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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

$315,000

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

$158,000

Enjoy a peaceful country setting just minutes from downtown Middlesboro! Situated on approximately 2 acres, this rustic 3-bedroom, 1-bath cabin combines charm, usable outdoor space, and convenient access to shopping, dining, and medical facilities. Inside, hardwood floors complement the home's warm character, while the updated kitchen features stainless steel appliances. A pellet stove provides supplemental heat, and the washer and dryer are included. Additional features include a metal roof, covered front porch, mature trees, and a spacious, level backyard with room for gardening or outdoor enjoyment. A 1-car garage, covered carport, workshop, and storage building provide ample space for parking, tools, and hobbies. The unfinished basement offers additional storage. Bring your personal touches and make this country retreat your own!

3 Beds ⋅ 1 Baths ⋅ 1356645 MLS

Enjoy a peaceful country setting just minutes from downtown Middlesboro! Situated on approximately 2 acres, this rustic 3-bedroom, 1-bath cabin combines charm, usable outdoor space, and convenient access to shopping, dining, and medical facilities. Inside, hardwood floors complement the home's warm character, while the updated kitchen features stainless steel appliances. A pellet stove provides supplemental heat, and the washer and dryer are included. Additional features include a metal roof, covered front porch, mature trees, and a spacious, level backyard with room for gardening or outdoor enjoyment. A 1-car garage, covered carport, workshop, and storage building provide ample space for parking, tools, and hobbies. The unfinished basement offers additional storage. Bring your personal touches and make this country retreat your own!

180 Stevenson Branch Rd, Middlesboro

$158,000

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

$575,000

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

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

$169,000

Don't miss your chance to own this beautifully updated 3-bedroom, 2-bathroom residence situated in the heart of Middlesboro, KY. Seamlessly blending modern convenience with classic charm. Step inside to an open and light-filled floor plan featuring brand-new flooring, fresh paint, and updated lighting fixtures throughout. The spacious living area flows effortlessly into a modernized kitchen complete with new cabinetry, updated countertops, and sleek appliances--perfect for daily living and easy entertaining

3 Beds ⋅ 2 Baths ⋅ 1355373 MLS

Don't miss your chance to own this beautifully updated 3-bedroom, 2-bathroom residence situated in the heart of Middlesboro, KY. Seamlessly blending modern convenience with classic charm. Step inside to an open and light-filled floor plan featuring brand-new flooring, fresh paint, and updated lighting fixtures throughout. The spacious living area flows effortlessly into a modernized kitchen complete with new cabinetry, updated countertops, and sleek appliances--perfect for daily living and easy entertaining

810 1/2 Rochester Ave, 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

$235,000

3 bed, 2 bath ranch style home located in a great neighborhood in the historic town of Middlesboro, Ky. Nice level lot with a fenced in back yard for your pets and privacy where you can enjoy the mountain views. Just minutes from the hospital and shopping as well as Lincoln Memorial University.

3 Beds ⋅ 2 Baths ⋅ 1354108 MLS

3 bed, 2 bath ranch style home located in a great neighborhood in the historic town of Middlesboro, Ky. Nice level lot with a fenced in back yard for your pets and privacy where you can enjoy the mountain views. Just minutes from the hospital and shopping as well as Lincoln Memorial University.

800 S 28th St, Middlesboro

$119,900

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

$219,000

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

$17,000

If you've been looking for a project here it is! Handyman special, would make a super cute flip! Or at this price you can buy it for just the land! Please do not go without an agent. Buyer/Buyers agent to confirm all information

2 Beds ⋅ 1 Baths ⋅ 1352038 MLS

If you've been looking for a project here it is! Handyman special, would make a super cute flip! Or at this price you can buy it for just the land! Please do not go without an agent. Buyer/Buyers agent to confirm all information

110 Danbury 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

$59,000

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

$149,000

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

$70,000

Major Price Reduction!! Charming 2 bedroom, 1.5 bath home situated on a beautiful, quiet lot with plenty of potential and possibilities! This property features an extra-large carport, storage shed, and inviting front porch perfect for enjoying peaceful mornings or evenings outdoors. The large backyard offers plenty of space for entertaining, gardening, or relaxing, while the enclosed back mudroom/workshop provides excellent extra storage, hobby space, or room for projects. Inside, you'll find additional flexible living space upstairs that could easily serve as a third bedroom, home office, playroom, or bonus living area to fit your needs. Conveniently located just minutes from Lincoln Memorial University, shopping, and local amenities, this home combines privacy with convenience. Whether you're looking for a starter home, investment property, or rental opportunity, this property offers endless potential. The home could benefit from some updates, making it a fantastic opportunity to add your own style and value. Don't miss this affordable home with room to grow in a desirable location! *All information contained herein is deemed reliable but not guaranteed. Buyers to verify all information independently, but not limited to square footage, acreage, taxes, etc..

2 Beds ⋅ 2 Baths ⋅ 1340557 MLS

Major Price Reduction!! Charming 2 bedroom, 1.5 bath home situated on a beautiful, quiet lot with plenty of potential and possibilities! This property features an extra-large carport, storage shed, and inviting front porch perfect for enjoying peaceful mornings or evenings outdoors. The large backyard offers plenty of space for entertaining, gardening, or relaxing, while the enclosed back mudroom/workshop provides excellent extra storage, hobby space, or room for projects. Inside, you'll find additional flexible living space upstairs that could easily serve as a third bedroom, home office, playroom, or bonus living area to fit your needs. Conveniently located just minutes from Lincoln Memorial University, shopping, and local amenities, this home combines privacy with convenience. Whether you're looking for a starter home, investment property, or rental opportunity, this property offers endless potential. The home could benefit from some updates, making it a fantastic opportunity to add your own style and value. Don't miss this affordable home with room to grow in a desirable location! *All information contained herein is deemed reliable but not guaranteed. Buyers to verify all information independently, but not limited to square footage, acreage, taxes, etc..

123 Cawood Lane, Middlesboro

$35,000

Old home needs work with an attached older home that needs to be torn down. Great Location on Cumberland Ave behind Food City

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

$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

$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

$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

$595,000

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!

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