Riverside

True to its name, Riverside runs along the eastern shore of the Mianus River. This is an almost entirely residential neighborhood, with a train stop conveniently located in the center. Commuters will often stop for a coffee at Ada’s, next to the station, which sold penny candy for 58 years, until the eponymous Ada Cantavero died in 2008. The business, still owned by her family, is now a popular café. Houses south of I-95, closer to the train station and Long Island Sound, will generally command higher prices, while those north of the highway are smaller and touch more affordable. On either side though, properties are pretty, many on spacious wooded lots. Houses can range from straightforward 1920s cottages to elaborate new construction estates. Many residents here belong to the Riverside Yacht Club, the second oldest sailing club in Connecticut, which has a clubhouse with dining.

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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.