Rye

With roughly 15,000 residents, Rye is commonly referred to as one of Westchester’s smallest yet finest cities. With a long stretch of picturesque Long Island Sound beachfront, a refurbished colonial-style downtown district complete with upscale fashion boutiques, galleries, gift shops and its own exclusive “Restaurant Row,” Rye certainly lives up to its own reputation.

Predominantly populated by upper-middle class families, Rye stands out as a tranquil yet vibrantly family-oriented city with astonishing houses—some of the county’s most luxurious—and spectacularly scenic views all around.

Public interest points include the almost century-old Rye Playland amusement park with its contemporaneous, old-fashioned boardwalk, which has been referenced in both movies and music videos over the years. In addition to Playland, the city features its own public Oakland Beach and Rye Golf Club, the latter being equally as extravagant as the cities large share of private counterparts – but at a much more affordable price range. 

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