Real places, real neighborhoods and current market numbers, verified by broker Ryan C. Winslow.
What St. Augustine is known for
St. Augustine is the nation's oldest city, founded by Spain in 1565. People know it for the coquina walls of the Castillo de San Marcos, Henry Flagler's Gilded Age hotels, and a walkable historic district full of live music. Beaches on Anastasia Island and Vilano sit minutes from downtown.
Don Pedro Menendez de Aviles founded St. Augustine in 1565. The Spanish built the Castillo de San Marcos from coquina stone after nine wooden forts burned, and in 1738 Fort Mose became the first legally sanctioned free African settlement in what is now the United States. Henry Flagler's Hotel Ponce de Leon welcomed guests by 1888 and became Flagler College in 1968. Downtown mixes Flagler College students, longtime families, retirees and artists on brick streets, with live music in the bars most nights. Many residents live a short drive away on Anastasia Island, Vilano Beach or in newer communities north of town and head downtown for dinner and events.
Where to live
The colonial core around St. George Street, the Plaza and the bayfront. Older homes and condos sit among shops, restaurants and museums. Life here is walkable but busy, and historic preservation rules and downtown parking permits apply. (source)
A historic Black neighborhood just south of downtown and a major civil rights site, home to the Lincolnville Museum and Cultural Center on M. L. King Avenue. Expect older wood frame cottages and restored historic homes within walking distance of the bayfront. The city runs a Lincolnville Community Redevelopment Area here. (source)
A laid back beach community north of downtown, reached by scenic A1A. Locals have used this beach for more than two centuries. Waterfront restaurants, a riverside pier for sunsets and a quieter pace than the main beach. (source)
A separate small city on Anastasia Island along A1A Beach Boulevard with a beachfront park, pavilion, splash park and wide hard packed sand. A mix of beach cottages, condos and newer single family homes close to Anastasia State Park. (source)
A mostly residential, old Florida stretch of Anastasia Island south of St. Augustine Beach, centered on Cubbedge Road and A1A. Wide beach, easy parking and fewer crowds. Driving on the beach is allowed with passes and fees during part of the year. (source)
A master planned community north of the city developed by Hines, with a Village Center and The Palencia Club. It has an Arthur Hills designed golf course along the Intracoastal Waterway, three pools, tennis and a 30 acre park system with boardwalks and trails. (source)
Local favorites
The St. Augustine location of the family owned restaurant that dates to 1905, with hand painted tile and a Spanish style fountain. Open daily for lunch and dinner. (source)
Opened in 2010 by Genie and Jeff McNally and known for fresh, local ingredients in a casual setting. Now at its new location. Closed Tuesdays. (source)
Crab cakes, local fish and shrimp in the Worth House, built in 1790, with patio seating and evening live music across from the bayfront. (source)
Bayfront spot with Louisiana flavors and live music most nights in its courtyard. (source)
1920s themed pub with locally sourced bar food, craft cocktails, live music nightly and what it calls the longest bar in the city. (source)
Grass fed burgers, local seafood and cocktails with house pressed juices inside a 1927 ice plant building. Named to Southern Living's South's Best in 2019. No reservations. (source)
Downtown location of a barbecue group with eight North and Central Florida restaurants, pairing smoked meats with bourbon and blues. (source)
Locally owned beach restaurant with a weekend breakfast buffet, vegetarian and vegan menu, and a 3 to 7 pm happy hour. (source)
After hours
A treehouse style tavern above St. George Street with a balcony, pub food and live music all day, every day. It has hosted live music for more than 50 years. (source)
A downtown lounge that began as a folk club and now books rock, blues and some country bands on a monthly live music calendar. (source)
Founded in 1996 in one of Henry Flagler's old railway buildings at 157 King Street. Daily tours and tastings, plus a rooftop wine bar with live music. (source)
Founded by 20 local families inside Florida's oldest ice plant at 112 Riberia Street. Offers tours and makes bourbon, rum, gin and vodka. (source)
A downtown brewery and taproom at 77 Bridge Street with house beer, wine and canned cocktails. (source)
Shopping
The pedestrian street at the heart of the historic district, lined with shops, galleries and restaurants. Side streets hold more local shops away from the main crowds. (source)
Outlet center at I-95 and State Road 16 with 80 plus stores, including Nike, Coach, Polo Ralph Lauren and Levi's. (source)
Local chocolate maker with a factory store and tasting tours at 139 King Street, plus shops on St. George Street and Anastasia Boulevard. (source)
Saturdays 8:30 am to 12:30 pm at 1340C A1A South, with local produce, plants, handmade goods, coffee and live music. (source)
Outdoors
More than 1,600 acres of beach, tidal marsh, dunes and maritime hammock, with a historic coquina quarry, a kayak launch on Salt Run and 139 campsites. (source)
Site of the 1738 free African settlement, with a reconstructed fort, visitor center, birding boardwalks, kayak launch and the Flight to Freedom Trail. No admission fee. (source)
A coquina watchtower completed in 1742 guarding the southern approach to St. Augustine, plus about 300 acres of dunes, marsh and maritime forest. (source)
Quiet park on Pellicer Creek, a designated paddling trail, with a boat ramp, 30 campsites, nature trails and more than 100 bird species during migration. (source)
More than 76,000 acres of estuary and coastal habitat. The Guana River Road visitor center is open Tuesday through Saturday. (source)
Formal gardens with a 150 bush rose garden and reflection ponds, plus a shoreline of coquina rock formations. The visitor center is temporarily closed and some programs are paused in October 2026. (source)
National Park Service preserve of salt marsh, dunes and hardwood hammock that includes Fort Caroline and Kingsley Plantation. (source)
Things to do
The oldest masonry fort in the continental United States, built by the Spanish from coquina on Matanzas Bay. (source)
Climb the working 1874 lighthouse on Anastasia Island and see maritime archaeology exhibits and a wooden boatbuilding shop. (source)
Henry Flagler's former Hotel Ponce de Leon, now a college campus known for its Tiffany windows and murals. Tours are available. (source)
Art and history museum at 75 King Street inside Flagler's former Hotel Alcazar. (source)
Zoo on Anastasia Boulevard with alligators and crocodiles, a bird rookery and a zip line over the park. (source)
On the calendar
Millions of white lights cover downtown, from the ground to the rooftops. It is free and best seen on foot. (source)
Nearly a month of free live music with more than 100 performances at venues across St. Augustine, produced by the nonprofit behind the St. Augustine Amphitheatre. (source)
Greek food, culture and tradition at Holy Trinity Greek Orthodox Church. The 2026 festival is the 28th. (source)
Spanish wine, food and culture in the city Pedro Menendez de Aviles founded. (source)
An evening stroll through more than 26 downtown galleries with live entertainment and refreshments. (source)
Schools
John A. Crookshank Elementary School, Ketterlinus Elementary School, Osceola Elementary School, R. B. Hunt Elementary School, W. D. Hartley Elementary School, Otis A. Mason Elementary School, James A. Webster Elementary School
R. J. Murray Middle School, Sebastian Middle School, Gamble Rogers Middle School, Pacetti Bay Middle School
St. Augustine High School, Pedro Menendez High School
St. Joseph Academy (Catholic high school, Diocese of St. Augustine)
Listed for reference, not ranked. Confirm school zoning for any address with the district. (source)
Broker notes
I-95, US 1, State Road 16, State Road 207, State Road 312 and A1A (a designated All-American Road along the coast)
Jacksonville International Airport (JAX), about 1 hour north, with nonstop service from many U.S. cities.
Ryan C. Winslow, broker/owner of Winslow Homes. REALTOR® since 2009, 3,000+ homes sold, broker in FL, MA, CT and RI, U.S. Army Retired.
Researched and verified 2026-09-28. Businesses change; call ahead.