Around the Island

Living history and the choices we make

REPORTER FILE PHOTO  | The Shelter Island Historical Society’s Havens House. The August 5 house tour begins at the property on Route 114.

Seldom do we buy the house of our dreams. How we go about creating it is the theme of the Shelter Island Historical Society’s biennial house tour “Living with History/Making Choices,” which will be offered Saturday, August 5 from 2 to 5 p.m. On view will be five fabulous Island houses which present “choices” made, ranging from the minor to the radical. The homeowners will share their houses and their stories, showing how they went about creating their dreams and taking visitors on a trail that runs from the Heights to the end of Ram Island. 

“Every house has a story,” said Lily Hoffman, co-chairwoman of the tour. “The best thing about doing the house tour was getting to know — and then getting to tell the story.”

COURTESY PHOTO | Greatfields (Samuel Havens House).

• Two hundred and thirty years of incremental change is evident in Greatfields (Samuel Havens House).  Built in 1788, this “brother house” to the Shelter Island Historical Society’s Havens House was owned for many years by Sophia Truslow an architectural historian who wrote a thesis on the house for Columbia University, School of Architecture. Current owners an archeologist and lawyer turned interior decorator, have added today’s comforts such as a pool and removed dropped ceilings to uncover original beams, adapting a historic gem to modern living. The home was recently featured in a Wall Street Journal article.

COURTESY PHOTO | Tudor style home overlooking Dering Harbor.
COURTESY PHOTO | Tudor style home overlooking Dering Harbor.

• Two houses on the tour illustrate the possibility of totally re-envisioning a house and property. One is a formal Tudor style with a five-car garage (built by a Lincoln/Mercury dealer) on a bluff overlooking Dering Harbor. The current owners -— an architect and an art historian — have remade it into a relaxed summer home through extensive renovation, including repurposing a driveway as a patio.

COURTESY PHOTO | 1960s ranch turned Art Deco dream.
COURTESY PHOTO | 1960s ranch turned Art Deco dream.

• The other, a small 1960s ranch, is owned by a graphic designer who has made it into an Art Deco monument, inside and out. A steamship smokestack replaces the chimney while the second floor provides living area and more space for her fabulous collection of Deco furnishings and art. She aptly describes her house as an “ocean liner.”

COURTESY PHOTO | Rebuilt historic home.
COURTESY PHOTO | Rebuilt historic “Dering Farm” home.

• The final two houses on the tour feature the rebuilding of the old as new. First is the rebuilt “Dering Farm,” a venerable Island property which the owners lived in for 10 years before deciding, together with their local architect, to totally rebuild, drawing upon original plans and salvaged materials that show its provenance and celebrate its history.

COURTESY PHOTO | 1920s updated (and expanded) cottage on Ram Island.
COURTESY PHOTO | 1920s updated (and expanded) cottage.

• In the other home, an award-winning local architect/design team took another approach to “living with history” by combining pre-existing buildings — a one-room 1920s cottage with a contemporary indoor/outdoor living area — to create a “new” house, which was featured in the September 2016 issue of Hamptons Cottages & Gardens.

Tickets to the Shelter Island Historical Society’s “Living with History/Making Choices” house tour are $40. The tour begins at Havens Barn at 16 South Ferry Road (Route 114) where visitors will receive a map and brochure. Homes can be visited in any order and light refreshments will be served. The tour is not wheel chair accessible. Tickets can be purchased by visiting or at Havens Barn on the day of the event. For more information, call (631) 749-0025.