At Central Florida Foundation, we often say, “It’s not how much you give, it’s how you give it.” A thoughtful gift can extend far beyond a single moment. With the right structure and a clear sense of purpose, philanthropy can reflect a donor’s values and continue responding to the community for generations to come.
An Officer's Wife
Penelope Wilson, or Mrs. Wilson as she preferred to be called, is a powerful example of this idea.
After an adventurous life of living around the world, Mrs. Wilson and her husband, Lt. Col. USAF Ret. Winton Wilson, settled in Longwood, Florida. She described her lifelong career as "an officer’s wife," a life in which she took deep pride. When Mr. Wilson passed away in 2000, Mrs. Wilson relocated to the Mayflower Court Retirement Community in Winter Park.
Honoring Winton
The same year she moved to Winter Park, she decided to honor her husband by establishing a charitable fund at Central Florida Foundation (which, at the time, was called the Community Foundation of Central Florida). With a gift of $10,000, the initial contribution minimum at the time, she established the Penelope and Winton (Lt. Col. USAF Ret.) Wilson Fund at Central Florida Foundation, an area of interest endowment fund set to focus on populations that were underserved or economically disadvantaged.
During her years in Winter Park, the Penelope and Winton (Lt. Col. USAF Ret.) Wilson Fund made annual grants to nonprofits such as the Coalition for the Homeless and the Salvation Army.
She also went on to establish six charitable gift annuities with the Foundation, naming the Penelope and Winton (Lt. Col. USAF Ret.) Wilson Fund as the beneficiary. A charitable gift annuity, or CGA, provided her with a steady source of income during her lifetime, while ensuring that the remaining funds would ultimately support the community through her fund at the Foundation.
The Power of a Legacy Gift
At the age of 99, Mrs. Wilson passed away in 2015. She is remembered as a person who loved adventure, her husband, and this community she called home. In addition to the contributions from her CGAs, Mrs. Wilson had listed the Penelope and Winton (Lt. Col. USAF Ret.) Wilson Fund at Central Florida Foundation as a beneficiary of her estate.
The larger estate gift Mrs. Wilson left behind coupled with the power of an endowed area of interest fund structure has made the Penelope and Winton (Lt. Col. USAF Ret.) Wilson Fund at Central Florida Foundation a true force for good in the region.
With over $1.7 million invested in the community, the fund has supported economically disadvantaged communities through programs such as urban farming, affordable housing, financial literacy training for women, and food security.
Ready for the Unexpected
Most recently, the Penelope and Winton (Lt. Col. USAF Ret.) Wilson Fund helped ease the impact of the SNAP benefits disruption in the fall of 2025. This is where the value of an area of interest fund becomes clear. No one could have anticipated the crisis, but the fund’s flexible structure allowed Central Florida Foundation to move swiftly, deploying charitable dollars from the fund to food banks responding to immediate needs across the community.
Because the fund is endowed, Mrs. Wilson’s legacy of giving will continue for generations. Under the stewardship of Central Florida Foundation, the fund will remain a lasting reflection of her philanthropic values, supporting the evolving needs of Central Florida and the community she cared deeply about.
Over the last 26 years, the Penelope and Winton (Lt. Col. USAF Ret.) Wilson Fund has quietly created opportunity across the region. Mr. and Mrs. Wilson’s legacy is woven into the fabric of Central Florida, addressing needs that weren’t there when the fund was established, but are able to be addressed through thoughtful philanthropic planning.
