Three at the top of the market as the 2025 residential real estate sales season opens.

Story by Colin W. Sargent

Chasing Winthrop

Perhaps you’re frustrated by the lack of 15-bedroom single-family oceanfront homes for sale as the buying season opens. Maybe you’re just as frustrated when you ponder, “How lucky do I have to be to own a place like this?”

Dapper New York lawyer Winthrop W. Aldrich (1895-1974) was, like John Adams and Joseph P. Kennedy before him, the U.S. Ambassador to Great Britain. He was also a world-leading financier, serving for decades as president and chairman of the board of Chase National Bank.

He liked to sail whenever he could. Years after fighting during World War I as a Navy lieutenant, he was the principal owner of the legendary J Sloop Enterprise and served as her navigator when she thrashed Shamrock V in four straight races during the 1930 America’s Cup. In the 1940s, King George of England made him an honorary knight (GBE).

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