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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!

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

$195,500

This enchanting cottage home (Fully Remodeled) offers 2 large bedrooms and 2 bathrooms, with an open floor plan that highlights the spacious kitchen with new white cabinetry and a farmhouse sink. It has a gourmet gas range, a deep Oster oven with French doors, and a butcher block countertop that creates a study nook or speakeasy during meal preparation. The same area and bedrooms have convenient USB charging outlets. This generous semi-wooded lot is .4 acres, with approximately 804 square feet of living space in this open floor plan home, built in 1957. The home is connected to city water and public sewer. Home has all new gas lines for the heating system, gourmet gas range, and a 3-year-old 'hot water on demand' tankless hot water heater. All plumbing has been upgraded to Pex. Additional appliances include a 2-year-old stackable washer/dryer unit and Full-size refrigerator. The home features newly installed Window World windows throughout that tilt in for cleaning with full screens which have a transferable Lifetime Warranty. The windows feature custom blinds throughout. This property has a new breaker panel with all updated outlets and switches, some with USB ports. The roof is approximately 3-years old, installed by the previous owner. There are also newly installed gutters with gutter guards on the home. The garage has its own standalone sub-panel breaker box with 30-amp electrical service and new LED lighting. The bathroom upgrades include a huge low threshold walk-in shower with frosted glass block natural lighting, a free-standing designer bathtub, and custom sliding barn doors with frosted glass panels. The HVAC unit is fully upgraded and serviced with new circuit panels. There is an automatic sump pump under the house. This home is an excellent fit for first time home buyers, young professionals and students seeking a spacious lot and well-maintained property, 2 minutes from Walmart and Restaurants, and 12 minutes from LMU in Harrogate, TN . Contact us today to schedule a private showing.

2 Beds ⋅ 2 Baths ⋅ 1361722 MLS

This enchanting cottage home (Fully Remodeled) offers 2 large bedrooms and 2 bathrooms, with an open floor plan that highlights the spacious kitchen with new white cabinetry and a farmhouse sink. It has a gourmet gas range, a deep Oster oven with French doors, and a butcher block countertop that creates a study nook or speakeasy during meal preparation. The same area and bedrooms have convenient USB charging outlets. This generous semi-wooded lot is .4 acres, with approximately 804 square feet of living space in this open floor plan home, built in 1957. The home is connected to city water and public sewer. Home has all new gas lines for the heating system, gourmet gas range, and a 3-year-old 'hot water on demand' tankless hot water heater. All plumbing has been upgraded to Pex. Additional appliances include a 2-year-old stackable washer/dryer unit and Full-size refrigerator. The home features newly installed Window World windows throughout that tilt in for cleaning with full screens which have a transferable Lifetime Warranty. The windows feature custom blinds throughout. This property has a new breaker panel with all updated outlets and switches, some with USB ports. The roof is approximately 3-years old, installed by the previous owner. There are also newly installed gutters with gutter guards on the home. The garage has its own standalone sub-panel breaker box with 30-amp electrical service and new LED lighting. The bathroom upgrades include a huge low threshold walk-in shower with frosted glass block natural lighting, a free-standing designer bathtub, and custom sliding barn doors with frosted glass panels. The HVAC unit is fully upgraded and serviced with new circuit panels. There is an automatic sump pump under the house. This home is an excellent fit for first time home buyers, young professionals and students seeking a spacious lot and well-maintained property, 2 minutes from Walmart and Restaurants, and 12 minutes from LMU in Harrogate, TN . Contact us today to schedule a private showing.

407 S 38th St, Middlesboro

$260,000

Beautiful Brand-New Construction - Modern Living at Its Best! Welcome home to this stunning brand-new 3-bedroom, 2-bath home featuring a spacious open floor plan designed for comfortable living and effortless entertaining. The thoughtfully designed interior boasts beautiful quartz countertops, luxury laminate flooring, and a bright, welcoming layout. The spacious primary suite offers a private retreat, while the large laundry room provides added convenience and functionality. Step outside and enjoy the covered porch overlooking a large, level lot with plenty of room to relax, entertain, or enjoy outdoor activities. With modern finishes, a desirable layout, and everything brand new, this home is ready for its very first owner. Conveniently located within walking distance of Yellow Creek School and minutes to the hospital. Not to mention downtown and Lincoln Memorial university. Don't miss your opportunity to make it yours!

3 Beds ⋅ 2 Baths ⋅ 1361665 MLS

Beautiful Brand-New Construction - Modern Living at Its Best! Welcome home to this stunning brand-new 3-bedroom, 2-bath home featuring a spacious open floor plan designed for comfortable living and effortless entertaining. The thoughtfully designed interior boasts beautiful quartz countertops, luxury laminate flooring, and a bright, welcoming layout. The spacious primary suite offers a private retreat, while the large laundry room provides added convenience and functionality. Step outside and enjoy the covered porch overlooking a large, level lot with plenty of room to relax, entertain, or enjoy outdoor activities. With modern finishes, a desirable layout, and everything brand new, this home is ready for its very first owner. Conveniently located within walking distance of Yellow Creek School and minutes to the hospital. Not to mention downtown and Lincoln Memorial university. Don't miss your opportunity to make it yours!

117 Upper Gibson Lane, Middlesboro

$180,000

Two nice homes on this 2.50 surveyed acres. House #1 - This sprawling brick home has approximately 3,000 SF and includes on main level den with fireplace, formal living room, family room, 5 bedrooms, 3 full bathrooms, one of the bathrooms has a walk-in tub/shower custom built; kitchen, formal dining room, laundry area; theatre room in basement plus bonus room in basement and additional storage space in basement also; central heat and air; paved driveway, 2 storage buildings, koi pond with relax listening to trinkling water fall, back porch and front porch; amazing view of the city of Middlesboro; walking distance to Food City, private; This sprawling brick home has approximately 3,000 SF and includes on main level den with fireplace, formal living room, family room, 5 bedrooms, 3 full bathrooms, one of the bathrooms has a walk-in tub/shower custom built; kitchen, formal dining room, laundry area; theatre room in basement plus bonus room in basement and additional storage space in basement also; central heat (AC does not work), paved driveway, 2 storage buildings, koi pond with relax listening to trinkling water fall, porch and front porch; House #2 - 3 Bedrooms and 2 full bathrooms, living room, large kitchen with dining area; both properties have amazing views of the city of Middlesboro; this property has walking trails plus it is walking distance to Food City, private;

5 Beds ⋅ 3 Baths ⋅ 1360340 MLS

Two nice homes on this 2.50 surveyed acres. House #1 - This sprawling brick home has approximately 3,000 SF and includes on main level den with fireplace, formal living room, family room, 5 bedrooms, 3 full bathrooms, one of the bathrooms has a walk-in tub/shower custom built; kitchen, formal dining room, laundry area; theatre room in basement plus bonus room in basement and additional storage space in basement also; central heat and air; paved driveway, 2 storage buildings, koi pond with relax listening to trinkling water fall, back porch and front porch; amazing view of the city of Middlesboro; walking distance to Food City, private; This sprawling brick home has approximately 3,000 SF and includes on main level den with fireplace, formal living room, family room, 5 bedrooms, 3 full bathrooms, one of the bathrooms has a walk-in tub/shower custom built; kitchen, formal dining room, laundry area; theatre room in basement plus bonus room in basement and additional storage space in basement also; central heat (AC does not work), paved driveway, 2 storage buildings, koi pond with relax listening to trinkling water fall, porch and front porch; House #2 - 3 Bedrooms and 2 full bathrooms, living room, large kitchen with dining area; both properties have amazing views of the city of Middlesboro; this property has walking trails plus it is walking distance to Food City, private;

31 & 29 E 10th Lothbury St, Middlesboro

$285,000

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.

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

$175,500

Welcome to this charming 3-bedroom, 1-bath home tucked away as the last house on a quiet dead-end street--offering extra privacy and minimal traffic. Enjoy peace of mind with major updates already completed: a new heat pump, a new water heater, and a durable metal roof only 2 years old. Thoughtful extras include lights installed in both the attic and crawl space for easy access and maintenance. This property is not located in a flood zone and is served by public water and sewer--no well or septic worries. Solid, move-in ready home in a convenient Middlesboro location. Don't miss this opportunity!

3 Beds ⋅ 1 Baths ⋅ 1358653 MLS

Welcome to this charming 3-bedroom, 1-bath home tucked away as the last house on a quiet dead-end street--offering extra privacy and minimal traffic. Enjoy peace of mind with major updates already completed: a new heat pump, a new water heater, and a durable metal roof only 2 years old. Thoughtful extras include lights installed in both the attic and crawl space for easy access and maintenance. This property is not located in a flood zone and is served by public water and sewer--no well or septic worries. Solid, move-in ready home in a convenient Middlesboro location. Don't miss this opportunity!

114 E Rochester Ave, Middlesboro

$320,000

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.

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

$235,000

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.

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

$299,000

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!

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

$145,900

You just gotta see how cute this place is in person for yourself! Completely furnished and move-in ready, you will find this 3 bdrm 2 bath home with covered front porch and carport. You will LOVE this huge back deck, big enough for a ping pong table, bring your hot tub, add a big screen TV for the ultimate entertaining and game watching pad!

3 Beds ⋅ 2 Baths ⋅ 1356828 MLS

You just gotta see how cute this place is in person for yourself! Completely furnished and move-in ready, you will find this 3 bdrm 2 bath home with covered front porch and carport. You will LOVE this huge back deck, big enough for a ping pong table, bring your hot tub, add a big screen TV for the ultimate entertaining and game watching pad!

810 W Rochester Ave, Middlesboro

$145,000

Completely remodeled and move-in ready! This charming 2-bedroom, 1-bath home offers a fresh, updated interior with new laminate flooring and carpet throughout, along with a beautifully remodeled kitchen. Recent improvements include a new roof, siding, and fresh paint, providing peace of mind and modern appeal. Situated on a level lot in a great location, the property also features a detached one-car garage for convenient parking and additional storage. A wonderful opportunity for anyone looking for a low maintenance home.

2 Beds ⋅ 1 Baths ⋅ 1356312 MLS

Completely remodeled and move-in ready! This charming 2-bedroom, 1-bath home offers a fresh, updated interior with new laminate flooring and carpet throughout, along with a beautifully remodeled kitchen. Recent improvements include a new roof, siding, and fresh paint, providing peace of mind and modern appeal. Situated on a level lot in a great location, the property also features a detached one-car garage for convenient parking and additional storage. A wonderful opportunity for anyone looking for a low maintenance home.

305 N 15th St, Middlesboro

$199,000

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!

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

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.

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

$129,000

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 ⋅ 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

$89,900

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.

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

$215,000

Isn't she lovely?! Located right in the middle of Middlesboro Ky. 4 bedroom 2 bath home with a beautiful kitchen! Yard space for all the things on a quiet street. Excellent home to check out today!

4 Beds ⋅ 2 Baths ⋅ 1352799 MLS

Isn't she lovely?! Located right in the middle of Middlesboro Ky. 4 bedroom 2 bath home with a beautiful kitchen! Yard space for all the things on a quiet street. Excellent home to check out today!

812 Worchester Ave, Middlesboro

$279,000

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!

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

$199,900

Nice 3-bedroom 2 bath home just for the picking. Priced is right with the possibility of a 4th bedroom. The kitchen, dining room, living room, 3 bedrooms and 1 bath are on the main level. The bonus room (optional 4th bedroom), full bath with laundry facilities downstairs. This home has a back deck, patio and storage building. Don't let this one get away!

4 Beds ⋅ 2 Baths ⋅ 1348714 MLS

Nice 3-bedroom 2 bath home just for the picking. Priced is right with the possibility of a 4th bedroom. The kitchen, dining room, living room, 3 bedrooms and 1 bath are on the main level. The bonus room (optional 4th bedroom), full bath with laundry facilities downstairs. This home has a back deck, patio and storage building. Don't let this one get away!

140 Wellington Drive, Middlesboro

$359,500

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.!!!

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

$135,000

Cute as a button! This adorable cottage style home would make an excellent choice for a first home! Come see today!

2 Beds ⋅ 2 Baths ⋅ 1346436 MLS

Cute as a button! This adorable cottage style home would make an excellent choice for a first home! Come see today!

125 Cawood Lane, Middlesboro

$51,000

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.

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

$125,000

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!

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

$125,000

This beautiful 2 bed 1 bath with beautiful hardwood floors, sits only minutes away from downtown Middlesboro and the Cumberland Gap National Park. This home has had some great improvements such as a new roof and new windows installed. don't miss your opportunity to call this your own.

2 Beds ⋅ 1 Baths ⋅ 1342457 MLS

This beautiful 2 bed 1 bath with beautiful hardwood floors, sits only minutes away from downtown Middlesboro and the Cumberland Gap National Park. This home has had some great improvements such as a new roof and new windows installed. don't miss your opportunity to call this your own.

413 S 26th St, Middlesboro

$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

$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

$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

$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

$100,000

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

$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

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