South Pasadena Homes with Playground Community Features

South Pasadena Homes with Playground Community Features

Welcome to South Pasadena, Florida – a hidden gem nestled in the heart of Pinellas County. This charming coastal city offers a delightful blend of serene living and vibrant community life, making it an ideal destination for families, retirees, and everyone in between. With its picturesque streets lined with lush greenery and beautiful waterfront views, South Pasadena is a place where you can truly unwind and enjoy the beauty of Florida living.

One of the standout features of South Pasadena is its family-friendly atmosphere, particularly evident in its homes with playground community features. Imagine living in a neighborhood where children can safely play and explore, while parents connect with one another in a welcoming environment. These communities often feature well-maintained playgrounds, offering a perfect spot for kids to enjoy outdoor activities, make new friends, and create lasting memories.

South Pasadena is conveniently located close to the stunning beaches of St. Pete and the vibrant culture of downtown St. Petersburg, ensuring that you have easy access to shopping, dining, and entertainment options. The city's close-knit community fosters a sense of belonging, where neighbors become friends and local events bring everyone together.

Whether you’re looking for a cozy single-family home or a spacious townhouse, South Pasadena's real estate market has something for everyone. With its enchanting charm, family-oriented amenities, and proximity to the beautiful Gulf Coast, South Pasadena is not just a place to live – it’s a place to thrive. Discover your dream home in this idyllic city today!

Newest South Pasadena Homes with Playground Community Features

$1,300,000
3 Beds ⋅ 3 Baths ⋅ Boca Ceiga Park SubDv. ⋅ 33707 Zip Code
Welcome to a turnkey, income-producing coastal retreat in the heart of Gulfport's Historic Waterfront Arts District. This Key West-inspired residence offers 3 bedrooms, 3 bathrooms, and 3,051 square feet of light-filled living space with sweeping views of Boca Ciega Bay and Veterans Park just steps from the front door. Currently operating as a successful short-term rental, the home is being sold fully furnished and rental-ready — a rare opportunity to step into an established, cash-flowing vacation rental from day one. Existing bookings, guest reviews, and operating history are available to qualified buyers upon request, making this an ideal acquisition for investors, 1031 exchange buyers, or second-home owners seeking offset income. Inside, soaring cathedral ceilings, a spacious great room, warm wood flooring, and a whole-house reverse osmosis system deliver the elevated finishes today's guests and homeowners expect. Multiple porches and balconies showcase the water views and capture Gulf breezes, while the layout comfortably sleeps a full group without sacrificing privacy. Location is everything: a one-minute walk to Veterans Park and the Gulfport waterfront, minutes to the shops, restaurants, art galleries, and live music of Beach Boulevard, and a quick drive to St. Pete Beach, downtown St. Petersburg, and Tampa International Airport — the exact walkability and lifestyle that keep this property booked. Whether you're expanding a short-term rental portfolio or looking for a coastal residence that pays for itself between visits, 5417 Essex Ave S is a rare turnkey offering in one of Florida's most sought-after small-town waterfront communities. STR certificate and licenses in place and transferable subject to city approval.

5417 Essex Avenue S, Gulfport
$399,500
2 Beds ⋅ 1 Baths ⋅ Pasadena Gardens Gulfview Sec SubDv. ⋅ 33707 Zip Code
Welcome to this charming 2-bedroom GULFPORT COTTAGE with a versatile bonus room that can be used as a home office, guest space, or potential 3rd bedroom. Enjoy the Florida lifestyle from the SPACIOUS SCREENED IN BACK PORCH (permitted 2022), plus two large sheds offering plenty of additional storage in the FULLY FENCED in backyard. This Property is NOT LOCATED IN A FLOOD ZONE that requires flood insurance. The house has no history of flooding. Located less than a mile from Gulfport's beaches, restaurants, shops, and entertainment, approximately 10 minutes from Downtown St. Pete, and a short drive to some of FLORIDAS TOP RATED GULF BEACHES. Major upgrades include ROOF (2022), A/C (2024), WATER HEATER (2024), TUFF SHED (2022), and MAIN SEWER LINE replacement (2026). A great opportunity to own a well-maintained home in one of Gulfport's most desirable locations.

1907 53rd Street S, Gulfport
$114,900
1 Beds ⋅ 1 Baths ⋅ Les Chateaux Condo SubDv. ⋅ 33707 Zip Code
Welcome to your beautifully reimagined retreat! A fully renovated ground-floor one-bedroom, one-bathroom condominium that blends contemporary style with effortless Florida living. Step inside to find an inviting, open-concept living space dressed in wood-look luxury vinyl plank flooring, which adds warmth and character while maintaining easy-care durability. The brand-new kitchen will impress with sleek shaker-style cabinetry, elegant quartz countertops, and a timeless design that perfectly complements any décor. Whether preparing a quiet breakfast or hosting friends for an evening in, this kitchen strikes the ideal balance between function and sophistication. The spacious bedroom provides a serene retreat, featuring an oversized walk-in closet and an abundance of natural light. The bathroom has been rejuvenated with modern fixtures and a clean, polished aesthetic, echoing the home’s overall sense of calm and contemporary luxury. Peace of mind comes standard here, with a brand-new hot water heater, a new sliding glass door leading to your private patio, and a brand-new air conditioning unit ensuring comfort year-round. Every detail of this renovation has been thoughtfully planned to provide style, efficiency, and low-maintenance living. Located in South Pasadena, this condo offers convenient access to world-class dining, shopping, arts, and culture. Enjoy nearby waterfront parks, explore the vibrant downtown scene, or spend the day on St. Pete Beach; all just minutes from your door. Whether you’re seeking a primary residence, a seasonal getaway, or an investment opportunity, this fully remodeled condo offers the best of modern living in an unbeatable location.

1170 Rue Des Chateaux Unit 1A, South Pasadena
$299,000
2 Beds ⋅ 2 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
Unmatched Views & Value: Make This 10th-Floor Windsor Condo Your Own. Experience sweeping water views and incredible value in this 10th-floor, 2-bedroom, 2-bath residence located in the highly desirable Windsor House 55+ community at Town Shores of Gulfport. Unit 1002 is a fantastic opportunity for buyers looking to build equity and customize their waterfront living experience. This is the perfect blank slate for your modern upgrades and coastal vision. Step inside to an open-concept floor plan filled with natural light, offering commanding views of Boca Ciega Bay from nearly every room. The spacious living and dining areas open to large picture windows where you can watch daily dolphin shows and take in the vibrant sunsets over the iconic Don CeSar Hotel. The kitchen layout is ideally situated for entertaining and features generous storage, reverse osmosis water filtration, and a gas stove. Town Shores offers an active, maintenance-free coastal lifestyle with a full calendar of social events. Just outside your elevator-equipped building, you have access to resort-style amenities including four pools, a marina, a fitness center, a dog run, and courts for tennis, pickleball, shuffleboard, and bocce ball, plus a vibrant clubhouse featuring a library, billiards, card rooms, and a ballroom. This residence includes a covered carport to keep your vehicle shaded and offers ample guest parking. Best of all, you are just a short stroll from the charming downtown Gulfport waterfront district, brimming with award-winning dining, entertainment, and art. Secure premium views with the freedom to upgrade on your terms and create your coastal paradise.

6020 Shore Boulevard S Unit 1002, Gulfport
$178,000
1 Beds ⋅ 1 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
Welcome to your FURNISHED WATERFRONT RETREAT in the highly sought-after Lancaster Building at TOWN SHORES OF GULFPORT – an active and vibrant 55+ community, where comfort meets coastal charm. This UPDATED, BRIGHT AND SPACIOUS 1 bedroom, 1 bath condo offers an AIRY OPEN LAYOUT FLOODED WITH NATURAL LIGHT, creating a gorgeous, welcoming atmosphere from the moment you step inside. A QUEEN SIZE MURPHY BED IN THE FLORIDA ROOM provides flexible guest space along with A BEAUTIFUL WATER VIEW OF THE BAY to wake up to! Enjoy morning coffee or evening cocktails greeting dolphins, manatees and pelicans with sparkling Boca Ciega Bay and private marina views right outside your window — a daily reminder that you’re living in one of Gulfport’s most desirable waterfront communities. The expansive living and dining areas provide plenty of room for entertaining, relaxing, or simply soaking in the peaceful ambiance. Plus, the entire unit was recently upgraded with beachy driftwood tone vinyl plank flooring throughout ... practical, beautiful and easy to maintain. The spacious primary bedroom delivers comfort and privacy with a peaceful, laid-back boho/shabby-chic vibe, a large walk-in closet and a hall double closet for extra storage. The updated full bath with tub and rainhead shower features a beautiful new dove gray vanity, white quartz countertop, and gorgeous champagne gold vanity lighting, faucet hardware and modern cabinet pulls. The kitchen was also recently updated with white cabinetry, granite countertops and glass and champagne bronze hardware. This condo’s open design, gorgeous upgrades and extra-large footprint set it apart from typical 1-bedroom units, giving you space to breathe, move, and truly enjoy your home. Plus, this unit comes with the extra bonus of a deeded carport. Residents of Town Shores enjoy resort-style amenities including four heated pools, a private marina, tennis and pickleball courts, kayak storage, an active clubhouse with weekly social events, fitness areas, and walkable access to Gulfport’s vibrant shops, dining, and waterfront activities. With its unbeatable location, spacious interior, and bright coastal feel, this condo is the perfect place to embrace relaxed and vibrant Florida living!

5925 Shore Boulevard S Unit 405, Gulfport
$400,000
3 Beds ⋅ 2 Baths ⋅ SubDv. ⋅ 33707 Zip Code
Welcome to **1714 55th Street S, Gulfport, FL 33707**, where comfort, convenience, and the Florida lifestyle come together in one exceptional opportunity. Whether you're searching for a primary residence, seasonal retreat, or investment property, this move-in-ready **3-bedroom, 2-bath home** offers outstanding value with **no deed restrictions**, giving you the flexibility to truly make it your own. From the moment you arrive, you'll appreciate the peace of mind that comes with major updates already completed. The **roof was replaced in 2021**, a **4-point inspection has just been completed**, and for added confidence, the seller is including a **one-year home warranty** for the new owner's protection. Best of all, this home is **ready for immediate occupancy**, allowing you to move in and start enjoying the Florida lifestyle right away. Inside, you'll find a functional floor plan with comfortable living spaces, generous bedrooms, and two full bathrooms designed to accommodate families, guests, or those who simply appreciate extra space. Natural light fills the home, creating a warm and inviting atmosphere that's ready for your personal touches. One of this home's greatest advantages is its incredible location in the heart of Gulfport. Known for its vibrant arts community, welcoming small-town charm, and beautiful waterfront, Gulfport has become one of Pinellas County's most desirable places to live. Spend your weekends strolling along the Gulfport Marina, exploring the eclectic shops and local art galleries, dining at award-winning waterfront restaurants, or enjoying live music and community festivals that take place throughout the year. The city's famous Tuesday Fresh Market and First Friday Art Walk create an atmosphere unlike anywhere else on Florida's Gulf Coast. Outdoor enthusiasts will appreciate the nearby parks, walking trails, pickleball and tennis courts, kayak launches, and waterfront recreation opportunities. Enjoy spectacular sunsets over Boca Ciega Bay, launch your boat from nearby public ramps, or simply relax along the scenic waterfront while watching dolphins play. Beach lovers will appreciate being just a short drive from some of Florida's most beautiful white-sand beaches, including **St. Pete Beach, Treasure Island, Pass-a-Grille, Madeira Beach, and Fort De Soto Park**. Whether you enjoy boating, fishing, paddleboarding, or simply soaking up the sun, you'll have endless opportunities just minutes from your front door. The location also provides quick access to vibrant **Downtown St. Petersburg**, where you'll enjoy world-class restaurants, rooftop bars, museums, breweries, shopping, waterfront parks, entertainment venues, and professional sports. Visit the renowned Salvador Dalí Museum, catch a Tampa Bay Rays game, explore Beach Drive, or enjoy concerts and events at the St. Pete Pier—all just a short drive away. Commuters will appreciate convenient access to I-275, making travel to Tampa, Clearwater, and both Tampa International and St. Pete-Clearwater International Airports simple and convenient. With **no HOA or deed restrictions**, valuable recent improvements, immediate availability, and an unbeatable location close to Gulfport's waterfront, Downtown St. Petersburg, and the Gulf beaches, this home offers an incredible opportunity to enjoy everything Florida's Gulf Coast has to offer. Schedule your private showing today and discover why so many people are proud to call Gulfport home.

1714 55th Street S, Gulfport
$257,000
2 Beds ⋅ 2 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
WATERFRONT PARADISE IN THE HIGHLY SOUGHT-AFTER MANCHESTER BUILDING AT TOWN SHORES! Welcome to 6025 Shore Blvd S, Unit 106, Gulfport, FL 33707 — a rare opportunity to own a first-floor FULLY REMODELED waterfront residence in one of Town Shores’ most desirable buildings. Perfectly positioned directly on the water, this unit offers breathtaking views and front-row seats to Florida’s spectacular sunsets right from your own patio. Located in the coveted Manchester Building, this home combines convenience, comfort, and an unbeatable waterfront lifestyle. Enjoy easy first-floor access with no elevators required while taking advantage of the serene waterfront setting that makes Town Shores one of Gulfport’s premier 55+ communities. Wake up each morning to sparkling water views and enjoy watching dolphins, seabirds, and boats pass by from the comfort of your home. The open and inviting layout is ideal for both everyday living and entertaining guests. Immaculately remodeled with gorgeous cabinetry in the bedroom for extra storage, beautiful granite countertops with stainless steel appliances, crown molding throughout, brand new tile flooring and on site laundry facilities. Town Shores offers an exceptional array of amenities, including multiple heated pools, a clubhouse, fitness center, tennis and pickleball courts, shuffleboard, social activities, walking paths, and a marina. The HOA covers water, gas, trash, recycling, cable and internet!!! Just minutes away, you’ll find the vibrant waterfront downtown Gulfport district, known for its charming restaurants, art galleries, boutiques, festivals, and beach. Whether you’re seeking a year-round residence, seasonal retreat, or waterfront investment opportunity, this exceptional Manchester Building condo delivers the very best of Gulf Coast living. Don’t miss your chance to own one of the most desirable waterfront locations in Town Shores!

6025 Shore Boulevard S Unit 106, Gulfport
$4,999,000
4 Beds ⋅ 5 Baths ⋅ Pasadena Point Estates Ph Ii SubDv. ⋅ 33707 Zip Code
A MAGNIFICENT LUXURY WATERFRONT ESTATE SUPPORTED BY AN IMPRESSIVE DEEP-WATER DOCK WITH MOORINGS FOR A 100FT YACHT! Located in renowned Pasadena Yacht and CC, south Pinellas County’s only gated golf and boating community, this remarkable Windstar Home rests on a wide, 1 ½ lot footprint, with beautiful open water view of Boca Ciega Bay. Step up to the elevated courtyard entry and take in rich cast stone and travertine exterior finishes. Soaring 25 feet high, the majestic rotunda foyer introduces exquisite cherrywood and marble floors, dazzling faux paintwork, elegant detailed woodwork, radiant lighting, brilliant custom ceilings and unforgettable waterviews. The superb CEO-quality executive office provides extensive sumptuous built-ins, wonderful matching coffered ceilings and a double-sided fireplace. Lovely casual waterfront dining is complemented by a gorgeous formal dining room with 12ft-high ceilings. The sublime chef’s kitchen is a deeply-satisfying culinary experience. Artisan quality raised-panel wood cabinetry and superb Ogee-edge granite surfaces support high-end Gaggenau steam, convection and gas cooking, Subzero refrigeration, built-in Miele coffee system, warming drawers, refrigeration drawers, large walk-in pantry, and a built-in workstation center. You’ll love the fabulous butler’s pantry, multi-level breakfast bar (with beverage chiller and ice maker), and dedicated wine closet that support this incredible kitchen. Relax in the resplendent waterfront living room with custom designer entertainment center, rich marble-encased fireplace, fine coffered ceilings, and terrific window treatments (all windows are elegantly encased in wood). Step out to the enticing 450sqft covered waterfront balcony with remote controlled sunshades. Balcony offers a built-in tumbled marble/granite gas cooking center, and spacious seating/dining areas. Huge guest bedroom suite has a lavish, adjacent luxury bath. Upstairs, you’ll discover a spectacular owner’s suite: a full-height cast stone double-sided gas fireplace separates the bedroom from the plush sitting area with Juliette balcony and magnificent built-in entertainment center. The grand walk-in closet system features numerous built-ins and a generous center island dresser. The owner’s bath is a posh, pampering retreat with commanding views of the water, exceptional marble/granite surfaces, built-in microjet spa tub, custom designer vanities, a dedicated sit-down cosmetics center, and a superb glass-enclosed marble rain shower/steam room. Bedrooms 3 & 4 are oversized and en suite, with beautiful, luxurious baths. Your massive lower level is ideal for fitness/gaming/storage. Lushly landscaped, out back you’ll find the perfect blend of luxury, entertainment and waterfront adventure. A 460sqft covered lounging/dining deck transitions to a stunning Pebbletec pool/elevated spa overlooking the water. An expansive composite dock supports a 16,000 lb boat lift with cat walk, shore power, water, lighting, shower and deep water mooring with tie poles for yacht with 22ft beam. This luxury estate is a true rarity and boasts countless amenities and highly-desirable extras. One of the finest waterfront homes in Tampa Bay! Pasadena Yacht & CC enjoys an extensive list of world-class amenities including golf, tennis, fitness center, marina, restaurant, community pool and clubhouse. A great location and an extraordinary community! Dimensions are estimates, buyer to verify.

6224 Pasadena Point Boulevard, Gulfport
$685,000
3 Beds ⋅ 3 Baths ⋅ Curns W J Sub SubDv. ⋅ 33707 Zip Code
In the heart of Gulfport, with its vibrant arts scene, waterfront marina, locally loved restaurants, and independent shops, this home offers a rare blend of character, functionality, and resort-inspired living. Check out the curb appeal — a fresh exterior framed by lush tropical landscaping and a low-maintenance xeriscape front yard. A brick walkway leads you through the covered entry to immediate sightlines of the bright living room offering soaring ceilings and beams, engineered hardwood floors, and a fireplace layered in natural textures. Light pours throughout the open-concept layout, flowing into the dining area. The adjacent kitchen balances functionality with style, featuring linen-toned cabinetry with dovetail drawers, double convection ovens, and a Samsung stainless steel refrigerator. Windows overlooking the patio continue the home’s connected indoor-outdoor feel. Off the main living spaces, a step-down flex room with patio access and built-ins lends itself to a relaxed family room, media lounge, or home office. Three bedrooms include two spacious primary suites. The first primary retreat features a lounge with custom closets that opens into the bedroom where original terracotta tile flooring adds warmth and timeless character. Its ensuite bath features textured stone tilework and earthy organic finishes. The second primary suite offers private access to the carport and an ensuite bathroom with a gorgeous custom door and a stunning clawfoot tub. A third bedroom continues the home’s design language with Art Deco-inspired glass wall accents and double glass sliders opening directly to the patio. The outdoor space is centered around an expansive screened patio. Paver flooring, a covered lanai with large spa, multiple lounging and dining areas, and a shade sail overhead create an atmosphere that feels resort-inspired. The home interior offers a laundry closet with a full-size stackable washer and dryer, and the nearby oversized garage offers more versatility, including additional storage, a full pool bath, kitchenette, and second laundry area — ideal for entertaining, extended guest stays, or multigenerational living. The pool bath itself showcases vibrant tilework by noted tropical artist Monica Watson. This property has been thoughtfully designed for both functionality and sustainability including kayak, canoe, and bike racks, raised garden beds, rain barrels, and mature landscaping that includes various tropical fruits. It offers underground power and utilities, and abundant parking, including space for large trailers or RVs with a 30-amp hookup. Extensive upgrades include whole-home solar power with a Tesla backup battery system, impact-rated windows and doors, whole-house surge protection, new ductwork, UV air purification system, reverse osmosis water filtration, and irrigation on well and tap. The property also boasts extensive integrated security system with cameras, control keypads, infrared monitoring, and integrated smoke detectors, all hardwired into the home’s solar infrastructure. Distinctive, flexible, and deeply connected to the creative coastal spirit of Gulfport, this is far more than a traditional three-bedroom home — it is a private retreat designed for gathering, creating, hosting, and living exceptionally well. Just minutes from downtown St. Petersburg and Gulf beaches, Gulfport offers a uniquely creative and laid-back lifestyle that feels worlds away from typical suburban Florida living.

5005 24th Avenue S, Gulfport
$215,000
2 Beds ⋅ 2 Baths ⋅ Les Chateaux Des Rois SubDv. ⋅ 33707 Zip Code
LES CHATEAUX DES ROIS | SOUTH PASADENA – FULLY RENOVATED 2BR/2BA - Now with a NEW ROOF! One of the most extensively updated condos in Les Chateaux, this 2-bedroom, 2-bath condominium offers a level of finish and livability that stands apart from typical inventory in the community. With approximately 960 square feet, this larger floor plan provides functionality and flexibility not found in the more common one-bedroom units. The interior has been thoughtfully upgraded throughout, anchored by a completely redesigned kitchen featuring new cabinetry, granite countertops, tile backsplash, and a full suite of stainless steel KitchenAid appliances. Both bathrooms have been tastefully renovated, and luxury vinyl plank flooring runs seamlessly throughout the home, creating a clean, modern feel. Major system upgrades add significant long-term value and peace of mind, including hurricane-rated impact windows and doors, a newer water heater, and in-unit washer and dryer. The private rear balcony has also been improved with new flooring and screening, offering a comfortable outdoor space to relax. Plus the condo association is replacing the rook and front entrances to all of the building within Les Chateau Des Rois. Not an age-restricted community, Les Chateaux offers flexibility for both full-time residents and seasonal ownership. The location is exceptionally convenient within walking distance to shopping, dining, and everyday essentials, and just minutes to the beaches of South Pasadena. Gulfport, St. Pete Beach, and downtown St. Petersburg are all easily accessible, placing waterfront parks, restaurants, and entertainment within a short drive. A move-in ready opportunity with meaningful upgrades, larger living space, and a location that supports both lifestyle and long-term value.

7001 Place De La Paix Unit 2A, South Pasadena
$865,000
3 Beds ⋅ 2 Baths ⋅ Villa De Maria SubDv. ⋅ 33707 Zip Code
Are you tired of paying sky high electric bills, expensive HOA fees and blowing your budget at the gas pump? STOP SCROLLING!!! ECO FRIENDLY SANCTUARY ~ UNDER $100 ELECTRIC BILLS ~ VOLUMINOUS WORKSHOP ~ LOW-MAINTENANCE ELEVATED LIVING ~ Welcome to a truly one-of-a-kind, engineered HAVEN offering ultimate freedom and storm resilience just moments from the Pasadena Yacht & Country Club. Designed for those who value independence, security, and low-overhead luxury, this exceptional custom residence features paid-off solar panels, a 2024 Generac emergency generator, natural gas connection, EV charging capability, and hurricane-impact protection. Unwind across multiple private upper decks framed by tropical canopy, delivering seamless indoor-outdoor living with LITTLE weekend YARD maintenance. Inside, soaring ceilings and high-end finishes create an airy, light-filled SPACE. IN EVERY ROOM ONE IS SURROUNDED BY VIEWS OF NATURE WITH A treehouse ambiance. The crown jewel for makers, collectors, or adventurers is the massive, fully enclosed 1,600+ SF lower-level, workshop, PLAY AREA and flex storage space. CAPABLE of housing SPORTS AND EXERCISE EQUIPMENT, SMALL BOATS, kayaks, or a world-class workshop , this level provides utility rarely found in coastal Pinellas County. Located outside mandatory HOA restrictions, steps from Gulfport’s vibrant downtown waterfront, dining, and marina. Experience high-spec coastal living with maximum security and LOW MONTHLY MAINTENANCE costs. (NOTE: this property does not currently have a pool. Pool-possibility renderings have been provided by Sunshine City Pools.)

2613 59th Street S, Gulfport
Start Your Search