Naumkeag is the former Berkshire estate of New York City lawyer and U.S. Ambassador to Great Britain, Joseph Hodges Choate, and his wife Caroline, located in Stockbridge, Massachusettes. The Choate’s, who were part of the newly-rich, traveled in well-to-do social circles. They decided to build a 44-room shingle-style “cottage” with brick and stone details, designed by the architect of the day, Stanford White.

The Village is one of New York’s most historically rich neighborhoods and it has architecture spanning all eras. It is almost like a time capsule that has embraced culture and counter-culture alike. Originally attracting artists, writers, musicians and actors, this area is full of old New York charm with buildings tucked away on winding streets created before the existence of the grid.

Ruth Livingston Mills and Ogden Mills owned homes in Paris, Newport, Manhattan and California, but it is this 65-room Beaux-Arts Gilded Age mansion that five generations of Livingstons lived and entertained. The 40,000 square foot mansion was originally a smaller house, built in 1832 and greatly altered and expanded to what it is today.

In 1895, Frederick W. Vanderbilt purchased the Langdon estate, comprised of 153 acres, a structurally unsound house, a farm and 459 acres on the east side of Post Road. Hyde Park was the name of the stately home he commissioned for himself and his wife, Louise and it was built between 1896 and 1899 on approximately 600 acres. The mansion on a bluff overlooking the Hudson River in Hyde Park, N.Y., this was one of several homes owned by the couple.

Westbook Farms started when William Bayard Cutting purchased the George C. Lorillard estate on the Connetiquot River in the Long Island town of Great River. Cutting was a New York City lawyer and sugar beet refiner, who made his fortune in railroads and in the development of the Red Hook, Brooklyn waterfront.