Jennifer Caulfield

Jennifer is a successful and dedicated real estate agent with William Pitt Sotheby’s International Realty in Essex, Connecticut, with a thirty-year track record in the sale of residential real estate. She began her career as the Assistant to the Director of the Darien Library in Darien, Connecticut, developing the skill set of dealing with non-profits and their Boards. She has enjoyed many varied positions, including Assistant to John Denver’s personal manager and the Executive Assistant to the President and Tournament Director of the Volvo International Tennis Tournament, where she developed her expertise in sponsor relations and overseeing the sales and marketing group.

Equally devoted to the community and to her clients, she contributes her time and assistance to several area organizations, including Child and Family Services, the Florence Griswold Museum and The Lyme Academy College of Fine Arts. She is long-standing Board member of the Connecticut River Museum, with a focus on development and fund-raising, and is a member of the Old Lyme Country Club, the Essex Yacht Club and the Black Hall Club. Golfing is a pleasure, but the water has always been a draw. Her first boat was a Concordia yawl and she enjoys chartering in the BVI’s with friends and family.

Jennifer is a long-time resident of Old Lyme with her husband, Chris, and they have two children and are the proud grandparents of five.