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116 Edgewood Rd, Middlesboro
$200,000
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

Listing courtesy of Megan Stanaford of Black Diamond Realty.

140 Wellington Drive, Middlesboro
$199,900
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

Listing courtesy of Janice Pratt of Fathom Realty TN LLC.

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

1102 W Chester Ave, Middlesboro

Listing courtesy of Kevin J Bisceglia of Coldwell Banker Bisceglia Real.

1102 W Chester Ave, Middlesboro
$199,000
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

Listing courtesy of David Gambrell of Coldwell Banker Bisceglia Realty & Auction Co.

114 E Rochester Ave, Middlesboro
$175,500
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

Listing courtesy of Melanie Mullins of Backwoods Realty & Development.

114 E Rochester Ave, Middlesboro
$175,500
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

Listing courtesy of Melanie Mullins of Backwoods Realty & Development.

1801 & 1801 1/2 Exeter Ave, Middlesboro
$175,000
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

Listing courtesy of Victoria Allen of Century 21 Virginia Wilder Real Estate.

8 Castleford Way, Middlesboro
$160,000
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

Listing courtesy of Victoria Allen of Century 21 Virginia Wilder Real Estate.

810 W Rochester Ave, Middlesboro
$145,900
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

Listing courtesy of Nichole Goins of Heartland Real Estate, LLC.

305 N 15th St, Middlesboro
$145,000
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

Listing courtesy of Mike Hensley of REMAX PROFESSIONAL'S.

312 Blakely Ln, Middlesboro
$139,000
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

Listing courtesy of Ann Robinson of Mountain Realty Group LLC.

2002 Winchester Ave, Middlesboro
$135,000
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

Listing courtesy of Sheila Durham of Coldwell Banker Bisceglia Realty & Auction Co.

125 Cawood Lane, Middlesboro
$135,000
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

Listing courtesy of Misti McGrath of Realty Group.

708 W Chester Ave, Middlesboro
$129,000
3 Beds ⋅ 1 Baths ⋅ 1354572 MLS
Great little 3 bedroom house in a wonderful neighborhood in historic Middlesboro, Ky. Very convenient to downtown and Lincoln Memorial university. Fenced in back yard and large eat in kitchen make this a good option for just about anyone. Would also make a great opportunity for someone wanting to purchase a rental property.

708 W Chester Ave, Middlesboro

Listing courtesy of Mike Hensley of REMAX PROFESSIONAL'S.

64 Dunlap Hollow Rd, Middlesboro
$125,000
4 Beds ⋅ 2 Baths ⋅ 1343957 MLS
This home is turnkey and ready to move right in; it has been well maintained over the years. This home has 4 Bedrooms, 2 Full Baths, Dining Room and a Kitchen that comes with Range, Refrigerator, Dishwasher and Microwave plus the laundry room has a washer and dryer set that will stay with home. Step out the back door and just a few steps up the hill is a wonderful workshop and a storage shed. Home has a country setting with a private drive in the front and a right of way to the property from the back. Public water and septic system, internet is available, great views and close to Wal-Mart, hospital, churches and much more!

64 Dunlap Hollow Rd, Middlesboro

Listing courtesy of Virginia Wilder of Century 21 Virginia Wilder Real Estate.

413 S 26th St, Middlesboro
$125,000
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

Listing courtesy of Brad Cawood of Backwoods Realty & Development.

2354 State Highway 441, Middlesboro
$120,000
2 Beds ⋅ 1 Baths ⋅ 26030686 MLS
Welcome to 2354 State Highway 441 or also known as the belt-line, this small home located right inside of city limits would make the perfect starter home, also great option for those looking to downsize! This home is 5 minutes from shopping, restaurants, schools, and a hospital! This home features a beautiful stone fireplace, beautiful hardwood floors, and a huge storage building! don't miss out on this deal call or text today to make it yours!

2354 State Highway 441, Middlesboro

Listing courtesy of Victoria Allen of Century 21 Virginia Wilder Real Estate.

215 S 21st St, Middlesboro
$120,000
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

Listing courtesy of Megan Stanaford of Black Diamond Realty.

412 N 24th St, Middlesboro
$105,900
3 Beds ⋅ 2 Baths ⋅ 26025309 MLS

412 N 24th St, Middlesboro

Listing courtesy of Dawn Risner of Turn Key Realty.

405 S 37th St, Middlesboro
$100,000
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

Listing courtesy of Kevin Bisceglia of Coldwell Banker Bisceglia Realty & Auction Co.

405 S 37th St, Middlesboro
$100,000
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

Listing courtesy of Kevin J Bisceglia of Coldwell Banker Bisceglia Real.

252 Chasteen Drive, Middlesboro
$97,000
3 Beds ⋅ 2 Baths ⋅ 1316842 MLS
Welcome to this versatile 3-bedroom, 2-bathroom home offering 1,296 sq. ft. of living space in a convenient Middlesboro location. With a new roof and a freshly painted exterior, this property is move-in ready and full of potential. Step inside to find a layout that offers both comfort and flexibility. The home features multiple kitchens and laundry areas, creating the unique opportunity to easily convert the property into two rental units or maintain it as a single-family residence with extra convenience. The outside is just as impressive, with a spacious fenced backyard, perfect for gatherings, pets, or a garden. You'll also appreciate ample off-street parking, seasonal mountain views, and plenty of storage space throughout. Located close to schools, shopping, and town amenities, this property combines practicality with investment potential. Whether you're looking for a family home or an income-producing opportunity, 252 Chasteen Drive is a must-see!

252 Chasteen Drive, Middlesboro

Listing courtesy of Aaron Rose of Realty Network, Inc.

706 Ilchester Ave, Middlesboro
$89,900
3 Beds ⋅ 2 Baths ⋅ 1353618 MLS
This brick ranch style home has 3 bedrooms, 2 bathrooms, living room has a fireplace which adds beauty but is inoperable. The kitchen is spacious with lots of kitchen cabinets, pantry and a nice spacious laundry room. This property is nice and level and includes a paved driveway, storage shed in back yard. Home has a heat pump, internet available, nice double pane windows, city water and city sewer, home is conveniently located, close to hospital, shopping and LMU in Harrogate.

706 Ilchester Ave, Middlesboro

Listing courtesy of Virginia Wilder of Century 21 Virginia Wilder Real Estate.

816 W Chester Ave, Middlesboro
$74,900
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

Listing courtesy of James Martin of Century 21 Pinnacle.

518 S 43rd St, Middlesboro
$51,000
2 Beds ⋅ 1 Baths ⋅ 1345724 MLS
Two bedroom, 1 bath home located in a great neighborhood. Large bedrooms, living room, and kitchen. Don't miss the opportunity to make this home your own.

518 S 43rd St, Middlesboro

Listing courtesy of Mike Hensley of REMAX PROFESSIONAL'S.

LOTS 12 & 13 Sams Mountain RD., Middlesboro
$30,000
1328410 MLS
LOCATION!! LOCATION!! Ready to build your dream home. Property is located minutes from Middlesboro. Wooded lot with electric and water available. Close to shopping, restaurants and hospitals. Minutes from LMU main campus. Buyer to verify acres!

LOTS 12 & 13 Sams Mountain RD., Middlesboro

Listing courtesy of Sharon K Teaney of Century 21 Virginia Wilder Real Estate.

2107 Winchester Ave, Middlesboro
$29,000
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

Listing courtesy of Sheila Durham of Coldwell Banker Bisceglia Realty & Auction Co.

Bowling Rd, Middlesboro
$25,000
1359116 MLS
0.9 Acres Partially cleared with wooded area in back for privacy. City limits. All utilities available. Perfect location for a home or two right next to the mountains!

Bowling Rd, Middlesboro

Listing courtesy of Misti McGrath of Realty Group.

526 Balmoral Rd, Middlesboro
$22,500
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

Listing courtesy of Megan Stanaford of Black Diamond Realty.

109 Bloomsbury Ave, Middlesboro
$21,000
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

Listing courtesy of Megan Stanaford of Black Diamond Realty.

Listings courtesy of Spartanburg Association of Realtors as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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