Penelope Moore
Licensed Associate Real Estate Broker
(631) 749-5801
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Home > Listings > 42 Prospect Avenue and 23 Serpentine Drive

42 Prospect Avenue and 23 Serpentine Drive

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Built in 2002, “Treetops”, an AIA Archi Award winning classic modern, possesses arguably the best views on Eastern Long Island to the North Fork, Peconic Bay, Long Island Sound and Connecticut. Designed by noted architect, Frederick Stelle who elaborated on the original building by avant garde architect Peter Schladermundt, who also designed structures for the famed 1964 New York World’s Fair, the home sits at an elevation of 162 feet on “Divinity Hill” in Shelter Island Heights, one of the highest points on Shelter Island. The concept consists of two volumes joined by a glass pavilion and a few select materials including stone, steel and glass, used in pure and elegant ways. On the water view side, there is a pavilion offering unobstructed views, wrapped in 9-foot high walls of glass spanning from floor to ceiling, punctuated by anodized aluminum windows, hand made aluminum in-laid moulding and solid core doors. The main living area offers an open layout with fireplace, radiant heat floors, screened dining area with access to outdoor dining, built in barbecue deck, elevated kitchen with Poliform cabinets and above standard appliances, butler’s pantry, family room with fireplace, powder room, laundry, office/library and first floor en-suite bedroom. A delicate, open bluestone stairway with treads suspended one inch from a glass wall allows light from 19-foot-tall acid-etched glass windows to filter between the materials, offering a graceful ascent to the master bedroom, an aerie above the treetops. With a covered rooftop terrace, steam shower, soaking tub and Scandinavian propane stove, it provides the ultimate in privacy. The at-grade lower level has recently installed travertine floors, guest bedroom with doors to the pool, mirrored gym-exercise area, Finnleo sauna, full bath, second laundry area, walk in cedar closet, Eurocave 150 bottle wine cooler, and Sub-Zero side by side refrigerator-freezer. A 57-foot freeform heated Gunite pool with recently installed Arizona buff stone is framed by picturesque perennials with paths to a separate garden with multilevel decking in bluestone and grandfathered steel cord rails. Hamptons Cottages & Gardens wrote, “This place is indeed divine, not only in the sense of ‘oh how divine’ but also in its distinctive sense of other worldliness. Here the air, the light, the very atmosphere, feels celestial. Clouds floating by overhead appear within reach and the sunsets are cinematic events.” A rare offering on Shelter Island, which includes a protective vegetative buffer. 2020 annual Heights water, sewer, highway and beach club fees are for 42 Prospect Ave. $4314.35 and 23 Serpentine Dr. $177.56

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Property Details

Price: $8,100,000
Address: 42 Prospect Avenue and 23 Serpentine Drive
City: Shelter Island Heights
State: NY
Zip: 11965
MLS#: 10914673
Pool: Yes
Waterfront: Yes
Beds: 3
Baths: 3.5
Square Feet: 4133
Garage: n/a
Year Built: 2002
Acres: 3.41
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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