The Enchantment of Shelter Island Heights

Last week I spent time with a client along with her trusty dog and two friendly cats on the veranda of her Heights home. Although the weather was hot, the American flag, hung between colorful flower baskets, moved with the breeze and seemed an idyllic image of Norman Rockwell's Americana.This visit inspired me to spend a morning in the Heights and reconnect with some of the things that made me fall in love with Shelter Island. From the North Ferry to Goat Hill there is so much to love – the quiet little streets shaded by old trees, the expansive water vistas from Serpentine Drive, the smell of flowers,greenery and even the scent of wood wafting out from the doors of Our Lady of the Isle.

The layout of the streets and parkland were designed by famed landscape designer Frederick Law Olmsted, who also designed Central Park in NYC, and Robert Morris Copeland. The Heights Beach Club is a treasure for both kids and adults, with swimming dock, cabanas, refreshments, lockers, basketball area, playground, a sandy beach with a walkway,and a covered sitting area. The Heights tennis courts are a short distance away and in the last several years have gone up a notch under the management of Moussa Drammé. 

Union Chapel, the oldest public building on Shelter Island, is surrounded by parkland and historic homes. A majestic Copper Beech tree across the street in the front yard of a home I sold a little over a year ago is one of the most incredible old trees on the Island. On Sundays,when there is a service in progress, the rustling of the congregation and music playing harken back to the days of The Shelter Island Grove and Camp Meeting Association, when clergymen from Brooklyn organized a Methodist Episcopal Church summer resort area, much like Oak Bluffs in Martha's Vineyard and Oak Grove in New Jersey.

While many homes have been restored, some to a very high standard with nearly every amenity, there are still many built at the turn of the century that are virtually intact and unblemished by renovation. One such home,presently listed for sale, on Wesley Avenue overlooking the Grove is like looking through a portal to another age, having exposed beams,screened porch, ball and claw tub, outdoor dining area adjacent to flowering shrubs,and shaded rooms that always seem to stay comfortable, even on the hottest summer day.  Another home that was once for sale had a brick oven and sleeping area in the kitchen, as well as a partially finished attic with a stained glass window streaming colored sunlight onto faded 1940's magazine clippings of Betty Grable, Rita Hayworth and Alice Faye pinned to the masonite wall.

There have been some wonderful homes to purchase in the Heights in recent memory, with several available today. One in particular that is now in contract, has been bought, renovated,and sold four times in the last 15 years and is still referred to as the home of the family who owned it from the 1960s through the 1990s, in true Shelter Island fashion.

Every year, there are many Heights homes available for rent, each one enchanting in its own way, and filled with history. If you listen closely enough, you can even hear the laughter of fun summer times in years gone by.