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Single family home for sale at 344 Oak Dr, Waynesburg, KY 40489 | MLS# 26021686 | Listing updated on 2026-10-09
Photo 1 of Single family home for sale at 344 Oak Dr, Waynesburg, KY 40489 | MLS# 26021686 | Listing updated on 2026-10-09
Photo 2 of Single family home for sale at 344 Oak Dr, Waynesburg, KY 40489 | MLS# 26021686 | Listing updated on 2026-10-09
Photo 3 of Single family home for sale at 344 Oak Dr, Waynesburg, KY 40489 | MLS# 26021686 | Listing updated on 2026-10-09
Photo 4 of Single family home for sale at 344 Oak Dr, Waynesburg, KY 40489 | MLS# 26021686 | Listing updated on 2026-10-09
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$969,995

Monthly Est:$4,828

  • Beds Icon5 Beds
  • Beds Icon
    5 Baths
  • Beds Icon6,888sqft

344 Oak Dr, Waynesburg, KY 40489

$4,828/moEst:

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  • 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 Lexington Bluegrass AOR (Imagine) MLS-KY

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Lincoln County

  • City

    Waynesburg

  • 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

DateEventPrice

10/09/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26021686

Price Decreased

$969,995 -0.51%

$141/sqft

10/06/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26021686

Price Decreased

$974,995 -0.51%

$142/sqft

09/16/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26021686

Price Decreased

$979,995 -1.01%

$142/sqft

09/04/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26021686

Price Decreased

$989,995 -1.00%

$144/sqft

08/27/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26021686

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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