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Meet Tom

Sara Littlefield
About Tom Castiglione

As a member of the Sara Littlefield team, Tom brings deep, local knowledge of the luxury real estate market from a unique perspective. For 30 years, Tom has been a professional sailor and top-earning sail consultant at North Sails. XX in addition to managing three full house renovations in Rowayton and Norwalk. “Tom has been immersed in local real estate since the 1990s as a successful sales agent in New York specializing in bank owned properties (REOs) as well managing and investing in several complete home renovations. With 30 years in the luxury sailing industry, Tom is no stranger to the fine points of a client’s needs.

Attention to details rules the day is Tom’s motto.

“As a Rowayton resident for 20-plus years, Tom has an insider perspective of current and future real estate values with an eye to the greatest return-on-investment (ROI) and overall enjoyment in one’s home, reveals Sara Littlefield. “Tom truly loves to share with everyone he meets why Rowayton and Darien are so special. His keen insights earned from his personal and professional connections and his personal real estate transactions, Tom is a natural to share with others his successes in this role.”

As a well-connected and local resident of Fairfield County for the past 20 years, Tom is well versed in the sales history of the area and what buyers are looking for in today’s market. “Tom is a great addition to the team because he is so educated about our marketplace and what the area has to offer. One of the most valuable things we bring to a client’s experience is the market knowledge they can’t read on Zillow or The value of a home is so much more than the black and white of bedrooms, baths, and square footage. Tom knows first-hand how to transform a property into a statement one and has the critical eye when reviewing properties to help guide clients in this critical step and the process after the sale as well,” says principal Sara Littlefield.

Buying and selling a property is an exciting moment in most people’s lives, but it can also be wrought with stress. In a recent study, 44% of American home buyers reported that it is the most stressful event in modern life. “Tom is an adept problem solver coupled with his attention to all details,” says Sara Littlefield. “As a client and friend for over 20-years, Tom is truly adept at bringing buyers and sellers to a closing table for a win-win for all.”

Tom is a graduate of Dowling College in New York, earning a bachelor’s of arts in business.

When Tom isn’t working with luxury clients or helping his luxury sailing clientele, he enjoys time with his partner Karen and her daughters as well as volunteering at the local rescue dog foster care and rehabilitation. He is active member at New York Yacht Club and Storm Trail Club and also enjoys skiing, mountain biking and road cycling on his limited time off.

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