Jenny Windsor was born and raised in Roanoke, Virginia.
She graduated from the College of William and Mary. After working for five years in Washington, DC, she moved to Virginia Beach, began raising a family and studying art Old Dominion University. She has been painting for over thirty years.
Her works have been featured in numerous galleries and juried shows selected by jurors as diverse as artist Faith Reingold, artist William Berry, curator Brooks Alexander, artist Sondra Freckelton, and Tom Armstrong, Director Emeritus of the Whitney Museum. She has received awards from many jurors including a Best-in-Show Award at the Mid-Atlantic Show in Norfolk, chosen by William Hennessey, Director of the Chrysler Museum. Her works are held in over a dozen corporate collections including Norfolk State University, Duke University Hospital, Austin Peay State University, Central Carolina Bank and Smithfield Foods.