[2] During the Revolutionary War, the Motts, a Quaker family, ran a gristmill at the far end of Premium Mill-Pond in the area now known as Pryer's Bridge on the border of New Rochelle and Larchmont.

[citation needed] After the Civil War, The New York Yacht Club established a shore station on Long Island Sound, which began to attract more and more sailing activity to the area.

At the same time, shorefront properties along Premium Point became prime locations for summer homes of wealthy New Yorkers including Henry Holt, CC Buell, TS Billings and JP Morgan.

On race days, excursion steamers were chartered from Starin's Glen Island Park so that hundreds of New Rochelleans could follow Iselin's boats as they left Premium Point for New York and the start of the contests.

[8] The area became more of a suburban destination in the late 1800s when the New York & New Haven Railroad opened a line along the sound shore of Westchester, building a stop in New Rochelle.

The area's homes are a mix of architectural styles from Spanish-style Mediterranean mansions to French Provincial palaces, as well as a number of more modern, 'boxy' designs.