By Amy Howell
Realtor & Team Lead · O.N.E. Florida Group
Facts checked October 21, 2026

My answer, with the tradeoffs attached

If I were moving to the St. Augustine area again, I would still start with TrailMark. What makes it right for me is the life I actually use there: walks, trees and a nature-oriented setting. That answer comes with a CDD, an inland location and a close look at the street around any home.

When the Navy brought us to Florida, I specifically told our Realtor that I did not want to live in the woods. Then we drove into TrailMark. The trees were the part that changed my mind.

Our budget mattered just as much. In the homes we compared at the time, TrailMark gave us more house for the money. That is my experience from that purchase, not a promise about today’s prices. The useful lesson is to compare actual homes and the lives around them, rather than deciding from a community’s headline.

In my new video, I change the priorities on purpose. My own answer stays TrailMark; the alternatives reveal what I would need to want differently.

What stayed useful after the move

I chose something I would do often.

I love a simple walk around the community. A spectacular amenity can make a memorable tour, but it earns its place in your budget when you use it. I knew that a lazy river could look beautiful in photographs and still be something we used only occasionally.

The distinction is personal. If your ideal week includes resident events, waterpark time and a connected Town Center, the amenities may be central to your choice. If it includes a walk after work, the route from your own front door deserves just as much attention.

TrailMark’s official guidance describes its trails and amenities as reserved for residents and authorized guests. For a visit, start with the Welcome Center and arrange a tour. A map pin does not give a visitor amenity access.

TrailMark’s current access and tour guidance ↗

The part I wish we had understood earlier

The payment needs the whole story.

In the video, I explain how the CDD affected our own ownership costs. Our first mortgage bill was higher than we had expected, and a later increase mattered to our budget. That experience is one reason I ask buyers to put two homes side by side before deciding which one is affordable.

Asking prices do not show all the differences. A comparison needs current mortgage principal and interest, taxes, HOA obligations, CDD or other assessments, insurance and maintenance. It also needs a check for expenses already included in an escrow estimate.

A CDD can have debt and operations/maintenance components. Use the applicable district’s documents and get a current property-specific figure. Do not assume a seller’s old payment becomes your payment after purchase.

Six Mile Creek CDD ↗ · How Tolomato describes its assessment components ↗ · Our two-home cost worksheet →

Three changes that would change my tour

My shortlist would follow my priorities.

If avoiding a CDD moved to the top

I would give SilverLeaf a serious look. The developer advertises no CDD fees and a wide range of neighborhoods and home types. I would still compare the actual HOA, taxes, insurance and maintenance. I would also test the errand routes in the specific section, instead of treating all of SilverLeaf as one interchangeable place.

SilverLeaf developer’s community facts ↗

If I wanted a fuller amenity routine

I would tour Nocatee and ask which amenities I would actually use in an ordinary week. The valuable thing would be the way the home, paths, parks, events and errands connect. That is the reason to compare the actual village and its costs, not just the biggest attraction in a promotional photo.

Nocatee’s arranged tour information ↗

If the river became the point of the move

I would put RiverTown on the tour. And if I were considering a 55+ neighborhood, I would want to see WaterSong. Its own amenity layer and the broader RiverTown setting deserve a separate conversation from wanting ocean access.

I would ask for the specific home’s association and maintenance documents, too. An active adult label is not a promise that lawn care or every exterior task is included. Eligibility, access and the full fee structure need to be confirmed.

WaterSong’s official neighborhood information ↗