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$449,900
3 Beds ⋅ 2 Baths ⋅ 26019393 MLS
Escape to the beauty of Lake Cumberland with this charming 3 bedroom, 2 bath home with spacious 2 car basement garage situated on 2.439 acres in the Cumberland Ridge area. Whether you're searching for a full time residence, a relaxing vacation getaway, or a potential Airbnb investment, this property offers endless possibilities and can comfortably accommodate 8-10 guests. Enjoy beautiful views of Lake Cumberland and Conley Bottom Marina from the large bay window in the living room or while relaxing on the front porch. Recent updates include new LVP flooring, new windows in 2022, new gutters in 2025, new garage doors/side doors/front door/storm door in 2023, and a new partial wood privacy fence in 2026. The oversized basement garage offers plenty of space for vehicles, storage, a home gym, or an entertainment area. Located just minutes from Conley Bottom Marina and nearby boat ramps, this home provides easy access to boating, fishing, and all the recreation Lake Cumberland has to offer!

2247 Ky-2393, Monticello
$999,000
26009297 MLS
Positioned on one of the busiest streets in the county, this +-6,720 sq ft medical office building delivers exceptional visibility and consistent traffic flow, directly across from Tractor Supply Company. Located just off Main Street, the property offers strong accessibility and a commanding commercial presence. The upper level is fully configured for medical use with 14 rooms, a reception area, spacious waiting room, break room, dedicated X-ray room, two half baths, and additional storage closets. The lower level adds flexibility with two full bathrooms and a large concrete vault room, well suited for secure storage, records, or specialized equipment. The building is supported by three HVAC units, single phase 400 amp electric service, city water, and sewer. A large blacktop parking lot provides space for 30 plus vehicles, offering convenience for both staff and clients. Recent improvements include a newer roof, gutters, and water heater, helping minimize upfront costs. Whether expanding a medical practice or establishing a wellness, mental health, therapy center, or insurance agency, this property offers the layout, location, and infrastructure to perform.

1104 N Main St, Monticello
$329,000
4 Beds ⋅ 3 Baths ⋅ 26006388 MLS
Welcome to your perfect getaway or full-time retreat in the highly desirable Golden Pond Resort area! This beautifully updated 4 bedroom, 3 full bathroom home offers the ideal blend of comfort, functionality, and proven income potential. Step inside to a spacious, open-concept layout featuring a warm and inviting living room with hardwood flooring and seamless flow into the kitchen and dining area—perfect for entertaining or hosting guests. The kitchen is well-appointed with abundant cabinetry, generous countertop space, and comes fully equipped with all appliances. Just off the main living space, you'll find comfortable bedrooms and updated bathrooms designed with both style and convenience in mind. This home is uniquely suited for large gatherings or short-term rental use, with the ability to comfortably sleep multiple guests. Currently operating on a successful rental program, this property presents an excellent opportunity for immediate income or continued investment. Outdoor living truly shines here with a large screened-in back deck, offering a private and relaxing setting to unwind. The hot tub conveys, creating the ultimate space to relax after a day on the lake. The home also includes a 2-car attached garage and ample parking space for guests. Located just minutes from multiple public boat ramps and less than 5 minutes to Conley Bottom Resort, this property is perfectly positioned for lake lovers and vacationers alike. Additional features include: • Kitchen appliances convey • Washer & dryer convey • Hot tub conveys • Triple bunk bed conveys • Updated flooring throughout • Proven short-term rental performance Whether you're searching for a primary residence, vacation home, or income-producing property near Lake Cumberland, this one checks all the boxes. Don't miss your chance to own a turnkey property in one of the area's most sought-after locations!

235 Golden Pond Rd, Monticello
$375,000
4 Beds ⋅ 3 Baths ⋅ 26005589 MLS
BACK ON THE MARKET!!!!Beautiful, lightly secluded 4-bedroom, 3-bath brick home offering space, versatility, and unique features for both comfort and functionality. This property includes a partially finished basement, along with a large unfinished room that can easily be completed to add even more living space. The spacious primary bedroom features a private sitting area and a walkout sliding door leading to the deck—perfect for enjoying peaceful mornings or relaxing evenings. The basement is equipped with a window A/C unit and baseboard heating, and also includes a flue cleanout, making it ready for a wood-burning stove or gas heating option. A standout feature of this home is the walk-in cooler—ideal for wild game enthusiasts, homesteaders, or anyone interested in processing and storing their own meat. Located less than one mile from a public boat launch, this property is perfect for outdoor lovers. Additional highlights include: •A walkout basement with a full kitchen, full bath with laundry room and 2 full size bedrooms. A detached 2-bay garage with 10-foot-high doors, underground electric, and a separate meter • An attached workshop or game room, perfect for hobbies or entertaining • An additional outbuilding that can serve as a workshop with side storage for boats, ATVs, mowers, or equipment This property offers a rare combination of privacy, practicality, and recreational convenience—making it a must-see! New flooring in basement living area.

815 Jr Phipps Rd, Monticello
$224,900
3 Beds ⋅ 2 Baths ⋅ 26008258 MLS
Welcome home to your 131 Golden Pond Road lake getaway, where you can't wait for the weekends to arrive! This is one of the most coveted Lake Cumberland resort communities in Wayne County. Step inside this lake area home that has been well taken care of, and has an open floor concept that offers the idyllic setting for hosting and entertaining guests. There is an expansive screened in back porch to enjoy the atmosphere that our beautiful Lake Cumberland has to offer. The main level offers a spacious Great Room, Eat-in Kitchen, 2 Bedrooms, 1 Full Bath, and a Laundry/Utility Room. The lower level features a Family Room, 1 Bedroom, 1 Full Bath, a Bonus Room, and an Attached Garage equipped with a 9x12 door suitable for housing your pontoon, boat & watercrafts, saving you a storage bill! There are community amenities available, for a fee, if you desire to utilize the tennis court, swimming pool, and common areas. Conley Bottom Resort & Marina is only 5 minutes away, offering close access for boating access. There are additional accessible boat ramps in the area that are available. Don't miss this opportunity to own your vacation getaway, permanent residence, or your possible VRBO Income Producing Property! Schedule your private tour today!

131 Golden Pond Rd, Monticello
$282,000
3 Beds ⋅ 3 Baths ⋅ 25503942 MLS
3 bedroom, 3 bath Home and boat slip! You won't find homes like this for sale often, Located on a scenic road with views of Lake Cumberland, this property offers a relaxing setting for daily living and entertaining. The large master suite is on the main floor, and wrap-around decks provide lake views from multiple rooms including the Master Bedroom, living room and Kitchen. With approximately 3,400 square feet of finished space and living rooms upstairs and downstairs, there's plenty of room for gatherings or extended family. This home has an attached 2 car garage for parking and storage, including a storm shelter on the bottom level for extra storage and safety. Additionally, a boat slip at a recently renovated private community dock is available with no waitlist, offering immediate access. The property borders the Army Corps of Engineers land, allowing for lake views from multiple rooms and decks. Located just minutes from Conley Bottom and Beaver Creek Marina by boat, this home is ideal for lake enthusiasts.

607 Old Lck 21st Rd, Monticello
$319,900
5 Beds ⋅ 3 Baths ⋅ 26011322 MLS
MOTIVATED SELLER! This home is just minutes from Conley Bottom and Burnside Marina! It would make the perfect vacation home or VRBO or Air B&B Rental! WIth both the attached and detached garages there is plenty of room for your boat and lake toys as well as your cars! Welcome to 2371 Highway 1568, where breathtaking views of rolling farmland, mountains, and mature trees create the perfect private country retreat. This well-built home offers 2,683 square feet of comfortable living space with 5 spacious bedrooms and 3 full bathrooms, providing room for everyone to spread out and enjoy. The main level features a welcoming living room, kitchen, dining room, 3 bedrooms, and 2 full baths. Downstairs, the partially finished basement includes 2 additional bedrooms, a large family room, utility room, and garage space, offering flexibility for guests, extended family, or additional entertaining areas. You'll appreciate the abundance of storage throughout the home, along with recent updates including new luxury vinyl flooring and new carpet. Enjoy the peaceful surroundings from the two back porches — one enclosed for year-round enjoyment and one open-air porch perfect for relaxing and taking in the beautiful scenery. Situated on 3.11 Non- Restricted acres, this property offers both privacy and opportunity. The mature timber has never been logged, creating potential future income possibilities. In addition to the attached garage, there is an impressive detached 1,376-square-foot garage providing excellent space for vehicles, equipment, hobbies, or workshop use. Additional features include a Silent Guard security system that is owned and can convey with the property. If you are looking for a spacious home with scenic views, quiet surroundings, and endless possibilities, this beautiful country property is a must-see.

2371 State Highway 1568, Monticello
$394,000
4 Beds ⋅ 3 Baths ⋅ 26002403 MLS
Welcome home to this beautiful, well-maintained 3,416 sq ft bi-level home sitting on a spacious 1.2- acre corner lot with room to breathe and features that are hard to find! This property offers 4 bedrooms, 3 full bathrooms, two full kitchens, and a layout that is perfect for multi-generational living, entertaining, or hosting guest. The main level features a bright and open floor plan with a large living room, spacious dining area, and a warm, inviting kitchen. you'll love the mix of gorgeous hardwood flooring, new carpet, and tile, along with the comfort of a wood-burning fireplace. The main level includes 3 bedrooms and 2 full baths, including updated handicap-accessible walk-in tub with a door for added convenience. Downstairs, the fully finished walk-out basement is like a second home, complete with a second kitchen, full bathroom, laundry room, 1 bedroom, and a very large living room with a second fireplace. This level is ideal for a in-law suite, guest space, or extra entertaining area. This home also features a built-in central vacuum system with vacuum hookups conveniently located throughout the house, making cleaning easier and more efficient. Step outside and enjoy the back deck, a yard with fruit trees, and an outbuilding for storage, hobbies, or a workshop. Both driveways are blacktop, and the attached 2-car garage adds even more functionality. Recent updates include a new roof and update screened gutters, giving buyers peace of mind. This one truly has it all, space, update, charm, and versatility. A MUST-SEE PROPERTY!!

35 Guinn Dr, Monticello
$489,000
6 Beds ⋅ 5 Baths ⋅ 26007152 MLS
Welcome to this impressive in-town property on Sunset Blvd offering nearly 4,000± sq ft of well-designed living space on a level 0.97± acre lot—an increasingly rare combination of space, functionality, and convenience in today's market. From the moment you step inside, the home sets itself apart with a grand entry and soaring ceilings that create an open, upscale feel throughout the main living area. Designed for both everyday living and entertaining, the layout flows seamlessly between the living room, formal dining area, and spacious kitchen featuring ample cabinetry, a breakfast bar, and dedicated dining space. The main-level primary suite offers both comfort and convenience, highlighted by a fully remodeled bathroom (2024) that delivers a clean, modern finish. Recent updates throughout the home include fresh interior paint (2022), plantation shutters in the living room, updated fixtures, three updated toilets, a new dishwasher (2025), and a new hot water heater (2026). Upstairs provides additional bedrooms, bathrooms, and flexible living space, while the fully finished walk-out basement significantly expands the home's functionality with a second living area, kitchenette, bedroom, bathroom, bonus room, and storm shelter—ideal for guests, extended family, or multi-generational living. Additional features include a 3-car garage, generous storage throughout, and multiple indoor and outdoor living spaces. Enjoy both an elevated deck and lower-level patio overlooking the spacious yard—perfect for relaxing or entertaining. Homes offering this level of space, layout, and recent updates—especially in a convenient in-town location—are rarely available. Schedule your private showing today.

575 Sunset Blvd, Monticello