South Pasadena Homes with Pickleball Court(s) Amenities

South Pasadena Homes with Pickleball Court(s) Amenities

Welcome to South Pasadena, Florida – a hidden gem nestled in the heart of Pinellas County! Known for its charming small-town atmosphere and close-knit community, South Pasadena offers a unique blend of coastal living and suburban comfort. With its picturesque streets lined with beautiful palm trees and vibrant local businesses, this city is a perfect retreat for those seeking a relaxed lifestyle while still enjoying easy access to the bustling nearby areas of St. Petersburg and Clearwater.

One of the standout features of South Pasadena is its commitment to outdoor recreation, particularly for those who enjoy an active lifestyle. The city is home to several homes with pickleball courts, an increasingly popular sport that combines elements of tennis, badminton, and ping-pong. Imagine stepping out of your beautifully designed home and onto your private court, ready to challenge friends or unwind with a leisurely game. This amenity not only promotes a healthy lifestyle but also fosters a sense of community as neighbors come together for friendly matches and social gatherings.

In addition to pickleball, residents of South Pasadena can enjoy nearby parks, scenic waterfront views, and access to some of Florida’s most beautiful beaches. With a range of dining options and cultural attractions just a stone’s throw away, you’ll find that this charming city has everything you need for a fulfilling life.

Whether you’re a retiree looking for tranquility or a family seeking a vibrant community, South Pasadena's homes with pickleball court amenities offer the perfect blend of comfort, recreation, and connection. Come discover your new home in this delightful Florida city!

Newest South Pasadena Homes with Pickleball Court(s) Amenities

$250,000
1 Beds ⋅ 1 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
Welcome to the highly sought-after Fairfax Building in Town Shores of Gulfport! This beautifully renovated first-floor condo offers the perfect blend of modern luxury and effortless Florida living. Every detail has been thoughtfully updated, making this home truly move-in ready. The stunning interior features porcelain tile flooring throughout, hurricane-impact windows and exterior doors, interior doors and baseboards, and a beautifully redesigned kitchen with shaker cabinetry, quartz countertops, a large movable island with abundant storage, a farmhouse sink, and stainless steel appliances. The bathroom showcases a spacious walk-in shower with glass enclosure, a new vanity, updated fixtures, and designer finishes. Additional improvements include a 2025 HVAC system, an updated electrical panel, and ceiling knocked down and re-done (NO popcorn).Enjoy assigned covered parking in the newly updated carports, coffee on your patio and an unbeatable location just steps from one of the community's four heated pools. The Fairfax Building also offers exceptional value with a new roof, low monthly maintenance fees, completed Milestone Inspection and Structural Integrity Reserve Study (SIRS), no pending assessments, and a pet-friendly community. Nestled in Historic Gulfport, Town Shores offers a vibrant, walkable lifestyle just moments from charming restaurants, unique boutiques, art galleries, and the beautiful waterfront along Boca Ciega Bay. Residents enjoy an active social calendar and exceptional amenities, including four heated pools, tennis and pickleball court, bocce ball, shuffleboard, a clubhouse, fitness center, and first-come, first-served boat slips when available. Ideally located just 15 minutes from St. Pete Beach, vibrant downtown St. Petersburg, premier shopping, and only 25 minutes from Tampa International Airport, this exceptional location offers the very best of Florida's Gulf Coast lifestyle. Whether you're searching for a seasonal getaway or your full-time Florida home, this condo is an outstanding opportunity.

5935 30th Avenue S Unit 104, Gulfport
$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
$185,000
1 Beds ⋅ 1 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
Welcome to your 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 extra-large 1 bedroom, 1 bath condo offers an airy, open layout flooded with natural light, creating a bright and inviting atmosphere from the moment you step inside. Enjoy morning coffee or evening cocktails with sparkling water and 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. A Murphy Bed in the Florida Room provides flexible guest space along with an upfront and close amazing water view to wake up to! 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
$555,000
2 Beds ⋅ 2 Baths ⋅ Harbourside Condo SubDv. ⋅ 33707 Zip Code
This is a well maintained waterfront unit in Harbourside Condos in South Pasadena INCLUDING A DEEP WATER BOAT SLIP/LIFT (there are only 87 slips total for 800 units). It's a 16,000 lb Deco all aluminum and stainless steel cradle lift. Harbourside is a resort-like condo community on the intracoastal waterway 5 minutes from St Pete Beach. This unit's features are: HVAC system (2025), Stainless steel appliances, Hurricane shutters, Hurricane impact windows, 9' Ceilings and Dining and Living room combination with a Split Bedroom plan. The western view from the private balcony has beautiful Florida sunsets! The guest bedroom and kitchen also have beautiful water views. This desirable complex is guard gated (24 hour) with many amenities including 6 pools, his and hers fitness centers, shuffleboard, pickleball, tennis, hot tub, electric car charging stations, car wash stations, clubhouse with many social events throughout the year, library, card room, billiards room, arts and crafts room, wood working area, yoga and water exercise classes. There is a 1.5 mile walkway around the complex along the waterfront which is lit up for nightly walks. Come see what resort living in Florida is all about. You can live your tropical, island dream here in Harbourside.

7984 Sailboat Key Boulevard S Unit 303, St Petersburg
$535,000
2 Beds ⋅ 2 Baths ⋅ Harbourside Condo SubDv. ⋅ 33707 Zip Code
****PRICE ADJUSTMENT**** LET'S GO! **** “BEACHWALKER” -Most desirable location in all of Harbourside— resort style living in one of South Pasadena’s finest waterfront communities. An immaculate, beautifully maintained, DIRECT WATERFRONT 2-bedroom 2- bath has been thoughtfully updated and cared for, providing comfort and quality. Plenty of natural daylight. West facing balcony with beautiful sunset views, enhanced by new gemstone floor coverings and protected with hurricane impact WINDOWS and electric shutters on both the balcony and primary bedroom— (shutter motor updated in 2023). Unit features newer stainless-steel appliances, updated ceiling fans and light fixtures, plantation shutters on all windows and the balcony, solid surface kitchen counters, and a granite vanity top in the primary bath. Additional upgrades include newer garbage disposal, kitchen faucet, and custom shelving in all closets. The AC (2019) and hot water tank (12/2022) ensure efficient, reliable performance. CONVENIENT UNDER BUILDING ASSIGNED PARKING SPACE #94. Complete Elevator modernization in 2025. A gated community with Exceptional amenities including Swimming pools and Spa's, EV charging stations, pickleball courts, tennis courts, shuffleboard, an active clubhouse, and miles of waterfront walking paths. Boat slips, guest boat docks (available on a first come-first serve) fishing pier, and a rare opportunity to own a pristine unit in a vibrant, amenity rich waterfront, community—perfect for full-time coastal living. Just minutes to the finest GULF Beaches. Oh, and a PET FRIENDLY community. Perfect timing to send out invites for the Pasadena Christmas boat parade that passes by right in front of your balcony. In addition, this unit is sold with a full wall media cabinet/bookcase with electric remote-control fireplace, plus a kitchen dinette table and 2 chairs. A MUST SEE! Schedule your showing.

7984 Sailboat Key Boulevard S Unit 306, St Petersburg
$370,000
1 Beds ⋅ 2 Baths ⋅ Harbourside SubDv. ⋅ 33707 Zip Code
Virtually Staged. Welcome to resort style living in the community of Harbourside! From the moment of parking your car in the assigned end space just a few steps away from your ground floor entryway (no elevator aggravation), you’ll enter this well maintained and updated unit with an immediate view through the living room wall of window sliders and view of the lovely community green space and water. The kitchen with west facing hurricane impact window, shelved pantry, wood cabinetry and stone countertops is immediately available upon entry for ease of arranging your groceries. A storage room with HVAC (installed 6/26), water heater (2024) and laundry across the hall allows you to multi task if you wish. The guest bath, living room and bedroom walls have been updated with lovely shiplap. The dining room/living room combination with a wall of mirrors provides a comfortable space with engineered hardwood throughout and an end wall of hurricane impact sliders leading to the porch. A Murphy bed cabinet (no mattress included) can be utilized for those occasional guest visits or used as storage. The master bedroom is ample and can accommodate a king size bed with nightstands; the east facing wall has a hurricane slider looking out to the lanai and lovely landscaping, walking trail but can the window treatment provides heavy coverage for days of sleeping in. The master bath was uniquely updated with a walk in shower and the walk in closet styled with extra shelves for additional storage. The community has a marina for your vessel (slips are owned/leased by residents) and clubhouse providing something for everyone, from a library, 2 fitness centers, craft room, woodworking shop, gathering area, pool, spa, and tennis and pickleball courts, EV charging stations, car wash/vacuum & air. Enjoy the fresh air as you take a stroll or run around the community along the waterfront 1.5 mile trail. Safe and secure with 24/7 security manned gate. Conveniently located to nearby shopping and restaurants and just minutes to the Gulf beaches.

7897 Sailboat Key Boulevard Unit 107, South Pasadena
$215,000
1 Beds ⋅ 1 Baths ⋅ Bay Island Group 14 SubDv. ⋅ 33707 Zip Code
Virtually Staged. ***HIGH and DRY - NO HURRICANE DAMAGE - NO WATER INTRUSION***SPECTACULAR LUXURY WATERFRONT CONDO with AMAZING DIRECT VIEWS of the BOCA CIEGA BAY*** Life is Great when you’re living in Paradise at the meticulously maintained Bay Island community. It’s a gated community with 24/7 security personnel. This gorgeous unit is located in the 8-story premier Presidential building. It’s a roomy 855 square feet of open plan with 1 Bedroom and 1 Full Bath. New LVP flooring was just installed throughout the condo. As a bonus…there is WASHER & DRYER laundry set inside the unit. Enjoy the sunsets and evening views of the Intracoastal waters from your private Balcony that's protected with a motorized HURRICANE SHUTTER for a high-level of protection. The timeless Kitchen was previously remodeled by prior ownership with solid-wood cabinets and beautiful countertops. The central HVAC system is only 1 year old. This unit comes with a dedicated Storage Closet big enough to store bicycles, beach chairs and small furniture. Your assigned covered parking spot is only a few steps away directly in front of the building’s entrance. Bay Island is a very active community for residents 55 years YOUNG or above. It boasts 6 heated swimming pools, 2 hot tubs, tennis and pickleball courts, shuffleboard, separate men and women fitness centers with locker rooms, a Clubhouse with party rooms, ping-pong tables, billiard tables, library and a full calendar of social events. There’s also an on-site MARINA for your boat - separately leased and subject to availability. The world-class Gulf Beaches of St Pete Beach, Treasure Island, Madeira Beach and Clearwater Beach are only minutes away and the famed Sunday Corey Ave Market is a stone’s throw across the iconic drawbridge. Come and enjoy the many beach bars with live bands or dine at the immense variety of restaurants that suit your taste. Downtown St. Petersburg is only a short drive where you can experience the many museums, theaters, parks, marinas, sidewalk dining, and cultural events – or come watch the Tampa Bay Rays play baseball and the Rowdies in a soccer match. Tampa International Airport (TPA) and the Clearwater-St Pete Airport (PIE) are about 30 minutes away. The MILESTONE INSPECTION REPORT and Structural Integrity Reserve Study are done. So come and enjoy life at this Waterfront Paradise with a Peace of Mind. Life is Good at Bay Island.

7600 Sun Island Drive S Unit 603, South Pasadena
$179,000
1 Beds ⋅ 1 Baths ⋅ Bay Island Group 2 SubDv. ⋅ 33707 Zip Code
Waterfront oasis in a tropical paradise; complete low-maintenance, full-of-enjoyment lifestyle here at Bay Island. Located in the little City of South Pasadena, FL; nestled between St Petersburg and St Pete Beach - you have the best of all worlds being only minutes to the pristine beaches of the Gulf, and under a 20 minute drive to the emersed culture of Downtown St Petersburg. Upon entering this first floor unit, you will LOVE the open-concept/layout of the Kitchen, Dining, Living space. You'll notice the beautifully newly installed luxury vinyl tile in the main living space, with a fully renovated kitchen and bath. The Kitchen comes complete with white shaker cabinets, beautiful stone countertops, and brand-new stainless steel appliances. Enjoy your early morning coffee, or late afternoon night cap on the breeze filled patio that is just off your back Hurricane Rated sliding glass doors. Take an early am or pm walk around the 1.5 mile sea wall that has amazing views of Boca Ciega Bay all the way around, pop into the His/Hers gym for a quick workout, or stop in the sauna, then enjoy your afternoons by one of the 5 pools/2 spas, or at the clubhouse where there is a pickleball league, a full-scale billard, a library, card-room and entertainment room upstairs for regularly scheduled events!! The HOA dues cover all of you main utilities including Cable, Internet, Sewer, Trash, Water, Exterior Insurance and Maintenance and much much more. The cost of living in this lifestyle abundant community is quite low compared to single family homes and inflation on utilities. Oh and don't forget to enjoy the Sunday morning markets at Corey Avenue; or the frequent live music events at the clubhouse, or at Horan Park - both just a short walk from this community. You will absolutely love your decision to come live in Paradise!!

7425 Bay Island Drive S Unit 107, St Petersburg
$819,000
3 Beds ⋅ 2 Baths ⋅ Harbourside Condo SubDv. ⋅ 33707 Zip Code
PRICED TO SELL! Penthouse with Unbelievable Water Views at BayWatch at Harbourside. Discover luxurious penthouse living in this unique 1,990 sq. ft. condo, one of only 10 on the island. Enjoy panoramic water views from the living room, dining room, kitchen, and both bedrooms. The unit features an open floor plan, is move-in ready, and comes furnished. This is your opportunity to experience the best of BayWatch at Harbourside with resort-style island living. • Abundant Marine Life: Frequent sightings of dolphins, manatees, and various sea birds are common in the calm, protected waters of the Intracoastal Waterway and shallow bay areas. • Stunning Sunsets: West-facing balconies provide prime, unobstructed views of the sun setting over the water. • Active Waterways: You can watch a constant parade of sailboats, yachts, and other vessels, making the view dynamic and interesting • Interior highlights Flexible living space: Two bedrooms, two baths, and a den that can function as an office, media room, or third bedroom. • Gourmet kitchen: Includes a central island with cabinets, two pantries, a wall oven, a microwave, reverse osmosis filtration, and eat-in space. • Custom dining room: Features built-in cabinets with a granite countertop, a snack bar, and double sliders leading to a private balcony. • Spacious primary suite: Offers two walk-in California closets and a third wall closet. The en-suite bathroom includes a water closet, two vanities, a soaking tub, and a separate walk-in shower. • Convenient laundry: A full-size side-by-side washer and dryer with storage are located in a room off the kitchen. • Quality construction: Solid steel reinforced concrete construction was used by JMC Communities, the original builder, rather than concrete blocks. Penthouse exclusives • Two assigned parking spaces: One covered carport (#118) and one space under the building (#98). • Sixth-floor storage unit: A large, conveniently located storage unit near the elevator is also included. • Private balcony: Accessed by double sliders from Primary bedroom and both the dining room and living room. Resort-style amenities • Pools and recreation: Six swimming pools, five tennis courts with two pickleball courts, and shuffleboard. • Fitness and relaxation: Two fitness centers, a Jacuzzi, and saunas. • Convenience for residents: Three outdoor grills, a three-station car wash with vacuum and air, and electric car charging stations. • Waterfront access: The marina has three docks and 87 deeded slips, which are available for rent or purchase from other owners. • Clubhouse features: A card room, billiard room, library, woodwork shop, and a grand room with a kitchen for events. • Outdoor activities: A 1.5-mile walking trail around the island offers a chance to see dolphins, manatees, and seabirds. • Pet-friendly policy: Allows one pet per unit, 20 pounds or under. This is your opportunity to experience the best of BayWatch at Harbourside and resort-style island living.

7872 Sailboat Key Boulevard S Unit PH602, South Pasadena
$259,000
1 Beds ⋅ 2 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
A million dollar view out the windows of this special condo, with the Don ce Sar Hotel (the pink one) right in the center. And look down to see dolphin, manatee, rays and other sea creatures right in front of your home. It's amazing! You also have the "old fishing village" of Gulfport with tons of nice shops and restaurants , live music everywhere, and a Tuesday fresh market year round. This could be your winter "get away" or your full time residence with all the space in this oversized one bedroom home. The monthly maintenance includes everything except your electric which makes budgeting easy. Town Shores has all the amenities and includes four heated pools, clubhouse with billiards, small gym, lounge and meeting/party space and adjacent are the tennis, pickleball, bocce and shuffleboard courts. The marina is quite nice and first come, first served. And a mere 12 minutes or so away is downtown St Pete and about 12 min. in the other direction you have your choice of sandy beaches. Museums and restaurants or sand in your toes and a good book - either way is fun , interesting and so easy to get to. And also easy to get to are the Pinellas/Clearwater Airport or Tampa Airport at about 25 min. from our special little town of Gulfport. Come check us out and stay and play.

5980 Shore Boulevard S Unit 909, Gulfport
$279,900
2 Beds ⋅ 2 Baths ⋅ Bay Island Group 1 SubDv. ⋅ 33707 Zip Code
Virtually Staged. ### Waterfront Luxury Meets Resort-Style Living in South Pasadena Welcome to **7400 Sun Island Drive S, Unit 111**, a beautifully updated **2-bedroom, 2-bath waterfront condominium** nestled within the highly sought-after **55+ gated community of Bay Island**. This first-floor end unit offers the perfect blend of comfort, convenience, and coastal lifestyle with breathtaking water views and an abundance of natural light. Step inside to discover an inviting open-concept layout featuring a spacious living and dining area, stylish tile flooring, ceiling fans throughout, and a bright kitchen complete with **granite countertops, stainless steel appliances, two-tone cabinetry, and a charming breakfast nook**. Both bathrooms have been tastefully updated with granite countertops and modern vanities, while the primary suite offers a walk-in shower and private access to one of two outdoor patio spaces. The guest bathroom features a walk-in therapeutic tub for added comfort and accessibility. Enjoy Florida living at its finest with **two private patio areas**, including a peaceful retreat off the primary bedroom and an additional paver patio accessible from the living area—perfect for morning coffee, evening sunsets, or simply enjoying the waterfront setting. Bay Island is renowned for its resort-style amenities, including: * 24-hour gated security * Six heated swimming pools * Two hot tubs * Clubhouse and social activities * Fitness center * Tennis and pickleball courts * Marina and fishing areas * Scenic waterfront walking paths * Billiards, card rooms, and hobby spaces * Active social calendar and community events Ideally located just minutes from **St. Pete Beach, Corey Avenue shops and dining, Gulf beaches, downtown St. Petersburg, and endless entertainment options**, this home offers the perfect opportunity to enjoy maintenance-free waterfront living in one of Pinellas County's premier active adult communities. Whether you're looking for a seasonal retreat or a full-time residence, this move-in-ready waterfront gem delivers the lifestyle you've been dreaming about. Schedule your private showing today!

7400 Sun Island Drive S Unit 111, South Pasadena
$229,900
1 Beds ⋅ 1 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
Live the Gulfport lifestyle in this beautifully renovated first-floor Deluxe 1 bedroom, 1 bath unit in Town Shores of Gulfport! Offering just under 1,100 square feet (1060), of thoughtfully designed living space, this move-in-ready home perfectly blends modern updates with the charm and convenience of coastal living. Inside, you'll find fresh interior paint, new tile and luxury vinyl flooring, new 5-inch baseboards, updated kitchen and bathroom cabinetry, and new interior doors throughout. Additional improvements include ceiling knock down, (popcorn ceiling is gone), impact-rated exterior doors, newer impact windows, closet organizers in each closet, a new HVAC system, and new electrical panel.The spacious kitchen is designed for both functionality and entertaining, featuring abundant cabinetry with built-in pantry storage, stunning quartz countertops, a movable island with additional storage, stainless steel appliances, and a gas stove. Step outside to your private first-floor patio with an awning—the perfect spot to enjoy your morning coffee, or unwind after a day exploring Gulfport's vibrant waterfront. Town Shores of Gulfport is a welcoming waterfront 55+ community known for its active lifestyle and unbeatable location. Residents enjoy an impressive array of resort-style amenities, including four heated pools, tennis/ pickleball courts, shuffleboard, kayak storage, community events, and first-come, first-served boat slips with a waitlist. Best of all, you're just a short stroll from Gulfport's charming waterfront district, where colorful shops, local restaurants, art galleries, live music, festivals, and breathtaking sunsets create a true "Old Florida" coastal experience. Whether you're seeking a year-round residence, a seasonal escape, or the perfect place to embrace the Florida lifestyle, this exceptional home offers the opportunity to live where others vacation and enjoy your own slice of paradise. The Chatham building is pet-friendly, allowing one dog or cat up to 20 pounds. Seller is a licensed real estate salesperson.

3018 59th Street S Unit 103, Gulfport
Start Your Search