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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.

$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.

$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.

$80,000
6 Beds 4 Baths 26007707 MLS
Excellent income-producing opportunity! This property features two 3-bedroom, 2-bath mobile homes on one lot, previously used as rental properties and ideal for investors or owner-occupants seeking additional income. Homes offer approximately 924 sq ft and 1,140 sq ft and feature total electric utilities, central heat & air, and front and rear porches. Conveniently located just 10 minutes from Pineville and Hwy 25E, providing easy access to shopping, dining, and employment while maintaining a quiet country setting. A versatile property with strong rental or multi-family living potential. The stated acreage has been estimated by the (Local Property Valuation Administrator / boundary deed description / Agriculture Soil Conservation Service). The estimate is not the result of a survey and cannot be relied upon for accuracy. The property is selling by its boundary deed description.

6461 Ky-66, Arjay

Listing courtesy of Jason Rains of WEICHERT REALTORS - Ford Brothers.

$140,000
2 Beds 1 Baths 26014101 MLS
Charming 2-bedroom, 1-bath home located just minutes from Downtown Pineville! Offering approximately 1,100 square feet of comfortable living space, this home features a functional floor plan, spacious rooms, and plenty of natural light throughout. A full unfinished basement provides excellent storage space and endless potential for a workshop, hobby area, or future expansion. Step outside and enjoy the brand-new back deck, perfect for relaxing, grilling, or entertaining family and friends. There is also a newly added large outdoor shed which has full sized rolling doors to allow storage of mowers, tools and outdoor equipment. Conveniently situated near local shopping, dining, schools, and everyday amenities, this property combines comfort, value, and location. Whether you're a first-time homebuyer, looking to downsize, or seeking an investment opportunity, this well-maintained home is one you won't want to miss. Schedule your private showing today and discover all that this Downtown Pineville gem has to offer!

522 W Virginia, Pineville

Listing courtesy of Kortlyn A Barrineau of KY Real Estate Professionals, LLC.

$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.

$209,900
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.

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.