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918 E Cumberland Ave, Middlesboro

Listing courtesy of Steve Mason of REMAX PROFESSIONAL'S.

This home is located in the city of Middlesboro minutes away from the hospital, close to downtown. Walmart, LMU are minutes away. It's located in a very safe neighborhood. The home includes a 364' single care garage.

3 Beds ⋅ 2 Baths ⋅ 1336350 MLS

This home is located in the city of Middlesboro minutes away from the hospital, close to downtown. Walmart, LMU are minutes away. It's located in a very safe neighborhood. The home includes a 364' single care garage.

913 Doncaster St, Middlesboro

Listing courtesy of Janice Pratt of Fathom Realty TN LLC.

$455,000

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!

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

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.

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.

$135,000

Great little 3 bedroom house in a wonderful neighborhood in historic Middlesboro, Ky. Very convenient to downtown and Lincoln Memorial university. Fenced in back yard and large eat in kitchen make this a good option for just about anyone. Would also make a great opportunity for someone wanting to purchase a rental property.

3 Beds ⋅ 1 Baths ⋅ 1328773 MLS

Great little 3 bedroom house in a wonderful neighborhood in historic Middlesboro, Ky. Very convenient to downtown and Lincoln Memorial university. Fenced in back yard and large eat in kitchen make this a good option for just about anyone. Would also make a great opportunity for someone wanting to purchase a rental property.

708 W Chester Ave, Middlesboro

Listing courtesy of Mike Hensley of REMAX PROFESSIONAL'S.

$229,500

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.

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.

$115,000

Newly remodeled 2-bedroom home located just minutes away from downtown Pineville.

2 Beds ⋅ 1 Baths ⋅ 1327446 MLS

Newly remodeled 2-bedroom home located just minutes away from downtown Pineville.

1093 Old Bell High Rd, Pineville

Listing courtesy of Mike Hensley of REMAX PROFESSIONAL'S.

$250,000

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.

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

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.

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.

$69,900

Has the up stairs new flooring some new windows roof 7 years old hot water 7 years old new gutters with gutter guards. Bring your vision and bring this fixer upper back to life. Great duplex for rental or 2 families, Walking distances to everything. Live in one and rent one out. Check it out.

1324983 MLS

Has the up stairs new flooring some new windows roof 7 years old hot water 7 years old new gutters with gutter guards. Bring your vision and bring this fixer upper back to life. Great duplex for rental or 2 families, Walking distances to everything. Live in one and rent one out. Check it out.

417-A&B Avondale Ave, Middlesboro

Listing courtesy of Nancy Maiden of Mountain Realty.

$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.

3 Beds ⋅ 3 Baths ⋅ 1323427 MLS

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.

$97,000

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!

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.

$85,000

2 bed, 1 bath, manufactured home sitting on a large level lot. Conveniently located to shopping and Harrogate, TN.

2 Beds ⋅ 1 Baths ⋅ 1311219 MLS

2 bed, 1 bath, manufactured home sitting on a large level lot. Conveniently located to shopping and Harrogate, TN.

310 Barkley Drive, Middlesboro

Listing courtesy of Mike Hensley of REMAX PROFESSIONAL'S.

$270,000

Beautiful Traditional Brick Ranch with Basement! This home has 1698sq/ft on the main floor with an additional 1476sq/ft in the basement. Nestled in the center of Middlesboro with a curved driveway and a 2 car carport with a storage unit between them. The home has two entrances from the carport for easy entry. There are two bonus rooms with a formal living room and formal dining area. The main suite has a beautiful walk-in shower with overhead sky-lights for natural lighting. Also in the main suit has a walk-in closet. There is a galley kitchen with built-in appliances. The basement can be an in-law suite with a studio apartment set-up and full kitchen. This is a charming home! Schedule an appointment today!

3 Beds ⋅ 3 Baths ⋅ 1277166 MLS

Beautiful Traditional Brick Ranch with Basement! This home has 1698sq/ft on the main floor with an additional 1476sq/ft in the basement. Nestled in the center of Middlesboro with a curved driveway and a 2 car carport with a storage unit between them. The home has two entrances from the carport for easy entry. There are two bonus rooms with a formal living room and formal dining area. The main suite has a beautiful walk-in shower with overhead sky-lights for natural lighting. Also in the main suit has a walk-in closet. There is a galley kitchen with built-in appliances. The basement can be an in-law suite with a studio apartment set-up and full kitchen. This is a charming home! Schedule an appointment today!

113 Hollywood Drive, Middlesboro

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