South Pasadena Homes with Tennis Court(s) Community Features

South Pasadena Homes with Tennis Court(s) Community Features

Welcome to South Pasadena, Florida—a charming coastal city nestled in the heart of Pinellas County. Known for its serene atmosphere and picturesque surroundings, South Pasadena offers a perfect blend of small-town charm and modern convenience. With its close proximity to the sparkling Gulf of Mexico, residents enjoy easy access to beautiful beaches, vibrant parks, and a plethora of recreational activities. The city’s rich history is reflected in its quaint architecture and welcoming community spirit, making it an ideal place to call home.

One of the standout features of South Pasadena is its exclusive homes with tennis courts, perfect for both avid players and casual enthusiasts. Imagine stepping out of your backyard and onto your own private court, ready to engage in a friendly match or enjoy a leisurely game with friends and family. These properties not only provide a unique lifestyle but also foster a sense of community among residents who share a passion for the sport.

In addition to tennis facilities, homes in this delightful area boast spacious layouts, lush landscaping, and many modern amenities. Residents can enjoy nearby shopping, dining, and entertainment options, all while relishing the tranquility of suburban living. Whether you're looking for a cozy retreat or a family-friendly abode, South Pasadena offers a variety of options to suit your needs.

Embrace the South Pasadena lifestyle, where every day feels like a vacation, and the perfect home with a tennis court awaits you! Explore the possibilities today and discover why this hidden gem in Pinellas County is the ideal place to live, play, and thrive.

Newest South Pasadena Homes with Tennis Court(s) Community Features

$195,000
2 Beds ⋅ 2 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
Bring your personal style and discover the possibilities in this 2-bedroom, 2-bath condo in the Avalon Building at Town Shores of Gulfport. With a solid foundation and plenty of potential, just a few thoughtful updates could transform this home into a fresh, inviting Florida retreat tailored to your taste. Some of the work is already done. The shared bath has been refreshed with newer tile, a walk-in shower, and an updated vanity, and French doors open from the primary bedroom into an enclosed Florida room, a bright bonus space ready to become a home office, reading nook, hobby room, or guest retreat. An assigned carport space keeps your car covered and close to home. Located in a beautifully maintained 55+ waterfront community along Boca Ciega Bay, the Avalon Building offers a friendly atmosphere and convenient access to everything that makes Town Shores such a desirable place to call home. Whether you're looking for a full-time residence or a sunny Florida getaway, this condo presents an opportunity to update at your own pace while enjoying the community and lifestyle from day one. Town Shores is known for its impressive collection of resort-style amenities, including four heated swimming pools, tennis and pickleball courts, a fitness center, shuffleboard, billiards, a library, marina, and scenic waterfront walking paths. Spend your mornings strolling along Boca Ciega Bay, your afternoons by the pool, and your evenings enjoying everything nearby Gulfport has to offer. Just minutes away is Gulfport's colorful waterfront district, filled with locally owned restaurants, boutiques, art galleries, entertainment, and popular markets and community events. Browse the Tuesday Fresh Market on the bay, catch a dance or concert at the historic Gulfport Casino Ballroom, or paddle the mangroves at Clam Bayou Nature Preserve. Stetson University College of Law is right around the corner, the Gulf beaches of St. Pete Beach are about 10 minutes away, and downtown St. Petersburg is roughly 20 minutes by car, making this Gulfport FL condo an easy home base for 55+ living in Pinellas County.

5840 30th Avenue S Unit 201, Gulfport
$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
$3,375,000
5 Beds ⋅ 4 Baths ⋅ SubDv. ⋅ 33707 Zip Code
Must-see Italian Riviera-style villa offering exceptional coastal living in the amazing gated community of Pasadena Yacht & Country Club! This spectacular 5-bedroom, 4-bath residence offers 4,895 square feet of living space and is one of the largest one-story homes in the community. Set on one of the neighborhood’s largest lots at nearly half an acre, the highly desirable U-shaped design provides exceptional privacy while creating a seamless connection between the spacious interior and remarkable outdoor spaces. The resort-style backyard is truly an entertainer’s dream. The expansive area features a heated saltwater lap pool (resurfaced in 2024), Jacuzzi, outdoor kitchen, gas fire pit and abundant space for entertaining, dining, or simply relaxing and enjoying the Florida lifestyle. From the moment you enter the inside the impressive scale of the home is immediately apparent. The open floor plan features an elegant living room, formal dining area, and beautifully appointed wet bar. The bar includes an ice maker, quartz countertops, peninsula with seating space, two refrigerators and abundant cabinetry. The adjacent living room features beautiful wood flooring and soaring cathedral ceilings. The formal sunken dining area is framed by dramatic ceilings rising more than 20 feet and is complemented by a dedicated wine room with a Thermador wine cooler. Movie nights become an experience in the state-of-the-art media room, complete with a huge screen and surround sound. The gourmet kitchen is equally impressive, featuring a Sub-Zero refrigerator, Wolf gas range with double ovens, granite countertops, large island, peninsula with seating, and an abundance of cabinetry. Just off the kitchen is a SECOND dining area and living room, giving multiple spaces for privacy or to entertain guests in. Next to that also includes a versatile bedroom that can easily function as a children’s playroom, home office, library, or family room. The private south wing is dedicated to the primary suite and additional bedrooms. The enormous primary retreat features his-and-her closets with custom organizers, dual sinks with powder area, and a whirlpool tub overlooking the marina. An indoor shower and separate outdoor shower add a distinctive resort-style touch. Two additional generously sized bedrooms on this wing provide comfortable accommodations for family and guests. A spacious three-car garage offers ample storage, an epoxy-coated floor, and dedicated work area. Other upgrades include: full-home generator, hurricane-impact windows/sliders/doors, block home, full-home security system, water softener, irrigation/sprinkler system, dual HVAC systems, central vacuum, ceiling-mounted sound system, laundry room, large driveway, pest-control service. Pasadena Yacht & Country Club offers an exceptional private-club lifestyle with 18-hole championship golf course, tennis and pickleball courts, Olympic-size swimming pool, fitness center, and an active calendar of social events. The club is planning a new state-of-the-art fitness center as well as updates to the golf course and marina in 2027. New owners have the ability to bypass the current membership waitlist, which is reportedly more than two years long. Close to downtown St. Pete, St. Pete Beach, easy drive to Tampa, Bradenton, and Sarasota, and walking distance to charming downtown Gulfport. Home never flooded during the seller’s ownership and sits notably higher than many surrounding homes.

6320 Pasadena Point Boulevard, Gulfport
$175,000
1 Beds ⋅ 1 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
Welcome to EXQUISITE WATERFRONT living in Unit 304 of the Manchester building in Town Shores, an exceptional 55+ community in the CHARMING town of Gulfport. This PARADISE is located directly on Boca Ciega Bay. This one bedroom, one bathroom unit provides nearly 1100 square feet of OPEN FLOOR PLAN living space! The MURPHY BED in the living room conveys with the sale and makes it a breeze to host guests. You won’t believe the OVER-SIZED living room, which boasts an entire WALL OF WINDOWS emphasizing the beautiful water view and inviting in tons of natural light and Florida sunshine. The large bedroom is complimented by a WALK-IN closet. The bathroom has been remodeled with a modern style vessel sink, large vanity, built in shelves, walk-in shower, and tile floors. Enjoy the convenience of a gas stove in the updated kitchen, which is highlighted with PENDENT LIGHTS at the bar, NATURAL STONE counters, and a large PANTRY. UNIT 304 HAS A DEEDED, COVERED PARKING SPACE. The Manchester building has a PRIVATE COURTYARD for lounging, grilling, and enjoying the waterfront. The building provides 2 laundry rooms, a building-specific Book Nook, allows for 1 indoor cat, and allows for LEASING within HOA approval and availability. The HOA includes water, gas, trash, recycling, cable, wifi, insurance, grounds, exterior, and pool maintenance. The Town Shores complex includes an array of RESORT STYLE AMENITIES including multiple heated pools, a MARINA, tennis courts, PICKLE BALL courts, shuffleboard, bocce ball, kayak storage and rental, art programs, a billiards room, library, clubhouse with a host of planned activities and social events for active living. Town Shores is positioned literally steps to GULFPORT BEACH and just a few blocks from Gulfport’s Beach Boulevard district. Gulfport is known as a small, colorful, walkable town with an Old Florida and artsy COASTAL CHARM. The Beach Boulevard district provides a host of casual dining, fine dining, art galleries, independent shops, and a vibrant night life. DON’T MISS THIS OPPORTUNITY TO HAVE IT ALL!

6025 Shore Boulevard S Unit 304, Gulfport
$625,000
2 Beds ⋅ 2 Baths ⋅ Harbourside Condo SubDv. ⋅ 33707 Zip Code
Virtually Staged. Breathtaking, wide expansive waterfront views and stunning sunsets greet you the moment you step into this fully renovated 2BR/2BA coastal oasis. Completely upgraded in 2019 with an uncompromising eye for detail, this move-in ready condo offers high-end modern finishes and total peace of mind. The gorgeous open kitchen boasts premium quartzite countertops, sleek shaker-style cabinetry, new stainless steel appliances, and added pantries and base cabinets for abundant storage. Both the primary and guest bathrooms have been completely upgraded with Calcite countertops, new elongated toilets, pristine glass enclosures, and walk-in showers dressed in modern designer porcelain tile. Premium upgrades continue with all-new A/C and water heater installed in 2026, high-impact windows, and protective storm shutters on the balcony sliders. Sparkling water views can be enjoyed from the kitchen, guest bedroom, living room, and the private balcony with cool decking coverage. The primary bedroom features its own spectacular wide-water backdrop. Complete with under-building parking space #18 and two private storage units (one on the balcony and one steps away by the elevator), this turnkey property truly has it all! Harbourside Community has a 24/7 Gate access with on duty Guard, the Amenities include, 6 swimming pools, 5 tennis courts with Pickle ball courts, 2 fitness centers, Men and Women's, Gyms, Jacuzzi, saunas, Shuffle board, outdoor grilling, 3 car wash station with vacuum & air, Car Charging station and Marina. There is no deeded slip to this unit but there may be slips available to rent or purchase from other owners. A Clubhouse with a full social agenda, Card Room, Library, Billiard room and wood working shop. This Paradise has a 1.5 mile waterfront walking trail around the Island. Harbourside is located just minutes from the Popular Pristine West Coast Fl beaches and Minutes from I 275 and Downtown St Petersburg where you can enjoy the St Pete Pier, Museums, Art Galleries, Dining and all the History of the City of St Petersburg. Come and enjoy Resort style living at it's best.

7922 Sailboat Key Boulevard S Unit 206, South Pasadena
$399,000
2 Beds ⋅ 2 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
Breathtaking Boca Ciega Bay views and beautiful sunsets take center stage in this oversized condo located in the highly sought-after 55+ community of Town Shores of Gulfport. From the moment you enter, your eyes are drawn to the expansive water views from the generous living and dining area, creating a beautiful backdrop for everyday living and entertaining. The primary suite features a walk-in closet, tons of natural light, and a private ensuite bath, while the spacious guest bedroom also offers a walk-in closet with a full guest bath conveniently located just outside the bedroom. The kitchen provides plenty of cabinet space and pantry. This condo has been thoughtfully updated with luxury vinyl flooring, a newly replaced bay window, and new HVAC in 2026. Additional conveniences include a private storage area and designated parking space. Town Shores is known for its impressive resort-style amenities, including four swimming pools, a marina with boat slips available for rent subject to availability, tennis, pickleball, bocce ball, shuffleboard, a fitness room, his-and-her saunas, and an expansive clubhouse featuring a large billiards room, multiple meeting spaces, and generous common areas. Best of all, you are just minutes from vibrant downtown Gulfport, where you can enjoy locally owned restaurants, shops, art, community events, and Gulfport Beach. Whether you are relaxing at home watching the sun set over Boca Ciega Bay or taking advantage of everything this active waterfront community has to offer, this is Florida living at its best.

6020 Shore Boulevard S Unit 211, Gulfport
$259,000
1 Beds ⋅ 2 Baths ⋅ Bay Island Group 10 Condo Unit 202 SubDv. ⋅ 33707 Zip Code
Welcome to your personal paradise at Bay Island Condominiums, a premier 55+ resort-style community in South Pasadena, Florida. Located just across the bridge from the powder-white sands of St. Pete Beach, this second-floor, 1-bedroom, 1.5-bathroom waterfront retreat in the Commodore Building delivers sweeping views and effortless coastal living. Step through the front door and your eyes will be drawn straight to the sparkling waters of Boca Ciega Bay. The open-concept floor plan flows seamlessly from a large, well-equipped kitchen—featuring elegant marble countertops and included appliances—through the bright dining area and into the inviting living room. Low-maintenance tile flooring runs throughout the entire home for easy beach-life cleanup. Slide open the doors to your private, screened balcony to experience the ultimate Florida lifestyle. It's the perfect front-row seat for watching dolphins and manatees play, observing passing sailboats, and taking in Florida’s famous nightly sunsets. For ultimate peace of mind, the balcony features an integrated, powered hurricane shutter, alongside a convenient private storage closet. The spacious primary suite serves as a relaxing haven, complete with an attached owner’s bathroom and a generous walk-in closet. Guests will appreciate the convenient half-bath located near the entry foyer, which sits adjacent to your in-unit washer and dryer. Convenience is key with an assigned, covered parking space situated just steps from the building's entrance. Bay Island provides unparalleled 24-hour gated security and luxury amenities, including a scenic 1.5-mile waterfront walking path, six swimming pools, two spas, tennis and shuffleboard courts. The beautifully updated clubhouse features a billiards room, card room, ballroom, commercial kitchen, and his-and-hers fitness centers. Conveniently located just 30 minutes from Tampa International Airport and moments from local dining, shopping, and entertainment, this waterfront oasis is ready for you to call home.

7700 Sun Island Drive S Unit 202, South Pasadena
$220,000
2 Beds ⋅ 1 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
Welcome to beautifully updated living in Town Shores, a sought-after 55+ community in the charming town of Gulfport! This move-in-ready 2/1 condo has been thoughtfully refreshed throughout, offering a fresh, modern feel from the moment you walk in. The completely remodeled kitchen features new appliances and updated finishes, creating a stylish and functional space for everyday living and entertaining. Brand-new luxury vinyl plank (LVP) flooring flows throughout the condo, complemented by new baseboards and fresh interior paint for a clean, cohesive look. Located in the desirable Town Shores community, residents enjoy a relaxed Florida lifestyle with an array of amenities and activities. Just minutes from the waterfront, Gulfport's vibrant downtown, restaurants, shops, and beaches, this condo offers the perfect combination of comfort, convenience, and community. Whether you're looking for a full-time residence, seasonal getaway, or a place to enjoy the best of Florida living, this beautifully updated condo is ready to welcome you home!

3010 59th Street S Unit 306, Gulfport
$169,900
1 Beds ⋅ 1 Baths ⋅ Bay Island Group 9 SubDv. ⋅ 33707 Zip Code
PARADISE IS CALLING ~~ Super cute, cozy, waterfront condo that is located in the well sought after ESSEX building in this popular, guard gated 55+ community of BAY ISLAND. This condo is perfect as a "WINTER GET-AWAY or a wonderful FULL TIME RESIDENCE. Enjoy the panoramic water views of Boca Ciega Bay and be entertained by the many dolphins that frolic in the waters below and the many birds that soar above the sparkling waters. This lovely unit provides a Great Room concept, open kitchen with 42 inch cabinets, appliance package, coordinating backsplash and breakfast bar for on-the-go snacking. The Bathroom is cheerful with a modern look offering a single sink vanity with cabinet storage, overhead accent shelf/cabinet and full tub/shower combination. Neutral in color ~ this provides a blank slate to make it your own by adding the calming coastal watercolor hues. Step into the Primary Bedroom which offers a full walk-in closet, sliders that lead to a private covered waterfront balcony and plenty of interior wall space to strategically place furniture for optimum usage. This easy care unit showcases full tile flooring throughout, neutral paint, storage closets in both the hall and bedroom. Electric storm shutters provide the ultimate in storm protection for the Balcony slider as well as the front Picture Window. A covered carport dedicated to this unit is also included in the sale. THE ESSEX at BAY ISLAND has an elevator, individual storage lockers for all units and a waterfront pool with outside bathrooms. There is also a workshop in the building for the owners to use, which is a welcome amenity. General Laundry facility in building. HOA FEES include water, sewer, trash and more. There is a scenic 1.5 mile waterfront walkway around the community, 6 pools, Clubhouse with Social Director, marina, fitness center with both women's and men's saunas, tennis courts, car wash and more! Enjoy the many social events and meet new friends in this active 55+ community. Bay Island is minutes to some of the beautiful beaches, artsy Gulfport, trendy downtown St. Petersburg and South Pasadena where you will find unique restaurants, shopping and more. Isn't it time to make this place YOUR PARADISE. Call for your private viewing today!!

7665 Sun Island Drive S Unit 409, South Pasadena
$359,000
2 Beds ⋅ 2 Baths ⋅ Bay Island Group 13 SubDv. ⋅ 33707 Zip Code
Waterfront -- Turn Key -- Available Furnished - Wake up to dolphins in the bay -- end your evenings with sunsets over the water — This fully renovated 1,480 sq ft, 2-bedroom, 2-bath condo offers the best of easy coastal living. This spacious, turnkey home can be purchased furnished and includes an office space that easily converts to a 3rd bedroom, plus two covered porches overlooking the water. The milestone inspection is complete and cleared, and the community maintains a fully funded reserve fund for peace of mind. --- Community features: Six pools, tennis and pickleball courts, men’s and women’s gyms, a clubhouse with ballroom, car wash, library, Tiki Hut grilling areas, a 1.5-mile waterfront walkway, and access to a private marina — all inside a secure 55+ gated neighborhood. This unit also includes two covered parking spaces right outside your door and an exclusive private storage room not found in other units. With convenient first-floor living and no stairs, you can enjoy comfort and independence for years to come. Don’t miss this opportunity to own a stunning, move-in-ready waterfront condo in one of the most desirable communities in St. Petersburg — schedule your private showing today! HOA fees include: Flood insurance, water, sewer, trash, cable, internet, and maintenance for all community amenities.

7930 Sun Island Drive S Unit 104, South Pasadena
$799,000
3 Beds ⋅ 2 Baths ⋅ Harbourside Condo SubDv. ⋅ 33707 Zip Code
Welcome to Beachwalker at Harbourside Building 9 unit 408. This corner unit has 2 Bedrooms, 2 Baths and Den or 3rd bedroom. There are two balconies, one with hurricane shutters on the West side and the East side balcony has a wraparound balcony off kitchen and den. Upgrades include: new washer dryer, two pantries in the eat in kitchen with stainless steel appliances, granite throughout including kitchen and baths. Both Primary & guest baths have been upgraded with tiled shower and flooring. Hardwood Flooring throughout except for bedrooms which have Carpet. Recessed lighting throughout, two niches one in Kitchen and one in Foyer. Custom built buffet in dining room and kitchen breakfast bar. Crown molding with casing around windows and doors, 4" baseboards, three ceiling fans with lights and remotes. AC 2018 and hot water heater 2006 Garage parking space #54 and assigned storage unit 408 on floor. Tenant in place, 30 days notice to vacate. This is your opportunity to experience the best of Beachwalker 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: • Spacious primary suite: Offers a walk-in California closet with built in storage. • Convenient laundry. • Quality construction: Solid steel reinforced concrete construction was used by JMC Communities, the original builder, rather than concrete blocks. Penthouse exclusives • One assigned parking space under the building (#54). •: A large, conveniently located storage unit near the elevator is also included #408 and another on balcony. 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 up to 20 pounds. This is your opportunity to experience the best of Beachwalker at Harbourside and resort-style island living.

7974 Sailboat Key Boulevard S Unit 408, South Pasadena
$244,900
2 Beds ⋅ 2 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
Welcome to the amazing waterfront community of Town Shores of Gulfport. This completely renovated 2-bedroom, 2-bath condo located on the second floor is waiting for you. The kitchen was beautifully renovated in 2022, windows were replaced in 2023, and new flooring was completed in 2024.The primary bedroom offers a spacious walk-in closet with a custom closet system for exceptional storage and organization and a bathroom renovated in 2024. The community has several pools, Tennis courts and many fun activities. You will spend your evenings watching the spectacular sunset. Enjoy easy Florida living in a beautifully updated home close to Gulfport’s charming waterfront, shops, restaurants, and beaches. Just a short drive to downtown St. Pete and Tampa. Don't miss out on the opportunity to own this wonderful updated condo today.

5840 30th Avenue S Unit 202, Gulfport
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