DeLand, FL

45 minutes north of Orlando, and apparently one of the best places to retire in America. Here's what's actually up there.

✦ Investopedia · Top 100 Retirement Towns ✦

You've probably driven past the DeLand exit on I-4 a hundred times without thinking twice about it. I used to do the same. Then last month Investopedia put DeLand on their list of the 100 best places to retire in America, and I figured I'd actually go see what was up there.

Short version: the locals call it the "Athens of Florida" and they're not really joking. It's got a walkable brick downtown, a theater from 1921 that still runs shows, Stetson University in the middle of it, a state park full of manatees fifteen minutes away. It doesn't feel like Florida. Or it feels like the Florida that existed before everyone figured out Florida.

So whether you're looking for a Saturday trip or you've got a parent in the "where should we retire" conversation, here's the rundown.

Mario

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~ chapter one ~

Small-town, not small-minded.

You can walk the whole downtown in about twenty minutes. Brick buildings, oak canopy, independent shops that don't exist anywhere else in the metro. Stetson's campus is a five-minute walk from the center, which means there's a steady pulse of students and professors mixed in with the retirees, and that mix is basically the whole vibe.

The four places worth knowing if you're only going to remember four things:

01

Woodland Boulevard

The main street. Brick buildings, big trees, local shops all the way down. Saturdays it fills up and it's got that unhurried Southern downtown feeling that most Florida towns have paved over.
02

Athens Theatre

Restored 1921 theater. They run touring Broadway shows, local productions, and $5 classic movie nights. A 500-seat venue in a town of 45,000 is a pretty wild thing when you stop to think about it.
03

Artisan Alley

Friday night farmers market plus local makers and food trucks. It's the after-work ritual for half the town. Go once and you get the place.
04

Stetson University

Private liberal arts school, founded 1883, right in the middle of town. Half the cultural events in DeLand happen on campus. Most of them are free.

~ by the numbers ~

$331K

avg. home value
vs. $360K nationally

45 min

to downtown Orlando
via I-4 or SunRail

0.78%

Volusia County
property tax rate

~45K

population,
22% age 65 or older

~ chapter two ~

How to do DeLand in one day.

A route through the best of it, start to finish.

01

9 a.m.

Blue Spring State Park

Ten minutes south in Orange City. The spring runs 72° year-round and if it's cold enough outside, the manatees show up by the hundreds. Get there before 10 because it fills up and they close the gate.
02

11:30 a.m.

Coffee on Woodland

Persimmon Hollow or Half Wall, both walkable downtown, both good. Sit outside if the weather's cooperating.
03

1 p.m.

Lunch and a walk

The Table is the local pick for lunch. After, just walk the blocks around the theater. Museum of Art, antique stores, a bookstore or two. The whole downtown is a six-block grid so you can't get lost.
04

3:30 p.m.

Hontoon Island or Stetson campus

Hontoon is a state park on an island you reach by free ferry, no cars, just trails. If you'd rather stay in town, Stetson's campus has some of the oldest oaks in the county and it's a nice loop on foot.
05

6 p.m.

Cafe DaVinci

Live music, drinks, usually a crowd. It's where the night lands. You'll be home by 9 or you'll stay for one more set and be home by 11.

one more thing, if you're thinking longer-term

The retirement angle is real.

Investopedia didn't rank it for nothing. Florida doesn't tax retirement income, so Social Security and 401K draws stay yours. Home prices run below the national average. Property taxes in Volusia County are 0.78%, which is on the friendly end for Florida.

There's a full AdventHealth hospital in town, and the SunRail station runs straight down to Orlando's medical centers if something needs a specialist. Over 20 independent living communities in the immediate area, most of them offering graduated care if that becomes necessary down the road.

If you're in the "where should we retire" conversation, or you've got a parent who is, DeLand is worth a weekend visit before you commit to anywhere else.

~ want to see what's for sale? ~

Homes in DeLand, right now.

Active listings, updated daily.

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