St. Augustine Neighborhood Guide: What Bailey Martin Knows About Heritage Landing, Trailmark, Silverleaf, and Anastasia Island That Most Buyers Never Ask

Choosing a neighborhood in St. Augustine or St. Johns County is not simply a matter of finding the right price per square foot. The communities in this corridor differ in meaningful ways: their ages, their amenities, their HOA and CDD structures, their resale dynamics, and above all, the lifestyle they offer day to day. Bailey Martin, founder of STA Sunrise Realty and a licensed Florida real estate broker who has spent the better part of a decade living and working across St. Johns County, has a gift for translating those differences into language that helps buyers make decisions they will not regret.

In a wide-ranging conversation on the Real Estate Excellence Podcast, Bailey walked through the key communities that dominate buyer conversations in northeast Florida. What follows is a neighborhood-by-neighborhood breakdown drawn from her direct experience, not brochures or builder marketing materials.

Heritage Landing: The Best Bang for Your Buck in St. Johns County

Heritage Landing sits inside the World Golf Village area and is one of the most established communities in the corridor. Built primarily in the mid-2000s, most homes in the neighborhood are now approximately twenty years old. That age is actually a significant advantage for certain buyers, particularly those who are not yet sure where they want to be five years from now.

"Heritage Landing is definitely gonna be your biggest bang for your buck. You can get a big home there for one of the cheapest prices compared to everything around it."

Bailey lived in Heritage Landing for eight years, so her knowledge of the community is not academic. She knows the two pools, including the one with the water slide. She knows the athletic amenities that allow kids to ride their bikes to soccer practice. She knows the difference between a floor plan that has been updated and one that has not, and she has seen identical floor plans sell $100,000 apart based on condition and upgrades alone. That price spread creates real opportunity for buyers who are willing to put in some work.

Heritage Landing also has a resale stability that newer construction communities cannot always match, precisely because the builder is long gone and the neighborhood has matured. For a buyer who might need to sell in three to four years, or who is not certain about their timeline, that predictability matters enormously.

The challenge Heritage Landing faces is its neighbors. Trailmark and Silverleaf sit essentially at its back door, and the builders in those communities are offering incentives that are very difficult for a resale home to compete with.

Trailmark: Community Life, Trail Systems, and a Lifestyle Coordinator

Trailmark is a newer master-planned community that Bailey described with genuine enthusiasm, the kind that comes from someone who has attended its events and paddled its kayak launch, not just sold homes there.

"I love Trailmark. I think it's a wonderful neighborhood. They have amazing amenities. They just built another pool. And one of the things that really sticks out about Trailmark is they have all of these trails throughout the woods in the neighborhoods."

The trail system is genuinely distinctive. Rather than walking along a sidewalk next to traffic, residents move through wooded paths that wind through the community and eventually connect to a kayak launch leading out toward the St. Johns River. Bailey knows this firsthand. She was on her paddleboard on that narrow creek when she came around a bend and found herself face to face with a family of river otters. It was, she said, a moment that made her heart race for all the right reasons.

What truly sets Trailmark apart is its full-time lifestyle coordinator, a paid position dedicated to planning community events throughout the year. Bailey attended many of these events even when she lived in Heritage Landing. One of her favorites, called The Groove in the Grove, brought residents together with live music, vendor booths, local food, and a community energy that feels rare in modern suburban development. She has also run the neighborhood's 5K seven years in a row with her daughter.

Trailmark is a CDD community, which means residents pay a community development district fee that funds these amenities and events. For buyers who value an active lifestyle and genuine community connection, that fee tends to represent strong value.

Silverleaf: No CDD, Multiple Price Points, and a Luxury Push

Silverleaf is the largest and fastest-growing development in the corridor. Bailey described it as a community of communities, with different builders, different price points, and different product types spread across a massive footprint that has been expanding for years.

One of Silverleaf's most appealing features for buyers who want strong amenities without the CDD fee is exactly that: no CDD. The community still offers amenities that are competitive with its neighbors, along with townhomes, single-family homes, and now a growing luxury component.

"There is a big push over there for 1.2 and above. Once Dream Finders sells out of Brooke Forest and Lennar finishes its single-family homes in the 400s and 500s, it's gonna be more focused on the townhomes and then the over 1.2, $1.3 million homes."

Bailey noted some concern about this shift. She sees a gap forming in the middle income range, the buyers looking in the $600,000 to $800,000 range, who may find fewer and fewer new construction options as Silverleaf's remaining buildable land tilts toward luxury and townhomes. Toll Brothers currently has some well-priced options in the Newbrooke section of Silverleaf, but Bailey expects those to sell out within the next couple of years.

Buyers interested in Silverleaf are strongly encouraged to act before that middle-market inventory disappears.

Rivertown: New Construction Just Up the Road

Rivertown, situated north of Heritage Landing and Silverleaf along the St. Johns River, rounds out the primary new construction corridor in St. Johns County. Bailey described it simply as another beautiful new construction community, with the scenic advantage of its riverfront setting. For buyers whose priority is new construction and who want to be slightly removed from the densest concentration of development, Rivertown offers a compelling option worth exploring.

The New Construction Resale Warning Every Buyer Must Hear

One of the most important pieces of advice Bailey offered applies to anyone buying in any new construction community in St. Johns County: plan to stay for at least five years, ideally longer.

The reason is straightforward. If a builder is still active in the neighborhood when a homeowner tries to sell, the resale property is competing against brand new inventory with builder incentives attached. Those incentives, including rate buydowns and full closing cost coverage, are extremely difficult to match.

"I'm seeing pretty much everybody who bought at the end of 2022, '23, '24, and '25 who are trying to sell, and they're losing money. They're having to bring cash to the table, especially in neighborhoods where they're competing against the builder."

This is not a hypothetical risk. It is a pattern Bailey is watching play out in real time with sellers who reach out to her, review the numbers, and realize they cannot afford to sell. The solution for those buyers is to wait, build more equity, and let the builder cycle complete before listing.

Anastasia Island and Downtown St. Augustine: A Completely Different Market

Bailey's move to Anastasia Island opened her eyes to how genuinely different the island and downtown St. Augustine market is from the master-planned community corridor she had been working in for most of her career.

Homes on the island tend to be older, many without HOAs, and priced according to proximity to the beach, flood zone designation, zoning for short-term rentals, and coastal lifestyle appeal. These are not factors that come up much in Heritage Landing or Silverleaf. On the island, they can make or break a purchase decision.

Bailey has spent more than a year learning the island's neighborhoods from the inside out. She knows which areas fall in flood zone X even two blocks from the ocean. She understands St. Augustine Beach's separate planning and zoning authority and how it governs short-term rental permits. She knows about the difference between neighborhoods with quiet deed restrictions and those with full HOA governance.

"You don't know what it's like to live on an island until you live on an island. And it's just so much more amazing than I really even imagined that it would be."

She also made a point that surprises many buyers: Anastasia Island is not exclusively a retirement destination. RB Hunt Elementary School, which has served island families for seventy years, is currently the top-rated elementary school in St. Johns County. Young families with remote work flexibility are increasingly choosing the island precisely because they can have beach access, great schools, and a lifestyle that feels like a permanent vacation.

How to Choose: The Tuesday Question

For buyers who are still unsure which community fits them best, Bailey has a question she returns to again and again. It is deceptively simple and consistently revealing.

"What do you wanna do on a typical Tuesday? Is your kid riding their bike up and down the street? Are you walking to the burger joint at the corner? Do you wanna watch the sunrise on the beach every morning?"

The answer to that question points directly to the right neighborhood. A buyer who wants a packed event calendar, a kayak launch, and woods trails belongs in Trailmark. A buyer who wants the largest possible home for their budget with mature landscaping and strong schools belongs in Heritage Landing. A buyer who wants to walk to the ocean before school drop-off belongs on Anastasia Island. A buyer who wants luxury new construction without a CDD fee is looking at Silverleaf's upper tier.

No online search algorithm can make that match. It takes a conversation with someone who has lived it. Bailey Martin has lived most of it, and she is currently living the rest. That is the kind of local knowledge that changes outcomes for buyers in St. Augustine and St. Johns County.