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Opportunity Alert! Whatever your business idea, this property has the potential to make it a reality. From location to actual usable space and even more property to expand, there is no shortage of boxes that this commercial property will check mark. Offering three separate buildings with large open spaces, office area, worship space plus a large apartment that could be rented or used by the new owner. These buildings are red steel buildings and have stood strong over the years with many years of life ahead of them. With all of the items mentioned above, this property could be used for a storage facility, boat and RV storage, turn it into a medical or health clinic, auto repair, even a possible church! Let your mind dream a little and then set up a showing to see how this listing can make it happen.

25008431 MLS

Opportunity Alert! Whatever your business idea, this property has the potential to make it a reality. From location to actual usable space and even more property to expand, there is no shortage of boxes that this commercial property will check mark. Offering three separate buildings with large open spaces, office area, worship space plus a large apartment that could be rented or used by the new owner. These buildings are red steel buildings and have stood strong over the years with many years of life ahead of them. With all of the items mentioned above, this property could be used for a storage facility, boat and RV storage, turn it into a medical or health clinic, auto repair, even a possible church! Let your mind dream a little and then set up a showing to see how this listing can make it happen.

3133 Us Highway 25e, Middlesboro

$598,000

Prime property with prime opportunity. This vacant land sits right on a main highway, just minutes from the upcoming Boones Ridge Wildlife project. Over 3 acres of land to build your dream business with thousands of eyes each day passing by, theres no better place than this property in Bell County.

25008609 MLS

Prime property with prime opportunity. This vacant land sits right on a main highway, just minutes from the upcoming Boones Ridge Wildlife project. Over 3 acres of land to build your dream business with thousands of eyes each day passing by, theres no better place than this property in Bell County.

Us Highway 25, Middlesboro

$469,900

Welcome home to an exceptional single-family residence that perfectly blends spacious living, thoughtful design, and breathtaking views in a peaceful Middlesboro neighborhood. This beautifully maintained 1994 brick home offers nearly 3,810 square feet of comfortable living space on a professionally landscaped 0.92-acre lot, creating an inviting setting where every day feels a little more relaxed. Step inside to an expansive open floor plan that flows effortlessly between the living, dining, and kitchen areas. Vaulted ceilings in the living room lend a grand, airy feel, while the chef's kitchen—seamlessly integrated into the heart of the home—makes entertaining as easy as everyday family meals. A generous walk-in pantry and expansive laundry room add practical elegance to the layout. The luxurious primary suite serves as a true private retreat, featuring a spa-like bath with a walk-in shower, soothing soaker tub, and a large walk-in closet. Two additional spacious bedrooms and a versatile bonus room provide flexibility for a home office, guest suite, playroom, or hobby space, while 2 full baths plus a half bath keep everything convenient. Energy-efficient geothermal heating and cooling deliver year-round comfort with lower utility costs. Outside, the elegant brick exterior and meticulously landscaped grounds create instant curb appeal. Multiple garage spaces—including an attached 2-car garage, an additional 1-car garage, and a 2½-car detached garage—offer abundant room for vehicles, tools, and recreational equipment. Nestled in a serene setting with panoramic views, this one-of-a-kind home combines classic charm, modern functionality, and an unbeatable location. Whether you're seeking a peaceful primary residence or a place to enjoy Middlesboro's mountain surroundings, 225 Sherwood Rd is ready to welcome you.

3 Beds ⋅ 3 Baths ⋅ 26029553 MLS

Welcome home to an exceptional single-family residence that perfectly blends spacious living, thoughtful design, and breathtaking views in a peaceful Middlesboro neighborhood. This beautifully maintained 1994 brick home offers nearly 3,810 square feet of comfortable living space on a professionally landscaped 0.92-acre lot, creating an inviting setting where every day feels a little more relaxed. Step inside to an expansive open floor plan that flows effortlessly between the living, dining, and kitchen areas. Vaulted ceilings in the living room lend a grand, airy feel, while the chef's kitchen—seamlessly integrated into the heart of the home—makes entertaining as easy as everyday family meals. A generous walk-in pantry and expansive laundry room add practical elegance to the layout. The luxurious primary suite serves as a true private retreat, featuring a spa-like bath with a walk-in shower, soothing soaker tub, and a large walk-in closet. Two additional spacious bedrooms and a versatile bonus room provide flexibility for a home office, guest suite, playroom, or hobby space, while 2 full baths plus a half bath keep everything convenient. Energy-efficient geothermal heating and cooling deliver year-round comfort with lower utility costs. Outside, the elegant brick exterior and meticulously landscaped grounds create instant curb appeal. Multiple garage spaces—including an attached 2-car garage, an additional 1-car garage, and a 2½-car detached garage—offer abundant room for vehicles, tools, and recreational equipment. Nestled in a serene setting with panoramic views, this one-of-a-kind home combines classic charm, modern functionality, and an unbeatable location. Whether you're seeking a peaceful primary residence or a place to enjoy Middlesboro's mountain surroundings, 225 Sherwood Rd is ready to welcome you.

225 Sherwood Rd, Middlesboro

$375,000

3,200 sf building in the city limits of Middlesboro. Built in 1998, this building is located on a high-visibility street behind the Middlesboro Mall. With lots of parking, this building would be an excellent opportunity to own your own business. This building would be great for retail, commercial or a restaurant.

26012603 MLS

3,200 sf building in the city limits of Middlesboro. Built in 1998, this building is located on a high-visibility street behind the Middlesboro Mall. With lots of parking, this building would be an excellent opportunity to own your own business. This building would be great for retail, commercial or a restaurant.

601 N 15th St, Middlesboro

$325,000

Location, Location, Location! Exceptional investment opportunity featuring a 12,210-square-foot commercial building in the Downtown Business District. A long-established restaurant tenant is already in place, occupying 4,070 square feet and providing immediate income potential. The remaining 8,140 square feet of open space offers outstanding flexibility for additional tenants, retail, office, or mixed-use development. The property boasts 141 feet of road frontage, excellent visibility, and ample on-site parking for customers and employees. With a proven tenant, significant leasable space available, and a prime downtown location, this property is well-positioned for both current cash flow and future growth.

26012876 MLS

Location, Location, Location! Exceptional investment opportunity featuring a 12,210-square-foot commercial building in the Downtown Business District. A long-established restaurant tenant is already in place, occupying 4,070 square feet and providing immediate income potential. The remaining 8,140 square feet of open space offers outstanding flexibility for additional tenants, retail, office, or mixed-use development. The property boasts 141 feet of road frontage, excellent visibility, and ample on-site parking for customers and employees. With a proven tenant, significant leasable space available, and a prime downtown location, this property is well-positioned for both current cash flow and future growth.

1803 W Cumberland Ave, Middlesboro

$299,000

Multi-unit rental property for sale. This instant money-maker has 4 apartments, all of which are rented. Tenants pay all utilities. Now is the perfect time to invest in rental property. Right now, there is no risk of your apartments sitting empty-schedule an appointment today before someone else realizes the potential in these units. Don't wait!

6 Beds ⋅ 4 Baths ⋅ 26022575 MLS

Multi-unit rental property for sale. This instant money-maker has 4 apartments, all of which are rented. Tenants pay all utilities. Now is the perfect time to invest in rental property. Right now, there is no risk of your apartments sitting empty-schedule an appointment today before someone else realizes the potential in these units. Don't wait!

312 W Chester Ave, Middlesboro

$295,000

Beautiful 5-Bedroom Home on 1.165 Acres - Middlesboro, KY Welcome to 717 Highway 441, a stunning custom manufactured home offering space, comfort, and modern charm—all set on a generous 1.165-acre lot. This gorgeous home features 5 spacious bedrooms and 3 full bathrooms, perfect for families of all sizes. Step inside to find large, open rooms, ample closet space, and beautifully designed bathrooms throughout. The heart of the home is a large, well-appointed kitchen, ideal for cooking, gathering, and entertaining. You'll also appreciate the oversized laundry room, adding convenience and extra storage. Enjoy outdoor living with a nice back deck, perfect for relaxing or hosting guests. A front deck is currently being completed, adding even more curb appeal and outdoor space. Additional features include: City water and sewer. Expansive lot with room to roam. This property combines comfort, space, and value in a peaceful setting. Call today to schedule your private showing—this one won't last long!

5 Beds ⋅ 3 Baths ⋅ 26006775 MLS

Beautiful 5-Bedroom Home on 1.165 Acres - Middlesboro, KY Welcome to 717 Highway 441, a stunning custom manufactured home offering space, comfort, and modern charm—all set on a generous 1.165-acre lot. This gorgeous home features 5 spacious bedrooms and 3 full bathrooms, perfect for families of all sizes. Step inside to find large, open rooms, ample closet space, and beautifully designed bathrooms throughout. The heart of the home is a large, well-appointed kitchen, ideal for cooking, gathering, and entertaining. You'll also appreciate the oversized laundry room, adding convenience and extra storage. Enjoy outdoor living with a nice back deck, perfect for relaxing or hosting guests. A front deck is currently being completed, adding even more curb appeal and outdoor space. Additional features include: City water and sewer. Expansive lot with room to roam. This property combines comfort, space, and value in a peaceful setting. Call today to schedule your private showing—this one won't last long!

717 Hwy 441, 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 ⋅ 26020657 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

$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 ⋅ 26020497 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

$275,000

1.695 flat acres in the city of Middlesboro. Zoned B3 (Central Business District). Some uses permitted are: Wholesale & Retail Trade, Sporting Goods, Banks, Theater, Auto Repair, Pharmacy, Hotel-Motel, Bed & Breakfast, and Multi Family

25012296 MLS

1.695 flat acres in the city of Middlesboro. Zoned B3 (Central Business District). Some uses permitted are: Wholesale & Retail Trade, Sporting Goods, Banks, Theater, Auto Repair, Pharmacy, Hotel-Motel, Bed & Breakfast, and Multi Family

321 Chester Ave, Middlesboro

$264,900

CHARMING VICTORIA HOME. Experience the timeless allure of this late-1800s Victorian masterpiece, where historic character meets expansive modern living. Boasting over 2,404 finished square feet—plus a versatile 600-square-foot finished attic space—this impressive residence offers a total of five spacious bedrooms, providing ample room for family, guests, or a dedicated home office. The primary bedroom is currently under renovation, offering the rare opportunity to add your final personal touch to the suite. While the primary bedroom bath has been completely remodeled with a walk in shower, bluetooth speakers, Step into your personal sanctuary with this top-of-the-line intelligent toilet. A seamless one-piece, skirted design, this smart fixture features a motion-activated lid that opens upon approach and an automatic, high-efficiency flush for ultimate sanitation. The integrated bidet offers customizable warm water cleaning, heated seating for year-round comfort, and an automatic air purifier to keep the atmosphere fresh and serene. The heart of the home flows through classic spaces designed for both grand entertaining and quiet retreats. Enjoy the traditional elegance of the parlor, a formal dining room for holiday gatherings, and a comfortable living room. Outside, the large wrap-around porch serves as the perfect vantage point for beautiful neighborhood views, while the screened-in porch and fenced in courtyard beautiful elegance to the home.

5 Beds ⋅ 3 Baths ⋅ 26010558 MLS

CHARMING VICTORIA HOME. Experience the timeless allure of this late-1800s Victorian masterpiece, where historic character meets expansive modern living. Boasting over 2,404 finished square feet—plus a versatile 600-square-foot finished attic space—this impressive residence offers a total of five spacious bedrooms, providing ample room for family, guests, or a dedicated home office. The primary bedroom is currently under renovation, offering the rare opportunity to add your final personal touch to the suite. While the primary bedroom bath has been completely remodeled with a walk in shower, bluetooth speakers, Step into your personal sanctuary with this top-of-the-line intelligent toilet. A seamless one-piece, skirted design, this smart fixture features a motion-activated lid that opens upon approach and an automatic, high-efficiency flush for ultimate sanitation. The integrated bidet offers customizable warm water cleaning, heated seating for year-round comfort, and an automatic air purifier to keep the atmosphere fresh and serene. The heart of the home flows through classic spaces designed for both grand entertaining and quiet retreats. Enjoy the traditional elegance of the parlor, a formal dining room for holiday gatherings, and a comfortable living room. Outside, the large wrap-around porch serves as the perfect vantage point for beautiful neighborhood views, while the screened-in porch and fenced in courtyard beautiful elegance to the home.

207 Arthur Hts, Middlesboro

$234,900

Welcome to this cozy and beautiful home nestled in Middlesboro Kentucky. Enjoy the appeal of a private outdoor space enhanced by a brand-new fence, perfect for relaxing or entertaining. Situated close to Lincoln Memorial University and within easy reach of all the everyday amenities Middlesboro has to offer, this charming property combines comfort with exceptional convenience. Schedule a showing today and experience the warmth and practicality of this inviting residence.

3 Beds ⋅ 2 Baths ⋅ 26029407 MLS

Welcome to this cozy and beautiful home nestled in Middlesboro Kentucky. Enjoy the appeal of a private outdoor space enhanced by a brand-new fence, perfect for relaxing or entertaining. Situated close to Lincoln Memorial University and within easy reach of all the everyday amenities Middlesboro has to offer, this charming property combines comfort with exceptional convenience. Schedule a showing today and experience the warmth and practicality of this inviting residence.

508 Worchester Ave, Middlesboro

$230,000

Welcome home to this spacious and inviting 3-bedroom, 1.5-bath property that offers both comfort and versatility! In addition to the three bedrooms, you'll find a bonus room that can easily serve as a 4th bedroom, home office, or flex space to fit your needs. This home features both a cozy living room and a separate den, providing plenty of space for relaxing or entertaining. The den is highlighted by a charming fireplace—perfect for gathering on cooler evenings. The eat-in kitchen offers a warm and functional space for everyday meals. Step outside to enjoy a large backyard complete with a swimming pool, an expansive deck, and a screened-in area attached to the deck—perfect for relaxing without worrying about pests while still enjoying the outdoors. Whether you're hosting guests or unwinding after a long day, this outdoor space has it all. With its flexible layout, multiple living spaces, and great indoor and outdoor amenities, this home has something for everyone. Don't miss your chance to make it yours!

3 Beds ⋅ 2 Baths ⋅ 26005639 MLS

Welcome home to this spacious and inviting 3-bedroom, 1.5-bath property that offers both comfort and versatility! In addition to the three bedrooms, you'll find a bonus room that can easily serve as a 4th bedroom, home office, or flex space to fit your needs. This home features both a cozy living room and a separate den, providing plenty of space for relaxing or entertaining. The den is highlighted by a charming fireplace—perfect for gathering on cooler evenings. The eat-in kitchen offers a warm and functional space for everyday meals. Step outside to enjoy a large backyard complete with a swimming pool, an expansive deck, and a screened-in area attached to the deck—perfect for relaxing without worrying about pests while still enjoying the outdoors. Whether you're hosting guests or unwinding after a long day, this outdoor space has it all. With its flexible layout, multiple living spaces, and great indoor and outdoor amenities, this home has something for everyone. Don't miss your chance to make it yours!

156 Wellington Dr, Middlesboro

$229,500

Excellent investment opportunity with a strong ~9% cap rate at asking price! This unique 4-unit property offers incredible versatility-perfect as a pure cash-flowing asset or an ideal opportunity to live in one unit while renting out the other three. The property consists of four fully occupied units: a main multi-family building featuring one 2-bedroom unit and two 1-bedroom units, plus a detached, standalone 2-bedroom, 2-bathroom manufactured home. All units have been historically well-maintained, feature newer appliances, and have received numerous updates and improvements over the years. Currently rented at stable, conservative rates, this property offers an immediate return on investment with substantial upside potential to increase rents to market value. A formidable long term opportunity.

6 Beds ⋅ 6 Baths ⋅ 26013646 MLS

Excellent investment opportunity with a strong ~9% cap rate at asking price! This unique 4-unit property offers incredible versatility-perfect as a pure cash-flowing asset or an ideal opportunity to live in one unit while renting out the other three. The property consists of four fully occupied units: a main multi-family building featuring one 2-bedroom unit and two 1-bedroom units, plus a detached, standalone 2-bedroom, 2-bathroom manufactured home. All units have been historically well-maintained, feature newer appliances, and have received numerous updates and improvements over the years. Currently rented at stable, conservative rates, this property offers an immediate return on investment with substantial upside potential to increase rents to market value. A formidable long term opportunity.

623 N 20th St, Middlesboro

$215,000

209 S. 19th Street, Middlesboro, KY 40965 Beautiful 2022 manufactured home offering approximately 1,352 sq. ft. of comfortable living space with 3 bedrooms and 2 bathrooms. The home is situated in a private setting while still conveniently located within town. Features include city utilities and a concrete block foundation. The PVA reflects approximately 0.50 acre; buyer to verify acreage and all property information. A great opportunity for buyers looking for a newer home with convenient in-town access and a private feel. Schedule your showing today

3 Beds ⋅ 2 Baths ⋅ 26022968 MLS

209 S. 19th Street, Middlesboro, KY 40965 Beautiful 2022 manufactured home offering approximately 1,352 sq. ft. of comfortable living space with 3 bedrooms and 2 bathrooms. The home is situated in a private setting while still conveniently located within town. Features include city utilities and a concrete block foundation. The PVA reflects approximately 0.50 acre; buyer to verify acreage and all property information. A great opportunity for buyers looking for a newer home with convenient in-town access and a private feel. Schedule your showing today

209 S 19th St, Middlesboro

$200,000

Mountain Views, Privacy & Endless Possibilities! Discover the perfect blend of privacy, space, and convenience at 116 Edgewood Road in Middlesboro. This spacious 2,154-square-foot home offers 3 bedrooms and 2 full bathrooms, nestled on approximately 0.75 acres while remaining within walking distance of downtown amenities. Step inside to find a versatile floor plan with multiple living areas and flexible spaces that can easily accommodate additional bedrooms, home offices, recreation rooms, or multi-generational living. The home's unique layout even presents the potential for conversion into separate living quarters, making it an attractive opportunity for homeowners and investors alike. Enjoy beautiful mountain, city, and park views from your property while experiencing the peace and privacy of a wooded setting where local wildlife is often seen. The home features central heating and cooling, a detached garage, ample parking, durable metal roofing, and city utilities. Recent improvements have already been completed, providing a solid foundation for the next owner to personalize and make their own. Whether you're searching for a spacious family home, an investment opportunity, or a property with room to grow, this unique Middlesboro residence offers exceptional value. Property Highlights 3 Bedrooms | 2 Bathrooms 2,154 Sq. Ft. of Living Space Approximately 0.75 Acres Detached Garage & Additional Parking Mountain, City & Park Views Central Heating & Air Conditioning Flexible Layout with Multi-Use Spaces Potential for Multi-Family or Income-Producing Use Convenient Access to Downtown Middlesboro Don't miss this rare opportunity to own a spacious home with privacy, views, and unlimited potential in the heart of Middlesboro. Schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ 26013326 MLS

Mountain Views, Privacy & Endless Possibilities! Discover the perfect blend of privacy, space, and convenience at 116 Edgewood Road in Middlesboro. This spacious 2,154-square-foot home offers 3 bedrooms and 2 full bathrooms, nestled on approximately 0.75 acres while remaining within walking distance of downtown amenities. Step inside to find a versatile floor plan with multiple living areas and flexible spaces that can easily accommodate additional bedrooms, home offices, recreation rooms, or multi-generational living. The home's unique layout even presents the potential for conversion into separate living quarters, making it an attractive opportunity for homeowners and investors alike. Enjoy beautiful mountain, city, and park views from your property while experiencing the peace and privacy of a wooded setting where local wildlife is often seen. The home features central heating and cooling, a detached garage, ample parking, durable metal roofing, and city utilities. Recent improvements have already been completed, providing a solid foundation for the next owner to personalize and make their own. Whether you're searching for a spacious family home, an investment opportunity, or a property with room to grow, this unique Middlesboro residence offers exceptional value. Property Highlights 3 Bedrooms | 2 Bathrooms 2,154 Sq. Ft. of Living Space Approximately 0.75 Acres Detached Garage & Additional Parking Mountain, City & Park Views Central Heating & Air Conditioning Flexible Layout with Multi-Use Spaces Potential for Multi-Family or Income-Producing Use Convenient Access to Downtown Middlesboro Don't miss this rare opportunity to own a spacious home with privacy, views, and unlimited potential in the heart of Middlesboro. Schedule your private showing today!

116 Edgewood Rd, Middlesboro

$199,000

Just listed 1480 sq ft historical spilt level home at 1102 W Chester Ave Middlesboro Ky. This home is in walking distance from downtown. It has three bedrooms and one bath and 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 dinning area.

3 Beds ⋅ 1 Baths ⋅ 26022803 MLS

Just listed 1480 sq ft historical spilt level home at 1102 W Chester Ave Middlesboro Ky. This home is in walking distance from downtown. It has three bedrooms and one bath and 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 dinning area.

1102 W Chester Ave, 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 ⋅ 26028237 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

$175,000

TWO HOMES FOR THE PRICE OF ONE!!! live in the recently remodeled 2 bed /1 bath homes while you renovate the other home on this parcel that has already been gutted for the new owner to start working on it! This is a great opportunity for real estate investors or those looking to get into rental properties! LMU (Main Campus) being just 15 minutes brings a huge demand for rental properties just like this! Less than 5 minutes to a hospital and downtown Middlesboro, also minutes away from National & State Parks! Don't miss out on this opportunity! Schedule your showing today!

2 Beds ⋅ 1 Baths ⋅ 26026368 MLS

TWO HOMES FOR THE PRICE OF ONE!!! live in the recently remodeled 2 bed /1 bath homes while you renovate the other home on this parcel that has already been gutted for the new owner to start working on it! This is a great opportunity for real estate investors or those looking to get into rental properties! LMU (Main Campus) being just 15 minutes brings a huge demand for rental properties just like this! Less than 5 minutes to a hospital and downtown Middlesboro, also minutes away from National & State Parks! Don't miss out on this opportunity! Schedule your showing today!

1801 & 1801 1/2 Exeter Ave, Middlesboro

$160,000

Welcome to 8 Castleford Way located in the beautiful subdivision Ambleside. This home is also conveniently located near National & state parks. This home includes a screened back porch and fenced backyard. Master Bed / Bath on main level of the home including the living room, kitchen, and laundry! Call or text today to schedule your showing!

3 Beds ⋅ 2 Baths ⋅ 26025315 MLS

Welcome to 8 Castleford Way located in the beautiful subdivision Ambleside. This home is also conveniently located near National & state parks. This home includes a screened back porch and fenced backyard. Master Bed / Bath on main level of the home including the living room, kitchen, and laundry! Call or text today to schedule your showing!

8 Castleford Way, Middlesboro

$139,000

Rare find! 5.33 ac of undeveloped land in Middlesboro! Land is zoned R-1 and is mostly level with a drop to the creek behind. Portion near the creek is in the flood plain. Several buildable sites above the flood plain. Easy access to Cumberland Ave but very private. Survey with flood plain distinction available on request.

26025959 MLS

Rare find! 5.33 ac of undeveloped land in Middlesboro! Land is zoned R-1 and is mostly level with a drop to the creek behind. Portion near the creek is in the flood plain. Several buildable sites above the flood plain. Easy access to Cumberland Ave but very private. Survey with flood plain distinction available on request.

312 Blakely Ln, Middlesboro

$135,000

CHARMING 2 BEDROOM/ONE BATH HOME! This charming 2 bedroom, 1 bath home offers a perfect blend of comfort and convenience, completely outside of the flood zone. Enjoy leisurely mornings on the large covered front porch or entertain guest on the back deck overlooking your private fully fenced in yard - perfect for pets or gardening. This move in ready property also features a detached 2 -car carport, providing ample shaded parking and storage. Don't miss this gem, conveniently located close to all the local amenities. Plus only a 10 minutes drive to LMU main campus.

2 Beds ⋅ 1 Baths ⋅ 26010030 MLS

CHARMING 2 BEDROOM/ONE BATH HOME! This charming 2 bedroom, 1 bath home offers a perfect blend of comfort and convenience, completely outside of the flood zone. Enjoy leisurely mornings on the large covered front porch or entertain guest on the back deck overlooking your private fully fenced in yard - perfect for pets or gardening. This move in ready property also features a detached 2 -car carport, providing ample shaded parking and storage. Don't miss this gem, conveniently located close to all the local amenities. Plus only a 10 minutes drive to LMU main campus.

2002 Winchester Ave, Middlesboro

$120,000

Investment Opportunity - Fire-Damaged Home at 215 S. 21st Street, Middlesboro, KY Investor Special! This property at 215 S. 21st Street, Middlesboro, KY has sustained significant fire damage and is being offered as-is. This is an excellent opportunity for experienced investors, contractors, or buyers looking for a major renovation or potential rebuild project. Situated in an established neighborhood, the property offers convenient access to schools, shopping, restaurants, and other local amenities. Property Highlights: * Heavily damaged by fire * Sold as-is * Ideal for investors, contractors, or rehab specialists * Potential renovation or redevelopment opportunity * Convenient Middlesboro location Buyers are encouraged to conduct their own inspections and due diligence to determine the best use of the property. If you're looking for your next project, this could be the opportunity you've been waiting for.

5 Beds ⋅ 4 Baths ⋅ 26011288 MLS

Investment Opportunity - Fire-Damaged Home at 215 S. 21st Street, Middlesboro, KY Investor Special! This property at 215 S. 21st Street, Middlesboro, KY has sustained significant fire damage and is being offered as-is. This is an excellent opportunity for experienced investors, contractors, or buyers looking for a major renovation or potential rebuild project. Situated in an established neighborhood, the property offers convenient access to schools, shopping, restaurants, and other local amenities. Property Highlights: * Heavily damaged by fire * Sold as-is * Ideal for investors, contractors, or rehab specialists * Potential renovation or redevelopment opportunity * Convenient Middlesboro location Buyers are encouraged to conduct their own inspections and due diligence to determine the best use of the property. If you're looking for your next project, this could be the opportunity you've been waiting for.

215 S 21st St, Middlesboro

$105,900

3 Beds ⋅ 2 Baths ⋅ 26025309 MLS

412 N 24th St, 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 ⋅ 26000834 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

$79,900

Ranch-style home built in 1950 offering over 1,200 square feet with 2 bedrooms and 2 full bathrooms. Features include a covered patio, a fireplace in the living room, and additional space suitable for a den or workspace. The home sits on an approximate 0.38-acre lot.

2 Beds ⋅ 2 Baths ⋅ 26001413 MLS

Ranch-style home built in 1950 offering over 1,200 square feet with 2 bedrooms and 2 full bathrooms. Features include a covered patio, a fireplace in the living room, and additional space suitable for a den or workspace. The home sits on an approximate 0.38-acre lot.

816 W Chester Ave, Middlesboro

$50,000

Lot on Edgewood road, can be purchased with 205 N 20th Street Middlesboro KY; former duplex was removed and now vacant land. City utilities available.

26006363 MLS

Lot on Edgewood road, can be purchased with 205 N 20th Street Middlesboro KY; former duplex was removed and now vacant land. City utilities available.

0000 Edgewood Rd, Middlesboro

$29,000

PRIME LOCATION, NO FLOOD ZONE! Discover the ultimate blank canvas within the city limits. This fully cleared, level, and build ready lot offers an exceptional opportunity to build your dream home, or next investment project. Situated entirely outside the FEMA flood zone, this lot offers peace of mind and reduced insurance costs. All city utilities are ready for connection. This lot would always be suitable for a double-wide manufactured home. Don't miss this opportunity to build in a premier location.

26009102 MLS

PRIME LOCATION, NO FLOOD ZONE! Discover the ultimate blank canvas within the city limits. This fully cleared, level, and build ready lot offers an exceptional opportunity to build your dream home, or next investment project. Situated entirely outside the FEMA flood zone, this lot offers peace of mind and reduced insurance costs. All city utilities are ready for connection. This lot would always be suitable for a double-wide manufactured home. Don't miss this opportunity to build in a premier location.

2107 Winchester Ave, Middlesboro

$22,500

Lot available within the city limits of Middlesboro KY; The Bell County Ky online PVA site shows approximately 0.355 of an acre more or less. City utilities are available. There was a home on the property but was demoed April 2025. Buyer to verify all pertinent information; sold as is where is.

25008692 MLS

Lot available within the city limits of Middlesboro KY; The Bell County Ky online PVA site shows approximately 0.355 of an acre more or less. City utilities are available. There was a home on the property but was demoed April 2025. Buyer to verify all pertinent information; sold as is where is.

526 Balmoral Rd, Middlesboro

$21,000

50x150 lot; used to have a home on premises but that has been removed. City utilities available, buyer to verify all aspects of the property.

26009366 MLS

50x150 lot; used to have a home on premises but that has been removed. City utilities available, buyer to verify all aspects of the property.

109 Bloomsbury Ave, Middlesboro

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