First question: which St. Augustine do you mean?

When someone tells me they want to live in St. Augustine, my first question back is, which one? There are really three. There is old town, the historic downtown with the cobblestone streets. There is the beach side. And there is the countryside west of town, farm and horse country that stretches all the way out to the St. Johns River. Those are three completely different lifestyles at three very different prices, so we sort that out before we look at a single house.

Why people fall for it

Most people already know St. Augustine is the oldest continuously occupied European settlement in the country. What they fall for once they get here is how much of that history you can still walk through. Henry Flagler built his grand hotels here to bring people down on his railroad, and one of them is now the heart of Flagler College, right in the middle of old town. Long before that, St. Augustine was a refuge for people escaping slavery in the colonies to the north. Martin Luther King Jr. was arrested here in 1964, during the St. Augustine campaign that helped push the Civil Rights Act through that summer.

The fort, the Castillo de San Marcos, is the oldest masonry fort in the continental United States, and it sits right where the bay opens up to the ocean. Stand there for a minute and it is obvious why the Spanish put it exactly there.

It is also a music town. There is a band playing somewhere almost every night, so if your idea of a good evening is dinner downtown, a drink after, and whoever is playing, old town gives you all of it on foot. There is a festival or an event of some kind most weekends.

Where I steer people

I will admit my bias. I love Lincolnville. That is where the big historic houses are, and from there you can walk right into old town and down to the bayfront. We call it the bayfront, but it is really the Intracoastal, and it opens out to the ocean right in front of the fort.

Where I am careful

There is really no bad part of St. Augustine, but there are low lying areas, and flood zones are one of the biggest conversations I have with buyers here. Some neighborhoods here took real flooding when the big hurricanes came through in recent years, and I will tell you which ones before you look. Flood zone X is where you want to be. The insurance is better and you are not lying awake in storm season. Anywhere lower than that, the cost of flood insurance has to be part of your affordability math from day one.

What it costs that the listing does not show

Historic homes are older homes. Expect more repairs, and do not expect the most efficient air conditioning, because it was added long after the house was built. Many homes and buildings downtown fall under the city’s historic review rules, so if you want to change something you need approval first, and that can be a slow process. Parking downtown is a real issue.

And St. Augustine is a tourist town. That is the thing that surprises people most after they have lived here a few months. Some times of year are much busier than others, and locals learn to plan around it.

Old town, the beaches, or the country

The beach side is beautiful, but unless you want a townhouse or a condo, homes on the water are very expensive. The value play is a townhouse in a community on the water. You may not have the ocean out your own back door, but you can walk to it, and as I write this those start somewhere around the mid $500s. That is a lot less than the same idea costs you up in Ponte Vedra.

Historic homes in Lincolnville do not come cheap. Those houses are special, and they are expensive to buy and to keep.

The countryside is where the deals are. Fifteen minutes or so outside downtown, you can buy real land. A lot of people here live an equestrian lifestyle, and you can find a nice piece of property with room for a proper horse setup.

Nights of Lights

If one thing sums up St. Augustine for me, it is Nights of Lights. From just before Thanksgiving into January, the whole city is lit up, and it is one of the largest holiday light displays in the South. Trolleys roll through town playing Christmas music and hand out special glasses that turn the lights into candy canes and snowmen while they tell you the history. The weather is finally cooler, too. That is when this town really shines.

Local tip: a lot of us skip driving downtown during Nights of Lights, because you will not find a parking spot. Take the trolley in.

What locals know

Where to eat. I always smile at the lines outside the places that simply have a good social media presence. Meanwhile O’Steen’s, a little fried shrimp place that has been around since 1965, has a line out the door without doing any advertising at all. It is cash only, and it is the best fried shrimp and hush puppies in the South. If you are not local, you probably would not know it is there.

The best seat for fireworks is on the water. If you have a boat, or friends with one, get out in front of the fort and watch them go off over the Castillo. It is absolutely beautiful.

The little shops downtown are half the fun: an olive oil shop that makes its own flavored oils and vinegars, Two Sparrows with its prayer wall, and good chocolate at Kilwins. It is also a very gluten free friendly town. The French Pantry opened a St. Augustine location on Granada Street, and Crème de la Cocoa is one of my favorites.

Is St. Augustine the right fit?

Old town is a walking life. It is carriage rides, trolleys, dinner and live music, date nights, and something going on most weekends. With Flagler College in the middle of it there is a young energy downtown, and plenty of graduates stay. It is also cobblestones, crowds in season, and a lot of walking, so be honest with yourself about how you like to live day to day. If you want more quiet, the beaches and the countryside are right there.

Nearby communities worth comparing

Palencia sits just outside historic downtown and gives you a gated golf community on the Intracoastal with the old city ten minutes away. World Golf Village puts you a short drive up I-95 with two championship courses and the county’s fastest growing retail hub. Ponte Vedra takes you north up the coast into the top of our market.

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