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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.

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

$299,900

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

3 Beds ⋅ 2 Baths ⋅ 26021660 MLS

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

100 Buffalo Trce, Monticello

$469,000

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!

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

$424,900

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!

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

$625,000

Welcome to the "Perfect Shade of Green" Home — a stunning custom-built log-style retreat featured in Log Homes Magazine. Completed in 2013 after years of thoughtful planning and craftsmanship, this extraordinary property sits on 3.43 acres in the desirable Hickory Point subdivision on beautiful Lake Cumberland. Positioned on a peninsula with breathtaking lake views, this spacious 5-bedroom, 3-bath home was designed for gathering, entertaining, and making lifelong family memories. From the moment you step through the front door, you'll be captivated by the soaring cathedral ceilings, floor-to-ceiling windows, and warm rustic charm throughout. The main level offers approximately 1,949 finished square feet and features two bedrooms, 2 full baths, and an impressive family room that opens onto a large deck with both open and covered entertaining spaces overlooking the lake. At the heart of the home is a chef's kitchen with a one-of-a-kind handcrafted wraparound bar offering abundant seating — perfect for hosting family and friends. The second floor adds approximately 830 finished square feet with three additional bedrooms and a full bath, providing plenty of space for guests and large families. One of the home's greatest opportunities is the 1,852-square-foot unfinished walkout basement, ready for a future owner to customize to their own style and needs. The basement opens to a spacious concrete patio and backyard area. This home also showcases unique custom wood finishes crafted from timber harvested directly from the property, adding authentic character you simply can't replicate. Built with efficiency and durability in mind, the home includes: 10-inch poured concrete basement walls 3-inch log veneers on both interior and exterior walls 6 inches of Styrofoam insulation between the veneers for excellent energy efficiency Located in an HOA-protected community in Wayne County, this property offers privacy, craftsmanship, and incredible potential. With a little TLC, this could become the ultimate lake home or family retreat. Property is being sold AS-IS. All inspections are welcome.

5 Beds ⋅ 3 Baths ⋅ 26010384 MLS

Welcome to the "Perfect Shade of Green" Home — a stunning custom-built log-style retreat featured in Log Homes Magazine. Completed in 2013 after years of thoughtful planning and craftsmanship, this extraordinary property sits on 3.43 acres in the desirable Hickory Point subdivision on beautiful Lake Cumberland. Positioned on a peninsula with breathtaking lake views, this spacious 5-bedroom, 3-bath home was designed for gathering, entertaining, and making lifelong family memories. From the moment you step through the front door, you'll be captivated by the soaring cathedral ceilings, floor-to-ceiling windows, and warm rustic charm throughout. The main level offers approximately 1,949 finished square feet and features two bedrooms, 2 full baths, and an impressive family room that opens onto a large deck with both open and covered entertaining spaces overlooking the lake. At the heart of the home is a chef's kitchen with a one-of-a-kind handcrafted wraparound bar offering abundant seating — perfect for hosting family and friends. The second floor adds approximately 830 finished square feet with three additional bedrooms and a full bath, providing plenty of space for guests and large families. One of the home's greatest opportunities is the 1,852-square-foot unfinished walkout basement, ready for a future owner to customize to their own style and needs. The basement opens to a spacious concrete patio and backyard area. This home also showcases unique custom wood finishes crafted from timber harvested directly from the property, adding authentic character you simply can't replicate. Built with efficiency and durability in mind, the home includes: 10-inch poured concrete basement walls 3-inch log veneers on both interior and exterior walls 6 inches of Styrofoam insulation between the veneers for excellent energy efficiency Located in an HOA-protected community in Wayne County, this property offers privacy, craftsmanship, and incredible potential. With a little TLC, this could become the ultimate lake home or family retreat. Property is being sold AS-IS. All inspections are welcome.

234 Cedar Point Ln, Monticello

$267,000

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.

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

$449,900

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.

3 Beds ⋅ 3 Baths ⋅ 26006822 MLS

Fully remodeled custom home or office offering 3 bedrooms, 2.5 baths, an eat-in kitchen, home office, laundry/mudroom, and three spacious living/entertaining areas, all on the main level. The updated kitchen features quartz countertops, stainless appliances, and modern finishes, while the primary suite includes a tiled walk-in shower, double vanities, and a walk-in closet. A 2,600+ sq ft unfinished basement provides endless potential. Situated on 1.25 acres in the heart of Monticello, this property also includes a wraparound blacktop driveway, propane fireplace, 30x30 detached garage, 24x28 attached garage, and a large backyard with room to add another detached garage. Would be a great commercial space for any business.

726 N Main St, Monticello

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