Penney Holland
Agent
A lifelong resident of the Eastern Shore, Penney Holland brings deep-rooted local expertise and a passion for helping others find their perfect home in Cape Charles and beyond. Having grown up in Cape Charles and lived in Northampton County for nearly her entire life, Penney offers an insider’s perspective on the area’s most sought-after properties, unique neighborhoods, and investment opportunities.
Penney’s journey in real estate began long before she earned her national and state certifications in 2021. Since 1996, she and her husband have been actively investing in Cape Charles real estate, giving her firsthand experience in the market’s evolving trends and opportunities. With a background at Virginia Tech’s Agricultural Research Center and the Virginia Cooperative Extension office, Penney brings a strong foundation in community development, problem-solving, and client service to her real estate career.
What Penney's Clients Have to Say
More About Penney
Where did you grow up?
I was fortunate enough to grow up right here in Cape Charles.
How long have you lived on the Eastern Shore?
I have lived in Northampton County here on the Eastern Shore for my entire life besides college years.
In what year did you begin your career in real estate?
I received my national and state certifications in the spring of 2021 and began my career as an agent in May 2021 with Chesapeake Properties. Prior to joining Chesapeake Properties, I worked with Virginia Tech both at the Agricultural Research Center and the Virginia Cooperative Extension office in Northampton County.
What originally got you interested in real estate?
My husband and I began investing in real estate in Northampton County in 1996. Most of our investments have been in the Cape Charles market. I love all of the unique aspects Cape Charles offers that you will not find anywhere else along the coast: the public beach, two deep water boat harbors, five square miles of golf cart access, a diversified commercial and residential market, the historical downtown and world class Palmer and Nicklaus golf courses.
What do you enjoy most about being a real estate agent?
Being able to showcase the town in which I grew up (Cape Charles), as well as all of Northampton County.
What is your favorite outdoor activity on the Eastern Shore?
I enjoy the outdoors on the Shore: boating, beaching, playing pickleball and golfing. I also enjoy exercising in the great workout facility options that we have in the area.
Do you prefer the seaside or bayside of the Eastern Shore?
Both the Bayside and the Seaside are unique in their own way and offer many positives based on peoples’ personal tastes and preferences.
Beach or boat – if you had to pick one, which would it be?
You can’t go wrong – a great decision either way!
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Ready to buy, sell, or just have questions? Penney is here to help—no pressure, just real advice. Fill out the form, and she’ll be in touch soon!