St Pete/South Pasadena/Gulfport/St Pete Bch Homes under $500,000

3 Beds ⋅ 1 Baths ⋅ Caldwells Rep SubDv. ⋅ 33707 Zip Code

Located in desirable Gulfport, this property sits on a spacious corner lot directly across from Wood Ibis Park and just five blocks from the sandy waterfront. The home features refinished oak hardwood floors, an updated kitchen, a remodeled bathroom, and mature landscaping. Enjoy relaxing or entertaining on the backyard deck, offering a private outdoor retreat. Experience the charm of Gulfport living with parks, beaches, and the community’s unique coastal atmosphere close by.

5879 27th Avenue S, Gulfport

$384,950

2 Beds ⋅ 2 Baths ⋅ Pasadena Gardens Gulfview Sec SubDv. ⋅ 33707 Zip Code

CHARM, CHARACTER, AND A FANTASTIC GULFPORT LOCATION! Situated on one of Gulfport’s beautiful tree-lined brick streets, this 2-bedroom, 1.5-bath home offers inviting living spaces, desirable updates, and easy access to everything that makes Gulfport special. The light-filled living room opens to an eat-in kitchen featuring newer stainless steel appliances. Just beyond, a bright breezeway provides flexible space for a sitting room or dining area and overlooks the screened, covered patio, perfect for relaxing or entertaining. A convenient half bath and indoor laundry are located just off the breezeway, with the washer and dryer included. Both bedrooms offer generous closet space and convenient access to the full bathroom. UPDATES AND FEATURES include a 2019 roof, double-pane windows installed in the main house in 2018, a water softener and filtration system, and rear alley access with a gated parking pad. LOCATION, LOCATION, LOCATION! Enjoy Gulfport’s vibrant downtown, locally owned restaurants, waterfront dining, boutiques, art galleries, and popular Tuesday Fresh Market. Spend your evenings strolling along the waterfront, enjoying Gulfport Beach, or watching the sunset from Williams Pier. Festivals, entertainment, and the community’s distinctive Old Florida charm are all part of the lifestyle. A HOME FULL OF CHARACTER IN ONE OF GULFPORT’S MOST CHARMING SETTINGS!

1619 53rd Street S, Gulfport

5925 Shore Boulevard S Unit 105, Gulfport

$177,900

1 Beds ⋅ 1 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code

DIRECT WATERFRONT LIVING WITH SPECTACULAR WATER VIEWS! Welcome to this beautifully remodeled, oversized 1-bedroom, 1-bath condo offering OVER 1,000 SQUARE FEET of living space in the desirable Lancaster Building at TOWN SHORES OF GULFPORT, one of the area's most sought-after 55+ waterfront communities! LOCATION, LOCATION, LOCATION! Perfectly positioned on the FIRST FLOOR and DIRECTLY ON THE WATER, this spacious residence offers beautiful waterfront views and a lovely rear patio where you can enjoy your morning coffee, watch the boats pass by, or simply relax while taking in the peaceful coastal surroundings. Imagine having the waterfront practically at your doorstep without ever having to take an elevator! Step inside and discover an inviting, remodeled interior with an exceptionally generous and open floor plan. The original sliding glass doors separating the Florida room from the main living area have been removed, seamlessly extending the living space and creating an even more open, airy atmosphere. Large windows invite natural light and showcase the beautiful waterfront setting, bringing the outdoors in. The expansive living and dining areas provide plenty of flexibility for entertaining guests, relaxing, or simply enjoying the incredible views. The generously sized bedroom offers a comfortable private retreat, while the home's oversized layout provides space rarely found in a traditional one-bedroom condo. Enjoy the convenience of FIRST-FLOOR LIVING combined with the charm of a waterfront retreat! Whether you're enjoying the views from inside or stepping out to your rear patio, this home offers the perfect setting to embrace Florida's relaxed coastal lifestyle. Town Shores of Gulfport is an active 55+ WATERFRONT COMMUNITY offering an impressive array of resort-style amenities, including FOUR HEATED SWIMMING POOLS, a private marina, tennis and pickleball courts, kayak storage, a clubhouse, fitness facilities, and an abundance of social activities. Enjoy an active lifestyle or simply spend your days soaking up the Florida sunshine! Just minutes away, you'll find Gulfport's charming waterfront arts district, featuring locally owned restaurants, eclectic boutiques, art galleries, a farmers market, and year-round community events. Beautiful Gulf beaches, downtown St. Petersburg, shopping, and entertainment are all within easy reach. DIRECT WATERFRONT VIEWS, OVER 1,000 SQUARE FEET, A REMODELED INTERIOR, AND FIRST-FLOOR CONVENIENCE — A RARE COMBINATION! Whether you're looking for a year-round residence or the perfect seasonal escape, this spacious waterfront condo offers an exceptional opportunity to enjoy the very best of Gulfport living!

5925 Shore Boulevard S Unit 105, Gulfport

$379,900

2 Beds ⋅ 1 Baths ⋅ Boca Ciega Estates Rep SubDv. ⋅ 33707 Zip Code

Beautifully Updated 2-Bedroom Home Near the Historic Gulfport beach community in a NON-FLOOD ZONE. Welcome to this beautifully updated 2-bedroom, 1-bath block-construction home offering 1,043 square feet of thoughtfully designed living space. Meticulously renovated with quality craftsmanship and high-end finishes, this home combines modern comfort with functionality in a highly desirable location. The stylish kitchen is a standout, featuring brand-new countertops, high-end appliances, abundant cabinet storage, and a layout designed for both everyday living and entertaining. The formal dining room provides a wonderful gathering space and offers convenient access to the attached one-car garage and spacious mudroom, complete with a built-in utility area, complete with a washer and dryer. Step outside to enjoy the large screened-in lanai—a perfect spot for morning coffee, outdoor dining, or relaxing year-round. Beyond the lanai is a huge backyard, offering plenty of room for outdoor activities, gardening, entertaining, or creating your own private oasis. (The large lot also conforms to the City of Gulfport’s 2026 planned ordinance (2026_4), allowing up to an 800sq ft ADU (Additional Dwelling Unit) (Buyer to verify and follow city permit process) Location is a major highlight. You'll be just minutes from shopping, public transportation, Stetson Law School and approximately one mile from the Historic Downtown that is the HIDDEN GEM OF GULFPORT, an unspoiled waterfront village brimming with independent boutiques and restaurants. Locals will tell you, “There’s always something going on in Gulfport!” You’ll delight in this charming small town’s art festivals; twice a month, market day; every Tuesday year-round, live music, delicious restaurants, beautiful parks and public pickleball and volleyball courts, plus a performing arts theater, art gallery, library and first-rate senior center all bordering the sandy beaches of the Boca Ceiga Bay. For commuters, travelers and to everyone that calls Gulfport home; location is everything as you are only 10 minutes away from the gulf beaches with access to I-275 being only approximately two miles away, putting downtown St. Petersburg within an easy drive. St. Pete-Clearwater International Airport is approximately 20 minutes away, while Tampa International Airport is approximately 30 minutes away. Updated, spacious and exceptionally well located—this home offers the opportunity to enjoy the best of Gulfport and the surrounding St. Petersburg, St. Pete Beach, Pass-a-Grille and Clearwater areas.

2109 58th Street S, Gulfport

6940 A Sunset Drive S Unit 1A, South Pasadena

$110,000

1 Beds ⋅ 1 Baths ⋅ Les Chateaux Condo SubDv. ⋅ 33707 Zip Code

Move-in ready and full of thoughtful features, this beautifully remodeled corner condominium offers the perfect combination of comfort, privacy, and convenience. The unit features two separate entrances, with the main entrance located in a hallway shared with only one other unit. A second, private entrance is located at the back of the unit, conveniently near the main road and the designated parking space. Remodeled throughout in 2026, the home features new appliances, a new HVAC system, and a new water heater, along with durable laminate flooring throughout. The kitchen offers plenty of storage, including a convenient pantry. The bathroom features a walk-in shower with security grab bars and a telescopic showerhead for added comfort and accessibility. The living room and bedroom both have ceiling fans, and the spacious bedroom walk-in closet provides excellent storage. An additional walk-in closet off the living room offers a great place to store a bicycle, beach chairs, umbrellas, and all your beach gear. A coat closet by the front entrance adds even more storage. The location within the community is another plus, with the unit conveniently close to the pool, laundry facilities, and clubhouse. Whether you're looking for a low-maintenance second home, a winter getaway from the cold, or a convenient place to enjoy long weekends near the beach, this corner unit is ready for you to move in and start enjoying the Florida lifestyle.

6940 A Sunset Drive S Unit 1A, South Pasadena

7300 Sun Island Drive S Unit 701, South Pasadena

$450,000

2 Beds ⋅ 2 Baths ⋅ Bay Island Group 15 SubDv. ⋅ 33707 Zip Code

Welcome to 7300 Sun Island Dr. #701 at Bay Island in South Pasadena. This sought after end unit residence features 73 feet of wrap-around balconies with spectacular water views of Boca Ciega Bay, the intercoastal waterway, and the Bay Island marina. This beautifully appointed condo is being sold fully furnished, turnkey and truly move-in ready - offering a seamless indoor-outdoor living space and Gulf coastal breezes! Thoughtfully renovated with attention to detail, featuring plantation shutters, plantation bifold doors, custom door casings and 6 inch baseboards. The updated kitchen features a generous open floor plan, newer stainless steel appliances, and east facing windows for your morning sunrises. The split-bedroom layout features a primary waterfront suite with an ensuite bath and walk-in closet. The second bedroom offers balcony water views and works well for guests or as a home office suite. At 1,375 sq. ft. the 2 bedrooms, living room and dining area are spacious, filled with natural light, all with expansive water views! An in-unit full size washer and dryer adds to your convenience, this unit also offers plenty of inside storage - plus a utility closet located off the balcony, and 2 additional assigned walk-in storage units, 1 on the ground floor and the other on the 7th floor next to the elevator. Reverse osmosis system under kitchen sink, HVAC 2018, both HVAC and reverse osmosis system recently serviced. 3 large flat screen TV's included, windows and doors 2020 and new Admiral building roof 2026. As an added bonus 701 features a private gated front entrance balcony with water and sunrise views. This residence comes with a covered parking space, just steps away from the building's front entrance and plenty of visitor parking for your family and guests. For your peace of mind and comfort this end unit comes with electric roll down balcony shutters, and hurricane impact windows and sliders. Entering the building you'll find a newly renovated lobby area, 2 large elevators and a large newly remodeled leisure room with water views and a full catering kitchen. The Admiral Building at Bay Island is a 55+ waterfront gated community that offers an almost endless list of amenities including 6 heated pools, 2 spas, tennis and shuffleboard courts, pickleball, waterfront walking and jogging trails, dog walking areas, on-site marina and fishing dock access, outdoor grilling stations and tiki huts, fitness center, clubhouse space, billiards, plus an active social calendar. Bay Island community has a rear axillary one-way exit bridge to Pasadena Ave. The Admiral building has passed the Milestone and Structural Integrity Reserve Studies. Just minutes from the 'Old Florida' charm of Gulfport, the beautiful sands of St. Pete Beach and Treasure Island, great restaurants, shopping, galleries, vibrant downtown St. Pete, and 2 International Airports - The Admiral at Bay Island is the perfect balance for today's Florida living. Buyer and buyer's agent to verify all information and measurements.

7300 Sun Island Drive S Unit 701, South Pasadena

$489,000

2 Beds ⋅ 2 Baths ⋅ Pasadena Shores SubDv. ⋅ 33707 Zip Code

Meticulously renovated with a sophisticated coastal style, this exceptional single-story concrete block home blends elegant finishes with extensive updates to include a complete electrical replacement with service upgraded to 200-amps, hurricane-impact double-pane windows and doors, Dam Easy Flood Barriers at the garage and all exterior doors, a new water heater, and completely renovated kitchen and bathrooms – providing enhanced protection, peace of mind, and worry-free enjoyment. Located in the highly desirable Pasadena Shores neighborhood of South Pasadena, this inviting home welcomes you with a spacious paver driveway accommodating up to six vehicles and a charming front porch. The thoughtfully designed floor plan offers 2 bedrooms, 2 full bathrooms—including a second full bath conveniently located in the garage—plus a light-filled Florida Room, screened-in lanai, and 1-car garage. Inside, luxury vinyl plank flooring, abundant natural light, plantation shutters, and custom craftsmanship trim details create a polished coastal style. The beautifully appointed kitchen features marble countertops and backsplash, solid-wood cabinetry with soft-close pull-out drawers, stainless steel appliances, a remote-control range hood, a gorgeous farmhouse sink, recessed lighting and a built-in desk. A true highlight is the Florida Room, surrounded by three walls of windows and a set of French doors. This versatile space can easily serve as a home office, exercise room, or guest accommodations. A pedestrian door provides seamless access from the Florida Room to your private screened lanai. The completely renovated hall bathroom features a modern walk-in shower, while two comfortable bedrooms are conveniently positioned off the main living area. Step outside to your own private tropical retreat. The covered screened lanai overlooks a fully fenced backyard with a paver patio and lush tropical landscaping—an ideal setting for relaxing, entertaining or enjoying Florida’s year-round outdoor lifestyle. A 220V electrical hookup has been installed for a future hot tub. The air-conditioned outdoor shed provides additional flexible space and storage. Following water intrusion from Hurricane Helene, the home underwent permitted renovations & upgrades, including professional remediation (2024); replacement of drywall to two feet throughout, all new interior and closet doors, fresh interior paint, new baseboards, new Kitchen cabinets and all appliances (dishwasher is approx. 2 years old), complete renovation of both bathrooms, complete electrical re-wire with 200 Amp service, new flooring and baseboard, washer and dryer, Dam Easy Flood Barriers, and new 4” cleanout to sewer pipe (2025). Additional valuable improvements: (2024) hurricane impact exterior doors and 13 hurricane impact double pane windows, electric water heater; (2023) Garage Door; (2022) Water Softener; (2018) Air Conditioning System w/Heat Pump, gutters, remove existing driveway, widen and replace with pavers, rear and side pavers, 6’ White PVC Fence; (2017) Exterior Stucco; (2015) Shingle Roof, Backyard Shed. Reclaimed water for irrigation. Pasadena Shores offers two waterfront community parks located at the ends of Pasadena Shores Drive and 14th Avenue S.—wonderful spots to watch the lighted boat parade, enjoy spectacular sunsets or cast a fishing line. Just minutes from our beautiful Gulf beaches, shopping, dining, parks and everyday conveniences.

1444 Corey Way S, South Pasadena

1847 Shore Drive S Unit 204, South Pasadena

$189,900

2 Beds ⋅ 1 Baths ⋅ Shore Crest Bldg SubDv. ⋅ 33707 Zip Code

How about trading Winter cold for Light and Bright Florida Living as soon as you walk in the door! Comfortable, open floorplan with 1120 Sq - 2 bed/ 1 bath, draws you to the Florida room with a magnificent southeastern view overlooking Boca Ciega Bay, it’s sure to be your Favorite spot to relax. Spacious Living / Dining area leads off to split bedrooms with abundant closet space and storage, and a nicely updated full bath . The current galley kitchen is efficient and has gas cooking plus a double wall oven. There are drawings showing options for a beautiful Kitchen update. Great news, a Washer & ventless Dryer can be added to the new kitchen design and you have a new electric panel and more GFI outlets already installed to work with! Luxury vinyl flooring, updated windows in the Florida room provides more time to relax and enjoy this wonderful condo. This +55 Community has been well managed – it’s a steel reinforced building has a new roof ( thanks Milton) and is currently being updated with trendy new exterior paint, new walkways surfaces. Recent updates include railings, plumbing and laundry and common room over recent years, All Milestone inspections completed. Laundry is available on floors 1, 5 and 8. ShoreCrest community has So much to do: premium Spectrum cable and hi-speed Internet included in monthly fee 2 heated pools, clubhouse, fitness center, library, shuffleboard, extensive waterfront with seating areas on Both sides of Shore Dr., gas grills and 2 piers to fish or just relax and a kayak launch. There are shared storage areas on each floor for bikes, beach supplies, etc. No pets and No rentals creates a community of friendly neighbors and an active social scene. Location provides easy access to our Gulfcoast beaches as well as to dining, sport activities, shopping, the theater and hospital, anything you might want to do! Also the SunRunner Express bus stops very nearby by for easy access to downtown St Petersburg and St Pete Beach, no driving required! If you’ve been dreaming of a waterfront lifestyle, condo #204 at Shore Crest is one to consider!

1847 Shore Drive S Unit 204, South Pasadena

$120,000

1 Beds ⋅ 1 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code

Freshly cleaned and painted condo. Well priced move in ready, partially furnished. New A/C System installed 3 years ago. Convenient curb parking. Town Shores features 4 heated pools. Updated Clubhouse, meeting rooms, pool tables, library, puzzle room, poker room and club room and kitchen for parties etc. Stroll to down town Gulfport daily for the Open Air Market on Tuesdays for fresh produce. Restaurants Vendors and Social Affairs. Live Theater, Library, Community and Senior Center for many activities.

3128 59th Street S Unit 203, Gulfport

6960 Sunset Drive S Unit 2A, South Pasadena

$95,000

1 Beds ⋅ 1 Baths ⋅ Les Chateaux Condo SubDv. ⋅ 33707 Zip Code

Virtually Staged. Welcome to this bright and inviting condo in a convenient St. Petersburg location. This well-maintained unit features beautiful bamboo flooring throughout the main living areas and bedrooms, a spacious open living and dining area, and plenty of natural light. The functional kitchen offers ample cabinet and counter space, while the comfortable Primary Bedroom includes a walk in closet for added storage. With a neutral interior, this home is ready for its next owner to add creative touches. Conveniently located near shopping, dining, beaches, and downtown St. Petersburg.. Schedule your showing today!

6960 Sunset Drive S Unit 2A, South Pasadena

$389,000

2 Beds ⋅ 1 Baths ⋅ Dolan Sub SubDv. ⋅ 33707 Zip Code

Virtually staged. Welcome to Charming Gulfport! This 2 bedroom, 1 bathroom home is 4 blocks from the town center. It is concrete block construction with new AC, new flooring and new hurricane windows. Enjoy the large screened porch and outdoor fire pit for entertaining. The art galleries, restaurants, theatres, parades, Tuesday Morning Market and waterfront beaches offer entertainment for all. This home is 2 blocks from Gulfport Marina, near Downtown St. Petersburg and Tampa International Airport. Come and enjoy the coastal spirit of Gulfport.

2907 49th Street S Unit A, Gulfport

7425 Bay Island Drive S Unit 105, South Pasadena

$214,500

2 Beds ⋅ 2 Baths ⋅ Bay Island Group 2 SubDv. ⋅ 33707 Zip Code

Bay Islands has so much to offer the +55 resident! A gated waterfront community in S Pasadena, a terrific location between the Gulf beaches and St Petersburg. This lovely updated 2 bed 2 bath - ground level condo enjoys a beautiful east view of the Pass that connects Boca Ciega Bay to the Intracoastal. Get to know the dolphins that pass by every day while you enjoy your coffee! This condo had very minimal water damage from the past storms, yet it has new kitchen and bathroom cabinets, quartz counters, new appliances, and gorgeous hurricane rated windows and 3 panel sliding doors, carpeting and interior paint. even the furnishings are available. There's a hook-up for a stack laundry near the guest bath. Your small pets are Welcome ( 2 pets, 1 dog + 1 cat Or 2 cats ) The Bahama building has owned solar panels on roof that offset everyone water bill. Bay Islands has 6 pools, a Very Active social vibe ! Gorgeous 2 story Rec Center, with Assoc Office - a banquet room with stage and kitchen, bar area, a library, billards and card rooms And his & her gyms with saunas. There is a 1.4 mile walkable seawall surrounding the community - multiple tennis courts and many areas to grill and picnic. And a marina - slips may be available. IF you need to wander, the SunRunner Express bus, just out front will zip you to locations in downtown St Petersburg as well as all along St Pete Beach. THIS could be the lifestyle you've been thinking about

7425 Bay Island Drive S Unit 105, South Pasadena

St Pete/South Pasadena/Gulfport/St Pete Bch Homes under $500,000

Newest St Pete/South Pasadena/Gulfport/St Pete Bch Homes under $500,000