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$855,000
2 Beds 2 Baths 26007225 MLS
Prime Multifamily Investment Opportunity Presenting a well-established commercial apartment building in the heart of Middlesboro, Kentucky. Built in 1990, this single-story property offers approximately 15,225 square feet of space ideally suited for residential rental units, providing stable cash flow in a convenient location. Strategically positioned on N 19th Street, the building benefits from easy access to local amenities, employment centers, and essential services in Bell County. Solid 1990 construction with a functional single-story design for easy maintenance and accessibility. This property represents an excellent value-add or turnkey investment for investors seeking entry into Kentucky's multifamily sector. Whether you're looking to maintain current operations or implement updates for higher rents, 725 N 19th Street delivers a solid foundation in a community with long-term housing needs.

725 N 19th St, Middlesboro

Listing courtesy of Beth Combs of Turn Key Realty.

$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.

$960,000
2 Beds 2 Baths 26007224 MLS
Prime Multi-Family Investment Opportunity - 508 & 512 Winchester Avenue, Middlesboro, KY This exceptional offering presents two adjacent multi-family apartment buildings totaling 13,392 square feet of living area on a combined 1.23 acres of land. Located at 508 Winchester Ave (6,696 sq ft on 0.55 acres) and 512 Winchester Ave (6,696 sq ft on 0.68 acres), these properties provide a rare chance to acquire substantial rental inventory in one convenient location. Built for efficiency and scale, each building offers significant square footage ideal for multiple residential units, making them well-suited for investors seeking strong cash flow potential in the Middlesboro market. The generous lot sizes allow for ample parking, green space, or future expansion opportunities. Situated along Winchester Avenue, the properties benefit from convenient access to local amenities, major thoroughfares, and the broader Middlesboro community. Whether you're an experienced multifamily investor or looking to expand your portfolio, this paired offering represents a solid foundation for long-term rental income and value appreciation.

508 & 512 Winchester Ave, Middlesboro

Listing courtesy of Beth Combs of Turn Key Realty.

$329,000
26011925 MLS
235.967 SURVEYED ACRES Discover ultimate freedom and natural beauty on this property which is next to the Kentucky Government Land Wildlife Management area with 30,661 acres. A rare, unrestricted gem offering endless possibilities, this prime property is a haven for outdoor enthusiasts and those seeking a private multi-use sanctuary. Only 22 miles from Royal Blue Unit of the North Cumberland Wildlife Management Area. The land Features rich vibrant foliage, mature vegetation, and a tranquil flowing creek that provides a steady water source for abundant local wildlife. With a well-established network of internal roads already in place , you can easily navigate and access the entire acreage. This property also has approximately 2,500 feet of road access and city water is available at the road. Whether you are looking for a world-class hunting retreat, a scenic homestead or a secluded site for recreational adventures, this unrestricted property gives you the space and freedom to bring your vision to life.

Hwy 3484, Pineville

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

$149,999
2 Beds 1 Baths 26015402 MLS
Charming Renovated Ranch in the Heart of Middlesboro! Welcome home to 1010 W Chester Avenue, a cozy and beautifully updated 2-bedroom, 1-bath brick ranch right in the heart of Middlesboro, KY. If you've been looking for that perfect blend of classic hometown charm and worry-free modern living, this is the one you've been waiting for. Step inside this solid traditional brick home and you'll immediately notice the inviting vibe. The entire house has been refreshed with updated paint throughout, creating a bright and airy atmosphere that lets the natural light pour in. Underfoot, you'll love the beautifully restored original hardwood floors paired with updated flooring that ties the whole home together perfectly. The heart of the home features a spacious eat-in kitchen complete with updated cabinets and a brand-new refrigerator added in 2024. For ultimate convenience, a brand-new dedicated laundry room has been added right off the kitchen. Around the corner, the living room serves up the ultimate cozy Appalachian factor with its classic brick, wood-burning fireplace—perfect for those crisp mountain evenings. Key Updates & Features: Brand New Roof (2024): Complete with durable 25-year shingles for total peace of mind. Modernized Kitchen & Bath: Features updated cabinetry, flooring, and a 2024 refrigerator. Convenient Layout: 1,275 sq. ft. of comfortable, main-level living space with an added laundry room and a convenient 1-car attached carport. Level Lot: A nice 50x140 level yard that's easy to maintain and perfect for relaxing. Tucked away on a great level lot near the West End, this property puts you just minutes from local schools, shopping, and all the dining downtown Middlesboro has to offer. Whether you're buying your very first home, downsizing, or looking for a solid investment in Bell County, this move-in-ready gem is ready for its next chapter. Don't wait on this one—call today to schedule your personal tour and let's go take a look!

1010 W Chester, Middlesboro

Listing courtesy of Russell Tribell of Fathom Realty KY LLC.

$264,900
3 Beds 2 Baths 26007901 MLS
This charming property offers the perfect blend of cozy indoor living and expansive outdoor space. Nestled in the heart of Middlesboro this home is situated on 1.5 acres. This brick ranch home with a basement has 1344 square feet, and features 3 bedrooms and 2 baths on the main floor along with the washer and dryer. The home provides plenty of room for family and guests. The heart of the home is designed for comfort and gatherings highlighting the fireplace in the dining area to create a warm inviting atmosphere. This home has built in shelving and natural wood cabinets in the kitchen along with an island. The potential is endless with an additional 634 square feet of living finished living space in the basement with a fireplace. The basement has a finished bathroom and additional 624 square feet unfinished that can be used as a workshop or other workspace. Walk out of the basement onto a large patio area. There is a short walk to the fenced in area and barn that can house many animal options. This home is near all the amenities including groceries, entertainment, shopping and restaurants. This is a rare gem in the heart of Middlesboro. Call for an appointment today!

127 Alpine Rd, Middlesboro

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

$325,000
26012876 MLS
Location, Location, Location! Exceptional investment opportunity featuring a 12,210-square-foot commercial building in the Downtown Business District. A long-established restaurant tenant is already in place, occupying 4,070 square feet and providing immediate income potential. The remaining 8,140 square feet of open space offers outstanding flexibility for additional tenants, retail, office, or mixed-use development. The property boasts 141 feet of road frontage, excellent visibility, and ample on-site parking for customers and employees. With a proven tenant, significant leasable space available, and a prime downtown location, this property is well-positioned for both current cash flow and future growth.

1803 W Cumberland Ave, Middlesboro

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

$124,900
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.

$279,000
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.

$229,900
3 Beds 2 Baths 26003725 MLS
This stunning home with a thoughtfull design offers the perfect blend of comfort, charm, and mountain beauty. The kitchen is a dream for any home chef, featuring granite countertops, abundant counter space, and elegant white cabinetry with generous storage. Beautiful hardwood floors flow throughout the home, adding warmth and character. The private primary suite is truly exceptional, complete with a customized en-suite bath designed for relaxation. Enjoy peaceful mornings and cool mountain evenings on the inviting wraparound porch. The home also offers a formal living room, a spacious family room, and a large laundry area for added convenience. Upstairs, you'll find a generously sized bedroom with direct deck access, perfect for looking at those morning mountain views. Location, lifestyle, and endless outdoor adventure—this home has it all! Just minutes from local schools, and the post office, you'll enjoy small-town convenience with modern perks like high-speed internet and Pineville city water. Love the outdoors? You're only a short drive from the breathtaking trails and scenic overlooks of Pine Mountain State Resort Park, tee time at Wasioto Winds Golf Course, exciting ATV trails, and local shopping. Adventure, convenience, and mountain charm are all waiting right here! Schedule your showing today!!!

15379 State Highway 190, Pineville

Listing courtesy of Sarah Richards of RE/MAX Preferred Group.

$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.

$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.

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.