344 Oak Drive, Waynesburg, KY 40489 (MLS# 26021686)

Comp Sale YN: No

Property Sub Type: Single Family Residence

Price Change Timestamp: 2026-10-19T15:49:29Z

Status Change Timestamp: 2026-08-27

Back on Market Date: 2026-08-27

County: Lincoln

Street Number: 344

Street Name: Oak

Street Suffix: Drive

State: KY

Zip Code: 40489

Zip +4: 9501

Directions: From Somerset take US 27 north toward Waynesburg. Turn right onto KY 1247 and then right onto Oak Drive. Follow Oak Drive to the dead end where it becomes the driveway for 344 Oak Drive. Barn and horse stable will be immediately on the left as you enter the driveway. Home will be at top of the hill.

Parcel Number: 58-103-01

Deed Book: 482

Deed Page: 386

Current Price: $969,999

Original List Price: 999995

Status: Active

Start Showing Date: 2026-08-11

Listing Contract Date: 2026-07-30

List Price: $969,999

Listing Agreement: Exclusive Right To Sell

Occupant Type: Occupied

Office Exclusive YN: No

List Price/SqFt: 140.82

Bedrooms Total: 5

Bathrooms Total: 5

Bathrooms Full: 5

Above Grade Finished Area: 5048

Below Grade Finished Area: 1840

Living Area: 6888

Living Area Source: Public Records

Basement YN: Yes

Fireplace YN: No

Garage YN: Yes

Garage Spaces: 4

Carport YN: No

Year Built: 2007

Accessibility Features YN: No

Lot Size Source: Public Records

Lot Size Acres: 25.738

Lot Size Square Feet: 1121147

Pool Private YN: Yes

View YN: Yes

Waterfront YN: No

Water Body Access YN: No

Horse YN: Yes

Cooling YN: Yes

Heating YN: Yes

Public Remarks: 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!

Amenity Fee YN: No

Showing Instructions: Please schedule showings via ShowingTime.

Bathroom 1 Level: First

Bathroom 2 Level: First

Bathroom 3 Level: Second

Bathroom 4 Level: Second

Bathroom 5 Level: Lower

Bedroom 1 Level: First

Bedroom 2 Level: Second

Bedroom 3 Level: Second

Bedroom 4 Level: Lower

Dining Room Level: First

Kitchen Level: First

Office Level: Second

Other Level: Lower

Primary Bedroom Level: First

Recreation Room Level: Lower

Utility Room Level: First

MLS Area Major: 024 - Lincoln County

Subdivision Name: Rural

High School District: Lincoln County - 24