sponsored by:
Douglas Elliman

Housewarming: Skye Weinglass

An Aspen native proves you can go home again—and love it

Like most kids from Aspen, Skye Bird Weinglass had no intention of sticking around the small town where she grew up. The daughter of Leonard “Boogie” Weinglass, a prominent philanthropist and retail entrepreneur, Weinglass spent her childhood in the legendary Merry-GoRound Ranch, a sprawling estate famous for the regulation basketball court inside its 13,000-sq.-ft. fitness center. She started working at her father’s iconic retail store and diner at 12, hawking designer jeans and matzo ball soup. But by the time she graduated from high school, she was ready to flee the nest.

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