Funky, artsy, and weird are just some of the many nicknames for Gulfport. This lively little bayside town embraces all the artisans and walks of life that enter its borders. It’s an area speckled with nightlife hot spots and independently owned stores. In addition, locals are just steps from Boca Ciega Bay and a quick drive to others. “The Philadelphia Inquirer wrote an article a few years back about Gulfport and referred to it as a new and upcoming little Key West,” says Gloria Hunter-Peroni, a local Realtor with RE/MAX Commercial. “It’s kind of quirky with many artists and great restaurants. That’s the draw: the bay, the art, the restaurants. You’ve got it all. And there’s always something going on in town.” These events could be live music along Shore Boulevard or the fun annual events.
Live music can be heard at many places in Gulfport neighborhood.
Sunsets are breath taking when living in Gulfport neighborhood.
Sit back & take in the views at Gulfport Beach recreation area.
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Shore and Beach Blvd for all things local dining
Stella’s is the spot for breakfast, serving an array of staples. Thanks to their dog menu, four-legged children can enjoy a simple meal. O’Maddy’s Bar and Grille is located along the waterfront, offering American cuisine favorites with a side of laid-back vibes. On top of the food, diners can also enjoy live music. Pia’s Trattoria is another popular sport along Beach Boulevard. This Italian restaurant takes people into Tuscany, offering fresh dishes in a cozy atmosphere. Grocery hauls can be done at the Save a Lot grocery or stop by the Gulfport Fresh Market on Tuesdays for fresh produce, bread, cheese and seafood.
Enjoy lunch throughout Gulfport on many beautiful patios.
Pia's Trattoria makes you fill like you stepped into Italy and serves delicious pasta.
O'maddy's bar & grill has indoor an outdoor sitting for you to enjoy near the water.
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GeckoFest and unique parades
There’s never a shortage of things to do in Gulfport. “There are so many events in Gulfport it would be hard for me to list them all,” says local broker Jody Caldwell Sepulveda with Caldwell Realty. “They shut the streets down for St. Patrick’s Day and Spring Fest. They also have dog rescue events, July fireworks, a boat parade, a golf cart parade, car shows and more.” One notable event is GeckoFest, which is held every Labor Day weekend. This street festival celebrates the area’s quirky atmosphere and unofficial gecko mascot.
Enjoy some time out with your pub & friends when living in Gulfport neighborhood.
Gulfport neighborhood is an artist town with many artist working outside.
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Colorful properties near the shore
Gulfport homes are as quirky and unique as their environment. “They range from starter homes to multimillion-dollar properties,” Sepulveda says. “There was a big building spree in the 20s and 50s. After the country club was developed, that’s when we got newer homes. The market is very competitive.” Common home styles are Spanish revival and Florida ranch homes in bright colors, which can go from $350,000 to $700,000. Condos can be found along the shoreline, and those can be under $300,000. Waterfront properties and gated communities offer upscale opportunities on larger lots; those stretch above $700,00 and peak around $1 million.
Spanish Revival Homes are found in the gated community in Gulfport Neighborhood and many of them sit on the waters edge.
A Private Gated community guarded by a security guard allows for the comfort of a more private home setting for those who like that feeling.
Colorful Art inspired homes are seen throughout the Gulfport Neighborhood.
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Aviation education in Pinellas County schools
Gulfport students can start their education in the Pinellas County Public Schools at Bear Creek Elementary, which holds a B on Niche. Azalea Middle School prides itself on its aviation and engineering program, offering a drone academy. The C-rated school is the first middle school to provide a Civil Air Patrol program, which partners with the U.S. Air Force to develop cadets and educate. Boca Ciega High holds an A-minus on Niche, priding itself on its robust AP and dual enrollment program.
Bear Creek Elementary School serves students in the Gulfport area if parents would like.
Welcome to Azalea Middle School in Florida.
The Boca Ciega High School is colloquially referred to as Bogie in the Gulfport neighborhood.
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Gulfport parks offer multiple recreation options
Spend some time outdoors at one of the many parks sprinkled throughout Gulfport. Chase Park offers playground equipment, pickleball, tennis courts, and a dog park. Along the coast of Boca Ciega Bay is where to find an abundance of recreation at the Gulfport Beach Waterfront Complex. Enjoy the sun on the soft sands, play a round of volleyball or bocce ball, or take the little ones to the playground. Clam Bayou Nature Park is an option for a canoe and kayak ride.
Take a stroll under the beautiful canopy trees covering the sidewalks through out Gulfport Neighborhood.
Living in Gulfport Neighborhood allows your to be on the water any day of the week.
Gulfport Beach Park has Picnic pavilions, beach volleyball courts and a beach for your enjoyment.
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Five miles from St. Petersburg
Those who need to get around the town have access to several bus routes that land at St. Petersburg Grand Central Station. Those who need to commute via car can hop on 275 from there. It’s about a five-mile drive. Interstate 275 stretches 60 miles through the rest of Tampa Bay.
Public Buses can be caught at many stops through out the Gulfport Neighborhood to get you around Saint Petersburg.
Check out 31st Ave S which is filled with many Restaurants and a park.
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Important to Know
Parts of Gulfport are located within the FEMA's 100-year floodplain map, which targets properties that may experience flooding during 100-year events from tropical cyclones and significant storms.
A Private Gated community guarded by a security guard allows for the comfort of a more private home setting for those who like that feeling.
Condominiums and Apartment living has many options for you to choose from in Gulfport neighborhood.
Beautiful Homes line the waters edge in Gulfport an give you your own private docks.
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Written By
Jessica Haddad
Photography Contributed By
Leila Sally
Interested in learning more about homes in this area?
Reach out to
Christopher Plummer,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Gulfport, FL sell after 88 days on the market compared to the national average of 56 days. The median sale price for homes in Gulfport, FL over the last 12 months is $368,000, down 2% from the median home sale price over the previous 12 months.
Located in the heart of downtown Gulfport, this 21st century Key West-style elevated home is picture perfect and blends seamlessly with the area’s eclectic charm. A custom wood gate welcomes you into a large, ultra-private courtyard filled with tropical plantings, creating a serene and beautiful setting that truly sets this home apart. Surrounded by masonry walls, this inviting outdoor space
This elevated key west style home is located just steps from the Gulfport Beach and Arts District which has many amazing restaurants, shops as well as events and festivals. The property itself features 3 large bedrooms and 3 full baths with two of the bedrooms having en-suite baths. A very open floor plan lends itself to entertaining with its spaciousness. The living room, as well as the Master
Bob Meyers, JrWEICHERT REALTORS EXCLUSIVE PROPERTIES
Jump at the chance to own this ENTERTAINER'S DREAM in the heart of Gulfport! This beautifully updated 3 bedroom, 2 bath POOL home sits on 2 lots and includes an oversized 2 car garage - a rarity in the Gulfport Marina District. With almost 2100 sq ft of living space, this home blends modern comfort with classic Florida character including 2 flex rooms that can be used for additional family rooms,
Opportunity meets charm in this ideally located Gulfport corner-lot property, perfectly positionedon a spacious 66 x 100 lot just minutes from the waterfront, vibrant downtown Gulfport, localdining, art galleries, and community events that make this area so highly sought after. This 2-bedroom, 2-bath concrete block home offers the solid foundation buyers want, with majorupdates
Welcome to this light-filled, airy 2-bedroom, 2-bath home with a sparkling private, enclosed pool and an open-concept layout perfect for coastal living. The beautifully renovated kitchen features modern finishes and flows seamlessly into the spacious living and dining areas. This home creates an easy indoor-outdoor vibe that's perfect for Florida living! A unique bonus artist studio or flex space
Live the Gulfport life in this charming, walkable home. Embrace the vibrant, laid-back Gulfport lifestyle from this beautifully renovated bungalow. Positioned for easy strolls to the downtown area, you can enjoy the Art District, restaurants, and the waterfront just blocks from your front door. This bright and airy 2-bed, 2-bath home blends classic Florida charm with modern updates. The luminous
One or more photo(s) has been virtually staged. Welcome to Villas Del Verde, a private, gated community that is located in a NO FLOOD ZONE. This pet-friendly neighborhood offers elegance, privacy, and resort-style amenities. Step inside and experience the luxury of a 3-bedroom, 2.5-bath, 2 car garage and spacious 2-story layout residence. The garage features multiple cabinets. A new water heater
Step into your own private tropical resort where an oversized open floor plan flows seamlessly to a heated pool, grass-thatched tiki bar, and a beautifully lit backyard paradise designed for unforgettable indoor-outdoor entertaining, in this beautifully updated block construction home designed for effortless Florida living. The oversized open floor plan creates a bright, spacious feel and offers
Completely renovated 2-bedroom, 2-bath pool home with dining/bonus room in Gulfport’ssought-after Marina District. The open-concept layout connects the living, dining, and kitchenareas, creating a bright, inviting space. The updated kitchen features modern appliances, amplestorage, and a breakfast bar, while the separate dining/bonus room offers flexible space forentertaining, a
Welcome to this move-in ready deluxe floor plan offering an open-concept layout and a light-filled bonus room surrounded by wall-to-wall windows — the perfect space for a home office,reading nook, or additional lounge area. Extra storage adds to the functionality of this bright andversatile space. Recent upgrades provide peace of mind and modern comfort, including
A LOT of PLUSES in this HOME...from the Covered Composite Floored Front Porch Through the Double French Doors with Mini-blind Inserts to the Open Floor Plan Family Room, Dining, Lving Room Open to the Kitchen. There is a Convienient 1/2 Bath off the Family Room. * Updated Windows Throughout * The Eat-in Kitchen is Loaded with Storage Cabinets, an Extra Countertop and an Extra Window for Abundant
Discover a unique opportunity in Gulfport: this 4-bedroom property with an office and 3 bathrooms offers excellent road frontage and exposure. Zoned for commercial/residential use, this property presents various mixed-use options such as retail, salon, spa, office, medical office, tattoo parlor, restaurant, daycare, Airbnb, and more. The front of the property can be used for large single-family
Classic Gulfport Charm with Limitless Potential! Nestled on a spacious corner lot, this solid 2-bedroom, 1 1/2 -bathroom residence offers the perfect canvas for your Florida dream home. Step inside to find original hardwood flooring throughout the living areas and bedrooms, exuding a warmth and character rarely found in modern builds. The vintage kitchen provides ample cabinetry and a cozy dining
LAST PRICE DROP! LESS THAN LAND VALUE. Hurry this Mixed use property in the heart of down town Gulfport wont last. Step into the charm of this enchanting cottage located in the heart of Gulfport! While the home requires some TLC (Flood damage from Helene), it offers endless possibilities to create your dream space. The expansive outdoor living area is a true showstopper, featuring mature
Charming Block Home on Oversized Corner Lot in the NO Flood Zone! This well-maintained single-story block home sits on a spacious corner lot in a desirable NON-FLOOD zone, offering peace of mind and plenty of outdoor space. Featuring 2 generously sized bedrooms with built in closets and 1 and 1/2 baths, this home provides 1,420 square feet of comfortable living. Recent updates include a new roof
NEW RENTAL LISTING - THIS 1 BEDROOM, 1 BATHROOM CONDO LOCATED IN THE ETON BLDG. ON THE 2ND FLOOR IS UNFURNISHED AND IS AVAILABLE NOW. This Condo checks all of your boxes wanted in a Rental; which includes, Easy maintainable Hardwood flooring from the Living room through the Florida Room, the Bedroom Features 2 closets, a large walk-in and the 2nd a double folding door design, in addition to a
Live like a local in the heart of Gulfport with this fully furnished 2-bedroom, 1-bath home available for short-term, month-to-month lease (1–3 months). Perfect for seasonal stays, relocations, or anyone looking to experience the charm of Gulfport without a long-term commitment.Inside, you’ll find comfortable, turnkey living with everything you need to settle in with ease. Step outside to
2 Bedroom / 2 Full Bath Condo for rent in the sought after Jamison Bldg in Town Shores. This unit is on the 5th Floor and had no damage in any storm (in fact there was no flooding to entire bldg.) It comes completely Turnkey. Unit is available for a 6 month minimum lease which is perfect for snow birds looking for the perfect place to spend their winter. Tenant can enjoy all of the features that
NEW TURNKEY RENTAL AVAILABLE FROM MAY 14, 2026 TO DECEMBER 31, 2026 - 2 bedroom 2 Full bathrooms, with an extra room that is used as an office or den. House also has a Washer and Dryer for your convenience. If you are looking for a great place, at an even better price, this rental is for you!
2180 Dolphin Blvd a true PASADENA PARADISE! This stunning 4-bedroom, 3-bath waterfront pool home in Pasadena Golf Club Estates offers breathtaking water views from nearly every room and has been thoughtfully updated from top to bottom—inside and out. The light-filled custom kitchen is a showstopper, featuring shaker cabinetry, touchless under-cabinet lighting, quartz countertops, sleek GE Café
Property Id: 1985552Fully Furnished 2BR Home in Gulfport - Utilities Included - Available April 1 through Dec 1, 2026Welcome to your Gulfport retreat! This charming 2 bedroom, 1 bathroom home is move-in ready and comes fully furnished — just bring your suitcase.-All utilities included: electric, water, high-speed WiFi, lawn care-Spacious layout with a freshly renovated
Charming 2/1 Gulfport Cottage close to the Historic District! Charming 2br/1ba single family home located in Gulfport. Home has been freshly painted with neutral paint, cooling effect and easy maintenance terrazzo flooring through out, ceiling fans and updated bath. Entry foyer can be used as extra sitting area and/or office space. Home has an open an airy floor plan with newer windows with lots
Property Id: 1760591Step into this beautiful 2-bedroom, 1-bathroom block home in Gulfport, FL. This home is open with a spacious living area that flows into the kitchen. The kitchen boasts stunning quartz countertops, complemented by sleek stainless-steel appliances. Gorgeous vinyl flooring throughout, providing durability and a modern touch. The home is situated in flood zone X (high
If you've been searching for a place where you can fully enjoy the Gulfport lifestyle—walk to dinner, the beach, and feel connected to a vibrant, welcoming community—this furnished monthly rental is the perfect fit. Ideally located just a short stroll from downtown Gulfport, the marina, local shops, and local favorites like Pia's Trattoria and O'Maddy's Bar & Grille, you can leave the car behind
Property Id: 2152894Great location- Walk to Gulfports Marina, Clam Bayou Nature Reserve. Right next to Pinellas bike trail. Short bike ride to downtown Gulfport.Brand new renovation. Great location. $2450/month unfurnished for a 12 month lease w/ tenant covering utilities.Seasonal rentals available. Fully furnished with High speed internet and all utilities included. 30+
Great updated 2nd floor studio apartment in Gulfport. There is a large living area, open kitchen with granite countertops, stainless appliances and an updated bath with a walk-in shower. The property is in close proximity to downtown Gulfport's, shoppes, restaurants and beach.
Welcome to your new home in the charming Gulfport area! This inviting property offers a perfect blend of comfort and convenience, ideal for those seeking a peaceful lifestyle near vibrant amenities.Key property features include spacious living arrangements with central heating and cooling to keep you comfortable year-round. With air conditioning and ceiling fans, you can enjoy a
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