This meticulously crafted Shelter Island 8.12 +/- acre estate property is currently configured with 3 substantial structures: a 3 bedroom, 4 bath primary residence, a 2-car carriage house with loft apartment, and a 3-stall horse barn with tack room and loft space. This is a rare opportunity to live your equestrian dreams or reimagine this C-Zone property as a sprawling compound with commercial/work options. The property can be subdivided into separate parcels. The pastures, paddocks, and cedar groves make this a true gem for horse enthusiasts, a compound with multiple dwelling options or a gym/yoga, art studio, or light commercial/work spaces. The centerpiece of this remarkable estate is the main residence, a 3,225 +/- af country home featuring 3 ensuite bedrooms and 4 bathrooms. The home also features a formal dining room, entryway, main floor laundry, and ample size living room. Also on the first floor, the primary suite features a beautiful sunroom with radiant heat floors, a large dressing room, and an extra-large ensuite bathroom with a soaking tub. The second floor hosts two ensuite bedrooms and a bonus media/lounge room as an optional 4th bedroom with high ceilings. The finished expansive lower level with a full bath is a walkout to the rolling property. Above the two-car garage, there is a loft space with high ceilings, a balcony overlooking the 18 x 44 gunite pool with a waterfall, a kitchen, and a full bathroom. In addition, the property has a functional horse barn with 3 stalls, a tack room, and loft space. This expansive Shelter Island property represents a rare opportunity to own a world-class equestrian estate in one of the most beautiful and sought-after locations in the region.