About this home

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.

Facts and features

Schools

• Riverhead Senior High School

  high · 9-12 · 2.5 mi

  3

• Riverhead Middle School

  middle · 6-8 · 2.6 mi

  3

• Pulaski Street Elementary School

  elementary · 5-6 · 2.9 mi

  2

• St Isidore School

  elementary · PK-8 · 2.5 mi

• St John Paul II Regional School

  elementary · K-8 · 2.5 mi

• Riley Avenue School

  elementary · K-4 · 1.0 mi

  2

Price history

• Sep 8, 2026 · Listed$2,490,000
• Jan 23, 2025 · Sold$1,650,000
• Aug 6, 2024 · Sold$1,650,000
• Nov 7, 2023 · Price Changed$1,900,000
• Jun 24, 2023 · Price Changed$2,500,000
• Jun 4, 2023 · Listing Removed$5,800,000
• May 14, 2023 · Price Changed$3,500,000
• Jan 19, 2023 · Price Changed$2,750,000

Tax history

• 2026$23,613 tax · $102,700 assessed
• 2025$23,613 tax · $102,700 assessed
• 2024$18,386 tax · $102,700 assessed
• 2023$14,461 tax · $102,700 assessed
• 2022$14,453 tax · $102,700 assessed
• 2021$14,072 tax · $102,700 assessed
• 2020$13,561 tax · $102,700 assessed
• 2018$13,551 tax · $102,700 assessed

Home value

$2,465,000

• Collateral Analytics$2,465,000
• Quantarium$2,294,052

Where it is