The Anastasia Island Neighborhood Guide

What it actually feels like to live in Anastasia Island

Anastasia Island doesn't feel like the rest of St. Johns County. Cross the Bridge of Lions or the 312 and the air gets saltier, the speed limit drops, and life reorganizes itself around the tide chart. Mornings are surfers checking the pier break, retirees walking the hard sand at low tide, and pickup trucks heading into Anastasia State Park. The St. Augustine Beach city core around A1A Beach Boulevard is bike-and-golf-cart territory — locals roll to the Wednesday farmers market at the pier, grab a coffee at The Kookaburra, and never put shoes on. Year-round residents skew a little older (median age in the low 50s) and lean toward retirees, remote workers, hospitality lifers, and longtime St. Augustine families who refuse to live anywhere else. In season the population swells with snowbirds and short-term renters; by mid-May the parking at the pier thins out and the island settles back into itself.

How Anastasia Island came to be

Anastasia Island has been working land since the Spanish first put a watchtower on the north end in the 1500s — the same tower Sir Francis Drake spotted before sacking St. Augustine in 1586. Beneath the dunes lies the Anastasia Formation, the layer of fossilized shell-rock called coquina that the Spanish quarried to build the Castillo de San Marcos starting in 1672, making it the only masonry fort in the continental U.S. built from shell. In 1763 the British granted island land to merchant Jesse Fish, who planted oranges at his El Vergel plantation. The coquina lighthouse from 1737 was replaced by the current black-and-white spiral-striped St. Augustine Light in 1874. For most of the 20th century the island was a sleepy beach town of fish camps, cottages, and the original Alligator Farm (founded 1893, one of Florida's oldest continuously operating attractions). The boom started in the 1980s and hasn't really stopped — but Anastasia State Park's 1,600 protected acres on the north end mean the island can never fully fill in.

What you'll see on the streets

The housing mix on Anastasia Island is genuinely all over the map. North end near the lighthouse and Davis Shores you'll find original 1920s-1940s coquina-block cottages and Mediterranean Revival bungalows that survived because the coquina walls just won't fail. Mid-island around St. Augustine Beach the dominant stock is 1960s-1980s concrete-block ranches and beach cottages — many on slab, many one block off A1A Beach Boulevard, most sitting in the $500K-$800K range depending on condition and elevation. Beachfront from Ocean Hammock down through Crescent Beach is a parade of stilted CBS single-family homes built post-2004, oceanfront condo towers like Sea Place, Ocean Gallery, and Anastasia Condominiums, and a handful of trophy new-construction homes north of $3M. Things to inspect: roof age and wind mitigation form (insurance hinges on it), flood elevation certificate, salt-air-corroded HVAC coils and railings, original aluminum windows on the 60s-80s stock, and any seawall or dune walkover on oceanfront. Polybutylene plumbing pops up on some early-1990s builds.

Where to eat and drink

The Anastasia Island dining scene is more substantial than a beach town this size has any right to be. Cap's on the Water sets the bar for Intracoastal sunset dinners; Salt Life Food Shack and Beachcomber own the casual oceanside lunch crowd; South Beach Grill is the Crescent Beach destination. Sunset Grille is the old-school anchor on A1A Beach Blvd — the minorcan clam chowder is a rite of passage. Locals fight quietly over the best taco at Mango Mango's Caribbean Grill and the best slice at Pizza Time. For coffee it's The Kookaburra or the locally-owned Anastasia Books & Coffee Co. Brunch at The Floridian Beachside or eggs at the Beachside Diner. When you want to dress up, drive 10 minutes to The Floridian or Catch 27 downtown — but most weekends you won't bother to cross the bridge.