Penelope Moore
Licensed Associate Real Estate Broker
(631) 749-5801
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Home > Listings > Shelter Island Pondfront with Dual Levels

Shelter Island Pondfront with Dual Levels

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Set on the gentle slope of a spring-fed pond, this Shelter Island residence, similar in ways to a duplex, reveals itself not all at once, but in a series of calm, considered gestures. One enters by way of a circular drive that curves around an old maple and up a short path to a home that understands the value of sunlight, privacy, and practicality. Inside, the main floor offers a living room where light from the west falls generously across books, armchairs, and a raised stone fireplace. A modest kitchen, thoughtfully arranged, adjoins a small breakfast area, a fine place for morning coffee and a quiet view. Down the hall, the primary bedroom includes its own bath, set apart in a way that grants quiet. At the rear of the house, a library lined with built-ins opens to a deck overlooking the water, where the pond’s surface shifts with wind and the passage of sunlight. Below, the lower level is wholly its own space – not merely an extension of the upstairs, but a dwelling with purpose. A living room, dining nook, full kitchen (one of two legally established in the house), bedroom, and bath occupy this floor, with sliding doors that open to a hidden stretch of land and a view that belongs almost entirely to ducks, frogs, turtles, and the birds that stop in from nearby Sachem’s Woods. The pond has its own rhythm; Spring-fed and self-sustaining, it hums with life. And while the property is not far from the ferry, from shops, or from the beach, it feels content to exist slightly apart, offering its new owner not just a house, but a setting in which to think, observe, and live quietly among living things.

Property Details

Price: $1,675,000
Address: 66A North Midway Road
City: Shelter Island
State: NY
Zip: 11964
MLS#: 11502807
Pool: No
Waterfront: Yes
Beds: 2
Baths: 3
Square Feet: 1488
Garage: Attached, 2 spaces
Year Built: 1976, Reno 2017
Acres: 1.00
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.

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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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