St. Augustine, Fla.: A Smart Place to Retire

Population: 14,576

Cost of living: Not available

Median home price: $343,000

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St. Augustine and the surrounding St. John’s County offer more than just surf and sand wedges. But retirees looking for fun in the sun will find it here in spades, along with plenty of cultural activities, affordable luxury living, and first-class health care.

12 Smart Places to Retire

The 42 miles of sand on St. John’s Atlantic coast offer something for everyone. St. Augustine Beach, located 10 minutes from downtown, is backstopped by laid-back restaurants serving up the day’s catch to folks in flip-flops. If a peaceful hammock is more your vibe, chill with the local wildlife on the secluded beaches of 1,600-acre Anastasia Island State Park.

A short drive north will land you in Ponte Vedra Beach, replete with ritzy beach clubs and golf courses. Here you’ll find TPC Sawgrass, home of The Players Championship, one of the PGA’s most prestigious annual events. The area is also home to the World Golf Hall of Fame and the PGA Tour Academy—for golf legends both real and aspiring.

You can’t walk very far in St. Augustine without being reminded that it is the oldest European-established city in the U.S.—one that houses more than 60 historic sites and attractions, including a town square that dates to 1573. The city is still very much alive, however. Pedestrian-only St. George Street, lined with bistros, boutiques and bars, bustles all day and well into the night, with live music coming from practically every other open door.

Also keeping the city young: Flagler College, which operates as a center for educational and cultural enrichment for students and locals alike. Retirees can take in free lectures, plays, musicals, concerts and art exhibitions on campus.

Living costs in greater St. Augustine aren’t cheap by national standards, but retirees—especially those from the northeast—are snapping up its relatively affordable beachfront property, says real estate agent Carrie Reynolds. Oceanfront condos with pools in St. Augustine Beach run about $500,000, compared with $1 million or more in Miami or Fort Lauderdale, she says. She recently showed a 2,222-square-foot, four-bedroom, three-bath house in nearby South Ponte Vedra Beach for $520,000. Residents can walk through a tunnel under the adjacent highway straight onto the beach.

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Florida has a plethora of health care providers. The Mayo Clinic’s Jacksonville campus, a five-star hospital, is about an hour from St. Augustine.

Florida is among the tax-friendliest states in the country for retirees. There is no state income, estate or inheritance tax.

For population figures, we used the most recent U.S. Census Bureau data. Cost-of-living data comes from the Council for Community and Economic Research (100 represents the national median). Median home prices were provided by Redfin, Zillow and local associations of Realtors.

Ryan joined Kiplinger in the fall of 2013. He wrote and fact-checked stories that appeared in Kiplinger's Personal Finance magazine and on Kiplinger.com. He previously interned for the CBS Evening News investigative team and worked as a copy editor and features columnist at the GW Hatchet. He holds a BA in English and creative writing from George Washington University.