On the premier estate lane with sweeping views over Peconic Bay, is a world-class home that transcends time and sets itself apart on all levels. This landmark residence rises from the head of a bluff with lush "green lawns" rolling from the wraparound porch to the shores of the Shelter Island Sound. Its flag pole is the mast from the vessel Sir Thomas Lipton raced in the 1930s for the America's Cup and an impressive maple tree by the entrance is a reminder of the long history this special home has lived. Built in 1880, this Queen Anne-style house is sited on 4.8+/- sound front acres with 400+ feet of water frontage, and an 80 foot L-shaped dock with a romantic boat house perfect for relaxing. The three-story 7000+ sq. ft. main house offers 7 bedrooms and 7 baths, living room with fireplace, multiple sitting rooms for both formal and informal gatherings, dining room with exquisite hand drawn etchings and chef's eat-in kitchen which gives to the round dining cabana. The windmill guest house has an entertainment level and guest suite with kitchen and living/dining area. The park-like grounds feature a waterside heated gunite pool with gazebo, spa, basketball court and har-tru tennis. With the most breathtaking sunsets and sumptuous water views, this gated property offers total privacy evoking quintessential Shelter Island beauty.
On the North Fork of Long Island, there's a place, where horses race, grapes ripen in the sun, livestock roam the pastures and everlasting memories are made. This breathtaking place, is called Big E Farm. What started as a thoroughbred horse farm, has evolved into 200 acres that possess incredibly diverse characteristics. Suitable for elegant country living, venue for social functions, corporate retreats, or a fully operational Award Winning Vineyard. 113 acres under vine - Certified Sustainable, 17 buildings, including 9 barns, Wine Club Gallery, Event Gallery, Tasting Room, Culinary Education Center and 3 cottages. In addition to all that is the Manor House which features professional chefs kitchen, commercial baking room, club room, 5 bedrooms including master suite w/ his and hers bathroom and closet, additional 4.5 baths, 4 fireplaces, foyer/solarium, porte-cochere, elevator, full basement with therapy/fitness pool, sauna, spa room, exercise room and wine cellar. Big E farm, where each day is an adventure, each night a celebration. Let your vision unfold... #120843
Cutchogue - Set on a bluff on coveted Oregon Road and overlooking the Long Island Sound, a rare offering of one of the most beautiful and private waterfront estates on the North Fork. Sold only in its entirety, it is comprised of a 10+ acre parcel with an elegant waterfront home and pool, an additional three waterfront parcels totaling approximately 111 acres with development rights intact, and a fifth 26+ acre reserve parcel planted with varietal vines. The home offers water views from all rooms, three bedrooms and three full baths including an expansive master suite, a gracious living room with fireplace, formal dining room, kitchen with breakfast area, and a high-ceilinged sunroom opening to multiple decks overlooking the pool, a broad lawn and the Long Island Sound beyond. With 1390+- feet of beach this is a truly majestic 147.5+- acres estate in an exquisite natural setting.
Located in Shelter Island's sought-after Dering Harbor, this stately 8 bedroom 8 bath Colonial built in 1930 exudes old world elegance and sits on 2 sprawling parklike acres. Face the soothing Sound on your own private waterfront retreat featuring a 312'-long dock (the longest on Shelter Island) with 4 platforms, and a one-of-a-kind 2725 sq ft waterside cabana that will thrill any boat lover and entertaining enthusiast. Welcoming you into the grand 3-story, 8000 sq ft residence is a large entry foyer with a graceful staircase that ascends to the airy second-level landing. Adorning the expansive formal rooms are classic moldings, rich hardwood floors, oversized windows, beautiful built-ins and fireplaces. The generously-sized living quarters offer versatility of use for a home office, library and den. Other highlights of this massive home include a lovely screened porch, and 4 car garage.
Dering Harbor is a sought-after community that lies on the north side of Shelter Island facing Greenport. The village and picturesque harbor that separates it from Shelter Island Heights were named after Thomas Dering, a prominent Boston merchant who married Mary Sylvester of Shelter Island's founding family on March 9, 1756. Dering became the town's second supervisor and went on to become a prominent member of the new nation's Congress, a supporter of the Declaration of Independence and member of the convention that forged New York's first state constitution. Dering Harbor was established on the site where the legendary Manhanset House hotel stood from 1874 to 1910 when it was destroyed by fire. Wealthy cottagers who lived around the hotel purchased the hotel site and formed the village in 1916. This is an amazing opportunity to own a piece of history and private haven on the water.