Old Greenwich

Known in the 1800’s as “Greenwich, Old Town,” this quaint waterfront community was originally regarded as a burgeoning summer resort spot. The roots of modern-day Old Greenwich date back to 1641, when the first European settlers arrived. Today, this picturesque and charming place is regarded less as an accessible vacation destination, and more of a year-round residential hamlet.

Most of this classic New England town sits on a peninsula that juts out into the Long Island Sound. It’s home to 6,600 people, many of whom were lured to the sunny shores from Manhattan.

Sound Beach Avenue shoots south of the historic train station and is lined with mostly small, local businesses. Radiating out from “the village” are narrow, curving roads (best traversed on foot) that lead to Old Greenwich’s beaches and eight miles of stunning shoreline.

A Jeffersonian-style building with a children’s section that resembles a village green, the Perrot Memorial Library is named after Old Greenwich’s first private schoolmaster and beloved by locals.

You’ll find Cape Cods and Colonials in the northern part of town under $1 million, but newly constructed houses and those on the waterfront (below Route 1) typically sell for exponentially more.

The town’s 147-acre Greenwich Point Park (also called “Tod’s Point” for a banker who once had his estate there and “Elizabeth’s Neck” before that for a founding settler) stretches out into the water and boasts beautiful trails and beaches.