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Hamptons.com
April 16, 2025

Shelter Island Award-Winning Modern With Unparalleled Views

Hamptons.comby Hamptons.com
in Real Estate, Trending
Home Real Estate

42 Prospect Avenue + Part 23 Serpentine Drive, Shelter Island, NY 11964
Saunders Exclusive: $7,950,000
View Listing

Built in 2002, “Treetops” is an AIA Archi Award-winning modern classic that boasts some of the most sweeping and unobstructed views on Eastern Long Island—stretching across the North Fork, Peconic Bay, Long Island Sound, and reaching to Connecticut.

Positioned at 162 feet above sea level on “Divinity Hill” in Shelter Island Heights, it sits at one of the island’s highest natural elevations.

The home is the result of a thoughtful evolution of an original design by Peter Schladermundt, renowned for his iconic structures at the 1964 New York World’s Fair, brought to its current form by noted architect Frederick Stelle.

The architectural concept centers around two clean-lined volumes joined by a glass pavilion, using a restrained palette of stone, steel, and glass, executed with clarity and elegance.

 

On the view-facing side of the home, a dramatic pavilion wrapped in 9-foot floor-to-ceiling glass walls provides unobstructed vistas. These are framed with anodized aluminum windows, hand-laid aluminum inlay mouldings, and solid core doors that reflect the home’s refined craftsmanship.

The main living area is open, featuring a fireplace, radiant heat floors, a screened dining area, and access to two decks, one with a built-in barbecue.

An elevated kitchen is outfitted with Poliform cabinetry, high-end appliances, and a butler’s pantry.

Additional spaces on this level include a family room with Scandinavian fireplace, powder room, laundry, office/library, and a first-floor en-suite guest bedroom.

A sculptural bluestone staircase, with treads subtly suspended one inch from a glass wall, rises beside 19-foot acid-etched glass windows, filtering natural light through the space, offering a graceful ascent to the primary en-suite bedroom.

An aerie above the canopy of treetops, this suite features a covered rooftop terrace, steam shower, soaking tub, and a Scandinavian propane stove, offering a serene and secluded experience.

The at-grade lower level includes recently installed travertine flooring, a guest bedroom with direct access to the pool area, a mirrored gym/exercise studio, Finnleo sauna, full bath, second laundry area, walk-in cedar closet, Eurocave 150-bottle wine cooler, and a Sub-Zero side-by-side refrigerator and freezer.

Outdoors, a 57-foot heated freeform Gunite pool is bordered by Arizona buff stone and surrounded by lush perennial gardens. Pathways lead to a separate garden with multilevel bluestone decking and grandfathered steel cord railings, blending natural and architectural elements.

As Hamptons Cottages & Gardens once 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 Shelter Island offering, “Treetops” is as much a sanctuary as it is a landmark, complete with a protective vegetative buffer and unmatched architectural pedigree.

 

PENELOPE A. MOORE
Licensed Associate Real Estate Broker
[email protected]
Cell: (917) 208-5519

 

For more information, Click Here

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LOCAL EVENTS

Events

19
Sep
19
Sep
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19
Sep

SoundWAVE – a bespoke sound bath hosted by WAVE WELLNESS Southampton

September 19 @ 05:45 PM - September 19 @ 06:45 PM
15b Hill Street Southampton NY
19
Sep
19
Sep
-
19
Sep

Dynamic Duos of the East End

September 19 @ 06:00 PM - September 19 @ 07:30 PM
830 Springs Fireplace Rd, East Hampton, NY 11937
19
Sep
19
Sep
-
19
Sep

Splitsville: Special Q&A with Director/Star Michael Covino

September 19 @ 07:30 PM - September 19 @ 10:00 PM
Sunset Theater - 2 Brook Rd, Westhampton Beach, NY 11978
19
Sep
19
Sep
-
19
Sep

Local Motion at The Stephen Talkhouse

September 19 @ 08:00 PM - September 19 @ 08:30 PM
161 Main St, Amagansett, NY 11930
20
Sep
20
Sep
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20
Sep

Honey Harvesting with Master Beekeeper (Cutchogue)

September 20 @ 10:00 AM - September 20 @ 12:00 PM
Downs Farm Preserve | 23800 Main Road Cutchogue, NY, 11935 United States
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2025 Long Island Restaurant Week: Spring Edition Guide

2025 Long Island Restaurant Week: Spring Edition Guide

  • Whether you are walking the fast-paced streets of New York City or taking a leisurely beach stroll in the Hamptons, there’s a slight chance you might run into Elias Friedman, known online as “The Dogist.” His adoration of dogs, combined with his passion for photography, has led him to gain over 7 million followers on Instagram. The audience at his recent Guild Hall show reflects how much people truly love their dogs and how Elias does so much more than simply take picture-perfect dog portraits. He can capture the beautiful bond between man and his best friend. His book, This Dog Will Change Your Life, is already a New York Times bestseller. Guild Hall’s lobby was filled with fans excited to get their copy signed.⁠
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His guests included local dog lovers and friends of ARF (Animal Rescue Fund of the Hamptons). Attendees had front-row seats to a “Dogist”-style encounter: a casual conversation about how the dog entered the owner’s life, followed by a quick photo shoot revealing Elias’ methods for capturing the dog’s attention (hint: It’s dog noises and treats).⁠
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I had the pleasure of talking to Elias about how “The Dogist” came to be, rescue organizations, and the Hamptons.⁠
⁠
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Let’s go back to the beginning. What inspired you to dive into photography?⁠
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We had a dark room because my dad was an amateur photographer, and I’d always liked cameras and gadgets. We had a couple of Labrador retrievers who were sort of my first muses and would happily sit for pictures. I was taking dog pictures from a young age and then fast forward to 2012 in New York City I was let go from my job and saw what other street photographers were doing like Humans of New York and The Sartorialist and thought why isn’t someone doing that for dogs and I thought I wanted to be the person, I dusted off my camera and the rest is kind of history. It took off pretty quickly because it turns out people like dogs just as much as I do.⁠
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Read the full interview at Hamptons.com (Link in Bio)⁠
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#dogist #arf #dogs #animalrescue #guildhall #hamptons
  • 167 Dune Road, Bridgehampton, NY 11932⁠
Saunders Exclusive: $42,500,000⁠
@jenniferwilsonhamptons 
@edbruehl @leemohlerehamptons 
@hamptonsrealestate 
⁠
Experience extraordinary coastal living with this exquisite oceanfront estate on Dune Road in Bridgehampton. ⁠
⁠
Designed by the renowned architect Francis Fleetwood, this remarkable property boasts 300 feet of private ocean frontage, complete with its own private boardwalk leading directly to the beach, all set on over 3 acres of prime land.⁠
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The charming shingle-style residence encompasses 4,200 +/- sq. ft. of luxurious living space, featuring 5 bedrooms and 5 full bathrooms, plus an additional half bath.⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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#duneroad #oceanfront #bridgehampton #realestate #hamptons #francisfleetwood ⁠
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  • The Hamptons have seen their fair share of collaborations and takeovers this summer. Still, nothing compares to The h.wood Group and Chase Sapphire Reserve’s transformation of Montauk hotspot Mary Lou’s into Delilah Montauk.⁠
⁠
The four-day takeover combined unforgettable dining experiences with show-stopping live entertainment featuring performances by Zack Bia, Alesso, Gwen Stefani, and DJ Pee.Wee (Anderson Paak). ⁠
⁠
Exclusively for Chase Sapphire Reserve cardholders, diners were treated to white glove hospitality and Delilah’s staples, including the famous chicken tenders and tuna tartare, and bold twists on Hamptons classics like lobster rolls, striped bass crudo, and crab and avocado toast. 

Check out more at Hamptons.com (Link in Bio)

#gwenstefani #alesso #djpeewee #chasesapphirereserve #delilahmontauk #montauk #hamptons
  • LVIS thrift shops are open Tuesdays through Saturdays 10 AM through 5 PM

donations are accepted Wednesday through Saturday 10 AM through 1 PM by appointment 

located at 95 Main St East Hampton
  • Check out the Top Hamptons Events This Weekend!⁠
⁠
🚗 The Bridge IX⁠
📅 Sat, Sept 13 | 2–7PM⁠
📍 The Bridge, Bridgehampton⁠
Over 300 rare automobiles showcased across stunning landscapes.⁠
⁠
🎬 23rd Annual Surf Movie Night⁠
📅 Fri, Sept 12 | 5:30–9PM⁠
📍 Southampton Arts Center⁠
Surfboard swap, live music & outdoor film screening. 🌊⁠
⁠
🍝 San Gennaro Feast of the Hamptons⁠
📅 Sat, Sept 13 – Sun, Sept 14 | 10AM⁠
📍 Hampton Bays⁠
Italian pastries, live entertainment & fireworks Sat @ 8:15PM 🎆⁠
⁠
🎭 In Process: Roderick George⁠
📅 Sat, Sept 13 | 7PM⁠
📍 Guild Hall, East Hampton⁠
A special in-process presentation of The Missing Fruit (Part I).⁠
⁠
🎤 Sheena Easton at WHBPAC⁠
📅 Sat, Sept 13 | 8PM⁠
📍 Westhampton Beach PAC⁠
Grammy-winning artist live on stage!⁠
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☕ Cars & Coffee⁠
📅 Sun, Sept 14 | 9–11AM⁠
📍 Bridgehampton Museum⁠
Classic & exotic cars, food, drinks & live music.⁠
⁠
🛍 Hampton Vintage⁠
📅 Sun, Sept 14 | 10AM–5PM⁠
📍 Westhampton Beach Village Green⁠
Shop unique vintage finds!⁠
⁠
🎶 Hamptons Festival of Music Finale⁠
📅 Sun, Sept 14 | 4PM⁠
📍 St. Luke’s Church, East Hampton⁠
Featuring Cimarosa, Berlioz & Beethoven.⁠
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🍷 Wine Dinner with Pradorey at R.AIRE⁠
📅 Tues, Sept 16 | 6:30PM⁠
📍 Hampton Bays⁠
Five-course tasting menu with exquisite wine pairings.⁠
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🎥 Toy Story 30th Anniversary Screening⁠
📅 Sept 12–15 | Various Times⁠
📍 Southampton Playhouse⁠
Celebrate Woody & Buzz’s timeless adventure!⁠
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Check out more events at Hamptons.com (Link in Bio)⁠
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#carshow #hamptons #sangennaro #sangennarofeast #winedinner #bridgeIX
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