299 South Road

Tucked away at the end of a long, private drive just 15 minutes from historic Kingston and 90 miles from New York City, this exceptional 24 acre compound offers a rare intersection of sleek contemporary architecture, tranquil natural beauty, and unmatched utilitarian luxury. Whether you are seeking a serene country sanctuary or a world-class estate to house a prized automotive collection, this property delivers on every level. The heart of the property is a striking 2-bedroom, 2-bathroom contemporary home designed to pull the outdoors in. Clean lines, expansive windows, and open-concept living spaces frame views of your own private pond. The main level offers an effortless flow between the high-end kitchen and the airy living spaces--perfect for intimate weekends or stylish entertaining. A custom stone fireplace runs floor to ceiling. The first floor primary has ensuite bath with radiant floors and walks out to a deck overlooking the pond. A full, finished basement with murphy bed expands the footprint significantly, offering flexible space ideal for a media room, home gym, wine cellar, or a quiet wellness studio. Recent upgrades include new roof and gutters, furnace and hot water heater. Directly above the attached two car garage sits a bright, fully independent apartment. Featuring its own separate entrance, this auxiliary unit is perfect as a high-earning rental, a private writer's retreat, or a dedicated luxury suite for hosting weekend guests from the city. The Automotive Pavilion & Guest Apartment For the enthusiast, the detached 5-bay garage is a crown jewel. Far beyond standard storage, this space features professional-grade infrastructure, including a hydraulic lift, soaring ceilings, and ample room for workshop customization or multi-car staging. Year round comfort with heat and a/c. The Acreage & Location Outside, 24 pristine acres of mature woodlands offer total seclusion. Spend your mornings drinking coffee by the pond, exploring your private woods, or enjoying the local culture. The whole house generator brings peace of mind. Positioned just moments from Kingston's vibrant waterfront, boutique shops, and dining, you enjoy the absolute best of upstate privacy without ever feeling isolated. A property of this caliber, infrastructure, and proximity to NYC is a generational find.