This meticulously crafted Shelter Island approximately 8.45-acre estate property is currently configured with three substantial structures: a three bedroom, four bath primary residence, a two-car carriage house with loft apartment, and a three-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, an approximately 3,225 square foot country home featuring three en suite bedrooms and four 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 three 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.