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$350,000
26022246 MLS
Investor Opportunity: Downtown Mixed-Use with Active STR Cash Flow + Clear Upside Exceptional value at $350,000 for this high-visibility mixed-use property at 110 W Kentucky Ave in the heart of Pineville's town square on HWY 25E. Approximately 5,943-6,250 SF total. The upper level operates as the established Boone Trace Inn short-term rental with 7 private bedrooms (coded entry), gathering room, fully equipped kitchen, dining area, and 2.5 baths—delivering current income while positioned to attract regional visitors and tourists. The lower level (~3,125 SF) offers flexible commercial space, partially configured as a vendor's mall and ideal for restaurant, retail, professional/medical office, pub, or multi-tenant uses. Prime downtown exposure and traffic create strong potential to grow both the STR performance and commercial income streams. Attractive basis well under $60/SF for an income-producing mixed-use asset with multiple paths to increased returns. Ideal for the investor seeking immediate cash flow plus value-add opportunity in a high-visibility location. Downtown town-square / HWY 25E location provides excellent visibility. Current STR baseline already exceeds typical Pineville market averages; the gap between current passive results and optimized performance is the primary value-add story. Strong candidate for investors focused on operational upside rather than pure turnkey yield.

110 W Kentucky Ave, Pineville

Listing courtesy of Tamara Hurst of SimpliHOM.

$439,000
4 Beds 3 Baths 26021440 MLS
Welcome to your next home—an exceptional 4-bedroom (bonus could be a 5th bedroom), 2.5-bath retreat offering the space, style, and everyday comfort today's buyers want most. Step inside and instantly feel the openness and quality throughout: beautiful hardwood floors, refined trim, and recessed lighting that brightens the main living areas with an airy, welcoming flow. The updated kitchen is made for hosting and everyday living, featuring custom cabinetry, a breakfast bar, a pantry, and stainless-steel appliances that bring both function and style to the heart of the home. Upstairs, you'll enjoy an open bonus room that's ideal for a home office, media space, play area, or guest-friendly flexibility. Outside, a spacious backyard and large deck create the perfect backdrop for summer barbecues, relaxing evenings, and gatherings—plus an enclosed yard that helps keep pets safely contained. And location matters here: you're positioned between Pineville and Middlesboro city limits while still feeling tucked away among the trees with beautiful mountain views. Enjoy nearby outdoor adventure at Pine Mountain State Resort Park and make it a lifestyle with golf just minutes away at Wasiota Winds Golf Course—this is the kind of home and location that buyers don't want to miss. Schedule your showing today and move quickly, because homes like this—updated, hosting-ready, and close to everything— this offers what most buyer's have on their bucket list of must have in their next home.

112 Woodland Trail Rd, Pineville

Listing courtesy of Donna Gregorich of CENTURY 21 Advantage Realty.

$180,000
1350764 MLS
This stately brick building sits in downtown Harlan, Kentucky and offer multiple possibilities. It once was a law office. The downstairs needs a little TLC. On the main floor there are 12 rooms plus 2 half bathrooms and a kitchenette, a front and back door. Upstairs, there are 2 large apartments. One the owner occupies, it has 2 bedrooms, one full bathroom, Livingroom, kitchen, laundry area and dining area. The other upstairs apartment has 2 bedrooms, one full bathroom, living room, dining area, laundry area and is vacant. With some TLC the second apartment would be ready to rent. The unfinished basement has a concrete floor. This building has city water and city sewer, high speed internet is available, a heat pump, nice windows, great visibility, walking distance to the courthouse. This is a golden opportunity!

107 E Mound St, Harlan

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

$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 Mountain Realty Group LLC.

$279,000
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.

$279,000
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.

$249,900
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

113 Wildwood Trl, 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.

$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.