Shelter Island: A Summer Family Hotspot

Shelter Island is known for being one of the most unique and charming places on the Eastern Seaboard. The island offers 8,000 acres of pristine landscape with glistening water views. Accessibility to the island is convenient by car and ferry from Sag Harbor on the South Fork or Greenport on the North Fork. Always a favorite family vacation spot and close-knit community, SI offers seclusion mixed with cultural events, fine dining and amazing sunsets.

Just back from a vacation/business in Europe, Angelo Piccozzi, of Dering Harbor Real Estate, said properties have been moving quickly. “Some homes are only on the market for a month. There are a lot of buyers; properties are being listed appropriately and investors are getting back in the game with the confidence that they will be able to achieve a 15–25% return on their investments,” shared Angelo.

If anyone should have a little insight on Shelter Island, Angelo definitely does. His family roots date back to the 1850s on his mother’s side and the 1920s on his father’s. “Shelter Island is a special place where many artists, architects and writers like to spend time—while families can enjoy sailing, tennis, paddleboarding or relaxing with a good book. Many people come back year after year and make lifelong friends here,” he continued.

There are so many beautiful properties available and the Little Ram Island estate is at the top of the list. Set on 2.9 acres of immaculately landscaped property, it boasts 6 bedroom, 4.5 baths and 3,900 square feet beauty. Overlooking Coecles Harbor and Gardiners Bay, this charming shingle-style home offers many luxurious amenities including a 20‘x 40’ gunite pool with slate surround, a grand waterfront porch, mooring, 150’ dock, a new 230’ seawall, plus a 570 square foot 1 bedroom, 1 bath and living room, guest house as an added bonus. In addition, there is an outdoor shower and two-car garage that are also part of this perfect package. Listed at $6.4M. For more information, please contact Angelo Piccozzi, Dering Harbor Real Estate at 631-749-2800 or visit

With a total population just a little over 2,000 residents, Shelter Island is one giant family. “One of my loyal clients has been vacationing on the island since childhood and now continues that tradition with her children. The children benefit from summering here, rather than camp, because they have so many options” shared Georgiana Ketcham, of Georgiana B. Ketcham Realty.

“Some people may refer to Shelter Island as the ‘Un-Hampton,’ I refer to it as the ‘New Hampton.’ The Perlman Music Camp, Sylvester Manor, great restaurants and local shopping have added to the island becoming a much more social environment.” Georgiana continued.

Georgiana has years of experience and a passion for life on Shelter that she likes to incorporate in her day-to-day business. “We have properties in all ranges,” she said. One of those properties includes the Shelter Island Creek Cottage at Sylvester Manor.  Highlights include a master suite with fireplace, his and hers closets and dressing room, washer and dryer upstairs, guest rooms and bathroom with separate entrance, formal living room, formal dining room, large eat-in kitchen with fireplace and gathering area, walk-in pantry, entrance foyer, home office steps to waterfront deck, little “nooks and crannies” here and there, two full basements, two separate heating and air conditioning systems, and a garden shed. All nestled on 1.8 acres allows for plenty of room for pool and tennis court, making this a truly one-of-a-kind residence on Shelter Island. Exclusive—appointment only. Listed at $1.6M. For more information, please contact Georgiana Ketcham at 631-749-2800 or visit

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