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$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
$315,000
4 Beds ⋅ 3 Baths ⋅ 1356915 MLS
Beautifully maintained with modern updates, lots of room to spread out, and an unbeatable location, this home is ready to raise its next family. Featuring 4 bedrooms 2.5 baths, gorgeous shiny kitchen with sliding glass doors taking you to the deck outside, this home would make a fabulous entertaining home. A formal living room with great natural lighting. A rock fireplace surrounded by a den worthy of all the days and all the naps. Located a stone's throw away from Middlesboro Schools, restaurants, hospital and the best 4-wheeling in our area, with LMU being only 6 miles away, Talk about convenient!

1015 Old Wilson Lane, 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
$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
$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
$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
$359,500
3 Beds ⋅ 2 Baths ⋅ 1348099 MLS
This beautiful brick has touches of class to enjoy for a lifetime. With all the beauty of her old style from big rooms, original cherry doors 9 1/2 foot ceilings and original hardwood floors. A fabulous front porch, a 2 car garage with a spacious and playful backyard. On the inside you will enjoy a kitchen that sparkles white with stainless steel appliances and a grand island for cooking and entertaining. The owner's suite hosts a 5-piece bathroom with a double vanity. Move in ready!!!! This house is a once in a lifetime purchase.!!!

2909 W Cumberland Ave, Middlesboro
$275,500
3 Beds ⋅ 2 Baths ⋅ 1348055 MLS
Welcome to 97 Joe E Dell RD, this beautiful BRICK home is nestled on a peaceful, tree-surround lot of 1.75a. Your very own personal paradise with a beautiful above ground pool, and deck for entertaining! Inside, this 3 beds 2 bath has all the touches of HOME.

97 Joe E Dell Rd, Pineville
$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
$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
$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
$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
$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
$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
$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