Windsor Forest: Where Neighbors Become Family and Families Come Back Home
By John Womeldorf, A.K.A. Mr. Williamsburg
For a family-friendly community with a central location, excellent schools, mature trees, and one of the most active social calendars in Greater Williamsburg, it’s hard to beat Windsor Forest.
But for me, Windsor Forest is more than a “great neighborhood.”
It’s home.
I’ve lived here for more than 25 years. My wife and I raised our two sons here. They learned to ride bikes here. They spent their summers at the pool here. They swam for the Windsor Forest Frogs from age six through their senior years in high school.
This is where our family story unfolded.
And after selling homes all over the region for more than two decades, I can honestly say:
Very few neighborhoods offer what Windsor Forest does — year after year, generation after generation.
A First Impression That Still Holds True
More than a decade ago, Heather Moore and her husband first drove through Windsor Forest while searching for a home.
They happened to arrive on the night of a swim meet.
“We could hear the hustle and bustle,” Heather recalls. “There were people everywhere. Kids, parents, neighbors walking dogs. It was clearly active and friendly. We felt immediately that this would be a great place to raise kids.”
Thirteen years later, Heather says that instinct was absolutely right.
That story is repeated again and again here.
People don’t just “find” Windsor Forest.
They feel it.
A Neighborhood Designed to Last
Windsor Forest spans more than 321 acres and is located off Longhill Road between Centerville Road and Route 199.
It was developed in the early 1970s by Robert S. Hornsby, Sr., a respected community leader and visionary developer.
Instead of clear-cutting land, Hornsby designed roads and lots around existing trees and natural contours. A wooded greenbelt still surrounds much of the community today.
He also sold lots to some of the best custom builders of the era — many of whom were building in Kingsmill, Ford’s Colony, and First Colony.
The result?
No two homes are exactly alike.
You’ll find mostly two-story Colonials, along with transitional and contemporary designs, on generous lots ranging from roughly half an acre to over an acre.
That diversity gives Windsor Forest its timeless character.
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Raising Kids in Windsor Forest
When our sons were growing up, Windsor Forest felt like the perfect environment.
Safe streets.
Sidewalks.
Bike rides to the pool.
Friends everywhere.
They had freedom — and community.
Both of our boys swam for the Windsor Forest Frogs from childhood through high school. Like many kids here, they grew up on that pool deck.
Over the years, dozens of Frog swimmers have gone on to compete in college, many on full scholarships. One former Frog even went on to compete in the Olympics.
That doesn’t happen by accident.
It happens when a community supports its kids.
The Pool: The Heart of Windsor Forest
The Windsor Forest pool and clubhouse remain the social center of the neighborhood.
It’s a 25-meter, competition-sized pool with lap lanes, a diving well, and a baby pool.
I had the privilege of serving as Pool Manager for 10 years and serving on the HOA Board for more than 14 years. That gave me a front-row seat to how much care and volunteer effort goes into making this place special.
Friday nights in summer are legendary.
As Heather once joked, “The pizza delivery guy is in and out all night.”
It’s been that way for decades.
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A Social Calendar That Actually Feels Social
Windsor Forest isn’t just a collection of houses.
It’s a real community.
Throughout the year, residents enjoy:
- Easter celebrations
- Christmas caroling and visits with Santa
- Holiday light contests
- Pool parties
- Clubhouse socials
- Tennis and pickleball gatherings
- Wine Wednesdays
- Ladies’ Luncheons
And then there’s the Fourth of July.
Our parade is legendary.
Decorated bikes. Wagons. Costumes. Neighbors lining the streets.
It’s not staged.
It’s genuine.
And it’s wonderful.
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Neighbors Helping Neighbors
One of the most meaningful parts of Windsor Forest is something you won’t find on a map.
It’s how neighbors take care of each other.
We have residents who welcome newcomers with directories and visits. We have the “From the Heart Club,” which organizes meals and short-term assistance for neighbors recovering from illness, surgery, or loss.
People notice when someone needs help.
And they respond.
A True Multigenerational Community
Windsor Forest is home to:
- Young families
- Established families
- Empty nesters
- Retirees
- Longtime residents
- Second-generation homeowners
More than 19 families currently living here grew up in Windsor Forest and moved back as adults.
In some cases, three generations have lived here at the same time.
That’s rare.
And it speaks volumes.
What Residents Say
John Womeldorf — Resident & Realtor
“There are families here who grew up, got married, and moved back. You see it most clearly on the Frogs swim team — new generations growing up together.”
“Christmas here is especially fun. We even have people competing for the ‘Griswold Award’ with their decorations. It’s serious — and hilarious.”
Dorothy Coleman — Retired William & Mary Professor
“I love the privacy from the trees, but I still feel connected to my neighbors. Everyone is generous and kind.”
“I often see deer when I pull into my driveway at night. It’s peaceful.”
Windsor Forest Amenities
- Competition-size swimming pool
- Clubhouse
- Playground
- Tennis and pickleball courts
- Soccer field
- Walking routes and green space
- Quarterly newsletter (The Forester)
- Active social committee
📊 Current Homes for Sale Windsor Forest
This section allows buyers to see what is currently available in Windsor Forest, including pricing, layouts, and condition.
Inventory here is often limited.
When homes come on the market, they tend to attract strong interest.
📈 Recent Sales in Windsor Forest
Reviewing recent sales in Windsor Forest helps buyers understand:
- Market trends
- True values
- Typical features
- Renovation levels
Past listings often provide insight into what may become available again.
Context matters.
Windsor Forest History
Windsor Forest was developed beginning in 1971 by Robert S. Hornsby, Sr., a respected civic leader.
His vision was simple:
Create a neighborhood that would still feel good 50 years later.
He succeeded.
Construction continued through the mid-2000s, maintaining high standards throughout.
Schools
Windsor Forest is served by the Williamsburg-James City County Public School System, consistently ranked among the top systems nationally.
Public Schools:
- J. Blayton Elementary
- James Blair Middle
- Lafayette High
Private Options:
- Walsingham Academy
- Hampton Roads Academy
- Williamsburg Christian Academy
- Williamsburg Montessori
- Providence Classical
Why I’ve Sold So Many Homes Here
Over the years, I’ve honestly lost count of how many homes I’ve sold in Windsor Forest.
It’s approaching forty at this point.
That’s not because I “specialize” here in some calculated way.
It’s because I love this neighborhood.
I know its rhythms.
I know its traditions.
I know its people.
I know what it feels like to raise kids here, to volunteer here, and to grow older here.
When I talk about Windsor Forest with clients, I’m not reciting bullet points.
I’m sharing lived experience.
If that helps someone fall in love with this place the way I did, then I’ve done my job.
And if Windsor Forest isn’t the right fit, I’m just as happy helping them find the place where they will feel that same connection.
That’s what real estate should be about.
If Windsor Forest Isn’t Your Perfect Fit…
If you’re drawn to older, established neighborhoods with large lots and custom homes, you may also want to explore:
- Queens Lake
- Kingsmill
- Kingspoint
- First Colony
- Ford’s Colony
- Banbury Cross
- Kingswood
I’m always happy to walk you through the differences.
Why I Write Neighborhood Pages Like This
Someday, I’ll retire.
But I don’t want my work to disappear.
I want there to be a lasting library of honest, firsthand information about Williamsburg neighborhoods — written by someone who actually lived in them.
Not marketing copy.
Real stories.
Real experience.
That’s what helps people make good decisions.
Meet Your Local Guide: Mr. Williamsburg
Psssst… I’ll let you in on a little secret.
I’m not a typical real estate agent.
I’m a local ambassador first.
Known throughout the region as Mr. Williamsburg, I combine deep community knowledge, storytelling, and practical market insight to help buyers and sellers navigate every step with confidence.
📞 Call/Text: 757-254-8136
📧 John@MrWilliamsburg.com
🌐 https://mrwilliamsburg.com
Your real estate journey is personal.
And it deserves to be treated that way.
Warmly,
John Womeldorf
A.K.A. Mr. Williamsburg