Penelope Moore
Licensed Associate Real Estate Broker
(631) 749-5801
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Home > Listings > Shelter Island Hidden Waterfront Traditional

Shelter Island Hidden Waterfront Traditional

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Set on 1.19± acres overlooking Fresh Pond, this traditional offers privacy, an elevated position overlooking the water, and southwest-facing light with sunset views. Largely hidden from the road, the property enjoys a quiet setting above one of Shelter Island’s treasured glacial freshwater ponds. A gravel circular drive approaches the cedar-shingled façade, framed by established landscaping and gabled rooflines. The interior has been updated in 2026, including refinished floors, renovated bathrooms, refreshed exteriors and freshly painted interiors. A gracious entry is framed by a covered porch and a central Palladian-style window above the front door, bringing natural light into the foyer and halls. The double-height living room is imbued with natural light from a wall of windows and glass doors, creating an open yet grounded gathering space centered on a fireplace with custom built-ins. Above, a connecting balcony spans the room, linking the upper level while maintaining a sense of separation between the bedroom wings. The kitchen includes a center prep island and a breakfast bar, with an adjacent dining area facing the pond. A laundry room and powder room are set just off the kitchen, with convenient access to the attached two-car garage. The first-floor primary bedroom includes a renovated bath and walk-in closet. Upstairs, two additional bedrooms reflect the home’s architecture, with varied ceiling lines that add dimension. The lower level has a finished office with separate entrance and an unfinished area with waterside windows that are ready for finishing. Outdoor amenities include a hot tub overlooking the water and a screened gazebo positioned for relaxed afternoons or casual gatherings. A path leads down to the pond and dock, offering access to the shoreline and the surrounding landscape.

Property Details

Price: $3,250,000
Address: 28 Lake Drive
City: Shelter Island
State: NY
Zip: 11964
MLS#: 11684925
Pool: No
Waterfront: Yes
Beds: 3
Baths: 2.5
Square Feet: 2300
Garage: Attached, 2 spaces
Year Built: 1998, Reno 2026
Acres: 1.19
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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