene setting with panoramic views, this one-of-a-kind home combines classic charm, modern functionality, and an unbeatable location. Whether you're seeking a peaceful primary residence or a place to enjoy Middlesboro's mountain surroundings, 225 Sherwood Rd is ready to welcome you.

225 Sherwood Rd, Middlesboro

Listing courtesy of Jonathan Evans of Mountain Realty Group LLC.

523 N 30th St, Middlesboro
$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.

1803 W Cumberland Ave, Middlesboro
$325,000
26012876 MLS
Location, Location, Location! Exceptional investment opportunity featuring a 12,210-square-foot commercial building in the Downtown Business District. A long-established restaurant tenant is already in place, occupying 4,070 square feet and providing immediate income potential. The remaining 8,140 square feet of open space offers outstanding flexibility for additional tenants, retail, office, or mixed-use development. The property boasts 141 feet of road frontage, excellent visibility, and ample on-site parking for customers and employees. With a proven tenant, significant leasable space available, and a prime downtown location, this property is well-positioned for both current cash flow and future growth.

1803 W Cumberland Ave, Middlesboro

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

103 Sherwood Rd, Middlesboro
$320,000
5 Beds ⋅ 3 Baths ⋅ 1357377 MLS
Here is your chance to meet 103 Sherwood Rd, the home with a huge personality. New construction and cookie cutter style lovers, I need you to look away. This home is unlike any other. The love this home has been shown truly shines, Updated to suit todays needs, but at the same time holding on to that mid century modern style. In addition to having 5 bedrooms and 3 baths you have a massive bonus room perfect for use as a den, family room, game room or theatre room, depending on your needs, Sitting on approximately half an acre right across from Fords Woods Park. Outside lighting, several brick flower beds, and a patio worth sharing with friends. This home packs a punch I can't even fully explain. You're going to have to see this one yourself, the pictures do not do justice. Buyer/Buyers Agent to verify all information.

103 Sherwood Rd, Middlesboro

Listing courtesy of Misti McGrath of Realty Group.

406 N 25th St, Middlesboro
$285,000
3 Beds ⋅ 2 Baths ⋅ 1358692 MLS
3 Bedrooms 1.5 Baths with not one but 2 bonus sunrooms! This home packs the charm of our older homes of Middlesboro only with an open floor plan you can't find just anywhere! (Speaking of floors, notice how solid these are during your walk through} Oversized rooms throughout the home, tall ceilings, wonderfully preserved doors with working transom windows create a nice, easy, light flow through the home, Gorgeous living room with wood burning fireplace that is sure to keep you super cozy. Lots of extra storage space in the full basement and attic but also hidden in the walls of the home. Outside you'll find the best front porch around. In the back you'll find a screened in porch and a big flat yard in case you need to store a pool or swing set or trampoline. Lots of room to play and grow in this beautifully maintained historic home.

406 N 25th St, Middlesboro

Listing courtesy of Misti McGrath of Realty Group.

400 Gloucester Ave, Middlesboro
$279,000
4 Beds ⋅ 2 Baths ⋅ 1350232 MLS
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!

400 Gloucester Ave, Middlesboro

Listing courtesy of Sheila Durham of Coldwell Banker Bisceglia Real.

400 Gloucester Ave, Middlesboro
$279,000
4 Beds ⋅ 2 Baths ⋅ 26020497 MLS
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!

400 Gloucester Ave, Middlesboro

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

515 Englewood Rd, Middlesboro
$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.

207 Arthur Hts, Middlesboro
$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.

119 Wagon Hollow Rd, Middlesboro
$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.

156 Wellington Dr, Middlesboro
$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.

623 N 20th St, Middlesboro
$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.

301 Doe's Crossing, Middlesboro
$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.

717 Hwy 441, Middlesboro
$220,000
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.

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.

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