Leslie Chesloff

Leslie treats her clients like friends and helps them find a slice of heaven in The Berkshires

After a successful 35-year career as a media executive, Leslie relocated to Great Barrington full-time over a decade ago and became a licensed real estate agent. She has quickly became one of the top producing agents in Berkshire County and in 2025 she was recognized as the number one advisor in Berkshire County for William Pitt Sotheby‘s.  Having gone through the construction process many times, Leslie built two homes in the Berkshires. She has also built three homes in Boston, Philadelphia and Short Hills NJ. She loves to help clients with interior design and the building process, as well as give recommendations for everything from the best painter to the best restaurant.  As a media executive in many high profile positions, Leslie brings to her real estate endeavors a well tuned set of negotiation and strategic planning skills, all suited for the Berkshire real estate market. She is a licensed agent in Massachusetts, New York, and Connecticut.

Leslie is happy to show you around and share all of her favorite things.