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Greenwich

As evidenced by its name, Old Greenwich is the oldest part of Greenwich. Like its coastal neighbors of Riverside and Cos Cob, Old Greenwich has its own postal name and zip code and exists in the minds of its residents as a bit of a separate entity from the rest of Greenwich. The neighborhood’s downtown, called “the village” by locals, is centered around its historic 1894 railroad station, still in use for the Metro-North New Haven line. Here, you won’t find any chains, but rather, small independent eateries and local boutiques. Closer to Long Island Sound is Greenwich Point Park, unofficially referred to as Tod’s Point, a 147-acre park and beach at the tip of Old Greenwich’s peninsula. Houses in Old Greenwich are closer together than in other parts of the city, and neighbors are friendly, sharing well-maintained beaches and evening walks.

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Living in Fairfield County

Fairfield County is often called Connecticut’s Gold Coast, referring to its string of waterfront towns that glisten in the sun, with hubs of finance interlaced with beach towns and nautical villages—albeit villages with some of the most prosperous populations in the country. The station names called off by the train conductors evoke images of ultimate suburbia: Greenwich, Stamford, Darien, Norwalk, and Westport. Residents have long been drawn to Fairfield County because of its proximity to New York City, thanks its many stops on the commuter rail. It also offers idyllic country acreage, much of it with views and access to the Long Island Sound. Houses here include aristocratic estates, where sailing and horseback riding is still a part of daily life; glass-walled Modernist icons; and solid, historic clapboard Colonials that might have been models for a 19th-century painting.