Douglas Elliman Mourns the Passing of Beloved Colleague Karen Chesleigh

It is with the heaviest of hearts that we share news that our dear friend and colleague Karen Chesleigh has passed away.

For almost two decades, Karen touched our lives in profound ways, both personally and professionally. As our Senior Vice President of Human Resources, she brought extraordinary empathy, tenderness and kindness to her day-to-day work on behalf of each of us. Karen exemplified what we mean when we describe Douglas Elliman as a family. We are a better company thanks to her, and she will be greatly missed.

Our hearts go out to Karen’s devoted and loving family and friends. We wish her husband, Christopher, and daughter, Kaitlyn, the strength and courage to endure this terrible loss.

Below are details for a service and memorial campaign honoring Karen’s life and legacy of love and kindness:

Saturday, August 13, 2022 at 10:30 AM
Our Lady Queen of Martyrs Church
110-06 Queens Blvd (Ascan Ave. entrance)
Forest Hills, Queens

Limited parking is available in the lot on 72nd Road, between Queens Blvd and Austin St.

In lieu of flowers, which the church does not accept, please consider honoring Karen with a donation to the GoFundMe campaign in support of her daughter’s education.

There are no words to adequately describe the sadness we feel. We can only hope that each of us finds some comfort in remembering Karen with the same love and kindness she shared with all of us.

In that spirit, we invite all who knew Karen to send thoughts, memories, photos and other tributes to We will collect and share them here and with Karen’s family as we receive them.

In Memoriam

To say that Karen was the heart and soul of Douglas Elliman would be an understatement.  She was the glue that kept us together. She had a wonderful way of connecting with everyone at DE, from those in corporate to the individual agents. She was the person we all went to when we needed to be heard. If something was on your mind and you weren’t sure where to go, Karen helped. She made time for everyone regardless of how many directions she was being pulled in. She listened with intent and she never made you feel invalidated. She had such a magical way of expressing understanding, concern and most of all, compassion.

To Karen’s family, I am so incredibly sorry for your loss. I hope you know how loved she was by those of us in her work family. Kaitlyn, your mom was and will continue to be, a beautiful soul.  You could not have been raised by a more wonderful woman.  I hope that gives you and your father some comfort.  May she rest in eternal peace.

Rachel Weiss

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I was so sad to hear the heart-breaking news that Karen had passed. She was one of the kindest people, with a warm smile and a gentle manner. She was always happy to make time for a chat and left a sprinkle of happiness everywhere she went. 

A beautiful person inside and out, I know her loss will be felt deeply by all that knew her. 

My thoughts and prayers go out to her family. 

She was taken far too soon

Stacey Watson xoxo

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Karen Fontana Chesleigh, a very special member of our Douglas Elliman family, has, all too soon, left us, and to all who knew and loved her, our hearts are broken. As Sr. VP of Human Resources, Karen was the first welcoming face to all new hires. Warm, loving and accessible, it was Karen who got many over their first day jitters. Our friendship was immediate when I joined DE approaching 19 years ago…both of us working mothers, we had so much in common & always kept in touch. Karen was the real deal. Genuinely caring of all and like the butterfly of her 813  was the personification of a loving human being. Eight letters, 3 words, 1 meaning❤️

Love you always, dear Karen and thank you for being there and gracing all who knew you. You made such a difference in every life you touched, now R.I.P. 🦋💔🦋💔 

Sincere condolences to Karen’s husband Chris, daughter Kaitlyn & brother Anthony.

Corinne Pulitzer

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My deepest condolences to Karen’s family and loved ones.

Scott James, Pasadena, Ca

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Karen was not just a client, she was a friend.  I owned a staffing agency and eight years ago I “cold called” Karen because I heard she was looking for an assistant for Dottie. Everyone in sales knows that no one ever returns sales voicemails, but sure enough Karen did! We clicked that minute and worked together ever since. Working with Karen was never work though. We knew so much about each other… her cooking school, European travel plans, how proud she was of her daughter and her commitment to 813.

Candidates adored Karen. They recognized her beauty inside and out and never once did anyone tell me they didn’t want to work for her.

Karen was such a special person, a bright light on a gloomy day. She exuded kindness, loyalty and love. We are all better for having known her.

My heart goes out to Chris and Kaitlyn and her Elliman family. I’m heartbroken and will miss her greatly.

May her memory forever be a blessing.

Jill Rosenfeld

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Karen is the most beautiful person inside and out that I’ve met in my lifetime. Truly a class act! I am fortunate to have had the privilege to have her in my life as a colleague and a good friend. I will miss her dearly! Our hearts and deepest condolences to Kaitlyn, Christopher and their family.

Sal Troia

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Karen was an extraordinary person, one the kindest, loveliest person I’ve ever known.  She was here when I started working at Elliman more than 20 years ago.  She made me feel so welcome and part of the family. 

I remember when we worked together at the welcome desk during the REINVENT Conferences every year at the Borgata in Atlantic City.  There was always a themed Costume Party and one year Karen came as Priscilla Presley with a life-size cut of Elvis.  The next year she came as Kate Middleton with a life size cutout of Prince William. She walked around all night with her “men”.   It was hysterical!  I remember thinking that only she could pull that off. I told her that and she laughed happily. 

At the Southampton Arts Center for our East End Spring Mixer this past April 26th, we talked for almost a half hour.  She gave generously of her time and was not in rush to move on to the next person.  She always made you feel special.  

I will miss Karen terribly.  She helped create the family atmosphere that we all enjoy and thrive in here at DE, by simply being exactly who she was.  A wonderful, caring, loving person.   Rest In Peace, Karen.  

Love, Barbara Mattson 

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Another Angel received her wings! 

Karen was a beautiful, intelligent, warm & loving soul! Her smile would light any room & melt the hearts of many! She looked over me & especially my son, Marquis, as a protective mother Wolf would watch over her Cubs! I know many of my Colleagues know exactly what I’m talking about! She will be truly missed!! 

My deepest condolences & prayers to her husband & daughter, may they find comforting in knowing that Karen will never be forgotten!

Rest in Peace my Friend,

Marjorie Campbell

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From the day I met Karen in 2006 she made me feel welcome loved and uplifted every moment we spoke.  Karen was truly an angel! What a Great loss!

She always put everyone before herself.  She was a great teacher and an example of kindness.

She was so gracious so kind so loving and grateful. She loved her family and appreciated everything she had in your life.

My prayers and deepest sympathy are with her husband, daughter, entire family and loved ones.

She will always be in my heart.

Silvia Aboud

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My deepest condolences to her family and loved ones.

Roya Oveisi

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Like many of my colleagues, Karen was the first person I met when interviewing here (in a VERY TINY OFFICE which was slightly claustrophobic).

Her warmth and genuine goodness was easy to see right away and she always made you feel special when she saw you and said hello.  Karen always had a calm and caring demeanor; you just knew she was looking out for everyone behind the scenes.

She always called me sweetie when she saw me, I think she probably called everyone that, but it always made me smile when passing her in the hall.   Karen always brought a smile to your face, even when it came to business discussions.  I keep a picture on my desk of Karen from my first Elliman event and I really cherish this photo as these are all people that I care very much about.  How many people get to wear hulk hands with the head of HR in their company?

I wish I could have told her all this, but I consider myself very fortunate to have known her, and that she saw enough in me to give me the opportunity to work at Douglas Elliman which has been rewarding beyond measure meeting so many wonderful people.  

Paul Nilsen

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Thank you, Karen for everything.

Your time, your laugh, your positivity, and especially for personally checking in on me when I underwent surgery last year. Your calls and texts were so fun to receive and truly appreciated. You made Elliman personable and compassionate. 

God Bless You, Your Family, and Your Elliman Colleagues who were fortunate to see you each and every day.

Most Sincerely, 

Lisa Rainis – Massachusetts

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To Karen’s family:

I love Karen!! She is the most beautiful person, inside and out! I cried so much when I heard about her passing! I remembered watching her on TV at The Chew, I jumped from my seat and we laughed so hard next day!!!.

I’ll always have fond memories of her, the pictures are from 2019 , when I Took her for lunch at The MoMa  restaurant to thank her and the group for being the best Professionals in the company! Today I can say I lost a friend and there is a hole in my heart! Douglas Elliman will never be the same without Karen!

While no one and nothing can fill the hole created by the loss of your loved one, I know that She would want you to think of all the joy, love, and laughter that remains in the world. I am thinking of you and sending heartfelt sympathies and condolences.

Marcos G Cohen

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We are absolutely devastated to hear this news this morning. After seeing such a beautiful and vivacious Karen at a recent Elliman event in the spring, we were so hopeful that she would overcome this horrible disease. Our hearts and deepest sympathies go out to her husband and daughter and all that were blessed to know her.


Todd Bourgard & Barbara Leogrande

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So fortunate to have been able to spend the past 7 years working with Karen. She was without a doubt the sweetest & funniest person I have ever had the pleasure knowing. Saying she will be missed is too much of an understatement. Sending much love & condolences to her family.

xoxo, Hal D. Gavzie

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I am so sorry to hear about Karen’s passing. I remember interviewing with her in 2006 when I was looking to relocate from another firm.  She was so warm, and inviting that I did not interview with any firms after that first meeting!  She made the choice to join DE incredibly easy for me!

She was truly a gem and will be greatly missed!  My deepest and sincerest condolences to her family, and loved ones!  May her memory be a blessing!

Kathy Koch-Pitlake

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To the Family of the late Karen Chesleigh,

I am so upset to hear the news of Karen’s passing. Having spoken with her and George Wathbun just last year where we had a conversation about work ethics.  Karen treated me with the utmost respect and dignity and for that I am grateful. I am so sorry for her loss and the unfathomable loss to her husband and children. May God continue to comfort them in this most difficult time.

“Weeping endures for a night, but Joy comes in the morning.”  Psalm 30:5

Remember to die is gain, to live is Christ.  Karen is absent from the body but is present with the Lord.

My condolences.

Mary Grady

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Thank you all very much for sharing the touching tribute to Karen. It is true that our hearts are very heavy and will deeply feel the loss of such a kind and insightful colleague and individual.  When faced with challenging situations, such as is often the case when Human Resources is involved, she was always professional, thoughtful, intuitive and kind. We will miss her deeply and send our sympathy to her family and to our many colleagues that worked with her on a daily basis.


Melody Newberry

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I am so sorry to hear this news. I spoke with Karen just once. But I’ve often reflected on her kindness and empathy in that one phone call. It was that real. Prayers for her, her family and everyone who knew her. — Thomas Healy

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So very sad about Karen. She was beautiful inside and out. Always had time for us, and so devoted to Elliman. It is a hole in our hearts. Rest In Peace, dear Karen

Jane and Joe Pontarelli

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Karen was extraordinarily helpful in helping me navigate department of state licensing last year, and when I saw this I remembered her immediately. I offer heartfelt sympathy to her family.

Nan Schiff-Eisenberg



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