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$969,995
Monthly Est:$4,828
5 Beds
- 5 Baths
5 full baths
6,888sqft
344 Oak Dr, Waynesburg, KY 40489
$969,995
$4,828/moEst:
Get Pre-Approved
Single Family Residence
Built in 2007
$-- HOA
25.74 acres lot
$141/sq.ft
Description
Experience the ultimate in luxury, privacy, and country living with this stunning custom-built estate! Situated on approximately 25+/- mostly wooded acres, this exceptional property offers the perfect blend of upscale living, recreation, and mini-farm potential. Boasting 6,888 sq. ft. of finished living space, this remarkable home is filled with quality craftsmanship and exquisite finishes throughout all three levels. The property features an enormous 60x80 four-bay RV/boat garage, barn/stable area ideal for horses or livestock, and a picturesque creek winding through the back of the property. Inside, you'll find radiant-heated tile floors, custom cabinetry, vaulted ceilings, grand staircases, a home theater, three ensuite bedrooms, and five full bathrooms. The main level offers an impressive open-concept living, dining, and kitchen area designed for both everyday living and entertaining. The spacious primary suite provides a private retreat, while a second bedroom and full bathroom, oversized laundry room, and additional living space complete the main floor. Upstairs, you'll find two additional bedrooms, each with its own full bathroom, along with a convenient secondary laundry hookup. The finished basement offers even more living and entertaining space with a full bar/kitchenette, spacious living room, bonus room currently used as a fifth bedroom, full bathroom, dedicated home theater, and two extra-large garage spaces. Step outside into your own private oasis, featuring a massive patio and entertaining area overlooking a spectacular 20x40 heated in-ground pool. Whether you're hosting family and friends, relaxing poolside, or enjoying the privacy of your acreage, this property is designed for exceptional indoor and outdoor living. Conveniently located approximately 15 minutes from Somerset and the Cumberland Parkway and just 20 minutes from Lake Cumberland's recreational areas, this property provides the privacy and space of country living while remaining close to shopping, dining, and recreation. With its impressive acreage, wooded privacy, creek, outbuildings, pool, expansive garage space, and luxurious custom home, this is truly a one-of-a-kind property with room to live, entertain, and enjoy everything the Kentucky countryside has to offer! New Roof just put on as of 8/30/2026!
- Houzeo last checked: 12 hours ago
- Listing updated: October 9, 2026 at 4:05 pm
- Listing Provided by: Tyler Chamings | Nexthome Realty Experts
- Source: Lexington Bluegrass AOR (Imagine) MLS-KY | MLS#: 26021686

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
2007
HOA Fees
-
Finished Area
6,888 sqft
Lot Size
25.74 acres lot
Basement Area
- sqft
MLS Name
Lexington Bluegrass AOR (Imagine) MLS
MLS Number
26021686
MLS Status
Active
Days on Market
44
Cumulative Days on Market
64

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 5
Bathrooms: 5
Interior
Heating
Heat Pump, Hot Water, Radiant
Flooring
Carpet, Tile
Window Features
Blinds, Insulated Windows
Cooling
Ceiling Fan(s), Central Air, Heat Pump
Exterior Features
Other
Appliances
Dishwasher, Microwave, Range, Refrigerator
Interior Features
Ceiling Fan(s), Walk In Closet(s), Wet Bar
Sewer
Septic Tank
Construction
Year Built
Year Built: 2007
Home type
Single Family Residence
Foundation Details
Concrete Perimeter
Roof
Dimensional Style, Shingle
Construction Materials
Brick, Stone, Other, Hardi Plank Type
Architectural Style
Craftsman
Utilities & Energy
Utilities
Cable Connected, Electricity Connected, Water Connected
Basement
Exterior Entry, Finished, Full, Walk Out Access
Pool Features
In Ground
Water Source
Public
Parking Features
Attached Garage, Detached Garage, Driveway, Garage Faces Rear
Laundry Features
Main Level
Other Features
Lot Features
Landscaped, Secluded, Wooded
Subdivision Name
Rural
Patio And Porch Features
Patio, Rear Patio
Price History
| Date | Event | Price |
|---|---|---|
10/09/2026 Source: | Price Decreased | $969,995 -0.51% $141/sqft |
10/06/2026 Source: | Price Decreased | $974,995 -0.51% $142/sqft |
09/16/2026 Source: | Price Decreased | $979,995 -1.01% $142/sqft |
09/04/2026 Source: | Price Decreased | $989,995 -1.00% $144/sqft |
08/27/2026 Source: | Listed for Sale | $999,995 $145/sqft |
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Based on information from the IMAGINE MLS® through Oct 09, 2026, 02:30PM. Copyrighted by the Imagine MLS®. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data on this website is deemed reliable but is not guaranteed accurate by the MLS. © 2026 IMAGINE MLS®. All Rights Reserved.
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