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Hamptons.com
August 15, 2024

Cotswold Cottage: A Shelter Island Masterpiece by Heiberg Cummings Now on the Market

David Andrewsby David Andrews
in Real Estate, Trending
Home Real Estate

The acclaimed design duo Heiberg Cummings is proud to announce the exquisitely restored Cotswold Cottage on Shelter Island (133 South Midway Road, Shelter Island, NY 11964) is now available for sale for just the second time. Building on the tremendous interest and successful sale of their latest new construction at Osprey House, this offering represents a unique opportunity to own and experience the visionary design and luxury in an enviable Hamptons location.

 

Originally built by hand in 1955, Cotswold Cottage emerged masterfully restored in 2022 by Heiberg Cummings Design, blending classic charm with contemporary elegance. Perched nearly 2 hilltop acres dotted by blueberry bushes and an apple orchard, this luxurious estate captures the essence of Shelter Island living, combining the tranquility of its surroundings with the sophistication and chic style that the designers are known for.

“This home is a testament to the power of place and has been the source of peace and inspiration for our work as designers,” says Bill Cummings. “We’ve poured our hearts into every detail, creating a space that feels both timeless and modern, a sanctuary that invites comfort and conversation.”

Cotswold Cottage offers bright living space across two stories, plus a finished lower level. The home features five bedrooms, two full baths, and one half bath, alongside a heated saltwater pool. The interiors are a testament to Heiberg Cummings’ dedication to craftsmanship, with antique copper light fixtures, high-gloss woodwork, and a grand wood-burning fireplace that serves as the focal point of the large living room. The kitchen, designed for today’s entertainer, marries the past with the present through custom cabinetry, premium appliances, and a stunning antique center island.

“The magic of Cotswold Cottage lies in its ability to marry the old with the new, the classic with the contemporary,” adds Bernt Heiberg. “It’s a chic and elevated take on coastal living, where every space has been thoughtfully crafted to invite light, joy, and effortless elegance into your daily life.”

The property’s outdoor spaces are equally as captivating, with a beautifully manicured backyard that includes a brick-paved dining patio, a fire pit, and a fully fenced gunite pool that is bathed in sunlight throughout the day. A serene Belgian stone sitting courtyard, anchored by an obelisk-shaped fountain, offers a tranquil retreat, perfect for enjoying the all-day sun in peaceful seclusion.

 

Stacey Cohen, who has represented many of the team’s properties, has been overjoyed by the positive response from buyers and brokers alike. “Osprey House was such an amazing example of what makes Heiberg Cummings so special – and clearly in-demand. Cotswold Cottage is its own expression of inspiration and luxury – highlighting how attractive Shelter Island is for today’s buyers. The interest in their work continues to grow, and I’m thrilled to bring this extraordinary home to the market.”

Located just beyond the South Ferry to Sag Harbor, Cotswold Cottage provides easy access to boutique shops, charming dining spots, beaches, and the natural beauty that defines the Shelter Island experience.

“Shelter Island is such a unique place in the Hamptons and we’ve seen how amazingly Stacey and Heiberg Cummings, the boys as she calls them, work together. Buyers are taking notice, and for good reason. Saunders is proud to help highlight how luxurious life on Shelter Island is with a property as elevated as Cotswold Cottage,” adds Steve Glick, Senior Vice President of Marketing at Saunders & Associates. 

 

For more information about Cotswold Cottage or to schedule a private viewing, please contact Stacey Cohen of Saunders & Associates.

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Learn To Play Mah Jongg with Gatherings Social Club

October 31 @ 01:00 PM - November 21 @ 03:00 PM
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Halloween Party for Kids in Westhampton Beach

October 31 @ 03:30 PM - October 31 @ 05:30 PM
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Aperitivo (Sunset Cocktails)

October 31 @ 05:00 PM - October 31 @ 08:00 PM
The Baker House 1650
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Calissa’s Annual Halloween in the Hamptons Party

October 31 @ 05:00 PM - November 1 @ 02:00 AM
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Top Hamptons Events This Weekend: August 16th, 2024

Top Hamptons Events This Weekend: August 16th, 2024

  • Dust off your favorite witch’s hat and opt for a paddleboard instead of a broom for Paddle Diva & Wych’s Bloom’s inaugural Witches Paddle on Wednesday, October 29, from 4–6 p.m. at Paddle Diva (10 Boat Yard Rd., East Hampton, NY). A portion of the proceeds will go to the Surfrider Foundation’s Eastern Long Island Chapter and its efforts to protect the world’s oceans, waves, and beaches through dedicated activism. ⁠
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We’ve all seen Witches Paddles grace our social media feeds, and now you can partake in the spooky fun! This tradition combines Halloween vibes with the healing power of nature as you glide and take in the beautiful Three Mile Harbor views.⁠
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Gina Bradley excitedly shared, “I am thrilled to be hosting this at Paddle Diva’s permanent location inside Swan’s Marina (formerly Vanderveer’s). This kind of paddle has been on my mind for many years, as I’ve seen them in all parts of the world, and it looks so cool seeing all the witches gracefully gliding along the water. This is particularly exciting because we’ve joined forces with Wych’s Bloom, a local herbal apothecary brand, and Surfrider to raise money and awareness for ocean and clean bay initiatives that are crucial for our waters on the East End of Long Island.”⁠
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“As an herbalist, Samhain, or Halloween, offers a special occasion for me to celebrate the healers who came before us to teach the wisdom of the plants in our region. I had seen people gathering for Witches Paddles all over the country, and as a surfer, I connected instantly with these events. When I texted Gina the idea, she was immediately in. That’s what I love about the women on the East End—they’re always up for an adventure,” shared Wych’s Bloom owner and Surfrider Foundation board member Christina Winters.⁠
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Join us in taking part in this one-of-a-kind event! Craft a witch’s outfit and set sail at the inaugural Witches Paddle for a great cause.⁠
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@paddlediva @wychs_bloom⁠
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#witch #witchespaddle #paddlediva #hamptons #halloween #easthampton⁠
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  • Check out the top Hamptons events this weekend!⁠
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🍎 Wölffer’s Cider Fest⁠
📅 Sat, Oct 25 | ⏰ 2–5PM⁠
📍 The Wine Stand, Sagaponack⁠
Sip cider, enjoy live music, games, and lobster rolls!⁠
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🍦 Buddhaberry’s Spooktacular Costume Party⁠
📅 Sat, Oct 25 | ⏰ 2–4PM⁠
📍 Buddhaberry, Southampton⁠
Bingo, trivia & costume prizes galore!⁠
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👻 Haunted Village⁠
📅 Sat, Oct 25 | ⏰ 11AM–4PM⁠
📍 Southampton History Museum⁠
Ghost stories, pumpkin carving & trick-or-treating!⁠
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🧙‍♀️ CMEE’s Halloween Bash⁠
📅 Fri, Oct 24 | ⏰ 4–6PM⁠
📍 CMEE, Bridgehampton⁠
Spooky crafts, games & costume contest!⁠
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🎬 The Horror Show at Sunset Theater⁠
📅 Oct 24–30⁠
📍 Westhampton Beach⁠
7 nights of scary movies 🍿⁠
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🎧 Halloween Silent Disco Dance Party⁠
📅 Sat, Oct 25 | ⏰ 7–10PM⁠
📍 Guild Hall, East Hampton⁠
3 channels, endless grooves—disco, funk & more!⁠
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🐾 Canines in Costume at LongHouse Reserve⁠
📅 Sat, Oct 25 | ⏰ 10:30AM–12:30PM⁠
📍 East Hampton⁠
Dress up your pup + enjoy treats & fun!⁠
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🎃 Bridgehampton Halloween Parade⁠
📅 Sat, Oct 25 | ⏰ 10–11AM⁠
📍 Hampton Library, Bridgehampton⁠
Trick-or-treat parade down Main Street!⁠
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🎸 The Cherry Bombs at The Stephen Talkhouse⁠
📅 Fri, Oct 24 | ⏰ 8PM⁠
📍 Amagansett⁠
Rock out all night! 🤘⁠
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🌲 Enchanted Forest Trail⁠
📅 Oct 25–26 | ⏰ 12–1:30PM⁠
📍 Quogue Wildlife Refuge⁠
Costume walk + crafts + games!⁠
⁠
🥁 Annual Ragamuffin Parade⁠
📅 Sun, Oct 26 | ⏰ 1PM⁠
📍 Sag Harbor⁠
Parade fun for all ages + pets!⁠
⁠
🐶 Little Lucy’s Annual Pet Parade⁠
📅 Sat, Oct 25 | ⏰ 1–4PM⁠
📍 Agawam Park, Southampton⁠
Prizes, live music & celebrity judges!⁠
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🕸️ Solé East’s Halloween Party⁠
📅 Sat, Oct 25 | ⏰ 8PM⁠
📍 Montauk⁠
Win a free weekend stay for best costume!⁠
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🍁 Centro’s Fall Festival⁠
📅 Sun, Oct 26 | ⏰ 12–5PM⁠
📍 Hampton Bays⁠
Pumpkin decorating, drinks & local vendors!⁠
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🔗 Click link in bio for more events at Hamptons.com⁠
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#hamptons #halloween #pumpkins #scarymovies #southampton #sagharbor #easthampton #costumes
  • East Hampton’s streets came alive with wagging tails and smiling faces for ARF’s 32nd Annual Stroll to the Sea Dog Walk. Families, friends, and their dogs gathered at the historic Mulford Farm, where the morning kicked off with vendors, photo ops, custom merchandise, contests, and prizes.

@arfhamptons 

#arf #hamptons #community #mainbeach #adoptdontshop❤️
  • Last Saturday, Wölffer held its annual harvest party at its scenic vineyard in Sagaponack. The annual fest brought together friends, families, and wine lovers to toast the season and harvest behind every bottle of Wölffer wine.⁠
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📸: Cameron Burton⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#wolffer #hamptons #wolfferwine #harvestparty
  • From Hollywood red carpets to Milan exhibits and Hamptons fashion shoots, Filbert Kung has photographed the world—but it’s his quiet, unguarded, and attentive nature that reveals the artist behind the lens.⁠ @filbert_kung 
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I met Filbert Diego Kung at a Grey/Ven fashion event in Amagansett last summer. He’s one of those rare photographers who instantly puts you at ease—calm, composed, and naturally good at making anyone feel like they belong in front of his lens. Had I known then just how in-demand Filbert is in the fashion and photography world, I probably wouldn’t have asked him to snap a few shots of me goofing off on the red carpet. But maybe that makes me a model? Either way, it was my first glimpse of how effortlessly he captures people as they are. In my case, goofy-but-make-it-chic.⁠
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Since then, I’ve seen him popping up around the Hamptons, often between flights to LA, Miami, or wherever the next big editorial or campaign takes him. Originally from the Philippines, Filbert has spent over fifteen years building a career that bridges Hollywood red carpets, high-fashion editorials, and fine art portraiture. ⁠
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Read the interview at Hamptons.com (Link in Bio)⁠
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⁠#photographer #photography #hamptons
  • From fall festivals to concerts, a lot is happening in the Hamptons this weekend! ⁠
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Check out the top Hamptons events this weekend!⁠
⁠
🎃 Fall Festival at Good Ground Park⁠
📍 Hampton Bays | 🗓️ Fri, Oct 17 | 🕓 4–6PM⁠
Bring your pre-carved pumpkin & compete for prizes! Games, food truck, costume parade & more!⁠
👉 Link in bio⁠
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🍷 Wölffer’s Candlelight Fridays⁠
📍 Sagaponack | 🗓️ Fri, Oct 17 | 🕓 4–7PM⁠
Live music, seasonal pairings & cozy vibes 🍁⁠
👉 Link in bio⁠
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🖼️ Like No One: Michael McDowell Exhibition⁠
📍 East Hampton | 🗓️ Oct 17–19⁠
🎉 Opening reception: Sat, Oct 18 | 4–8PM⁠
Fine art lovers, don’t miss this!⁠
👉 Link in bio⁠
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📚 BookHampton: Caroline Sutton in Conversation⁠
📍 East Hampton | 🗓️ Sat, Oct 18 | 🕕 6PM⁠
Nature meets literature in this insightful author talk.⁠
👉 Link in bio⁠
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👟 Shelter Island Fall 5K Run/Walk⁠
📍 Shelter Island | 🗓️ Sat, Oct 18 | 🕚 11AM–2PM⁠
Run/walk for a cause—supporting Breast Cancer Awareness 💗⁠
👉 Link in bio⁠
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🏛️ 32nd Annual Landmarks Luncheon⁠
📍 Maidstone Club | 🗓️ Sat, Oct 18 | 🕦 11:30AM–2:30PM⁠
Hosted by LVIS, spotlighting the history of East Hampton’s Freetown.⁠
👉 Link in bio⁠
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🍂 Amber Waves’ Oktoberfeast⁠
📍 Amagansett | 🗓️ Sat, Oct 18 | 🕑 2–5PM⁠
Seasonal dishes, live music, dancing & games 🎶⁠
👉 Link in bio⁠
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🎻 BCM Autumn: Brooklyn Rider⁠
📍 Bridgehampton | 🗓️ Sat, Oct 18 | 🕔 5–6:30PM⁠
A powerful string quartet performance you won’t want to miss.⁠
👉 Link in bio⁠
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🍷 Cab Franc Forward Winemaker’s Dinner⁠
📍 Shelter Island | 🗓️ Sun, Oct 19 | 🕔 5PM⁠
Multi-course dinner + Cab Franc pairings = 🍽️🍇 perfection⁠
👉 Link in bio⁠
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✨ So much happening this weekend — which event are you heading to first?⁠
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#hamptons #fall #fallfestival #shelterisland #5k #wine #winedinner #amberwaves #wolffer
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