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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
$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
$674,000
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
$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
$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
$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
$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