Monticello Homes with Exterior Entry Basement

Monticello Homes with Exterior Entry Basement

Welcome to Monticello, Kentucky—a charming city nestled in the heart of Wayne County, where Southern hospitality meets stunning natural beauty. Known for its picturesque landscapes and friendly community, Monticello offers a serene escape from the hustle and bustle of urban life. With its rich history and vibrant local culture, this city is an ideal place to call home.

One of the standout features of Monticello is its diverse selection of homes, particularly those with exterior entry basements. These unique properties provide not only additional living space but also the convenience of easy access. Imagine having a cozy den, an entertainment room, or even a home office that you can access directly from the outside—perfect for guests or for enjoying those beautiful Kentucky summers without disturbing the rest of the household.

The homes in Monticello are surrounded by lush greenery and stunning views, making every day feel like a retreat. Whether you’re looking for a quaint cottage or a spacious family home, the real estate market here offers a variety of options to suit every lifestyle. Plus, with local amenities just a stone’s throw away, including parks, shops, and dining, you’ll find everything you need right at your fingertips.

Embrace the charm of Monticello, KY, and discover the perfect home with an exterior entry basement that complements your lifestyle. Experience the tranquility of small-town living while enjoying the modern conveniences that make life enjoyable. Welcome to your new beginning in Monticello!

Newest Monticello Homes with Exterior Entry Basement

3 Beds ⋅ 3 Baths ⋅ 26019876 MLS

Enjoy the perfect combination of privacy, comfort, and beautiful lake views in this custom-built 3,300+/- square foot home featuring 3 bedrooms and 3 bathrooms, situated on approximately 5 acres. This well-maintained property offers hardwood floors, two fireplaces, a bright sunroom, a spacious finished garage, and a recently replaced roof. The large back deck provides the perfect space for entertaining or relaxing while overlooking the scenic surroundings. Outside, you'll find two large greenhouses and plenty of room to enjoy the peaceful setting. Conveniently located just minutes from Conley Bottom Marina and several other public boat ramps, this exceptional property offers easy access to boating, fishing, and all the recreational opportunities of Lake Cumberland, making it an ideal full-time residence, vacation home, or investment opportunity. Call today to schedule a private showing!

202 Peaceful Cove Ln, Monticello

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

5 Beds ⋅ 3 Baths ⋅ 26010384 MLS

Welcome to the "Perfect Shade of Green" Home — a stunning custom-built log-style retreat featured in Log Homes Magazine. Completed in 2013 after years of thoughtful planning and craftsmanship, this extraordinary property sits on 3.43 acres in the desirable Hickory Point subdivision on beautiful Lake Cumberland. Positioned on a peninsula with breathtaking lake views, this spacious 5-bedroom, 3-bath home was designed for gathering, entertaining, and making lifelong family memories. From the moment you step through the front door, you'll be captivated by the soaring cathedral ceilings, floor-to-ceiling windows, and warm rustic charm throughout. The main level offers approximately 1,949 finished square feet and features two bedrooms, 2 full baths, and an impressive family room that opens onto a large deck with both open and covered entertaining spaces overlooking the lake. At the heart of the home is a chef's kitchen with a one-of-a-kind handcrafted wraparound bar offering abundant seating — perfect for hosting family and friends. The second floor adds approximately 830 finished square feet with three additional bedrooms and a full bath, providing plenty of space for guests and large families. One of the home's greatest opportunities is the 1,852-square-foot unfinished walkout basement, ready for a future owner to customize to their own style and needs. The basement opens to a spacious concrete patio and backyard area. This home also showcases unique custom wood finishes crafted from timber harvested directly from the property, adding authentic character you simply can't replicate. Built with efficiency and durability in mind, the home includes: 10-inch poured concrete basement walls 3-inch log veneers on both interior and exterior walls 6 inches of Styrofoam insulation between the veneers for excellent energy efficiency Located in an HOA-protected community in Wayne County, this property offers privacy, craftsmanship, and incredible potential. With a little TLC, this could become the ultimate lake home or family retreat. Property is being sold AS-IS. All inspections are welcome.

234 Cedar Point Ln, Monticello

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

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

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

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

3 Beds ⋅ 2 Baths ⋅ 26005928 MLS

Back on the market at no fault of the seller or property! Welcome to 875 Hwy 3106 in Monticello, KY—offering the perfect blend of country living, usable land, and modern updates. Situated on approximately 2.15 acres, this 3 bedroom, 2 bath home provides space, privacy, and versatility just minutes from town. Originally built in 1950 and thoughtfully updated, this home features a functional layout with over 1,400 square feet on the main level plus additional finished space in the basement—ideal for extra living, storage, or recreation. Inside, you'll find a warm and inviting feel with a mix of modern updates and classic character, along with a spacious kitchen and comfortable living areas designed for everyday living. The 3-bedroom with a bonus room layout offers flexibility for families, guests, or home office space. Outside is where this property really stands out—over 2 acres of usable land with room for gardening, recreation, or even small-scale hobby farming. A large detached garage/shop provides excellent space for vehicles, equipment, or a workspace, making this property ideal for those needing extra storage or functionality. Located in a peaceful setting while still being convenient to Monticello and Lake Cumberland, this property is perfect as a full-time residence, weekend getaway, or investment opportunity. Don't miss your chance to own a property with acreage, updates, and endless potential—schedule your showing today.

875 State Highway 3106, Monticello

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

2 Beds ⋅ 2 Baths ⋅ 26013532 MLS

Welcome to 93 Green Acres Drive! Check out this new to the market, charming remodeled vinyl home offering 1,275 sq. ft. of finished living space on the main level. Features include an Eat-in Kitchen with nice Pantry and Breakfast Bar, Formal Dining Room, Spacious Living Room with a corner nook with wire shelving for storage, 2 Large Bedrooms, 2 Full Baths, a roomy walk-in closet off the Primary Bedroom with lots of wire shelving, and a Laundry Area on the main level. There is a full unfinished basement with an exterior entrance. This property offers classic comfort with modern updates for everyday living and special gatherings. Renovations include thoughtful updates throughout, including a full bathroom addition, a bathroom remodel, a walk-in closet addition, cabinetry, updated faucets and lighting fixtures, that offer you peace of mind and a move-in-ready home. There are handicapped accessible features also, including a sturdy metal ramp leading to the front door. There is an attached 1-car carport, a concrete driveway that offers added parking space, a rear patio, and a nice level yard. You'll love living in the heart of Monticello and enjoy having access to the conveniences of town, medical facilities, Wayne County School Campus, dining and shopping. If you love the lake, you're only minutes from our beautiful Lake Cumberland, that's perfect for fishing, boating, and the weekend getaways that you'll look forward to. Call today to schedule your very own private tour!

93 Green Acres Dr, Monticello

3 Beds ⋅ 3 Baths ⋅ 26006822 MLS

Fully remodeled custom home or office offering 3 bedrooms, 2.5 baths, an eat-in kitchen, home office, laundry/mudroom, and three spacious living/entertaining areas, all on the main level. The updated kitchen features quartz countertops, stainless appliances, and modern finishes, while the primary suite includes a tiled walk-in shower, double vanities, and a walk-in closet. A 2,600+ sq ft unfinished basement provides endless potential. Situated on 1.25 acres in the heart of Monticello, this property also includes a wraparound blacktop driveway, propane fireplace, 30x30 detached garage, 24x28 attached garage, and a large backyard with room to add another detached garage. Would be a great commercial space for any business.

726 N Main St, Monticello

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

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