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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

22
Jun
22
Jun
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22
Jun

Penny Pond Hike

June 22 @ 09:30 AM - June 22 @ 11:30 AM
Meet at Red Creek Road off Rt 24, Hampton Bays.
22
Jun
22
Jun
-
22
Jun

Hampton Vintage at the Bridgehampton Museum

June 22 @ 10:00 AM - June 22 @ 05:00 PM
2368 Montauk Highway, Bridgehampton, NY, USA
22
Jun
22
Jun
-
22
Jun

The Hamptons Handbag Festival

June 22 @ 10:00 AM - June 22 @ 05:00 PM
American Legion 419 East Hampton, NY
22
Jun
22
Jun
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22
Jun

Screening of HALF NELSON at Sag Harbor Cinema

June 22 @ 11:00 AM - June 22 @ 02:00 PM
Sag Harbor Cinema, 90 Main Street, Sag Harbor, NY 11963
22
Jun
22
Jun
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22
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Upcoming Panel at Guild Hall Explores Legacy of Sculptor John Chamberlain

June 22 @ 02:00 PM - June 22 @ 03:00 PM
Guild Hall
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2025 Long Island Restaurant Week: Spring Edition Guide

2025 Long Island Restaurant Week: Spring Edition Guide

  • Sushi by Boū will offer just eight seats per table, a truly unique and memorable sushi experience inside Sydney’s “Taylor” Made Cuisine in Westhampton Beach. 

@sushibybou_westhampton 

#sushi #omakase #hamptons #dining #westhampton
  • Who’s excited for the Palm Tree Music Festival! ⁠
⁠
Check out the Top Hamptons Events This Weekend!⁠
⁠
🎶 5th Annual Palm Tree Music Festival⁠
📅 Saturday, June 21st | 🕑 2pm – 11pm⁠
📍 Shinnecock Indian Territory, Southampton⁠
🌴 Iconic music + luxury vibes + brand activations.⁠
📸: Rob Rich/SocietyAllure.com ©2025⁠
⁠
🛍️ Female Founders Market at The HUB⁠
📅 Saturday, June 21st | 🕘 9am – 6pm⁠
📍 2183 Montauk Hwy, Bridgehampton⁠
✨ Shop curated female-founded Hamptons brands.⁠
⁠
👡 Dolce Vita Pop-Up in Southampton⁠
📅 June 20–22 | 🕚 11am – 3pm daily⁠
📍 95 Main Street, Southampton⁠
🎨 Art, summer style, and new drops each month!⁠
⁠
👜 Kulson Pop-Up at Sage & Madison⁠
📅 Friday, June 20th | 🕒 3pm – 6pm⁠
📍 31 Madison Street, Sag Harbor⁠
🥂 Sip + shop Kulson’s Summer Capsule Collection.⁠
⁠
🍦 BuddhaBerry x Stocked Pop-Up⁠
📅 Friday, June 20th | 🕛 12pm – 5pm⁠
📍 125 Main St, Sag Harbor⁠
🍪 Salted cookie + froyo collab = YUM.⁠
⁠
👜 Hamptons Handbag Festival⁠
📅 Sunday, June 22nd | 🕙 10am – 5pm⁠
📍 15 Montauk Hwy, East Hampton⁠
👜 From vintage to designer. All price points.⁠
⁠
📚 Author Talk: Nellie Sciutto⁠
📅 Saturday, June 21st | 🕕 6pm – 7:30pm⁠
📍 East Hampton Library⁠
🎬 Hear Hollywood tales + get your book signed!⁠
⁠
🎭 Colin Quinn at WHBPAC⁠
📅 Friday, June 20th | 🕗 8pm⁠
📍 76 Main St, Westhampton Beach⁠
😂 Big laughs with the comedy legend.⁠
⁠
🎶 Ghost-Note at Talkhouse⁠
📅 Saturday, June 21st | 🕗 8pm⁠
📍 Stephen Talkhouse, Amagansett⁠
🔥 Don’t miss this epic jam session.⁠
⁠
🥾 Penny Pond Hike⁠
📅 Sunday, June 22nd | 🕤 9:30am – 11:30am⁠
📍 Meet at Red Creek Rd, Hampton Bays⁠
🌲 A beautiful trail to start your Sunday.⁠
⁠
Check out more events at Hamptons.com (Link in Bio)⁠
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#palmtreemusicfestival #hamptons #colinquinn #hub #dolcevita #weekend
  • Hosted in the Hamptons at Calissa, Ja Rule showed off his mixology skills, livin’ it up and serving craft cocktails from Amber & Opal as the premium whiskey brand launched in the Hamptons. 

@jarule 
@calissahamptons 
@amberopalspirits 

#jarule #whiskey #hamptons #calissa #hamptonsweekend #hamptonsevents
  • 24 Saddle Lane, East Hampton, NY 11937⁠
Saunders Exclusive: $2,795,000⁠
⁠
@hamptonsrealestate ⁠
@jenniferwilsonhamptons⁠
@edbruehl⁠
@edmondzenuni_⁠
⁠
This stunning contemporary home redefines modern living with its clean lines, dramatic vaulted ceilings, and walls of glass that flood the interior with natural light. ⁠
⁠
Fully renovated in 2016, the open-concept living area seamlessly blends indoor and outdoor spaces, creating an entertainer’s paradise.⁠
⁠
Imagine hosting gatherings on the expansive deck overlooking the heated pool and spa, or enjoying more intimate moments in the screened porch.⁠
⁠
Read the full article at Hamptons.com (Link in Bio)⁠
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#hamptonsrealestate #easthampton #hamptons #realestate⁠
  • Check out the Top Hamptons Events This Weekend!

🎤 Ja Rule Bar Takeover at Calissa
🗓️ Friday, June 13 | 7–9PM
📍 Calissa, Water Mill
Hip-hop icon Ja Rule takes over the bar to celebrate the launch of his new whiskey, Amber & Opal.
📸 Phillip Faraone/Getty Images for AVA Resort
#calissahamptons #jarule #amberandopal

🍷 Mavericks Montauk Winemaker Dinner
🗓️ Friday, June 13 | 6PM
📍 Mavericks, Montauk
Kick off the Summer Winemaker Dinner Series with Christophe Renard of Domaines Ott.
📸 Photo Credit: Michelle McSwain
#mavericksmontauk #domainesott #winemakerdinner

🌸 Hampton Water Rosé Day Tour
🗓️ Saturday, June 14 | 1–7PM
📍 Bounce Beach, Montauk
Show up in pink and celebrate National Rosé Day with tastings, giveaways & more.
#hamptonwater #roséday #montaukevents

🏃 Beacon of Hope 5K Run/Walk
🗓️ Saturday, June 14 | 9AM
📍 Camp Hero to Montauk Lighthouse
Support awareness and hope on this scenic 5K through Camp Hero.
#beaconofhope5k #montauklighthouse

📚 Book Signing with Julianne Moore & Jesse Eisenberg
🗓️ Saturday, June 14 | 3–4PM
📍 Southampton Playhouse
A special family reading and signing with two stars and authors.
#julianneMoore #jesseeisenberg #southamptonny

🐶 ARF’s Rescues & Rosé
🗓️ Saturday, June 14 | 4–7PM
📍 ARF, East Hampton
Rescue dogs + rosé = summer magic.
#arfhamptons #rescuesandrosé #eastenddogs

🎨 Father’s Day Arts & Crafts Fair
🗓️ Saturday, June 14 | 9AM
📍 Marine Park Drive, Sag Harbor
Shop handmade jewelry, furniture, paintings, home goods, and more.
#sagharborarts #hamptonscraftfair

🍋 Lucky One Lemonade Launch w/ Miss Peaches
🗓️ Saturday, June 14 | 2PM
📍 Shark Bar, Montauk
Meet adoptable dogs and sip dog-lover-approved lemonade.
#misspeaches #southamptonanimalshelter #sharkbarmontauk

🛍️ Alice + Olivia Sip & Shop
🗓️ Saturday, June 14 | 4–6PM
📍 68 Main Street, Southampton
Hosted by Sydney Sadick & Sylvia Hemingway to benefit SAC.
#aliceandolivia #sipandshop #southamptonvibes

🩰 Tiler Peck at Guild Hall
🗓️ Saturday, June 14 | 8PM
📍 Guild Hall, East Hampton
An evening of unforgettable performance and movement.
#tilerpeck #guildhall #easthamptonevents

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

#hamptonsweekend
  • Sydney Sadick, Founder, Editor-in-Chief, and Publisher of Spotlight Magazine has been a lifetime Hamptons goer who has created a platform centered around the community she knows and loves. Spotlight Magazine has strong roots with the East End and is a fresh product in an ever-changing landscape.⁠
⁠
Sydney is a fashion and lifestyle expert who regularly appears on television. She is the author of the memoir and educational guide Aim High, which has received praise and recognition in the fashion space, encouraging individuals to find their unique style and achieve their goals.⁠
⁠
Sydney discussed her background and why she decided to launch Spotlight, how the magazine has evolved and grown, and some upcoming projects she is excited to be involved in ahead of the 2025 summer season. ⁠
⁠
Read the full interview at Hamptons.com (Link in Bio)⁠
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#sydneysadick #hamptons
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