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$455,000
5 Beds 4 Baths 26020660 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

Listing courtesy of Kevin Carroll of Backwoods Realty & Development.

$279,000
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

Listing courtesy of Kevin Carroll of Backwoods Realty & Development.

$1,599,000
3 Beds 2 Baths 26020546 MLS
More than 200 Acres of Private Hunting & Fishing Paradise Discover true Appalachian seclusion on this expansive Bell County tract. Approximately 200+ acres of timbered land offers outstanding habitat for deer, turkey, and other game, with several established tree stands already in place so you can hunt productively from day one. Ridges, natural funnels, and mature cover create ideal stand locations and year-round recreational potential. Fishing opportunities are abundant both on the property and nearby. The property includes two large ponds stocked and loaded with fish. The home includes free gas service, a rare and valuable benefit. In addition, the owner receives a monthly royalty check, providing ongoing income from mineral interests. Conveniently located near Pineville yet private and unrestricted, this property is perfect as a hunting camp, family recreational retreat, timber investment, or secluded full-time residence with income potential.

4213 State Highway 1344, Calvin

Listing courtesy of Jonathan Evans of Action Realty.

$299,000
4 Beds 2 Baths 1350232 MLS
Nestled in the heart of downtown Middlesboro, this beautifully maintained 1930 home offers over 2,000 square feet of comfortable living space with 4 bedrooms and 2 full baths. The updated kitchen is designed for both style and functionality, featuring custom soft-close cabinetry, under-cabinet lighting, a double oven, and a French-door refrigerator with double freezer drawers. This kitchen also has a fill-pot feature next to the stove. The kitchen's backdown is where you will , find a covered deck--perfect for entertaining family and friends. Situated on a quiet dead-end street, this property combines the convenience of downtown living with the privacy and tranquility you've been looking for. The home offers a flexible floor plan with two bedrooms on the main level with cedar lined closets and two bedrooms upstairs. The foyer entryway offers a closet and space for coats and shoes to conveniently stored. A spacious living room with a fireplace creates a warm gathering space, while the formal dining room and vented sunroom provide additional areas for relaxation and entertaining. The basement includes a two-car garage, workshop, and ample storage space, offering plenty of room for hobbies and organization. Schedule an appointment TODAY!

400 Gloucester Ave, Middlesboro

Listing courtesy of Sheila Durham of Coldwell Banker Bisceglia Real.

$299,000
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

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

$60,000
26020294 MLS
Seller states there are 1.9 surveyed acres just outside the Sharps Woods Road Subdivision which is located off highway 190, Pineville KY. The property is accessed by Sharps Woods road but isnt restricted by the subdivision covenants since the land isnt part of the development. Pineville city water is available, area is serviced by KY Utilities and Spectrum internet or Starlink. 5 minutes to US25 and Wasioto Winds Golf course, Pine Mountain State Park, 8 minutes to the town of Pineville for shopping etc makes this property a great location to build your new home or install a manufactured home. The lot is mostly wooded and gently rolling. If you choose, remove a few trees and enjoy gorgeous views of the area. Bring your imagination and design your dream home and have the property you're wanting.

99999 Sharps Woods Rd, Pineville

Listing courtesy of Megan Stanaford of Black Diamond Realty.

$255,000
3 Beds 3 Baths 26019632 MLS
I found your new Home in Woodland Hills Subdivision, just outside Pineville KY. 3 spacious bedrooms, multiple living areas, deep walk-in closets, paved driveway and a 2-car garage to satisfy all your boxes you need to check off with your home search. This is the very last house at the end of the lane. Plenty of vacant yard space. ***Seller will give the buyer option to purchase an additional half-acre lot adjoining the property. This house is well-maintained through the years and offers the new home-owner an opportunity to update the interior to truly make this home theirs. Right at 3,000 sq feet of living space and a 900sqft garage. Will sell with or without adjoining lot, all offers considered. Will qualify for most if not all loan products. Call for your showing today

Pineville

Listing courtesy of Jarrod Nunnelley of New Beginnings Real Estate LLC.

$699,000
3 Beds 2 Baths 1349199 MLS
Hidden in the mountains of Kentucky is this gorgeous brick ranch style home that is totally secluded. It has 3 bedrooms (including primary suite), 2 full bathrooms, living room with cathedral ceiling adding to the beauty of this home, large kitchen with island and breakfast bar, all appliances stay with home (dishwasher needs repair) the kitchen extends to breakfast area and the formal dining room, large laundry room, primary suite has walk-in closet, plus the bathroom has walk in shower and jacuzzi tub, home has a 2 car attached garage, central heat and air installed new in 2022, city water, private septic system, internet available, double pane windows. Beautiful mountain views. This home sits on 26.8 acres with a pond and creek (ideal for horses or cattle). There are beautiful fields that homes could be placed on or fence fields for farm animals. This property is level, some rolling and some steep. Lots of wildlife on this property. The driveway is paved with concrete sidewalk at home, large concrete patio and concrete front porch. This is a must see!

412 Page School Rd, Pineville

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

$140,000
2 Beds 1 Baths 26019100 MLS
Motivated Seller! Bring Offers! Charming cornerlot home in the heart of Pineville offering comfort, convenience, and potential. This inviting property features a spacious living room with abundant natural light—perfect for relaxing or entertaining. Ideal for firsttime homebuyers or anyone looking to downsize, the home sits on a generous lot with two adjoining parcels available for purchase together or separately, providing room to expand or invest. There are no restrictions, allowing flexibility for future use. A second structure next door offers additional possibilities—it can serve as storage, be remodeled into a rental, or removed to open up more space. Located close to the hospital, shopping, and local amenities, this property is connected to public sewer and serviced by KU electric. Enjoy smalltown charm with big potential in this versatile Pineville home.

306 3rd St, Pineville

Listing courtesy of Josh Trosper of New Beginnings Real Estate LLC.

$315,000
4 Beds 2 Baths 26019014 MLS
Large property with finished basement, 4-bedroom 2-bath house has been remodeled from the inside to the out. With a new metal roof (2025) New Front porch (2025) New Gutters (2025) New vinyl fence around this beautiful inground salt water pool (2026) Kitchen has been remodeled (2025) and all the inside has been painted (2025) Setting on a little over 2 acres this property has been surveyed and a new chain link fence installed around the whole property. This is a move-in ready home as most all furniture conveys with the property. Within 5 miles to the New Boone's Ridge Wildlife Park. Weather your looking for some good riding or just a little country get away this property has it all. Conveniently located in between Pineville and Harlan this property makes getting to town a breeze. Call now because this won't last long.

144 Mathel Hill Rd, Pineville

Listing courtesy of Beth Combs of Backwoods Realty & Development.

$490,000
26012929 MLS
This convenient store and gas station is on a busy highway between Harlan and Pineville, Kentucky and a short distance to the soon coming Boone's Ridge Wildlife plus is close to ATV trails. This convenient store/gas station comes as a turn key business with the inventory and equipment. The store building is set up with a deli to include the grill and hood with fire suppression system and the capability to expand the deli. This building was built in 2018 and has a 10,000 gallon gas tank and diesel can easily be added. In addition to the restroom, there is an office and storage room. Heat pump is approximately 8 years old, public water, private septic system on property, lots of parking space. Plus This is an amazing opportunity to own your own businesses! Located on Hwy 119 between Harlan and Pineville, KY.

8249 Us-119, Calvin

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

$110,000
3 Beds 2 Baths 26014433 MLS
Hey Neighbors! If you've been looking for a solid property with room to build some serious sweat equity, you'll want to take a look at this one. Sitting on a spacious corner lot inside the Middlesboro city limits, this 1.5-story brick veneer home offers a massive 1,963 square feet of living space and sits on over half an acre 0.539 acres per (Bell County PVA). With a potential of 4 bedrooms, 2 baths, hardwood floors, and a sturdy metal roof, the foundational pieces are right here waiting for your vision. The home is being sold AS-IS, making it the perfect blank canvas for a dedicated house flipper, an investor looking to grow their rental portfolio, or a handy homeowner wanting to customize their dream space from top to bottom. Several of the rooms are currently unfinished and need to be updated, giving you the unique opportunity to choose your own finishes, layouts, and style without paying for someone else's recent choices. Sit back and sip some sweet tea on the welcoming front porch and plan some landscaping around the spacious yard. Opportunities at this price point with this much square footage don't come around every day in our neck of the woods. So bring your toolbelt, your imagination, and let's go take a peek at this properties potential!

901 Exeter Ave, Middlesboro

Listing courtesy of Russell Tribell of Fathom Realty KY LLC.

$132,000
26010965 MLS
This property is located in Kettle Island Ky; MLS doesn't recognize the address due to not having a physical 911 address because its vacant land only. Mapping comes from the Bell county ky PVA office and the OnX hunting app. Total acreage being sold is listed as 88 acres, per the PVA records. The parcels do not connect; one parcel has 48 acres and the other has 40 for the combined 88 acres. . This property is approximately 15 minutes from the county seat of Pineville in Bell County KY; Home of the KY mountain laurel festival, nearby you'll find Boone's Ridge which is being developed as a wildlife sanctuary for Elk, deer, bear etc. Kettle Island Ky is a beautiful community with hospitable folks. Come check out all the area has to offer. The land would make a great hunting property, homestead and more.

000 Mill Creek Rd, Pineville

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.