John Caulfield

John’s easygoing personality and Wall Street finance background well-equips him to provide expert guidance to his buyer, seller, and investor clients. John has over a decade of experience as a futures trader and co-founded a proprietary trading firm on Wall Street. This extensive experience gives him an advantage in buying and selling homes and predicting sound investments. It was John’s personal experiences with investing that led him to real estate. When he began to make property investments in Aspen, Colorado where he lived for more than a decade he discovered his passion for real estate.

Since moving to New York from Aspen, John, his wife, Jen, and their two young sons enjoy their daily beach life in Ditch Plains. John and Jen have become involved in the community, where their sons go to the local school and John coaches East Hampton Little League. You can find John playing 105 tennis, surfing, skiing, snowboarding, and golfing at the Downs or the Snowmass Club.

John has the pulse on the luxury market. Working with clients who like to invest and expand their real estate portfolios, his knowledge and local experience in the Hamptons and Aspen markets are a natural fit. He is proud to be a part of the Hamptons and Aspen Agency team and help find clients in both locales their next dream home, investment property, or primary/second/third home.