Monticello Homes with Exterior Entry Basement

Monticello Homes with Exterior Entry Basement

Welcome to Monticello, Kentucky – a hidden gem nestled in the heart of Wayne County. Known for its warm community spirit and breathtaking natural landscapes, Monticello offers a unique blend of small-town charm and modern conveniences. Surrounded by the picturesque beauty of Lake Cumberland, residents enjoy a wealth of outdoor activities, from fishing and boating to hiking along scenic trails. With a rich history and a vibrant local culture, Monticello is the perfect place to call home.

If you’re searching for a residence that balances comfort and functionality, look no further than our homes featuring exterior entry basements. These thoughtfully designed properties provide a seamless blend of convenience and versatility. Ideal for families, these basements offer abundant storage space, additional living areas, or even the potential for a private guest suite. Imagine hosting gatherings with friends and family, where everyone can enjoy the spacious surroundings.

The exterior entry allows for easy access, making it perfect for hobbies or a home office, while also providing a separate entrance for guests or tenants. With Monticello’s affordable housing market, you can find the perfect home that meets your needs without sacrificing style or comfort.

Whether you’re a first-time buyer or looking to relocate, Monticello’s welcoming atmosphere and beautiful homes with exterior entry basements are sure to captivate your heart. Come explore what this charming city has to offer and discover your dream home in Monticello today!

Newest Monticello Homes with Exterior Entry Basement

75 Hickory Hill Dr, Monticello
$345,000
4 Beds ⋅ 4 Baths ⋅ 26027010 MLS
Beautifully updated home located near historic Kendrick Avenue in one of Monticello's most desirable neighborhoods. Offering 4 bedrooms, 3.5 bathrooms, and a thoughtful blend of modern updates and timeless charm, this 3146 sq ft home provides comfortable living for families of all sizes. Step inside to an inviting great room that seamlessly combines the family room, dining area, and kitchen into the heart of the home. The stately kitchen is a chef's dream, featuring abundant cabinetry and countertop space, a convenient eat-at bar, and a stone fireplace ready for propane conversion. Just beyond, the spacious back deck with pergola creates the perfect setting for outdoor dining, entertaining, and relaxing. The adjoining family room features a second dual-sided fireplace, which can be enjoyed from both the family room and the adjacent flex space. This versatile area is ideal for a home office, den, library, or reading room. The main level primary suite offers a spacious en suite bath featuring dual vanities, a walk-in shower, and a large tub. Upstairs, you'll find three additional bedrooms, including one with a private en suite bath, along with a full hallway bath. The lower level adds valuable functionality with garage access through a mudroom entry, a laundry room, and a bonus room with a half bath, providing excellent space for hobbies, recreation, or additional living needs. Situated on a beautiful corner lot, the property offers gently rolling lawn, trees, a fenced area adjacent to the back deck, and a blacktop circular driveway that enhances both curb appeal and convenience. Recent improvements include new siding and roof in 2026, a new water heater in 2022, and an updated heat pump. The chimneys have been capped (new metal roof), and both fireplaces will require gas log conversion to become operational. Just minutes from both Lake Cumberland and Dale Hollow Lake, providing opportunities for fishing, boating, water sports, and year-round recreation.

75 Hickory Hill Dr, Monticello
100 Buffalo Trce, Monticello
$320,000
3 Beds ⋅ 2 Baths ⋅ 26021660 MLS
Wonderful Lake Cumberland 3.6 acre mini-farm only 3 miles from Conley Bottom Marina with several area ramps for easy lake access. Whether you use it to raise a horse or livestock or develop it out, it'd be a great property. You could ride your horse to the lake even. How cool would that be?! Spacious 3-bedroom, 2-bathroom single-level floor plan. Low maintenance brick so you can enjoy yourself and not work on things all the time. There is a basement garage for mower storage and a workshop. But one of the highlights of the property is the 30 X 40 garage with 9 & 10 ft. doors. There is another old barn on the property if you did need a place for your horses/livestock. As to development potential this would be a great spot for RV or STR short term rental cabins due to the proximity to Lake Cumberland. There is 300' feet of road frontage on Hwy 2393 for easy access. Make this dream of a property yours.

100 Buffalo Trce, Monticello
202 Peaceful Cove Ln, Monticello
$495,000
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
2247 Ky-2393, Monticello
$424,900
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
234 Cedar Point Ln, Monticello
$625,000
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
131 Golden Pond 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
607 Old Lck 21st Rd, Monticello
$273,000
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
2371 State Highway 1568, Monticello
$299,900
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
726 N Main St, Monticello
$449,900
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
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