top of page


3.5 Acre Waterfront Estate with 410' Bulkhead & Dock

2 Charlies Lane, Shelter Island


2 Charlies Lane Shelter Island.jpg


Heroic water views are just the prologue to the story that describes this idyllic 3.5-acre bayfront compound, awash in gentle onshore breezes with a bulkheaded waterfront looking west, southwest over the protected waters of West Neck Harbor. A gated drive welcomes you past a sea of verdant lawn onto the property that is home to a serene residence spanning over 410' of beachfront.

Initially designed by Bertrand Goldberg, a disciple of Frank Lloyd Wright, the one-level, 6,000 SF, 6+ bedroom modern edifice was rebuilt and expanded in 2002 by the extremely talented architect David Schefer and renowned East End builder John Caramagna. Heated stone floors fan out to a living room under soaring mahogany-clad ceilings. Anchored by a dramatic stone fireplace, this three-sided gathering room, while sundrenched by day with a vast liquid backdrop, will transform by evening into the focal point of all your entertaining. The completely outfitted eat-in kitchen with a large center island is more than adequate to service the dining room, large enough for both sides of the family.

2 Charlies Lane Shelter Island


Begin and end your days in the seclusion of your own master wing, offering a sleeping chamber with expansive water views, a seductive lounging area, a spalike bath, and a walk-in closet. Family and fortunate weekend invitees will enjoy five additional bedrooms, including a few with sitting rooms. This stunning retreat is complete with a media room, gym, powder room, and two-car garage.

If needed, the residence could be expanded significantly to support a second level and added living area on the first floor. Outside, both covered and uncovered patios look out to the bay and the 250' dock fashioned from imported Ipe that could accommodate multiple watercraft to ply the protected bay with easy access to the open waters beyond. For those who want a full-service facility for their larger boats, the Island Boatyard & Marina is just minutes away. A rear courtyard enjoys views of the recently built and beautifully conceived 14' X 74' heated pool, smartly designed and insulated for year-round use, and perhaps a future tennis court.

2 Charlies Lane Shelter Island.jpg


A 22,000-gallon underground cistern has permitted environmentally sensitive owners, who worked closely with horticulturalists and skilled gardeners, to cultivate an organic landscape plan that speaks to and supports its natural surroundings, which is environmentally sensitive, pesticide-free with low water usage, which include Long Island native meadow, cedar grove forest, bayside gravel garden and a beach sand fire pit.


Inquire about the one-acre parcel found at the gateway to the estate, currently home to the owners' vegetable garden, which could support that coveted guest house for the weekend overflow or staff needs. With protected views across the bay to the nature preserve of Shell Beach, easy access to both the North and South Forks, as well as proximity to the beaches, shops, and various restaurants that dot the 29 square-mile island oasis, this fully bulkheaded, rare waterfront compound awaits your personal tour. Get Swept Away today

2 Charlies Lane Shelter Island.jpg
2 Charlies Lane Shelter Island.jpg
2 Charlies Lane Shelter Island.jpg


2 Charlies Lane, Shelter Island, is offered at $13,950,000.


For more information or to schedule a private showing, please contact:


Gary DePersia

Licensed Associate Real Estate Broker

The Corcoran Group

T: 516.380.0538



Web Id: 894688

bottom of page