— City Guide
Gulfport
FL
You will know you have arrived in Gulfport the moment the commercial strip changes character. The dollar stores and auto-parts shops that line US-19 give way to hand-lettered sandwich boards, fairy lights strung between oak trees, and a row of pastel-painted storefronts along Beach Boulevard South. This is a city of about 11,800 people that has chosen, deliberately, to stay weird. The waterfront is Gulfport's anchor. Williams Pier stretches 1,600 feet into Boca Ciega Bay and is the most democratic fishing spot in Pinellas County — no charge, no permit. Just north of it, the 1930-vintage Gulfport Casino Ballroom hosts swing dances every Friday night, Tuesday night Latin sessions, and the occasional Saturday ballroom event. The building has never been a gambling hall; the name is old Florida for 'assembly place.' Show up at 7:30 on a Friday with $5 and you will find people who have been coming for 40 years. The Art Walk on the first Friday and third Saturday of each month is Gulfport's signature civic ritual. Beach Boulevard closes to cars, artists set up on the sidewalk, the galleries stay open late, and Pia's Trattoria typically has a line out the door. GeckoFest each Labor Day weekend is the city's end-of-summer blowout — 200+ vendors, live stages, and a parade of residents in gecko costumes that you simply have to see. For buyers, Gulfport occupies a sweet spot. It shares Pinellas County school districts with St. Petersburg, it is a 12-minute drive from downtown St. Pete and 10 minutes from St. Pete Beach, and it has none of the tourist-strip exhaustion of Treasure Island or Madeira Beach. The housing stock is a mix of 1940s–1960s Florida vernacular bungalows, updated cottages with painted porches, and a scattering of newer infill on double lots. You are not buying a McMansion here; you are buying a neighborhood.
Market context
Gulfport's median home sale price was approximately $305,000 as of mid-2025, a notable decline from the 2023 peak near $400,000. Hurricane Helene's September 2024 storm surge accelerated price softening in the flood-zone segments of the market, and homes in those areas are pricing in elevated flood insurance costs. Homes outside the surge zone — the higher-elevation inland blocks north of Beach Boulevard — have held value better. Average days on market runs around 60–75 days, giving buyers genuine negotiating room for the first time since 2020. For investors, the combination of lower prices, walkable character, and proximity to St. Pete Beach creates a compelling short-term rental calculus, though buyers should confirm current city STR ordinance status before underwriting.
Neighborhoods
Neighborhoods in Gulfport
Schools
Top-rated schools in Gulfport
- Boca Ciega High School3/10
Pinellas County Schools
From the blog
Reading about Gulfport
Buying a Waterfront Home in Florida: What to Check Before You Fall in Love
Waterfront is 20% of the price of a home. Before you make an offer, you need to know who owns the seawall, whether the dock permits are current, and what your flood insurance will cost — because these numbers move fast in Florida.
Moving to Tampa from Out of State: What You Need to Know
Tampa draws tens of thousands of out-of-state movers every year — mostly from New York, California, and the Northeast. No state income tax and lower housing costs are real. So are hurricane season, insurance sticker shock, and traffic on I-275. Here is the honest version.
Where Gulfport is
Gulfport, FL
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