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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.

412 Page School Rd, Pineville
$699,000
3 Beds ⋅ 2 Baths ⋅ 1349199 MLS
Hidden in the mountains of Kentucky is this gorgeous brick ranch style home that is totally secluded. It has 3 bedrooms (including primary suite), 2 full bathrooms, living room with cathedral ceiling adding to the beauty of this home, large kitchen with island and breakfast bar, all appliances stay with home (dishwasher needs repair) the kitchen extends to breakfast area and the formal dining room, large laundry room, primary suite has walk-in closet, plus the bathroom has walk in shower and jacuzzi tub, home has a 2 car attached garage, central heat and air installed new in 2022, city water, private septic system, internet available, double pane windows. Beautiful mountain views. This home sits on 26.8 acres with a pond and creek (ideal for horses or cattle). There are beautiful fields with MULTIPLE HOMES SITES on property, or you could fence the fields for farm animals. This property is level, some rolling and some steep. Lots of wildlife on this property. The driveway is paved with concrete sidewalk at home, large concrete patio and concrete front porch. This is a must see!

412 Page School Rd, Pineville

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

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.

105 Hwy 190, Pineville
$475,000
3 Beds ⋅ 3 Baths ⋅ 1323427 MLS
TWO HOMES FOR $525,000 - This property is in a perfect location for the golfer in you. Wasioto Winds Golf Course is immediately across the road from this property, and this property has access to Boone Trace Hiking Trail and is close to the Pine Mountain State Park. The main house has 3 full bathrooms and 3 bedrooms (2 bedrooms are suites) there are 2 stone gas log fireplaces, one in the Sunroom and the other in the living room, The living room has a gorgeous wood cathedral ceiling. The shining hardwood floors are an added bonus to the fine home, the amazing kitchen has an abundance of cabinets, there is an island in the kitchen, Kitchen extends to formal dining area and also leads to back covered porch. This home has a large spacious laundry room. There are lots of closets, double pane windows, 2 heat pumps that are serviced regularly, this home sits on a level yard with privacy from back porch, the front porch offers view of the golf course. Home has a handicap ramp for easy entry and has 36 inch doors for wheelchair access. High speed internet is available, public water, paved driveway with extra parking spaces. There is a 2 car garage/workshop and a 2 car carport on property. Gorgeous mountain views. Home has natural gas, cookstove is gas, all kitchen appliances stay with home plus washer and dryer. The second home has 2 bedrooms, one full bathroom, living room, family room and eat-in kitchen, laundry hookup, heat and air are wall units, wrapped porch with great views, septic system, public water. This home is ideal for additional income or to keep a family members close by. This property is close to downtown Pineville, hospitals and medical clinics as well as shopping.

105 Hwy 190, Pineville

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.

112 Woodland Trail Rd, Pineville
$429,000
4 Beds ⋅ 3 Baths ⋅ 26021440 MLS
Welcome to your next home—an exceptional 4-bedroom (bonus could be a 5th bedroom), 2.5-bath retreat offering the space, style, and everyday comfort today's buyers want most. Step inside and instantly feel the openness and quality throughout: beautiful hardwood floors, refined trim, and recessed lighting that brightens the main living areas with an airy, welcoming flow. The updated kitchen is made for hosting and everyday living, featuring custom cabinetry, a breakfast bar, a pantry, and stainless-steel appliances that bring both function and style to the heart of the home. Upstairs, you'll enjoy an open bonus room that's ideal for a home office, media space, play area, or guest-friendly flexibility. Outside, a spacious backyard and large deck create the perfect backdrop for summer barbecues, relaxing evenings, and gatherings—plus an enclosed yard that helps keep pets safely contained. And location matters here: you're positioned between Pineville and Middlesboro city limits while still feeling tucked away among the trees with beautiful mountain views. Enjoy nearby outdoor adventure at Pine Mountain State Resort Park and make it a lifestyle with golf just minutes away at Wasiota Winds Golf Course—this is the kind of home and location that buyers don't want to miss. Schedule your showing today and move quickly, because homes like this—updated, hosting-ready, and close to everything— this offers what most buyer's have on their bucket list of must have in their next home.

112 Woodland Trail Rd, Pineville

Listing courtesy of Donna Gregorich of CENTURY 21 Advantage Realty.

Hwy 3484, Pineville
$329,000
26011925 MLS
235.967 SURVEYED ACRES Discover ultimate freedom and natural beauty on this property which is next to the Kentucky Government Land Wildlife Management area with 30,661 acres. A rare, unrestricted gem offering endless possibilities, this prime property is a haven for outdoor enthusiasts and those seeking a private multi-use sanctuary. Only 22 miles from Royal Blue Unit of the North Cumberland Wildlife Management Area. The land Features rich vibrant foliage, mature vegetation, and a tranquil flowing creek that provides a steady water source for abundant local wildlife. With a well-established network of internal roads already in place , you can easily navigate and access the entire acreage. This property also has approximately 2,500 feet of road access and city water is available at the road. Whether you are looking for a world-class hunting retreat, a scenic homestead or a secluded site for recreational adventures, this unrestricted property gives you the space and freedom to bring your vision to life.

Hwy 3484, Pineville

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

Highway 3484, Pineville
$329,000
1342306 MLS
235.967 SURVEYED ACRES Discover ultimate freedom and natural beauty on this property which is next to the Kentucky Government Land Wildlife Management area with 30,661 acres. A rare, unrestricted gem offering endless possibilities, this prime property is a haven for outdoor enthusiasts and those seeking a private multi-use sanctuary. Only 22 miles from Royal Blue Unit of the North Cumberland Wildlife Management Area. The land Features rich vibrant foliage, mature vegetation, and a tranquil flowing creek that provides a steady water source for abundant local wildlife. With a well-established network of internal roads already in place , you can easily navigate and access the entire acreage. This property also has approximately 2,500 feet of road access and city water is available at the road. Whether you are looking for a world-class hunting retreat, a scenic homestead or a secluded site for recreational adventures, this unrestricted property gives you the space and freedom to bring your vision to life.

Highway 3484, Pineville

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

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.

802 Cirencester Ave, Middlesboro
$320,000
4 Beds ⋅ 3 Baths ⋅ 1361771 MLS
Welcome home to this spacious 4-bedroom, 2.5-bath brick ranch nestled in a fantastic neighborhood in historic Middlesboro, Kentucky! Offering approximately 1,960 square feet of main-level living space, this home combines classic charm with plenty of room to spread out. Beautiful hardwood floors, a large kitchen with an abundance of space and a pantry, and three fireplaces (one gas and two wood-burning) create a warm and inviting atmosphere. The partially finished basement provides additional living space and endless possibilities. A convenient two-car garage adds extra storage and functionality. Outside, enjoy the large fenced-in backyard featuring an in-ground pool currently covered by a removable wood deck, offering the opportunity to uncover and enjoy the pool once again. Location is another standout feature, with the Middlesboro Country Club and golf course just a five-minute walk away. Don't miss this opportunity to own a spacious home in one of Middlesboro's desirable neighborhoods!

802 Cirencester Ave, Middlesboro

Listing courtesy of Mike Hensley of REMAX PROFESSIONAL'S.

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.

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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