South Pasadena Homes under $400,000

South Pasadena Homes under $400,000

Welcome to South Pasadena, Florida—a charming coastal gem nestled in the heart of Pinellas County. Known for its picturesque waterfront views and vibrant community, South Pasadena offers a unique blend of small-town charm and modern amenities. Just a stone's throw away from the bustling beaches of St. Pete and the lively atmosphere of downtown St. Petersburg, this delightful city provides residents with the perfect balance of relaxation and excitement.

One of the most appealing aspects of South Pasadena is its diverse real estate market, particularly for those seeking homes under $400,000. Here, you will discover a range of options, from cozy condos with stunning water views to quaint single-family homes nestled in friendly neighborhoods. These affordable properties make South Pasadena an ideal choice for first-time homebuyers, retirees, or anyone looking to enjoy the Florida lifestyle without breaking the bank.

The community is enriched by its local parks, shops, and dining options, making it easy to enjoy leisurely strolls along the waterfront or indulge in delicious cuisine from nearby eateries. Residents also appreciate the city's commitment to maintaining a friendly atmosphere, where neighbors become friends and community events bring everyone together.

With its beautiful scenery, welcoming vibe, and affordable housing options, South Pasadena is not just a place to live—it's a place to thrive. Come explore this hidden treasure in Pinellas County and discover your dream home today!

Newest South Pasadena Homes under $400,000

1619 53rd Street 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
2109 58th Street S, 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
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
3128 59th Street S Unit 203, Gulfport
$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
2907 49th Street S Unit A, Gulfport
$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
2960 59th Street S Unit 215, Gulfport
$184,900
2 Beds ⋅ 2 Baths ⋅ Jamison House SubDv. ⋅ 33707 Zip Code
WELCOME to your ultimate coastal oasis in the prestigious Town Shores community of Gulfport, Florida! This beautiful 2-bedroom 2-bathrooms, 1250 sq ft end unit condo is perfectly positioned to offer the absolute best of Florida Living. located on the highly desirable sf the second floor of the Jamison building this unit provides the ultimate convenience-giving you the freedom of a quick and easy walk-up if you prefer to by-pass the elevator. Step inside to an expansive, airy floor plan a clean, beautifully staged interior with large tile flooring stretching across the primary living spaces a, sweeping water views of Boca Ciega Bay. Relax in your living area and watch the sky lights up with spectacular sunsets every single day over the tranquil bay. This property represents the best value on the market today. Rare corner unit end unit, you will enjoy a boost in natural sunlight, a more private atmosphere and gorgeous featuring Every day a beautiful with the big windows looking directly at Boca Ciega Bay and also the daily sunsets are amazing! A Premium Waterfront Lifestyle with Total Financial Peace of Mind. Third floor Corner unit with Beautiful Views. Stunning sunsets are your almost every day and intracoastal views from this light filled residence, enhanced by abundant windows and natural light though out. The open plan showcases a beautifully updated kitchen with modern appliances and updated windows. Incudes a carport. The impressive primary suite features an oversized, a large walk-in closet and a private ensuite bathroom. The secondary bedroom is generously sized and offers double closets, ideal for quests or a home office. An oversized hallway closet provides exceptional storage rarely seen in a condo. Unit also comes with a separate storage area. Additional highlights include smooth ceilings throughout, neutral décor, custom ceiling fans and beautiful maintenance-free flooring. Natural gas (which is not common in condos) is included in the monthly condo fee, providing energy for both cooking and heating. Town Shores offers an active and vibrant lifestyle with a large clubhouse hosting social events and activities, four heated pools, a fitness center with sauna, library, bocce ball, tennis/ pickle ball and shuffleboard courts. Ideally located within walking distance to downtown Gulfport, you’ll enjoy ease access to fine dining, cages, shops, galleries and waterfront activities. Live the Good Life in this bright with dazzling views of Boca Ciega Bay and only a short walk to Gulfport Beach. This waterfront condo has 2 bedrooms and 2 bathrooms in this 55+ Community of Town Shores of Gulfport. Skip the hassle and expense of moving trucks and furniture shopping. This condo features contemporary selection of high-end furnishings purchased just 2 years ago for over $25,000. The entire package is meticulously maintained and is completely negotiable to be included with the sale, offering you a seamless, walk-in ready. BUY WITH TOTAL FINANCIAL CERTAINTY. Unlike many coastal Florida hurdles, the Jamison Building offers you complete financial security. Fully Funded Reserves: The association reserves are 100% funded in accordance with State Compliance Laws. The building has successfully passed the mandatory Milestone inspections.

2960 59th Street S Unit 215, Gulfport
5980 Shore Drive S Unit 901, Gulfport
$375,000
3 Beds ⋅ 3 Baths ⋅ Town Shores SubDv. ⋅ 33707 Zip Code
Diplomat building, newly painted, newer flake & Epoxy flooring on walkways and laundry rooms, carport roofing recently cleaned (power washed), lush maintained landscaping, breathtaking views of Boca Ciega Bay and glorious sunsets. Enjoy living in this beautiful east end unit at Town Shores of Gulfport. You have your own oasis at the end of the hallway with full water views, loads of shade and privacy. The condo is protected with hurricane shutters for those yearly storms we may get in the summers. Stone countertops speak of an updated kitchen, upgraded maple cabinets, dishwasher, microwave, refrigerator featuring all the comforts of home. Enjoy the bonus of a full size Washer and Dryer. What a benefit for a new owner. A must see for anyone thinking of buying a waterfront condo.

5980 Shore Drive S Unit 901, Gulfport
1893 Shore Dr. Drive S Unit 216, South Pasadena
$140,000
2 Beds ⋅ 2 Baths ⋅ Shore Plaza Bldg SubDv. ⋅ 33707 Zip Code
Waterfront Value on Shore Drive: Priced to Sell! Why pay $180K+? The last 2/2 in this community sold for just over $180K, and this second-floor unit is priced at $140K. Waterfront living on Boca Ciega Bay at a price you won't see often. This 2-bed, 2-bath condo in a sought-after 55+ waterfront community is move-in ready. Sip your morning coffee in the spacious Florida room and watch dolphins, manatees, and boats drift by. St. Pete Beach, Treasure Island, and Gulfport are all just minutes away. Split-bedroom layout for privacy • Spacious primary suite with ensuite bath and large closet • Large windows and bright living space with bay views • Meticulously maintained* The community offers fantastic waterfront amenities, including: • Heated waterfront pool • Fishing pier and dock • Waterfront picnic areas with gas grills • Large clubhouse with fitness center, billiards, and event space • Laundry rooms on every floor Major community improvements include a new roof and dock/fishing pier (2018). The monthly condo fee provides tremendous value, covering cable, internet, gas, water, and more. The building also uses a central gas boiler, which helps reduce both building and individual unit insurance costs. Conveniently located near shopping, dining, medical facilities, and the SunRunner Express to downtown St. Petersburg. Affordable waterfront living in a prime location—rarely available at this value on Shore Drive. Schedule your private showing today and start enjoying the relaxed Florida coastal lifestyle.

1893 Shore Dr. Drive S Unit 216, South Pasadena
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