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.
Luxury. Location. Lifestyle. Your North Fork escape starts here.
An ultra-rare 2-bedroom, 2-bathroom ground-floor corner residence in one of the North Fork Wine Trail’s most desirable waterfront communities. Enjoy expanded outdoor living space, water views, exceptional proximity to the private beach, and the added privacy of a corner unit in one of the quietest buildings in the community—all while being perfectly positioned to enjoy everything the North Fork has to offer.
Enjoy relaxing nights by the fire or listening to records in the chic living room. Immerse yourself in the feel of a luxury hotel in your primary bedroom with a designer-quality ensuite bath complete with spa tub. Work in style or be the ultimate host with a secondary room that is easily convertible between office and guest quarters. Watch TV on the lanai, classic North Fork sunsets from the patio, and the abundance of wildlife in your backyard during cozy fall evenings.
The amenities make every day feel like a getaway, with a private beach, swimming pool, tennis courts, pickleball courts, and fitness center right at your fingertips.
Offered fully furnished and ready from Day 1 – this is a TRUE TURNKEY retreat equally suited as your full-time North Fork home, vacation escape, or a potential rental opportunity. Thoughtfully designed with an elevated coastal aesthetic and unmistakable North Fork flair, this is more than a home—it’s an opportunity to start living the lifestyle you’ve been waiting for.
Ever Dreamed of Owning a Vacation Home on Long Island? Now you can. This Charming Well Maintained Cottage offers Numerous Recent Updates Including Updated Electric, Plumbing, Washer & Dryer in New Cedar Enclosure, Custom Cedar Outdoor Shower With Sleek Black Stone Accents & Fixtures, New Retaining Walls, Parking for 2-3 Vehicles, Ample Outdoor Entertaining Area on your Covered Porch. Inside You will find Clean White Cabinetry, & an Open & Airy Living Space along with Two Bedrooms & a Full Bath w/Shower Stall. Private Beach access is just around the corner. Just an hour & 15 minutes from the NYC & With no shortage of Local Activities you will not be disappointed in with this Location. Located inside Desirable Seasonal Beachfront Community of Woodcliff park open April 15 -October 15. Cash Sales Only. Land is leased and not included in sale. Local attractions include: Beach, Golfing, Horseback Riding, Farm Stands, Wineries, Splash Splash Water Park, Aquarium, Outlet Shopping, & More!
NESTLED ON LONG ISLANDS NORTH SHORE BLUFF~ THIS LITTLE SLICE OF HEAVEN OFFERS THE TRANQUIL SOUND OF THE WATER WASHING ASHORE, UNOBSTRUCTED BREATHTAKING WATER-VIEWS AND BEACH VIEWS, This home was renovated in 2014 and additional Renovations done including Windows, & Sliders Added in 2023 to Accentuate THE WATERVIEWS. NEW ROOF, Updated Eat In kitchen W/White Cabinetry, Granite Counters, Subway Tile Back Splash, Updated Bathroom accented with Shiplap, Engineered Wide plank White Oak Floors, Vaulted Rustic Beamed Ceilings for the authentic cottage feel, Mini Split for Heat & air, Double SLIDERS to New entertainers Deck Also w/Wide Plank Boards, Stackable washer/Dryer, New Stove, New White Storage Cabinetry, 2 Sofas, & Captains Bed with Storage, Exterior Painted 2021 in a Soothing Blue Tone, Interior Freshly Painted 2024, Additional Tiered Deck Off Side for Sunbathing, Rose Bushes & Perennial Plantings offer charm & make it feel like home. Furnished & Ready to Use. Only 1 Hour & 15 Minutes to NYC. Jitney Bus is only 8 Minute Drive from Community. Community is Seasonal open April 15-October 15. Land is Leased at approximately $12,896 annually. Short term rentals Prohibited. Was two separate bedrooms but currently walls down and set up as Open Concept. Could be put back up., Additional information: Appearance:Mint
