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112 Woodland Trail Rd, Pineville
$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.

107 E Mound St, Harlan
$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.

515 Englewood Rd, Middlesboro
$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.

400 Gloucester Ave, Middlesboro
$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.

400 Gloucester Ave, Middlesboro
$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.

113 Wildwood Trl, Pineville
$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.

522 W Virginia, Pineville
$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.

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.

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.

9529 Hwy 92, Pineville
$97,500
3 Beds ⋅ 3 Baths ⋅ 26010902 MLS
All offers must be submitted by the Buyer's agent via the RES.NET Agent Portal. If your offer is accepted, you agree to be responsible for an offer submission technology fee of $225.00. The fee will be collected and disbursed by the settlement agent and disbursed at the closing and settlement of the transaction. To submit your buyer's offer, simply click the link below. If you already have a RES.NET Agent account, you will be prompted to log in. If not, you will be prompted to create an account. To begin, click or paste this link into your web browser: https://agent.res.net/Offers.aspx?-1807017 Escape to serenity with this 1,820 sq ft mountain retreat, perfectly nestled on 2± acres of lush, tranquil land in Southeast Kentucky. This 3-bedroom, 3-bath home offers the perfect blend of modern comfort and rustic charm, designed for peaceful living. A dedicated, functional laundry room adds to the convenience of daily living. The private primary suite acts as a true oasis, featuring a luxurious soaking tub for ultimate relaxation. Situated on 2 expansive acres, this property offers unparalleled privacy and mature trees, creating a peaceful backdrop for your morning coffee or evening sunsets. A standout feature is the large detached garage—providing ample space for vehicles, workshop, or storage.

9529 Hwy 92, Pineville

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

207 Arthur Hts, Middlesboro
$264,900
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

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

623 N 20th St, Middlesboro
$229,500
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

Listing courtesy of Derek Eisenberg of Continental Real Estate Group.

156 Wellington Dr, Middlesboro
$230,000
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

Listing courtesy of Megan Stanaford of Black Diamond Realty.

204 Greencamp Rd, Arjay
$65,000
2 Beds ⋅ 1 Baths ⋅ 26009843 MLS
Nestled in the hills of Arjay, Kentucky, this one-of-a-kind property offers the chance to own a true piece of Appalachian history. Originally built as a coal camp house, the home still holds its original structure at the core, with additions added over the years to create additional living space while maintaining its historic character. Homes like this carry a story you simply can't recreate, making it a unique opportunity for the right buyer. Surrounded by beautiful mountain views, the property offers a peaceful setting in a small, established neighborhood. Whether you're enjoying the scenery or looking for a quiet place to call home, this location provides that tucked-away Eastern Kentucky feel. This home is a fixer-upper and will need some TLC, but it is currently livable making it a great option for someone looking to renovate over time, invest, or restore a piece of local history. With a little vision and effort, this property has the potential to truly shine. Buyer to verify all aspects of the property.

204 Greencamp Rd, Arjay

Listing courtesy of Sydney Privett of Sester & Co 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.