# 344 Oak Drive, Waynesburg, KY 40489 > **TL;DR:** 5bd/5ba single family, $969,999 ($141/sqft), built 2007, 6,888 sqft. > Pool, A/C, 4-car garage. Est. $5,188/mo. Listed 95 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $969,999 | | Price/sqft | $141 | | Bedrooms | 5 | | Bathrooms | 5 full | | Square Feet | 6,888 | | Year Built | 2007 | | Lot Size | 1,121,147 sqft (25.74 acres) | | Stories | 3 | | Garage | 4-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 95 | ## Why This Home Stands Out - **Pool** - Pool listed; type not specified - **Large Garage** - 4-car garage ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $4,905 | | Estimated Insurance | $283 | | **Total** | **$5,188** | ## Nearby Schools - **Elementary:** Waynesburg - **Middle:** Lincoln Co - **High:** Lincoln Co ## Key Amenities - Pool - A/C - 4-car garage ## Property Highlights - Built in 2007 - 25.74 acre lot - 3 stories - Private pool ## Description ### Agent 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! ## Location - **Address:** 344 Oak Drive, Waynesburg, KY 40489 - **County:** Lincoln - **Neighborhood:** Rural - **Coordinates:** 37.325497, -84.648399 - **Google Maps:** https://www.google.com/maps?q=37.325497,-84.648399 ## Virtual Tour & Media - **Video Tour:** https://my.matterport.com/show/?m=UYN9ptS8BAU&mls=1 ## Listing Agent - **Name:** Tyler Chamings - **Brokerage:** Nexthome Realty Experts - **Broker Phone:** 2708428195 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/344-Oak-Dr_Waynesburg_KY_40489_M43301-91405?f=listhub&s=LBARKY&m=26021686&c=propsimple) ## Photos ![344 Oak Drive - Photo 1](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f2088203186r.jpg) ![344 Oak Drive - Photo 2](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f2430174796r.jpg) ![344 Oak Drive - Photo 3](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f1895498824r.jpg) ![344 Oak Drive - Photo 4](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f607779146r.jpg) ![344 Oak Drive - Photo 5](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f3145990097r.jpg) ![344 Oak Drive - Photo 6](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f1051979588r.jpg) ![344 Oak Drive - Photo 7](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f341068433r.jpg) ![344 Oak Drive - Photo 8](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f1354874524r.jpg) ![344 Oak Drive - Photo 9](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f3404969851r.jpg) ![344 Oak Drive - Photo 10](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f4053985931r.jpg) ![344 Oak Drive - Photo 11](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f3567596350r.jpg) ![344 Oak Drive - Photo 12](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f1578809653r.jpg) ![344 Oak Drive - Photo 13](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f838337482r.jpg) ![344 Oak Drive - Photo 14](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f3932740108r.jpg) ![344 Oak Drive - Photo 15](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f3548089379r.jpg) ![344 Oak Drive - Photo 16](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f2821487063r.jpg) ![344 Oak Drive - Photo 17](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f851872986r.jpg) ![344 Oak Drive - Photo 18](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f2212686579r.jpg) ![344 Oak Drive - Photo 19](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f630319647r.jpg) ![344 Oak Drive - Photo 20](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f1064051881r.jpg) ![344 Oak Drive - Photo 21](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f562923995r.jpg) ![344 Oak Drive - Photo 22](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f2018150618r.jpg) ![344 Oak Drive - Photo 23](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f923798426r.jpg) ![344 Oak Drive - Photo 24](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f3774585036r.jpg) ![344 Oak Drive - Photo 25](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f2308418223r.jpg) ![344 Oak Drive - Photo 26](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f1524017050r.jpg) ![344 Oak Drive - Photo 27](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f3171248351r.jpg) ![344 Oak Drive - Photo 28](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f2269969548r.jpg) ![344 Oak Drive - Photo 29](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f588856531r.jpg) ![344 Oak Drive - Photo 30](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f3005518871r.jpg) ![344 Oak Drive - Photo 31](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f2978316164r.jpg) ![344 Oak Drive - Photo 32](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f2889953892r.jpg) ![344 Oak Drive - Photo 33](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f26760630r.jpg) ![344 Oak Drive - Photo 34](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f725923351r.jpg) ![344 Oak Drive - Photo 35](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f3351216349r.jpg) ![344 Oak Drive - Photo 36](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f1252554612r.jpg) ![344 Oak Drive - Photo 37](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f3913838506r.jpg) ![344 Oak Drive - Photo 38](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f1063958667r.jpg) ![344 Oak Drive - Photo 39](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f684915502r.jpg) ![344 Oak Drive - Photo 40](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f2763647138r.jpg) ![344 Oak Drive - Photo 41](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f2445418563r.jpg) ![344 Oak Drive - Photo 42](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f2212347301r.jpg) ![344 Oak Drive - Photo 43](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f3908730241r.jpg) ![344 Oak Drive - Photo 44](http://lh.rdcpix.com/fe1d6ab2b6ae0b5219f15a54741f381el-f2812009695r.jpg) --- **MLS#:** 26021686 | **Updated:** 2026-10-31 **Source:** listhub *Copyright © 2026 ImagineMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/344-oak-drive-waynesburg-ky-40489-a2b8b6504a09496aa0c48ec9ade27c0d) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/344-oak-drive-waynesburg-ky-40489-a2b8b6504a09496aa0c48ec9ade27c0d#listing", "url": "https://www.propertysimple.ai/listing/344-oak-drive-waynesburg-ky-40489-a2b8b6504a09496aa0c48ec9ade27c0d", "name": "344 Oak Drive, Waynesburg, KY 40489", "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. 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