Penelope Moore
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(631) 749-5801
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Home > Listings > Shelter Island Waterfront with Deep Water Dock

Shelter Island Waterfront with Deep Water Dock

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At the end of a quiet lane, where the northern reaches of the harbor meet branching tributaries of the creek, with views toward a forever-green preserve, this expansive modern waterfront residence occupies an exceptional natural setting. Built upon a grandfathered foundation and renovated in 2026, the house has been conceived around its relationship with the water, with broad expanses of windows and multiple outdoor spaces bringing the surrounding landscape into nearly every part of the home. The entry foyer sets the tone with stone floors and sculptural pendant lighting set into an elevated ceiling well. Beyond, the house opens dramatically to a vaulted great room, where living and dining areas and the kitchen share sweeping water views. The chef’s kitchen combines high-end appliances and custom cabinetry, with distinctive counters embedded with shells and fossils. A guest bedroom and separate office complete the first floor. Upstairs, the landing becomes a comfortable lounge overlooking the living spaces below. Adjacent, there is an en-suite guest bedroom with water views and a skylit ceiling recess with sculptural pendant lighting. Farther along the hall, the primary en-suite bedroom occupies its own distinct wing, with a spacious spa-like bathroom, an elevated ceiling well inviting additional natural light, and glass doors opening to a dedicated deck. From here, access continues to a dramatic rooftop observation deck, offering an entirely different vantage point from which to take in the surrounding water and landscape. The lower level provides a practical housekeeping area with laundry center and overflow refrigeration, together with an adjacent mechanical room. The 415-sf garage has been partially finished to accommodate a gym and storage for sporting equipment. Outside, an expansive waterfront deck creates a series of places for dining and relaxing, including a shaded dining area, sunken hot tub and outdoor shower, all framed by established gardens. A path continues through the property to the 124+/- foot shoreline which has an 880+/- square foot span of bulkhead, and a 5ft x 90ft deep-water dock with 6×20-foot floating dock, equipped with power and water. Aesthetically connected to its pastoral waterfront setting, this home is designed around making its natural surroundings a part of everyday life. Recent renovations include siding, roof and solar panels. Turnkey and ready for its next chapter.

Property Details

Price: $4,945,000
Address: Undisclosed
City: Shelter Island
State: NY
Zip: 11964
MLS#: 11938578
Pool: No
Waterfront: Yes
Beds: 4
Baths: 3.5
Square Feet: 2407
Garage: Detached, 2 spaces
Year Built: 1954, Reno 2026
Acres: .43
Status: Active

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Penelope Moore

Penelope Moore

Since 1998, Penelope has been the driving force and leader in the Shelter Island real estate market, and is the go-to real estate broker for discerning buyers and sellers. She has experienced record-breaking sales in multiple categories over successive years, and her success has been distinguished not just by benchmark sales, but by volume in all categories.

Meet Penelope

Penelope Moore, Licensed Associate Real Estate Broker

9 Grand Avenue, PO Box 100
Shelter Island Heights, NY 11965-0100

(631) 749-5801
(917) 208-5519 Mobile

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