In loving memory of
Karen Jessop
April 15, 1953 – July 7, 2026
Celebration of Life with Live Stream
August 22, 2026
1:00 PM Eastern
Acclaim Independent Living
4801 Pretty Lake Ave., Norfolk, VA 23518
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Karen Jessop Obituary
Karen Jessop was born in Hartford, Connecticut, April 15th, 1953. She passed away in hospice care at Lake Taylor Transitional Care Hospital in Norfolk, Virginia, on July 7th, 2026. Born to Edward and Jean Jessop, Karen was the third child born after her sister Penny Jessop and her brother Peter Jessop and before her sister Kate (aka Kathy Jessop) Whitehead. Karen loved studying and learning, traveling, reading mysteries, watching NCIS and Murder She Wrote, doing arts and crafts and saving things. Central to all of these things was her love of friends and family. Her life was varied and full.
Karen grew up in Guilford, Connecticut, a quintessentially New England town on Long Island Sound. She never lost her love of the ocean and lighthouses. Some of her travels took her in search of the lighthouses of New England and the Mid-Atlantic States.
Throughout her schooling, Karen was an exceptional student. She once said that the only thing she had going for her was that she was the brightest kid in the room. One of the hardest things for her in the last year of her life was when she was no longer able to use her mind as well as she had used it in the early years of her life. It scared her and made her very sad.
Karen had a very creative side. She took great pride in making most of her clothes in high school. Later she enjoyed and was very competent at weaving. It was a great sadness to her that most of her weaving examples were lost in the floods in Florida that destroyed her home. As a young girl, her creativity extended to dance. Karen was in many recitals at Miss Bernice’s school of dance in Guilford.
Her best friend Wendy Gaylord reminded us that she and Karen were the first teenager girls ever to join the Democratic Party in Guilford. This was the foundation for her lifelong support of the ideals and principles of the Democratic Party.
Her exceptionally good grades and test scores garnered Karen a scholarship to Upsala College in New Jersey. There she studied premed/biology graduating with honors but undecided about going on to medical school. Karen made a big decision and moved to St. Louis, Missouri. She started working in the medical profession as a ward clerk in the emergency room at Barnes Hospital. There she met up with Connie Gaffkin and a fantastic group of nurses with whom she maintained a lifelong friendship. Someone suggested she look into medical records. Karen did just that, earning a second college degree in medical records administration. She was a highly respected medical records director for several major hospitals in the St. Louis area. Along the way she met up with great friends Kathy Oltmanns , Vincent McGrath and Bill Barron with whom she shared cherished friendships that supported her throughout the years.
Karen loved to travel. She went to Ireland, Italy, France, and all over the United States. Her trips to Europe were with her friend Sue Kraska. Karen used to joke that she was great to travel with except she couldn’t drive and she was a terrible navigator. They had some great adventures finding their way through some of those small country lanes. Karen had wonderful stories to share about those trips. Karen‘s greatest travel adventures were usually reserved for car trips. She loved to drive; to Connecticut and Florida to see her mother and stepfather, to the West Coast (with Vince) to see Kate and to New Orleans to see Penny. Even though she drove 50 miles each way to commute to her work in St. Louis, she never tired of long car trips to sightsee or visit family and friends. Each trip was a grand adventure for her.
Karen was an incredible saver and preserver of things. Much of the history and memorabilia that we still possess is because Karen saved things for us. For major life events, she produced the most amazing photo scrapbooks. Karen always said, she was saving things from the landfill.
After almost 40 years in St. Louis, Karen moved to Century 21, a manufactured home community in Fort Myers, Florida. It was a very special place to Karen. She was active in the arts and crafts group, card playing, hotdog Wednesdays, Potluck dinners, breakfast in the evening —- pretty much anything going on in the clubhouse and you’d probably find Karen there. Even when limited mobility became an issue, she got around everywhere on her electric scooter. She had a lot of friends in the park. People really loved her stories and her sense of humor. She wrote the humor column for the newsletter every month.
Shortly after arriving in Florida, her stepfather, Donald Sutherland, passed away. Karen immediately volunteered to take mom into her home. For the next nine years, Karen took care of her as mom’s Lewy body dementia advanced. It was a true labor of love. Her mother enjoyed a life of dignity, attention and compassion that few elderly people are fortunate enough to have. After the death of her mother, Karen continued to live in Fort Myers. Karen was blessed to have two wonderful aides, Milagros and Tatiana, during this time. Then in 2022, Hurricane Ian came through and destroyed the entire park, including both her home and her sister Penny’s home.
Then began a six week Odyssey of evacuation to a hotel in Fort Myers, then a further evacuation to a hotel in Fort Lauderdale and finally the decision to move to the Va Beach area with the help of Penny and her New Orleans friends Mary Ann and Charlotte. She chose Va Beach because it was where she had the loving support of family, her stepbrother Bob Sutherland, his wife Maureen and nieces and nephew and their kids.
Karen felt a true sense of loss on the death of her mother and the loss due to the hurricane of almost all her treasured possessions. So making the move to Virginia was painful and it was hard sometimes to find joy in the new place.
Karen moved into independent living at Acclaim at East Beach Norfolk. She enjoyed three wonderful years there and cherished all the friends she made playing Hand And Foot, being challenged at bridge, enjoying arts, and crafts, making Valentine’s for veterans, and all the other wonderful things that Acclaim had to offer.
After a diagnosis of breast cancer in 2023 Karen had a struggle with her other comorbidity and the cancer. Her life became very difficult. She was fortunate enough to find a physician, Dr. Marilyn Kellam, whom she absolutely adored and several caregivers, Kattia, Bianca and Dianna who were kind and compassionate and allowed Karen to have a life of dignity. Her sister Penny was happy to provide assistance and support as well.
In the summer of 2026 Karen made the decision that she needed more care than could be provided at Acclaim. She then moved to nursing level care at Lake Taylor Transitional Care Hospital. During that time, Karen continued to say, “I want to go home“. When asked what did she mean, she said (at different times) home meant Acclaim, Florida, Missouri, or Guilford. After five weeks, Karen passed away in peace and with family members present. Karen was finally home.
All of us who knew and loved her are going to miss Karen very much. But we recognize that she has gone on to a place where she will be without pain or handicap, with her full mental capacity restored, and unburdened from all of the things in life that were weighing her down. She has been reunited with her mother. For that, we are very thankful. We are also thankful that she was able to have people in her life who brought her joy and peace and love and friendship.
The Jessop, Whitehead and Sutherland extended families thank you for your love and support at this time and always. Donations can be made in Karen’s honor to the American Cancer Society.
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My acquaintance with Karen was short. It was a pleasure, may she rest now in peace. ann byerly
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may she rest in peace.
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What a beautiful eulogy you and Peter said about Karen ✨️ Karen would be so honored. Your prayer was beautiful said. You and Karen both had a wonderful life. Rest in Peace Karen 🙏 😇🙏You were so loved 😍 ❤️
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You are no longer with us, but you will always be a part of many people’s hearts. You will be missed and remembered forever. praying and thinking of the family through this difficult time of grief. Sending a big hug.
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I will always remember playing cards with Karen and what fun we had
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Prayers to the Jessup and Sunderland Families on Karen’s passing. Catching up with you by reading her obit and listening today to Karen’s service was special.
My days with you all go back to your Guilford days at GHS, First Congregational Church and PF.
Our parents laid the groundwork for us all with family connections at FCC.
Blessings for her life and all her wonderful memories. Thank you for sharing your words Penny with the support of Peter and Kathy.
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That was a beautiful service. Karen was certainly an inspiration for C21. Never will she be forgotten. Earl & Linda
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What a beautiful and inclusive tribute to Karen. I loved seeing her life through so many eyes. Thanks to all.
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Thank you to the whole family for such a wonderful service honoring Karen and her very full life.
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You honored Karen beautifully with this memorable and loving service.
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Karen was one of my favorite clients and people. Always in a good mood, even till the end. I needed her positive energy and gratefullness much more than she needed what we did for her. She will be truly missed. We will honor her legacy by using her estate to help better care for her siblings. That’s the way she would’ve wanted it to go
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Beautiful service! She was much loved!🙏🏻💓
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I’ll never forget visiting Karen in St. louis as a kid and she took me to the top of the arch. It was a remarkable day.
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My name is sandy liewe, I knew Karen from Alexia’s Brothers Hospital in St Louis. We traveled to Outer Banks,NC in early ‘90s with other friends. Karen loved playing in the ocean waves as I do.. her humor was wonderful, and she was talented in arts and crafts. Although I had not seen Karen for many years, she will be missed. Peace and love to all of Karen’s family and friends. 🕊️
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Good afternoon. My name is Milagros Aguilar, and I am one of the many people who had the honor of knowing Karencita. In March 2019, someone asked if I was interested in helping the sister of a fellow volunteer at the food pantry where I also volunteered—though I was warned that she was a very difficult person to deal with! I accepted anyway, and when I met her in person, I realized what a sensitive and loving person she truly was. Over time, we became friends and shared many special moments, despite the difficult health challenges she was facing. She enjoyed every activity we shared; for instance, she loved playing “beauty salon”—after her bath, I would put in her hair curlers and do her nails, especially when she had a dinner or outing planned with her little sister, Penny, whom she adored. We also cooked together; she particularly loved baking cookies, especially for Christmas, which was one of her favorite holidays to celebrate. Sometimes, as soon as I arrived at her home, she already had a project lined up for the art room—a space that took us over two years to organize. We would play music and start painting, cutting, or whatever else she had planned. You cannot imagine how much we enjoyed every day and every conversation. She taught me English, and I taught her Spanish—that was our agreement from day one. Karencita spoke of her mother with such love; at first, she would cry when remembering her, but over time, that sadness began to fade. I spent more than three years with Karen. She taught me that my own problems were nothing compared to the situation she was going through. Today, I thank God for bringing her into my life and for the many lessons she left me, and I pray for peace in the hearts of the family she left behind.
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I remember Karen as a great friend in high school. She, Wendy and I had some truly memorable times together (some unmentionable here!).
I’m sad to know that our time in St. Louis overlapped, and we never knew the other was there. I would have loved to have renewed our friendship.
But I’m happy to know she had a fulfilling life with many friends to love her brilliance and humor. I’ll always remember the home-made root beer I had at her home in Guilford.
My sincere condolences to Peter, Penny and Kate.
Jo-Nell [Silvestro] Labbienti
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Karen and I were friends in school in Guilford. We danced together at Miss Bernice’s School of dance. There were many activities we shared such as making our own clothes, being the family historian and crafts. She is now at her eternal home at peace with her departed family and friends. Cherishing the memories of Karen.
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Thinking of you all as you say a final farewell to Karen. I really enjoyed Karen’s conversations with me over the years. She was bright and intelligent and we always had so much to talk about.
She was always willing to help in C21 clubhouse and she’d zoom down Apollo in her wheelchair, draped in purple and had that lovely smile .
Christmas was special when we would sing carols around the park, stopping at all our Friends homes who needed some ‘ cheering up’ – including her mom sitting waiting for us on the deck….Karen is now a special memory …..Will meet her again in heaven. Thank you Karen for being our friend. From your Scottish friends Anne and Dorothy xxx
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I had the honor of knowing Karen and Wendy G. and a host of wonderful fellow students for only the senior year of HS when my family moved to Guilford. I cherish my time and memories there.
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Karen was always so friendly. And always had a smile. RIP Karen
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What a wonderful synopsis of her life
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Such an honor to know and love this beautiful lady. Walking with departed friends and relatives at last.
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May you Rest in Peace , My Kind Loving Friend!we had some good laughs! Miss you , love Judi Lumpp🙏🏻💕🥲