Penelope Moore
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Home > Listings > Quiet Shelter Island Renovated Cottage with Arboretum

Quiet Shelter Island Renovated Cottage with Arboretum

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Perched at the top of a gentle driveway on 2.3+/- quiet gated acres in Shelter Island’s estate section, this recently renovated 1954 cottage rests on a rise with visual advantages, surrounded by a landscape that has been nurtured with care and intention. The property is the result of years of dedicated stewardship by its current owners, who have propagated seeds collected from notable gardens across the country, cultivating an environment where native species and subtle beauty thrive. Winding paths lead through a setting where turkey hens nest undisturbed and turtles can often be seen on unhurried strolls. Indigenous orchids, documented by the Long Island Botanical Society, bloom quietly among oak, linden, beech, conifers and flowering perennial shrubs. An enclosed, raised vegetable garden is just beyond a shaded meditation area and is designed for seasonal harvests. The atmosphere is one of calm, a setting for contemplation and connection to the natural world – and just a short distance from sandy beaches and resort amenities. The single-story cottage is welcoming, with sunlit living and dining areas with natural pine overlooking the gardens and outdoor entertainment decks. A wood-burning Godin poêle anchors the common space, while the kitchen, updated in 2025, features granite countertops, custom cabinetry, and access to a deck that is well-suited to outdoor meals or quiet reflection. On one end of the home is a private bedroom with a half bath, and on the other, two additional bedrooms with a full bath, recently renovated. A full basement with garage access provides ample storage, functional space and future finishing possibilities. 2024-2025 renovations include: roof, siding, windows, kitchen, central air and bathroom. Located just a stone’s throw from the Pridwin Hotel, the Perlman Music Program, and the Crescent Beach, this home offers not just a place to live, but a place to observe, to preserve, and to appreciate the land and its quiet stories.

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Property Details

Price: $1,845,000
Address: 26 Rocky Point Road
City: Shelter Island
State: NY
Zip: 11964
MLS#: 11502766
Pool: No
Waterfront: No
Beds: 3
Baths: 1 Full, 1 Half
Square Feet: 1344
Garage: Yes, 2 spaces
Year Built: 1954, Reno 2025
Acres: 2.30
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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