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$499,000
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
$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
$699,000
4 Beds ⋅ 3 Baths ⋅ 26006968 MLS
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
$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
$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
$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
$774,900
6 Beds ⋅ 6 Baths ⋅ 26006647 MLS
New price!! Lakefront luxury can be yours in this breathtakingly gorgeous lake home that is completely furnished, all you'll need is your toothbrush! Lake Cumberland memories will begin and last forever as the nearly 5,000 sq ft of meticulously designed spaces will accommodate an abundance of friends and family! This stunning 6 bedroom, 5.5 bath custom built craftsman style home sits beautifully on 1.3 acres with a majestic view of the lake and lush surrounding hills. Enjoy these breathtaking views from nearly every room including the spacious great room, with soaring wood-beamed ceilings and a striking 2 story stone fireplace. The elegant kitchen features hardwood flooring, a huge bar and an expansive dining area, perfect for entertaining. Step outside onto the massive, wrap around screened porch, complete with a cozy stone fireplace and all the beauty and privacy that surrounds you. You can retreat to the private master suite or unwind in the finished walkout basement that features additional bedroom spaces (even a bunk room), a cozy family room and a large recreational area. Looking for income possibilities? If so, you may want to take advantage of the nightly rental opportunities as this is permitted in this upscale gated community!! With just a short drive to Beaver Creek Marina, this magnificent property offers both luxury and convenience for lake living at its finest. Don't miss a chance to own this exceptional Lake Cumberland retreat!

1166 Sandstone Point Trl, Monticello
$229,000
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
$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
$159,900
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
$498,000
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
$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
$889,900
8 Beds ⋅ 8 Baths ⋅ 26005198 MLS
Panoramic Lake Cumberland Views!! Custom Waterfront Home offering 8BR's 8BA's Rare opportunity to own a one-of-a-kind, custom-built waterfront home with breathtaking main channel views of Lake Cumberland. This 2-owner property offers the perfect lakeside retreat, comfortably accommodating up to 21 guests, making it ideal for family gatherings, entertaining, or a private getaway. Designed for both comfort and convenience, the home features an in-home elevator for easy access between levels. Multiple living and entertainment areas create inviting spaces to relax and unwind, including a study for quiet reflection, a game area with billiards and ping pong, and three cozy indoor fireplaces perfect for gathering with family and friends. The gourmet kitchen makes meal preparation a delight, while the outdoor kitchen and expansive decking provide the perfect setting for outdoor dining and enjoying the stunning lake views. Recent upgrades include: • New metal roof (2024) • New kitchen appliances (2025) • Culligan water system installed (2025) • New deck section with updated fencing • Entire deck freshly repainted • Garage doors, front door, and master bedroom doors freshly painted • Driveway resealed (Fall 2025) Front door, central alarm system and thermostat are Wifi Compatible, Safety Cameras added inside and outside. Furniture is negotiable, offering a potential turnkey opportunity. This property is more than a home—it's a private sanctuary where comfort, space, and the natural beauty of Kentucky's landscape come together. Enjoy peaceful lakeside living with panoramic views and unmatched serenity. Call today to schedule your private showing and experience this extraordinary Lake Cumberland retreat.

97 Black Walnut Ln, Monticello
$1,275,000
5 Beds ⋅ 6 Baths ⋅ 26014480 MLS
Rare Opportunity! Welcome to this stunning custom built waterfront estate being sold with 6.5 acres (4.5 acres added since previously sold) with magnificent views overlooking Lake Cumberland! Built by custom builder Marshall Todd, 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 7,808 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