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$235,000
3 Beds ⋅ 2 Baths ⋅ 1357154 MLS
Have you been looking for a home where you can raise your family? This might be what you have been dreaming of--a 3 bedroom, 2 bath home with a full unfinished basement waiting for your family to make some memories. This home is in move-in ready shape with beautiful hardwood floors throughout, brand new hardie board on the outside, and a brand new shingle roof This home was made to accommodate a family with 2 full bathrooms and huge walk-in closets! The outside space is just as welcoming. A large deck with new railings and a large yard with a greenhouse that stays with the property. Make this one a 'must-see'. Don't let someone else get there first!

320 Cypress St, Pineville
$235,000
3 Beds ⋅ 2 Baths ⋅ 1357060 MLS
Welcome home to this beautifully updated 3-bedroom, 2-bathroom property offering approximately 1,600 square feet of comfortable living space. Recent improvements include a new roof, new HVAC system, new laminate flooring, and an updated kitchen featuring new cabinets and granite countertops. Outside, enjoy a large yard with beautiful mountain views, providing plenty of space for outdoor activities, entertaining, gardening, or simply relaxing and taking in the scenery. With its spacious layout, modern updates, and picturesque surroundings, this home offers a wonderful combination of comfort, style, and peaceful outdoor living.

88 Tracy Ridge Rd, Middlesboro
$299,900
4 Beds ⋅ 3 Baths ⋅ 1356392 MLS
Beautiful historic home in the heart of Middlesboro. Within walking distance of Fords Wood Park and downtown Middlesboro, this home is an undiscovered gem. With 4 bedrooms and 2 1/2 bathrooms, this exceptional home has lots of room for a growing family. The large unfinished basement has lots of room for storage and has the washer and dryer (which stays with the home). Every inch of this home was built for comfort and sophisticated living. Lovingly cared for over the years, you don't want to miss your personal tour of this beauty. Come let us show you your new home!

412 Englewood Rd, Middlesboro
$225,000
3 Beds ⋅ 2 Baths ⋅ 1355982 MLS
Discover the charm and character of this beautifully remodeled 1,312 sq. ft. Lustron home in a desirable neighborhood in historic Pineville, KY. This unique home blends its distinctive mid-century design with thoughtful modern updates, including new flooring throughout and fire-resistant sheetrock installed throughout much of the home. One bedroom features a newly added private en-suite bath, providing an extra level of comfort and convenience. The kitchen includes a gas cooking range, while a ventless fireplace creates a cozy gathering space. Outside, the property offers two large lots, a new patio area perfect for relaxing or entertaining, and a detached garage providing additional storage and parking. With its rare Lustron construction, updated interior, spacious grounds, and convenient Pineville location, this property offers a unique opportunity to own a piece of local history with modern comforts.

107 Ridgewood Circle, Pineville
$199,000
3 Beds ⋅ 1 Baths ⋅ 1355810 MLS
1480 sf spilt level home at 1102 W Chester Ave. This home is within walking distance to downtown, schools and hospital. It has three bedrooms and one bath, with a large den with a beautiful fireplace. The eat-in kitchen is right off the den area. There is a covered, screened-in porch just off the dining area. Lots of room for a growing family--don't let someone else take advantage of this opportunity!

1102 W Chester Ave, 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
$575,000
3 Beds ⋅ 2 Baths ⋅ 1355383 MLS
Welcome to 2010 Twin Fawn Trail in the beautiful mountains of the New phase III of Vista Venado!!! This barndominium style NEW BUILT home sits on 2.74 A of beautiful land with breathtaking views for as far as you can see. This beauty offers 2016 sq ft of open-concept living space, perfect for every day living or entertaining. With touches of class in every room, this 3 bedroom 2 bathroom has a detached 2 car oversized garage with a bonus room over top!!This house has water provided by VV SO NO water bill comes with this house. With LMU minutes away and shopping just outside your front door this front porch is one you wont want to miss. Truly the opportunity of a lifetime!!! Call Today

2010 Twin Fawn Trail, Middlesboro
$129,000
3 Beds ⋅ 1 Baths ⋅ 1354572 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
$119,900
3 Beds ⋅ 2 Baths ⋅ 1353618 MLS
This brick ranch style home has 3 bedrooms, 2 bathrooms, living room has a fireplace which adds beauty but is inoperable. The kitchen is spacious with lots of kitchen cabinets, pantry and a nice spacious laundry room. This property is nice and level and includes a paved driveway, storage shed in back yard. Home has a heat pump, internet available, nice double pane windows, city water and city sewer, home is conveniently located, close to hospital, shopping and LMU in Harrogate.

706 Ilchester Ave, Middlesboro
$139,000
1353424 MLS
This land is Private and Beautiful with 23.7 acres already has a septic system and public water and electricity. High speed internet is available. This property is secluded and joins the ''Kentucky Ridge State Forest'' with trail from this property. Three adjoining parcels make up this acreage. There are great scenic views. Bring your RV or Build your dream home or place a manufactured home on this property - unrestricted. Wonderful country setting with lots of wildlife on this property. In the country yet close to downtown Pineville, Kentucky.

TBD Gobblers Knob, Pineville
$110,000
2 Beds ⋅ 1 Baths ⋅ 1352226 MLS
This 2 bedroom, 1 bath property is located in the heart of Pineville KY just minutes away from downtown. Whether you are looking for your next home or a high-demand rental investment, this property delivers incredible value in a great location. Schedule your showing today!

509 W Tennessee Ave, Pineville
$299,900
5 Beds ⋅ 2 Baths ⋅ 1350786 MLS
Looking for a HOME and not just another house? This is it! With 5 bedrooms, 2 baths, a bonus room to use as a den or rec room, and even special features like a light equipped with a built-in blue tooth speaker in the master bathroom. This home was built with 'family living' in mind. The kitchen is equipped with a new island/breakfast bar that seats six and blends seamlessly with the dining area. With lots of room inside plus a pool with nice deck and patio in the back, you have a great blend of inside and outside living. Put this one on your must-see list--it may be the last one you have to look at to find your perfect home.

926 Doncaster 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
$299,900
5 Beds ⋅ 3 Baths ⋅ 1350193 MLS
Historic home in Pineville! Lovely 2 story historic home with old-world charm and modern upgrades. This beauty has 5 bedrooms and 3 full baths with hardwood and new carpet throughout. The combined kitchen and dining area has upgraded appliances and modern lighting and cabinets that maintain the ''historic'' feel of the home. The bathrooms are amazing--the perfect blend of function and beauty. Even the front porch feels like home. This family-friendly neighborhood would make the perfect place to raise your family. Let us give you a tour of the home you have been dreaming about for years--now is the time!

307 Catalpa St, Pineville
$137,000
3 Beds ⋅ 2 Baths ⋅ 1350003 MLS

137 Horseshoe Drive, 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
$339,000
5 Beds ⋅ 3 Baths ⋅ 1347217 MLS
Beautiful two-story home with a fantastic front porch view of the mountains. Secluded but only 5 minutes to Pineville. Beautiful kitchen, 5 bedrooms 3 baths. large Master Suite, Hardwood floors New shingle roof in 2024 Only 10 minutes from shopping, dinning and 14 from LMU. This could be your dream home. Space for living comfortably with family and friends. Outdoor entertaining with a beautiful pool, patio and covered back porch.

56 Horizon Estate, Pineville
$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
$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
$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
$229,000
3 Beds ⋅ 3 Baths ⋅ 1343063 MLS
3-bedroom home with 2 full bathrooms and one-half bath located just minutes outside of the city of Pineville, Ky and the Pine Mountain State Park. Also convenient to Harlan Kentucky and local ATV trails. Oversized 3 car attached garage is perfect for storing all those toys or for your own workshop. Very private back patio area and large swimming pool are perfect for entertaining or just relaxing after a long day.

2953 U.S. 119, 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
$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
$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
$299,900
5 Beds ⋅ 4 Baths ⋅ 1329199 MLS
Pristine home on over an acre of land! This beautifully maintained home with over 3,000 sf of living space has all the space you could need for your family. This home has 3 bedrooms and 3 bathrooms on the main floor, with 2 more bedrooms and 1 bathroom in the basement. Featuring 2 living rooms, a dining room, a sunporch and a den, you don't want to miss this beauty. Included with the home is a 952 sf apartment behind the extra-large 3 car detached garage. This is the kind of home people wish for--move in ready and ready to make your dreams come true.

184 Osborne Rd, Pineville
$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
$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
$22,500
1326178 MLS
Great location just behind the Golf Course

Walnut Lane, Pineville
$525,000
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
$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