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Hamptons.com
July 5, 2025

Iconic Waterfront Estate

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

5 North Menantic Road, Shelter Island, NY 11964
Saunders Exclusive: $6,750,000
View Listing

 

A rare offering on Shelter Island, this waterfront estate represents a legacy of architectural pedigree and enduring luxury. Built in 1860 and renovated over the years, the home is a singular blend of history and Hamptons elegance, set on nearly 3 acres with western-facing water views, a deepwater dock, and every hallmark of refined coastal living.

In an iconic Shelter Island location on West Neck Bay, this timeless model of Federal-style architecture offers 3,157 +/- sq. ft. of living space on 2 levels, 6 bedrooms, 4.5 baths, an attached 2-car garage, 3 fireplaces, a waterside heated gunite pool, and a deep-water dock.

Further expansion is possible, and there is room for tennis on the property. The first level has a traditional floor plan with a living room, dining room, kitchen, ensuite primary and guest bedroom.

Enjoy all-day sun from the multiple patios, including a beautiful attached gazebo porch for dining al fresco and morning coffee. Bedrooms are each well-sized and bathrooms have been updated, including a bedroom and a bath with waterviews. Upstairs, the open third floor awaits your imagination.

The restored interiors have been beautifully preserved, the original high ceilings with crown molding, wide-plank pine floors, marble mantelpieces, and even bannisters and newel posts-imbuing the estate with provenance and character and ready to be improved and updated to suit your lifestyle.

The estate’s park-like grounds showcase everything that makes Summers on Shelter Island so special – peace, privacy, with direct access to the water in West Neck Bay.

This outdoor oasis is the ultimate luxury, a highlight of every season with brilliant color changes, migrating songbirds, and extraordinary all-day light. The exceptionally well-considered heated gunite pool and bluestone patio are located perfectly to capture western light and water views without interrupting the open vista lawn stretching down to the water. Here, find a boaters’ paradise with a deepwater dock and western-facing waterfrontage on Westneck Bay.

From lawn games and late-night dancing under the stars to elegant dinners with guests arriving by boat, the property has long served as both a vibrant social hub and a serene private retreat.

Shelter Island offers an abundance of seasonal pleasures-sailing, fishing, nature trails, and beaches so peaceful they often feel private. The island’s charm extends beyond summer; the estate is particularly enchanting in the shoulder seasons, when West Neck Creek glows with shifting light and the surrounding landscape turns vibrant with spring blossoms or autumn foliage. A haven for wildlife and inspiration alike, it’s a rare retreat that feels both expansive and deeply personal, year-round.

 

MYLES REILLY
Licensed Associate Real Estate Broker
[email protected]
Cell: (631) 786-9419
 

 


NANCY MIZRAHI
Licensed Associate Real Estate Broker
[email protected]
Cell: (917) 854-9933

 

For more info, click here.

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LOCAL EVENTS

Events

07
Oct
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Oct
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07
Oct

October 7th Mitzvah Day

October 7 @ 01:00 PM - October 7 @ 03:00 PM
13 Woods Ln, East Hampton, NY 11937, USA
09
Oct
09
Oct
-
09
Oct

Aperitivo (Sunset Cocktails)

October 9 @ 05:00 PM - October 9 @ 08:00 PM
The Baker House 1650
09
Oct
09
Oct
-
09
Oct

Emilio Moro Wine Dinner at R.AIRE

October 9 @ 06:30 PM - October 9 @ 08:30 PM
259 East Montauk Hwy, Hampton Bays, NY, 11946
09
Oct
09
Oct
-
09
Oct

R.AIRE Wine Dinner with Emilio Moro

October 9 @ 06:30 PM - October 9 @ 09:30 PM
259 E Montauk Hwy, Hampton Bays, NY 11946
09
Oct
09
Oct
-
09
Oct

“The First Science from the Vera Rubin Observatory” (A Free, Virtual Lecture)

October 9 @ 07:00 PM - October 9 @ 08:00 PM
Hamptons Observatory with Suffolk County Community College (online)
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Southampton Hospital Foundation’s 3rd Annual Summer of Wellness to Feature DanceBody, Pickleball Tournament and More!

Southampton Hospital Foundation’s 3rd Annual Summer of Wellness to Feature DanceBody, Pickleball Tournament and More!

  • When: Fri, Oct 3rd – Sun, Oct 5th, 2025
8am – 5pm

Where: Levain Bakery, 354 Montauk Hwy, Wainscott, NY

Levain Bakery is introducing a new cookie for a limited time: Peanut Butter Dark Chocolate Chip – a decadent mix of creamy and chunky peanut butter with rich dark chocolate chunks. Originally created to celebrate the opening of Levain’s Beverly Hills Bakery, this indulgent new flavor will now be available for just three days only, October 3–5, at all retail bakery locations.

To make the weekend even sweeter, guests who purchase a cookie will receive a Levain Bakery mini tote (while supplies last), a fan-favorite collectible sure to go quickly.

#levain #levainbakery #cookie #minitote #tote #hamptons
  • From world premieres at the Hamptons International Film Festival to SouthamptonFest! ⁠
⁠
Check out the Top Hamptons Events This Weekend!⁠
⁠
🎬 33rd Hamptons International Film Festival⁠
📅 Oct 3 – 13, 2025 | 9AM – 10PM⁠
📍 Various Locations⁠
A global lineup of films, shorts & documentaries.⁠
⁠
🍪 Levain Bakery⁠
📅 Oct 3 – 5, 2025 | 8AM – 5PM⁠
📍 354 Montauk Hwy, Wainscott⁠
Try the Peanut Butter Dark Chocolate Chip cookie + snag a mini tote (while supplies last).⁠
⁠
🎉 13th Annual SouthamptonFest⁠
📅 Oct 3 – 5, 2025 | 10AM – 7PM⁠
📍 Southampton Village⁠
Arts, culture, food & family fun all weekend long!⁠
⁠
🎶 SpringsFest⁠
📅 Oct 4, 2025⁠
📍 1 Parsons Pl, East Hampton⁠
Live music, raffles, crafts, blacksmith demos & more.⁠
⁠
💃 Salsa Social @ The Clubhouse Hamptons⁠
📅 Oct 4, 2025 | 9PM – 11:30PM⁠
📍 East Hampton⁠
Dance the night away w/ DJ Chile & more!⁠
⁠
🐚 34th Annual Largest Clam Contest⁠
📅 Oct 5, 2025 | 12PM – 3PM⁠
📍 Amagansett Life Saving Station⁠
Taste clam chowder, clam pies & cheer on the winners!⁠
⁠
🎷 East Meets West Jazz Jam Session⁠
📅 Oct 5, 2025 | 2PM – 5PM⁠
📍 Southampton Cultural Center⁠
Free community jazz jam – all are welcome.⁠
⁠
🌕 Full Hunter’s Super Moon Hike⁠
📅 Oct 6, 2025 | 6:30PM – 7:30PM⁠
📍 SOFO Museum Parking Lot⁠
Guided evening hike under the moonlight.⁠
⁠
✨ Which event are you most excited for?⁠
⁠
Check out more events at Hamptons.com (Link in Bio)⁠
.⁠
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.⁠
#hamptons #hamptonsinternationalfilfestival #hiff #jazz #fullmoon #hike #film #levainbakery #community
  • So many fun fall activities in the Hamptons 🎃

@fairviewfarmatmecox 
@corwithsfarmstand 
@milkpailfarmorchard 

Check out our fall guide at Hamptons.com (Link in Bio)

#hamptons #fall #applepicking🍎 #pumpkin #maze #pettingfarm
  • As summer winds down and the cool breezes of fall approach, jewelry enthusiasts and fashion lovers alike are looking for the latest seasonal trends. Yael Fraynd, founder and president of Yaya Publicity, offers an insider’s perspective on what to expect this fall — especially for those embracing the chic lifestyle of the Hamptons.⁠
⁠
Looking ahead to fall, Fraynd described the evolving styles with enthusiasm. For fall, expect to see bold statement pieces, rich gemstone colors like orange and a playful mix of metals. ⁠
⁠
She also noted the influence of pop culture on jewelry trends, including celebrities like Taylor Swift, who is recently engaged, saying, “It could also be just, you know, with Taylor Swift, who has such a big effect on what people like.”⁠
⁠
On the seamless transition from summer to fall styles, she observed, “In the summer, you see a bit of Western-inspired pieces, and I think that they really do kind of transition into fall really nicely. ⁠
⁠
@yayapublicity⁠
⁠
Read the full article at Hamptons.com (Link in Bio) ⁠
.⁠
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#fall #falltrend #falljewelry #hamptons⁠
  • Apollo in the Hamptons returned with a celebratory evening at the EHP Resort & Marina (Si Si Restaurant) in East Hampton. The annual fundraiser supported Apollo’s year-round artistic and educational programs and its first full-scale renovation and restoration. ⁠
⁠
📸: Danté Crichlow for The Apollo⁠
⁠
Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#apollo #apollotheater #hamptons #easthampton #benefit #fundraiser
  • L’AGENCE’s Fashion Director Tara Rudes-Dann hosted a cocktail shopping event at Blue & Cream in Sag Harbor, welcoming a mix of VIP brand fans and tastemakers. Guests wore pieces from the brand’s latest ready-to-wear collections while enjoying cocktails and getting an exclusive preview of the brand’s upcoming Fall 2025 collection.⁠
⁠
📸: Photo Credit: BFA/Madison McGaw⁠
⁠
Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#lagence #fashion #sagharbor #hamptons #bluandcream
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    • Hampton Bays, Ponquogue Beach
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    • Long Island Aquarium | Coral Reef
    • Long Island Aquarium | Penguins
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