Leslie Chesloff

Leslie Chesloff Final Offer Certified About Leslie Final Offer Certified

Real Estate Salesperson

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.

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Our agents are recognized in the communities they serve for their deep knowledge, expert guidance and commitment to excellence.

  • Lives In Great Barrington, MA
  • Born In Short Hills, NJ
  • Favorite Movie The Big Chill
  • Passion Great food and friends

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In The News

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Privacy and elegant simplicity in a home for all seasons…

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The Berkshire Eagle

Sotheby’s real estate salesperson Leslie Glenn Chesloff earns national recognition…

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BUSINESS BRIEFS: Lion’s Den reopens; Kripalu celebrates 50; BWB honorees; The Venture Out Project buys…

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Live 95.9

Stunning $4M Lakefront Home in the Berkshires with Tennis, Gourmet Kitchen is a Dream…

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  • Leslie Chesloff

    Leslie Chesloff

    Real Estate Salesperson
    M.
    Great Barrington
    306 Main Street
    Great Barrington, MA 01230
    Lenox
    26 Church Street
    Lenox, MA 01240

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