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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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Top Hamptons Events This Weekend: August 16th, 2024

Top Hamptons Events This Weekend: August 16th, 2024

  • 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! ⁠
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Check out the Top Hamptons Events This Weekend!⁠
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🎬 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).⁠
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🎉 13th Annual SouthamptonFest⁠
📅 Oct 3 – 5, 2025 | 10AM – 7PM⁠
📍 Southampton Village⁠
Arts, culture, food & family fun all weekend long!⁠
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🎶 SpringsFest⁠
📅 Oct 4, 2025⁠
📍 1 Parsons Pl, East Hampton⁠
Live music, raffles, crafts, blacksmith demos & more.⁠
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💃 Salsa Social @ The Clubhouse Hamptons⁠
📅 Oct 4, 2025 | 9PM – 11:30PM⁠
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Dance the night away w/ DJ Chile & more!⁠
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🐚 34th Annual Largest Clam Contest⁠
📅 Oct 5, 2025 | 12PM – 3PM⁠
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Taste clam chowder, clam pies & cheer on the winners!⁠
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🎷 East Meets West Jazz Jam Session⁠
📅 Oct 5, 2025 | 2PM – 5PM⁠
📍 Southampton Cultural Center⁠
Free community jazz jam – all are welcome.⁠
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🌕 Full Hunter’s Super Moon Hike⁠
📅 Oct 6, 2025 | 6:30PM – 7:30PM⁠
📍 SOFO Museum Parking Lot⁠
Guided evening hike under the moonlight.⁠
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✨ Which event are you most excited for?⁠
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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.⁠
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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. ⁠
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📸: Danté Crichlow for The Apollo⁠
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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.⁠
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📸: Photo Credit: BFA/Madison McGaw⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#lagence #fashion #sagharbor #hamptons #bluandcream
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