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

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.