Monticello Homes with Finished Basement

Monticello Homes with Finished Basement

Welcome to Monticello, Kentucky, a charming city nestled in the heart of Wayne County, where small-town warmth meets stunning natural beauty. Known for its picturesque landscapes and friendly community, Monticello is the perfect place to call home. With its rich history and vibrant local culture, residents enjoy a relaxed lifestyle surrounded by a wealth of outdoor activities. From fishing and boating on Lake Cumberland to hiking in nearby state parks, adventure is just around the corner.

One of the standout features of Monticello’s real estate market is the availability of homes with finished basements. These versatile spaces offer endless possibilities, whether you envision a cozy family room, a home office, or a recreational area for entertaining guests. Finished basements provide extra square footage that enhances your living experience, allowing you to maximize both space and functionality.

In Monticello, you’ll find a variety of homes that cater to diverse tastes and budgets. Many properties boast beautiful craftsmanship and modern amenities, all while maintaining the charm of the region. With a strong sense of community and a welcoming atmosphere, Monticello is a fantastic place to settle down.

If you're searching for a home with a finished basement in Monticello, you’re not just investing in a property; you’re embracing a lifestyle filled with warmth, adventure, and community spirit. Explore the possibilities that await you in this lovely city, and discover why Monticello is truly a hidden gem in Kentucky!

Newest Monticello Homes with Finished Basement

42 Lands End Dr, Monticello
$339,000
3 Beds ⋅ 3 Baths ⋅ 26027659 MLS
Welcome to 42 Lands End Drive in the beautiful Cumberland Vista Subdivision. This Beautiful Cape Cod style home has year round lake views with a gravel roadway to Lake Cumberland that is restricted to tract owners and their guest only. The well - known local Builder of this home was Phillip Kinnett. This 2nd home has been used as a (personal lake house), with typical stay of around 2 days per month. The home offers 3 bedrooms, 3 baths, with a Murphy bed in basement offering more sleeping area. Large windows to view the lake and outdoor privacy. Large rear deck with a remote awning. Other features include an added garage for RV and storage, hot tub, fireplace with gas logs. Call today to view this beautiful home.

42 Lands End Dr, Monticello
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
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
305 Beech St, Monticello
$1,645,000
5 Beds ⋅ 4 Baths ⋅ 26016942 MLS
Welcome to 305 Beech Street, a truly special Tudor-inspired home tucked along year-round Elk Creek in the heart of Monticello. Located within the city limits, this 23 +/- acre unique property offers the convenience of town with the peaceful feel of country living. Lovingly designed and enjoyed for generations, it is a place filled with beauty, character, and history. A winding asphalt driveway shaded by mature dogwood trees and lined with carefully trimmed evergreens welcomes you home. Inspired by the owners' travels through Europe, the grounds feature expansive lawns, mature shade trees, and a beautiful formal French garden with brick-lined beds, statuary, boxwoods, flowering arches of Sweet Autumn Clematis, a vegetable garden, and an automated irrigation system. In the spring, hundreds of daffodils bloom throughout the property, while the shady creekside setting provides the perfect place for picnics, cookouts, and simply enjoying nature. Built of native mountain stone, stucco, and custom milled fir trim, the home reflects exceptional craftsmanship and timeless style. A two-level screened gazebo porch with sliding glass windows creates a wonderful space to enjoy in every season. Inside, soaring beamed ceilings, hand-painted details, custom stained glass, beautiful millwork, and Italian porcelain flooring create a warm and inviting atmosphere. The spacious great room is centered around a striking custom stone fireplace with a heatilator system and flows easily into the dining room overlooking Elk Creek. The kitchen is both beautiful and functional, featuring custom cabinetry, quartz countertops, a center island, walk-in pantry, GE Monogram dual-fuel six-burner range with double ovens, KitchenAid appliances, and a cozy bay window breakfast area with views of the creek. The main-level primary suite offers an 11-foot beamed ceiling, stone fireplace with gas logs, sitting area, private deck, large walk-in closet, and a luxurious bath with heated floors, double shower, and clawfoot soaking tub. A guest bedroom and bath are also conveniently located on the main level. Upstairs is an additional private suite with custom built-ins, dormer windows, abundant storage, and its own bath. The walk-out basement provides generous additional living space with a fireplace, recreation areas, two more bedrooms, including one with an en suite bath, and plenty of storage. Additional features include three separate HVAC systems, an automatic generator, oversized garage, city water and sewer, and a new roof installed in May 2026. Rich in local history and surrounded by natural beauty, 305 Beech Street is more than just a house. It is a place where memories have been made for generations and where the next owners will have the opportunity to enjoy a truly remarkable setting along Elk Creek. Convenient location near Lake Cumberland in South Central Kentucky!

305 Beech St, Monticello
856 New Fall Creek Rd, Monticello
$649,900
4 Beds ⋅ 3 Baths ⋅ 26006968 MLS
Motivated Seller! Income-producing barndominium just 1 minute from New Fall Creek boat ramp and 7 minutes to Conley Bottom Marina. Featuring an open floor plan with soaring ceilings, 4 bedrooms, 3 baths, lake views, and a wraparound porch. Includes a 30x40 garage perfect for a boat and camper. Selling fully furnished and currently operating as a successful short-term rental with strong bookings in place.

856 New Fall Creek Rd, Monticello
137 Indian Cave Rd, Monticello
$654,000
5 Beds ⋅ 5 Baths ⋅ 26010372 MLS
Elegant Colonial Estate on 8 Acres with Exceptional Amenities... Discover this stunning two-story brick home set on 8 acres of mixed open and wooded land, offering the privacy and tranquility of a private estate. Featuring over 5,000 square feet of living space, this 5-bedroom, 4.5-bath home combines thoughtful updates with timeless elegance. The property includes a finished basement, an attached oversized 2-car garage, a detached 2-car garage, and an additional lawn/cart building, perfect for vehicles, toys, and storage. Energy efficiency is ensured with a well-maintained geothermal heating and cooling system. Inside, the home has been refreshed with new paint, crown molding, updated flooring, Franklin Brass hand-forged finishes, and select blown-glass light fixtures. The kitchen has been thoughtfully updated with new tile flooring, abundant cabinetry, custom rollout drawers, modern lighting, and an upgraded appliance package. The main living areas feature vaulted ceilings, abundant natural light, and a gas log fireplace flanked by built-in wood bookshelves. The spacious floor plan includes two large living rooms, an enclosed all-seasons room, a screened back porch, and a backyard courtyard with a fire pit—ideal for entertaining or relaxing. The master suite offers a private retreat with a renovated bathroom and ample closet space. A full secondary suite, located in its own private wing, provides comfort and privacy for guests or family. The grounds are thoughtfully landscaped with a "green fence" of Magnolia, Wisteria, Maple, and Crepe Myrtle trees, offering future privacy. Multiple flower gardens bloom nearly year-round with tulips, lilies, and roses, while a small orchard features pecan, almond, hazelnut, nectarine, pear, apple, and cherry trees. Enjoy scenic mountain views, abundant wildlife, and serene surroundings on this exceptional property. Additional highlights include a large attic/playroom, a 16x18 sunroom, a screened-in patio, a propane fireplace, and convenient proximity—just 3 miles to Conley Bottom Resort and multiple nearby boat ramps. Priced under $119 per square foot, this elegant Colonial estate offers both luxury and value. Don't miss the opportunity to experience this truly remarkable home.

137 Indian Cave Rd, Monticello
1104 N Main St, 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
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
510 Green Hill Estates Rd, Monticello
$1,250,000
5 Beds ⋅ 6 Baths ⋅ 26014480 MLS
RARE OPPORTUNITY + PREMIUM CLOSING INCENTIVES! Seller is willing to negotiate premium closing incentives with an acceptable offer. Welcome to this stunning custom-built waterfront estate, now being offered with 6.5 acres- 4.5 additional acres acquired since the property was previously sold- and magnificent views overlooking Lake Cumberland! This colonial-inspired exterior with grand columns and classic brick architecture encapsulates the grandeur of southern Kentucky living. Situated on 6.5 acres with year-round lake views and conveniently located just minutes from Burnside Marina and 15 minutes to Conley Bottom Resort, this impressive 5 bedroom, 6 bathroom home offers 7,809 sq ft with 3 levels of beautifully updated living space. When you step inside, the soaring two-story foyer welcomes you with an abundance of natural light. To the right, the formal dining room features beautiful marble tile offering warmth and versatility to transitional designs. The living room, office and playroom feature newly (2026) installed engineered hardwood flooring. The main level provides a seamless flow that transitions into what can only be described as the heart of the home. This one-of-a-kind chef's kitchen boasts brand new modern lighting, gorgeous custom Hahn cabinetry and the current owners have extended the island with the same top notch woodwork for additional seating and entertaining. The new (2025) Quartz countertops and full Quartz backsplash create a seamless transition and statement of classic style that is sure to last for years to come. The new premium Cafe´ appliances in matte white with gold hardware provide a visually stunning, high-performance kitchen, including, a double oven induction cooktop with touch controls, smart 4-door french door refrigerator with dual dispense autofill pitcher, and double drawer dishwasher. On the second level, the master suite features double interior doors opening up into a spacious suite with incredible lake views from your master deck. The space boasts a walk-in tile shower, soaking tub, walk-in closet, his and her vanities and a spacious deck with breathtaking views of the region's highly sought after Lake Cumberland. The second bedroom includes its own private full bathroom, perfect for guests. The additional 3 bedrooms plus a bonus room offer the same great finishing touches alike, and all upstairs rooms feature newly (2026) installed carpet. Downstairs you are met with a generous 2000+ sq ft basement with endless potential and possibilities. Currently serving as a flex room, this space provides a home gym area, playroom with lounging, additional sleeping area and room for a game of pool or other indoor activities. Did I mention the full kitchen? The basement offers a full bathroom and fully functioning kitchen with sink, 4 burner electric range and refrigerator. This space could be further finished out with additional bedrooms or a generous in-law suite. This home offers the best of both worlds with a NEW ROOF in 2026 providing peace of mind, updated interior finishes and peaceful lake views from one of your multi-tier decks. The home features Pella windows, newly installed blinds throughout the home and new remote controlled motorized blinds over the second story foyer windows, Trex decking with a new staircase addition for outdoor access from the main deck to lower level and other updates throughout multi-level decking, (2) new HVAC installed in 2025, fresh paint to walls and crown molding throughout the home this year, (2) new garage door motors, and so much more. This is a rare opportunity to own a beautifully updated estate where timeless architecture meets modern comfort, while surrounded by the gorgeous waters of Kentucky's crown jewel, Lake Cumberland.

510 Green Hill Estates Rd, Monticello
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