Leslie Glenn Chesloff

Leslie Glenn Chesloff About Leslie Glenn

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 nine years ago and became a licensed real estate agent. She has quickly became one of the top producing agents in Berkshire County.  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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Agent Awards

  • 2021 Diamond Award
  • 2021 #1 Dollar Volume Berkshire Office
  • 2020 Platinum Award
  • 2019 Gold Award
  • 2019 #1 Units Sold Berkshire Office
  • 2018 Platinum Award
  • 2018 #2 Dollar Volume Berkshire office
  • 2017 Gold Award
  • Pricing Strategy Advisor

AGENT Highlights

Properties Sold

Avg Sales Price

Overall Sales Volume

My Listings and Solds

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Endorsements
Leslie is great to work with as this is my second home that I have bought through her. I recommend her to anyone who is looking to but a house in the Berkshires. Daniel Alan Leyden
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Endorsements
Leslie has represented us in 3 transactions and working with her is fantastic. She has consistently delivered outstanding results and helps make each step of the process - whether buying or selling - go smoothly. We recommend her to anyone looking to buy or sell in the Berkshires. Jill S. Straus Stephen A. Feldman
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Endorsements
Incredible! Leslie worked with me for 6 months to find just the perfect home. I’ve been in the business for 40 years and she is one of the best I’ve ever worked with. Great follow through and she treats every client as if they were her best friend!!! Cynthia Dale Fiscina
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Endorsements
Love that girl Leslie! She was are pick after our first encounter and we never looked back. We sold the house and got a new friend! Ira R. Adler Hilkka E. Adler
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Endorsements
Leslie did a fantastic job, couldn't be happier!! Mark Brunner
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Endorsements
Leslie Glenn Chesloff is an extraordinary agent and person. She treats you like family and looks out for your best interest, I fully trust she will do the best job to assist a seller and buyer. I will recommend her to everyone I know. I thank Leslie for a wonderful experience in selling our home. Michelle Laramee-Jenny Scott Jenny
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Endorsements
Leslie did an exceptional job ! She was patient, gave us pros and cons for each house visited and we had at all times the feeling that her goal was to find us the dream house and location and not necessary to make a rushed transaction. Work with her, she will find the best house for your family ! Dragos Zanchi Antonela Zanchi
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Endorsements
Leslie was awesome! Jennifer Patton
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Endorsements
Leslie did a nice job moving things along and meeting deadlines. She guided us through a checklist of items and was very responsive by phone and text. Everything went much quicker and smoother than we had expected. Anne and Edward Perkin
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leslie was very professional and very helpful Donna and Jerry Weiss
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Endorsements
I can think of no better real estate agent than Leslie Chesloff. Leslie is the consummate professional in every regard: she has a thorough knowledge of the marketplace coupled with a deep sensitivity to who the client is and what we need--whether we can articulate it or not. Leslie is always available and responsive--- our tireless advocate. And well beyond the requirements of an agent, Leslie is an astonishing ambassador for the Berkshires and a bottomless resource for setting up a home in a new place. Finally, she will remain our first and hopefully oldest friend in the Berkshires. Deborah Reinisch & Michael Theodore Deborah Reinisch Michael Theodore
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Endorsements
Leslie was excellent to work with! I would highly recommend her. Glenna Blackwell Glenna Blackwell
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Endorsements
Leslie was more than a realtor to us she was a friend who looked out for us. Guided us through the maze of buying not just a house but a home that fits our needs and that we can afford. She was very professional at all times, and kind as well. Sincerely, Marge & Dick Wallis Marjorie and Richard Wallis
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Endorsements
Leslie was a delight to work with. She was effective and helpful and got the job done! I highly recommend her to anyone. Barbara Stedman
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Endorsements
We had the most wonderful, positive, supportive experience with Leslie. We'd been house hunting for some time, using a different broker and agency, without much success. We decided to switch agencies, and to look in the Berkshires instead of in the Hudson area. Our first meeting with Leslie was immediately so much better than what we'd experienced previously. She was friendly, positive, and enthusiastic. We had narrowed to a handful down the dozen or more houses she'd sent us to see on our first day. She very quickly seemed to understand what it was that we were looking for. We saw the house we ended up buying on that first day. She made us feel supported and was extremely helpful, offering to do whatever we needed to make the process go more smoothly and quickly. She has an incredible spirit and can-do attitude, and even after the process was complete, she remains available and helpful to us in so many ways. We are so grateful to her and enthusiastically recommend her to anyone looking for a house in the Berkshires. If we could give her ten stars we would! SS - Sheffield
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Endorsements
Leslie was wonderful to work with! She is a consummate pro in every way––unfailingly generous, deeply knowledgable about the area, savvy and smart and patient. We were new to the area, and she made this process easy and fun and painless. I'd recommend Leslie to anyone. She's a genuine star. SN - Sheffield
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Endorsements
Leslie was amazing to work with. She was always available, trustworthy, gave us great advice, and went above and beyond what was expected to help us out throughout the process of buying a vacation home! Even now after the sale was finalized she is still helping us with the house! Leslie made the process easier than we could have ever imagined! NB - Sandisfield
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Endorsements
The search for a new home is such an adventure! Discovering opportunities, weighing pros and cons, and ultimately diving in. Leslie is a great guide through it all. At one point, we found ourselves moving towards the closing that, while starting well, became very complicated. We focused on how to make the deal work rather than on our feelings about this increasingly complex situation. She helped us come to our senses and then helped us find the property of our dreams. She proved to us that regardless of the question or challenge we encounter, she will always have our best interests at heart. We are clients for life! LS- Great Barrington
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Endorsements
It was such a pleasure working with Leslie. She was welcoming, knowledgeable and very responsive, both during the process and even after we closed. I've asked for recommendations for everything from plumbers to restaurants as we get to know our new home and community and Leslie has given us great advice. Call her! KD - Great Barrington
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Endorsements
Leslie was amazing in helping us to sell our home. We had moved away and she gave us great advice on what to set up in preparation for the sale so we could have extra time to manage things remotely. She actually networked to find a buyer before we ever made it to the listing date! Her true professionalism and calm supportive manner helped us though every step of the process. She is very clear spoken and honest. This helped to ensure we were realistic in our expectations. I can also happily confirm that everything she advised us on prior to the listing turned out to be spot on . Leslie knows the Berkshire market perfectly! KC - Stockbridge
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Endorsements
Leslie Chesloff has been our agent for approximately the last 18 months. She understood our likes and desires and was able to screen the available real estate very successfully. She did not forward any listings that were out of our price range or our preferred design. When an appropriate listing was available she thoroughly researched the property successfully for pertinent details. At all times she maintained a cheerful, confident, timely, professional manner. We could not have asked for a better agent. JW - Egremont
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Endorsements
Working with Leslie Chesloff has been a great experience and a great success! Not only is she a true professional who is very knowledgeable and dedicated to her clients needs, she is also a lot of fun to deal with. You can count on her to be available and responsive. She answered all questions quickly and honestly, and was responsible for selling our house above asking price. Couldn’t ask for more in an agent. We recommend her highly! IM - West Stockbridge
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Endorsements
Leslie was there every step of the way, including afterwards, helping steer us towards resources in the community. She is a wonderful person to have had welcome us into the community, and I would not hesitate to recommend her. Thank you, Leslie! EA - Great Barrington
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Endorsements
Leslie is professional, works hard for the client and she is industrious. You want her to be your broker; she will pull the the parties together to close the deal. Her attention to detail is superb! DO - Great Barrington
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Endorsements
It was a real pleasure to work with Leslie. She was extremely knowledgeable of the market and her style and approach really helped us purchase our property at a great price. I really enjoyed working with her and highly recommend her to anyone looking for real estate in the Berkshires. CD - Lenox
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Endorsements
Leslie was an pleasure to work with at every step of the process. She is not a high pressure salesperson which I very much appreciated. She is very knowledgeable about the process and was always extremely responsive and helpful with our myriad of questions. We would use her again in a heartbeat. AB - Stockbridge
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Endorsements
Leslie was super in helping us navigate the purchase of a beautiful home in Egremont. She was intensely knowledgeable, and worked quickly to get the answers to our questions about the property and the area. She gave us the straight scoop and was expert in understanding our needs. I would recommend Leslie to anyone searching for a home in the Great Barrington area. KM - Egremont
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Endorsements
We had the most wonderful, positive, supportive experience with Leslie. We'd been house hunting for some time, using a different broker and agency, without much success. We decided to switch agencies, and to look in the Berkshires instead of in the Hudson area. Our first meeting with Leslie was immediately so much better than what we'd experienced previously. She was friendly, positive, and enthusiastic. We had narrowed to a handful down the dozen or more houses she'd sent us to see on our first day. She very quickly seemed to understand what it was that we were looking for. We saw the house we ended up buying on that first day. She made us feel supported and was extremely helpful, offering to do whatever we needed to make the process go more smoothly and quickly. She has an incredible spirit and can-do attitude, and even after the process was complete, she remains available and helpful to us in so many ways. We are so grateful to her and enthusiastically recommend her to anyone looking for a house in the Berkshires. If we could give her ten stars we would! user2718750
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Endorsements
The search for a new home is such an adventure! Discovering opportunities, weighing pros and cons, and ultimately diving in. Leslie is a great guide through it all. At one point, we found ourselves moving towards the closing that, while starting well, became very complicated. We focused on how to make the deal work rather than on our feelings about this increasingly complex situation. She helped us come to our senses and then helped us find the property of our dreams. She proved to us that regardless of the question or challenge we encounter, she will always have our best interests at heart. We are clients for life! zuser20150816055040927
double quote
Endorsements
Leslie was wonderful to work with! She is a consummate pro in every way––unfailingly generous, deeply knowledgable about the area, savvy and smart and patient. We were to new to the area, and she made this process easy and fun and painless. I'd recommend Leslie to anyone. She's a genuine star. zuser20160328065235673
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Endorsements
Leslie was there every step of the way, including afterwards, helping steer us towards resources in the community. She is a wonderful person to have had welcome us into the community, and I would not hesitate to recommend her. Thank you, Leslie! eaber
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Endorsements
Leslie was super in helping us navigate the purchase of a beautiful home in Egremont. She was intensely knowledgeable, and worked quickly to get the answers to our questions about the property and the area. She gave us the straight scoop and was expert in understanding our needs. I would recommend Leslie to anyone searching for a home in the Great Barrington area. kennethmurphy1
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Endorsements
Leslie was an pleasure to work with at every step of the process. She is not a high pressure salesperson which I very much appreciated. She is very knowledgeable about the process and was always extremely responsive and helpful with our myriad of questions. We would use her again in a heartbeat. alisonrbaker
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Endorsements
Leslie was amazing to work with. She was always available, trustworthy, gave us great advice, and went above and beyond what was expected to help us out throughout the process of buying a vacation home! Even now after the sale was finalized she is still helping us with the house! Leslie made the process easier than we could have ever imagined! naomib27
double quote
Endorsements
Leslie was amazing in helping us to sell our home. We had moved away and she gave us great advice on what to set up in preparation for the sale so we could have extra time to manage things remotely. She actually networked to find a buyer before we ever made it to the listing date! Her true professionalism and calm supportive manner helped us though every step of the process. She is very clear spoken and honest. This helped to ensure we were realistic in our expectations. I can also happily confirm that everything she advised us on prior to the listing turned out to be spot on . Leslie knows the Berkshire market perfectly! choate555
double quote
Endorsements
Leslie is professional, works hard for the client and she is industrious. You want her to be your broker; she will pull the the parties together to close the deal. Her attention to detail is superb! zuser20140321164731844
double quote
Endorsements
Leslie Chesloff has been our agent for approximately the last 18 months. She understood our likes and desires and was able to screen the available real estate very successfully. She did not forward any listings that were out of our price range or our preferred design. When an appropriate listing was available she thoroughly researched the property successfully for pertinent details. At all times she maintained a cheerful, confident, timely, professional manner. We could not have asked for a better agent. jweiss155
double quote
Endorsements
It was such a pleasure working with Leslie. She was welcoming, knowledgeable and very responsive, both during the process and even after we closed. I've asked for recommendations for everything from plumbers to restaurants as we get to know our new home and community and Leslie has given us great advice. Call her! zuser20140216172842525
double quote
Endorsements
It was a real pleasure to work with Leslie. She was extremely knowledgeable of the market and her style and approach really helped us purchase our property at a great price. I really enjoyed working with her and highly recommend her to anyone looking for real estate in the Berkshires. carlosdpublic

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  • Leslie Glenn Chesloff

    Leslie Glenn 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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