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$485,000
4 Beds ⋅ 4 Baths ⋅ 26019708 MLS
Rare opportunity to own a one of a kind property on approximately 2.5 secluded, wooded acres just minutes from two concrete boat ramps on beautiful Lake Cumberland. Whether you're looking for a full time residence, vacation home, or investment property with short term rental potential, this unique estate offers endless possibilities. The custom built primary home features soaring 12 foot ceilings, crown molding, stained glass windows, custom built-ins, abundant cabinetry and countertop space, a walk-in pantry, steam room, laundry chute, an oversized walk-in shower in the primary suite, and a built-in bed with integrated storage. An unfinished upper level with 12-foot ceilings offers excellent potential for additional bedrooms, a game room, home office, or expanded living space. The detached guest house is located above the oversized two-bay garage and is ideal as a mother-in-law suite, private guest quarters, or income-producing Airbnb. It features a full kitchen, spacious living area with king-size sleeping space, a full bath with a walk-in shower, two built-in twin window beds, and a loft for additional sleeping accommodations. The garage level also includes a laundry area and convenient half bath. Outside, you'll enjoy multiple decks, two covered porches, a screened-in porch, beautifully landscaped grounds, peaceful sitting areas, and a fire pit. This would be perfect for entertaining or relaxing after a day on Lake Cumberland. Underground utilities and city water provide modern convenience while preserving the property's private, natural setting. Properties offering this combination of privacy, acreage, proximity to Lake Cumberland, guest accommodations, and short-term rental potential are hard to find. Schedule your private showing today.

1560 Bell Phipps Rd, Monticello
$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
$115,000
25008019 MLS
Located in Monticello, Ky on the edge of Lake Cumberland, is this beautiful 10.17 acres with NO RESTRICTIONS! Only 15 minutes away from Beaver Creek Marina! The developer has already installed underground water and electric right to the property! You would own nearly 600' of shoreline that touches the ''Corp of Engineers''. With minimal clearing efforts, you could have an absolutely breathtaking view of Lake Cumberland. While it is uncertain how much, there is mature and marketable timber on the property. Whether you want to place a camper, a mobile home, a garage, barndominium, or even a custom built home, there is endless potential here! Call today for more information and to schedule a tour!

128 Sandstone Pt, Monticello
$130,000
2 Beds ⋅ 1 Baths ⋅ 26018568 MLS
Welcome to 183 Shoemaker Lane where you will find privacy and seclusion. This property has a lot to offer with 2 m/l acres of land, you will find a workshop, garage that has additions added to each side and a porch on the back. You will also find another cute building with storm shelter underneath, a cute playhouse, and chicken house. The home is a 1990 Clayton Mobile Home with an addition that has been started on the end. The home offers open concept with large living and kitchen, 2 bedrooms, bath and laundry area. In February of 2022 a new HVAC was installed, water heater was replaced in 2023. Home has front and back porch. Home has no carpet, laminate and vinyl flooring, At the back of the home you can walk down to Beaver Creek with waterfall that lots of folks enjoy seeing but is not part of this property. Lots of wooded areas behind the property, most of the outbuildings have electricity. Located close to the Sportsman Club this property has lots of potential. On the left as you enter the property there use to be another residence - mobile home site with electric, etc.

183 183 Shoemaker Ln Lane, Monticello
$1,645,000
5 Beds ⋅ 4 Baths ⋅ 26016949 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
$209,000
3 Beds ⋅ 2 Baths ⋅ 26013815 MLS
Looking for a small farm of 11.26 acres that is all cleared and within 2 miles of downtown Monticello. Property has 2 barns, 2 sheds, and a detached garage. Property also has a main house, with another house and a tiny home that is wired for electric, but is not hooked up. All structures may need some TLC. The farm has multiple uses, and has currently been used for goats and horses. This property would make a great investment for multi family farm, live in one home and rent out the other 2, or purchase and rent out the homes and the land. The choice is yours and priced to sell !

1434 Hwy 167 Se Highway 167 Highway, Monticello
$1,250,000
24017677 MLS
Looking for acreage close to Lake Cumberland!! Check out this hard to find, large tract of land that consists of 50.73 acres. Half of the acreage is cleared and the other half in timber. This property backs up to CORP property, making the location great for a campground, or your own private residence. Property is within 2 miles to Safe Harbor, (Beaver Creek Dock), less than 1/2 mile to boat ramp at the end of Dug Road (known as the orchard) less than 8 miles from Monticello, for shopping, medical, schools, etc. Call today to take a look at this larger tract of land.

371 Dug Road Rd, 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
$299,000
23008839 MLS
Trail Riding, Hunting, Hiking, Timber, Cleared Land. This 156 Acre tract m/l could be used for multiple purposes. With an abundance of wildlife this could be your own private Hunter's Paradise. Property contains a logging road that connects up with miles of a vast trail system that can give you endless hours of satisfaction. Even though the timber was cut a few years ago, there appears to be some marketable timber still to cut. The tract also includes a seven-acre hay field. This would be the perfect place for an RV site. Utilities border this cleared field, so building would not be an issue. Unlimited Possibilities!

Chesnut Grove Rd, 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
$160,900
3 Beds ⋅ 1 Baths ⋅ 26015160 MLS
Freshly Remodeled & Move-In Ready! Welcome to 370 Green Acres, Monticello, KY 42633—a beautifully updated 3-bedroom, 1-bath home that offers modern comfort in an unbeatable location! Step inside to discover a completely refreshed interior featuring a stylish new kitchen with brand-new appliances, updated flooring, fresh paint, and a beautifully remodeled bathroom. The partial basement provides plenty of room for storage, a workshop, or future possibilities. Location is everything, and this home delivers! You're just minutes from beautiful Lake Cumberland, the Wayne County Hospital, local schools, shopping, restaurants, and everything downtown Monticello has to offer. Whether you're looking for your first home, a place to retire, or a vacation getaway near the lake, this property checks all the boxes. Property Features: • 3 Bedrooms | 1 Bathroom • Freshly remodeled throughout • Brand-new kitchen appliances included • Beautifully updated bathroom • Partial basement for storage or hobbies • Convenient location close to Lake Cumberland, schools, hospital, shopping & dining • Move-in ready! Don't miss your opportunity to own this charming home in one of Monticello's most convenient locations. Schedule your private showing today!

370 Green Acres Dr, Monticello
$124,900
26002345 MLS
16.57 acres of secluded land featuring an off-the-grid cabin and a 24x30 detached garage to store side by sides, tractors and any other toys. A great setup for hunting with plenty of wildlife, riding 4-wheelers, or just getting away from it all. The cabin is wired for generator use, giving you a functional base camp while staying off the grid. The property includes a pond and three natural springs, is fenced, and offers plenty of room to explore and enjoy the outdoors. Private, quiet, and hard-to-find acreage like this with improvements already in place.

1657 Dry Hollow 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
$219,900
26009134 MLS
72 acres of unrestricted land offering privacy, recreation, and multiple opportunities with this exceptional tract in Monticello, Kentucky. Whether you're searching for a premier hunting property, a weekend getaway, or the ideal spot to build your dream homestead, this land checks a bunch of boxes. This property is predominantly wooded, offering excellent cover and habitat for wildlife, making it a prime location for hunting and outdoor recreation. Established trails wind throughout the acreage, providing easy access for ATVs and hiking. A small hunting building is already in place, giving you a ready-made basecamp for your outdoor adventures. In addition to its recreational appeal, this property offers several acres of cleared area with level areas perfectly suited for building. Whether you envision a secluded cabin, a full-time residence, or a garage for storing equipment and lake toys, the groundwork has already been laid. The property has successfully passed a perc test, and both water and electric are already run onto the property, saving you time and expense as you plan your build. Along the road frontage, you'll find fencing in place with two gated entrances, offering both security and convenient access. With its combination of natural beauty, functional improvements, and close proximity to Lake Cumberland, this property is a rare find in today's market. Just a short 15-minute drive to multiple boat ramps on beautiful Lake Cumberland. Don't miss your chance to own a versatile piece of land that offers immediate enjoyment in Southern Kentucky.

1051 Kelley Ln, Monticello
$350,000
3 Beds ⋅ 2 Baths ⋅ 26005409 MLS
Highlights: This property offers a charming cabin-style 3 bed/2 bath home and barn situated on over 36 +/- unrestricted acres, complete with a spring-fed pond. If you've been looking for a place where life can slow down and the outdoors take center stage, this property is worth a look! The home features classic hemlock siding and a large front porch, some recent kitchen updates, and a few new light fixtures, but the land itself is the true highlight—partially wooded with untouched timber. Whether you enjoy hunting, exploring, or simply being immersed in nature, this property delivers. A picturesque spring-fed pond sits just outside your dining room window, your own personal fishing hole and a serene backdrop for everyday life. While the home could use a little TLC, it provides a foundation for a rustic getaway, hunting cabin, or full time residence for those seeking a simpler lifestyle. A barn on the property adds additional functionality, perfect for covered storage, equipment, or hobby farming. If you're dreaming of wide-open spaces in a part of the world that moves a little slower, come see 656 Thompson Road in friendly Monticello, Kentucky! *Property is located on a dead-end road, so there is no through traffic coming by the house. *There are multiple places on the property that would be suitable building lots. *Suitable for cattle or horses; no fencing currently.

656 Thompson Rd, Monticello
$185,000
3 Beds ⋅ 2 Baths ⋅ 26004521 MLS
This beautiful property offers a charming home set in a peaceful country setting with plenty of features to enjoy. The property includes a barn and silo, along with an additional property hookup that already has septic, water, and electric connections in place. The home sits on a permanent block foundation and has been updated with a new roof, new facias, gutters, and vinyl siding, adding both durability and curb appeal. Inside, the spacious home features generously sized bedrooms and a cozy living room that is perfect for relaxing or entertaining guests. The dining area provides a wonderful space for family meals and gatherings, while the kitchen offers ample cabinet space for storage and functionality. Large walk-in closets add extra convenience, and the spacious primary bathroom provides comfort and room to unwind. The home comes fully equipped with all appliances, including a refrigerator and range, making it truly move-in ready. Enjoy the quiet and beauty of country living while still being just a short 10-minute drive from shopping, restaurants, and hospitals. For outdoor recreation, the property is also located about 20 minutes from the boat dock at beautiful Lake Cumberland, offering easy access to boating, fishing, and lake activities. This well-maintained home combines peaceful surroundings with modern conveniences, making it a wonderful opportunity you won't want to miss.

1115 Kentucky, Monticello
$299,000
2 Beds ⋅ 1 Baths ⋅ 26005932 MLS
Unique lake property situated on three lots featuring a 2-bedroom, 1-bathroom home plus a detached garage with plenty of room for a boat up to 26 ft. The garage has a finished guest quarters offering an additional 1 bedroom and 1 bathroom. Built in 2021 and tucked into a peaceful, golf-cart friendly Lake Cumberland community, this move-in-ready property offers flexibility, privacy, and lake lifestyle convenience all in one package. The main home features 2 bedrooms, 1 full bath, and an open-concept living/kitchen layout with durable LVP flooring throughout. The kitchen offers white shaker cabinetry, butcher block countertops, subway tile backsplash, stainless appliances, and recessed lighting, creating a clean, modern lake-cottage feel. The living area is bright and inviting with double doors leading to a spacious covered porch - perfect for relaxing after a day on the water. The full bath includes a tiled walk-in shower with glass door and updated vanity, continuing the low-maintenance, newer-construction appeal. Outside, enjoy extensive covered porch space with ceiling fans, composite decking on the house porch, ideal for entertaining or unwinding in the wooded setting. A major bonus is the detached garage with finished guest quarters, offering 1 bedroom, 1 bath, and its own mini-split HVAC system - perfect for guests, or private workspace. Also deck space beside garage for grilling, entertaining guest and relaxing. The property sits on three lots being sold together (approx. 1.32 acres +/-) and includes an additional lot already equipped with a RV hookup with septic, electric, and water in place, providing incredible flexibility for overflow guests or additional income potential. Located just minutes from Conley Bottom Marina and close to two private boat ramps, this home is ideal as a full-time residence, weekend getaway, or short-term rental investment near Lake Cumberland. If you've been looking for newer construction, extra space for guests, and lake access convenience - this one checks the boxes.

81 White Oak Ln, Monticello
$575,000
25014370 MLS
Approximately 327 acres of woodland m/l by PVA. 221.74 Acres of that has been surveyed. Timber was cut on the surveyed portion 12-15 years ago. The remaining acreage has not been surveyed and the timber has not been cut. Located in the Spann Hill area of Wayne County off Hwy 3285.

1111 Hwy 3285, Monticello
$1,398,000
25009320 MLS
106 Acres - A Hunter & Angler's Paradise - !!You can walk or ride to the water from this property!! Escape to your own private retreat with this stunning 106-acre tract, bordered by ±230 acres of landlocked U.S. Army Corps of Engineers property—providing unmatched seclusion and abundant wildlife. Whether you're chasing trophy bucks or casting a line, this property delivers the ultimate in outdoor recreation. A public boat ramp is just under a mile away, giving you quick access to Lake Cumberland, with Beaver Creek Marina just minutes downstream. All the essentials are within reach, with town only 15 minutes away. If you've been dreaming of a hunting and fishing haven, this is it. Many lakefront building lots. Call for your private tour.

333 Acreyville Rd, Monticello
$269,000
3 Beds ⋅ 2 Baths ⋅ 26002825 MLS
If you are looking for quite country living with an open view of the countryside and farms then stop! Take a look at this beautiful bedford stone home that has been remodeled to with all amenities that you could want. Large open floor plan for kitchen/dining/living room. 3 large bedroom with large walk-in closets for each bedroom. 2 full baths with one walk in shower. This home has raised ceilings that brings the newer modern living vibe. There is a large laundry room tied with large pantry off of the kitchen for functional daily living. This home boast 3 coverd porches to sit out relax and enjoy the view. One cover screened in porch to enjoy the nighttime atmosphere without the insects. Outside boast a 576 sq ft 2 car garage with a shed attachment. There is a poured concrete pad to add to the property. This can be used as a base for extra storage shed, provide fencing to make a dog kennel. If you are wanting to start your own garden ther is lots of room to have a large garden . Ample ground to have chickens, goats, sheep or other livestock. This home has too many things to offer to list. Even comes with 2 cute built in bed.

1169 Old Bethel Church Rd, Monticello
$185,000
3 Beds ⋅ 2 Baths ⋅ 26014817 MLS
This 3 bedroom, 2 bath brick home is located in a beautiful rural setting in Wayne County and offers an affordable opportunity for the right buyer. The home features approximately 1,447 sq ft of living space, a full unfinished basement, attached 1.5 -car garage, covered front porch, rear deck, fireplace, and poured concrete foundation. With its brick exterior, full basement, garage, and peaceful rural location, this home has tons of potential

10113 Kentucky 92, Monticello