Some properties are defined by what they include. This one is defined by what cannot be built again.
Officially designated as a Horse Farm on the Town of Riverhead’s assessment roll, 291 Deep Hole Road stands apart not by virtue of size alone — but because the combination it represents is no longer achievable. Current zoning and permitting conditions across Long Island’s East End have effectively closed the door on new construction of a residence of this scale on an agriculturally classified parcel. What exists here exists permanently, and on its own terms.
The Hollenbeck-designed, MAB Custom Built residence commands its 5.1 acres with quiet authority. Eighteen-foot ceilings draw the eye upward through sun-filled open volumes shaped by a passive solar philosophy — spaces that live generously across all seasons, grounded by Mexican terra cotta flooring and anchored by two fireplaces. The primary suite occupies its own world within the home: angled high ceilings, a southern and western exposure calibrated for year-round light, and glass sliders opening to dual private decks above the grounds. Four bedrooms, three and a half bathrooms, a four-car garage with nine-foot clearance — every element scaled to the life this property supports.
The equestrian infrastructure needs no embellishment. A 42 x 70 foot Morton barn — twelve rooftop skylights, insulated roof, six 10 x 12 stalls, dedicated tack room — serves rolling, fenced, and gated pastures backed by a natural southern woodland line that will never be developed. At the center of the operation: an 80 x 120 foot indoor riding arena, purpose-built, professional in every dimension, and irreplaceable in today’s regulatory environment.
This is not a property that competes. It occupies a category of its own on the North Fork.