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Five Fab Historic Homes

The five oldest homes in Westport

Susan Wynkoop's home, known to be Westport's oldest at 187 Long Lots Road

With roots reaching deep into colonial history, Westport has its fair share of old houses. But which are believed to be the oldest of the old? For an answer we went to Robert Weingarten, the Westport Historical Society’s historic house specialist and a realtor with Raveis in Westport. Here are Bob’s top five.

1. The one-story clapboard at 187 Long Lots Road that Susan Wynkoop shares with husband Morgan flies a 13-star early American flag flies on the front lawn. Weingarten says the pine flooring in the original rooms pegs the home’s age at no later than 1687, the year England made it illegal for colonists to cut down pines, needed for the king’s ships. Susan, who recently stepped down as president of the Westport Historical Society, says “it’s a real privilege to live in a historic house,” adding that there’s a “warmth and authenticity” to the original “pumpkin pine” paneling and floors that’s “soothing to the soul.”

2. Interior designer Andrea Cross is proud that her circa 1700 colonial at 46 Kings Highway South has presented the same “iconic” façade to passers-by for more than 300 years. But to provide an alternative to the home’s low ceilings and limited natural light, Andrea and husband David added a rear family room with a high ceiling, large windows and more privacy. Andrea, an interior designer, says the original rooms are outfitted with furniture in a variety of styles because period pieces would be a tad expensive and impractical.   

3. Built in 1710, the central-chimney cape at 38 Compo Road North is now the office of Westport architect Kevin Huelster. When Huelster and landscape architect Katherine Kamen bought the house, they gutted the interior, removing three centuries’ worth of sheetrock and plaster, and built a new home on the property for their residence. Huelster makes his work space, with its exposed, hand-hewn beams and girders, sound inviting. “It’s beautiful, warm, intimate and cozy,” he says.       

4. The cape at 81 Clapboard Hill Road that Judith Reid shares with her artist husband Charles, built in 1727, also features a central chimney, but with three working fireplaces. When her children were at Greens Farms School, Judith would host annual field trips where the pupils sat around the fireplace and saw how colonial families cooked meals. Like Susan Wynkoop, Reid also considers it a “great privilege” to live in an old house. “My view is we’re just borrowing it for a time,” she says.

5. The white saltbox at 46 Kings Highway North, built around 1730, comes with an interesting history. In 1777, it was seized by rebellious colonists after owner Nathan Bears and his family had “gone and joined themselves with the enemy.” Today the home is owned by Michelle Kelley and Elisabeth Abeson and rented to Betsy Barrett. “It embraces you…it’s so cozy and welcoming,” says Barrett, who has fun imagining “the lives of the different people who have lived here and what it was like for people then,” especially on bitter cold days like those earlier this month.

One of my memories of growing up on Compo Road South was playing in the attic of our next door neighbors, whose home dated to before the American Revolution, and finding musket balls stuck in the roof beams. The neighbors’ son and I figured they had been fired by British soldiers on their way to burn Danbury.