Lilly Roberta Webb

June 7, 1920 - July 16, 2022

Funeral Details:

Lilly Roberta Webb (nee Wilson)

Lilly in her 94th year passed away peacefully with her 3 daughters at her side on July 16, 2022 at Hospice Simcoe.  Lilly was the loving wife of the late Elwood Webb; Loving mother of Lynn and the late Dennis Underwood, Karen and John Kelly, Gayle and Ted Fairbank; Dear Nanny of Tyler, Amanda, Audrey, and Abigail Pitcher; Lindsey Pitcher and Austin, Nathan, and Riley Cook;  Michael Kelly and Stacey Withrow and Kenzie, Aiden, Avery, Brayden, Addison, and Blaire; David, Sarah, William and Lauren Kelly;  Nicole and David Shukster and 3 children; Adam and Jacquie McLennan and 2 children; Amber Fairbank and Rob Moore and 2 children; Joshua Fairbank.  Lilly will be missed by her sister-in-law Meril Cunningham.

Lilly worked alongside her husband and Bob and Hazel Webb at Webb Brother’s Service Station.  With Lilly’s smile and outgoing personality, she made friends easily.  Lilly was very active in her younger years playing golf and winning the Southern Ontario Ladies Curling championship.  She was an active member of St. James United Church in Stroud, Eastern Star and Stroud Seniors.  She loved nothing better than playing a game of bid euchre with family or friends.

Due to Covid numbers the funeral will be by invitation only.

A special thanks to Dr. Kotchetkov and Chrissy at the Simcoe Muskoka Regional Cancer Centre.

In lieu of flowers a donation to either Hospice Simcoe or the Simcoe Muskoka Regional Cancer Centre would be appreciated.

Online memories and condolences may be made at

Peaceful Transition Simcoe


12 Condolences
  • Doug & Heather Wice
    Posted on: Saturday, July 23, 2022 Reply

    To the entire Webb family, please accept our condolences on the passing of Lily. Webbs Service Station was a Painswick fixture while we grew up, and Lily was a big part of its success. Cherish the memories.

  • Gladys McKay
    Posted on: Saturday, July 23, 2022 Reply

    Beautiful smile ,kind heart and a generous spirit What a great lady! They are together again in heaven ! G McKay

  • Chris Sheard
    Posted on: Saturday, July 23, 2022 Reply

    Sending my condolences to the entire family. I remember Mrs. Webb from the service station in Painswick. We lived just two doors down. Blessings to the entire family.

  • Kathy French
    Posted on: Saturday, July 23, 2022 Reply

    Lynn, Karen, Gayle and families, please accept condolences from our family. Your mom was a wonderful and gracious lady and I fondly remember our 4H meetings in your kitchen, where she patiently taught us some of our first cooking skills. I am grateful that I got to see her a couple of weeks ago at the Griffith’s birthday celebration. I know she will be greatly missed.
    Kathy French

  • Karen & Steve Neely
    Posted on: Saturday, July 23, 2022 Reply

    We are sending our sincere condolences to all of the family with the passing of Lilly.
    Fond memories over the years
    May she Rest In Peace

  • John Chalmers
    Posted on: Sunday, July 24, 2022 Reply

    June Chalmers and Family,

    Lynn, Karen, Gayle and family, on behalf of the Chalmers family please accept our sincere condolences. Our memories are filled with love and our hearts are saddened with the news. Our families have spent so much time over the years, getting involved in community projects, baseball get togethers and the many card games. It was so nice seeing Lilly at the Allandale retirement station with Karen a few weeks ago. Thank you Lilly for the wonderful memories. We will all miss your beautiful smile and warm heart.
    Sincerely June

  • Marjory Nielen
    Posted on: Sunday, July 24, 2022 Reply

    Lilly and Elwood were wonderful next-door neighbours for 15 years. Always there for visits, watering gardens, cups of tea, playing bid euchre. I’m so grateful to have had a wonderful last visit with Lilly in late June. We shared many fond memories on that day. My sincere condolences to her wonderful family who she loved dearly.

  • Bob & Louise Cumming
    Posted on: Sunday, July 24, 2022 Reply

    Part of our growing up in Innisfil was visiting Webb’s Service Station several times a week minimum. Later when we operated Cumming Transport we were lucky to have Webb’s do repair/service work for us. Always done right and in a friendly manner. Thank you to the Webb family for this life experience. You have touched more people than you can imagine. Our thoughts are with you as you celebrate Lilly’s beautiful life.
    Bob and Louise Cumming.

  • Mary McIntyre
    Posted on: Monday, July 25, 2022 Reply

    My family was very lucky to have Lily and Elwood as next door neighbours in Kingswood. Lily was a lovely, happy , friendly person who had so much positive energy. She will be greatly missed!


    Ralph and Mary McIntyre

  • Di-Ann Hughes
    Posted on: Monday, July 25, 2022 Reply

    Sincere condolences to Karen, Lynn, Gail and the entire family. Lilly was a very friendly, warm and classy lady. Enjoy your happy memories. Rest In Peace Lilly. 🙏🏻

    Di-Ann Hughes

  • Joyce Rees
    Posted on: Tuesday, July 26, 2022 Reply

    My deepest sympathy to all the family, in the passing of Lilly. I knew her from 1972 in the Order of the Eastern Star, and always liked and admired her – many happy memories.

    Sincerely, Joyce Rees

  • Bernadette & Doug Lougheed
    Posted on: Wednesday, July 27, 2022 Reply

    Lynn, Karen, Gayle and families.
    Our sincere condolences on the loss of your mom…. what a wonderful lady!! Very glad to have seen her recently at Allandale Station when Karen was entertaining. She always looked after Doug when he visited Stroud Seniors luncheon’s…place set and ready to go! Her impact on the Painswick and Innisfil community will be long lasting. She will certainly missed by many beyond her family. Thinking of you at this difficult time.
    Bernadette & Doug Lougheed

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