St Pete/South Pasadena/Gulfport/St Pete Bch Homes with Pickleball Court(s) Amenities

St Pete/South Pasadena/Gulfport/St Pete Bch Homes with Pickleball Court(s) Amenities

Welcome to the enchanting region of St. Pete, South Pasadena, Gulfport, and St. Pete Beach, where sun-kissed shores and vibrant community life intertwine to create an idyllic Florida lifestyle. Nestled in the heart of Pinellas County, this coastal haven is renowned for its stunning waterfront views, eclectic arts scene, and an abundance of recreational activities, making it the perfect place to call home.

The charming neighborhoods of South Pasadena and Gulfport boast a unique blend of quaint shops, delightful dining options, and lush parks, all just a stone's throw away from the sparkling waters of the Gulf of Mexico. Whether you're strolling along the picturesque beaches of St. Pete Beach or exploring the lively atmosphere of Gulfport's art district, you'll find a warm and welcoming community ready to embrace you.

For those who enjoy an active lifestyle, homes in this region often come equipped with delightful amenities, including private pickleball courts. This popular sport, known for its friendly competition and social atmosphere, is perfect for residents looking to stay fit while fostering connections with neighbors. Imagine stepping out into your backyard to play a game of pickleball with friends or family, all while enjoying the beautiful Florida weather.

With a variety of homes available, from cozy bungalows to luxurious waterfront properties, you’ll find the perfect place to create lasting memories. Discover the vibrant lifestyle that awaits you in St. Pete, South Pasadena, Gulfport, and St. Pete Beach, where your dream home with a pickleball court is just around the corner!

Newest St Pete/South Pasadena/Gulfport/St Pete Bch Homes with Pickleball Court(s) Amenities

$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
$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
$150,000
1 Beds ⋅ 1 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
FULLY FURNISHED... And, completely UPDATED, this beautiful, like-new, condo has been renovated top to bottom! This spacious 1060 square foot interior features continuous luxury vinyl plank (LVP) flooring throughout, creating a stylish seamless look. Enjoy peace of mind with a walk-in shower, a beautifully updated kitchen featuring all new stainless-steel appliances. Move right in and enjoy the comfort and convenience of a truly turnkey home. The deeded carport is just steps and two guest spots right in front of your front door! Enjoy worry-free living with cable TV, internet, gas (for cooking and heating), and more... included in your monthly HOA fee... you only pay for electricity! Residents of Town Shores enjoy an impressive array of amenities including a fitness center (gym), billiards, room with a dozen pool tables, indoor shuffleboard tables, a library and multiple game rooms. Outdoor recreation options include shuffleboard, bocce ball, tennis and pickleball courts. The community also offers four heated pools (two right on Boca Ciega Bay) and a vibrant social clubhouse! Located just three blocks from the charming waterfront district of Gulfport, residents can easily enjoy a variety of local restaurants, boutiques, art galleries and entertainment. And don't forget the very active Senior Center located just a few blocks away, with many activities to enjoy daily! Convenient public transportation provides easy access to St. Petersburg, the nearby beaches and destinations throughout Pinellas County. Not to mention, only 10 minutes from award winning Gulf beaches, and 30 minutes to St Petersburg and Tampa International Airports. Call today to see this beauty in person! It won't last long at this price!

3018 59th Street S Unit 111, Gulfport
$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
$159,000
2 Beds ⋅ 2 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
A first-floor corner home in Gulfport's Town Shores with a covered carport spot (furnishings negotiable)—a welcoming 55+ waterfront community on Boca Ciega Bay—does not come along every day- this one. This bright 2-bedroom, 2-bath Jamison House residence offers 1,170 square feet, windows on three sides, mature landscaping and true ground-floor living. The lifestyle begins right outside your door with one of the community's four heated pools—The Jamison's pool was just renovated and is HEATED year round, directly off your back patio - plus tennis, pickleball, bocce, shuffleboard, fitness room, saunas, billiards, library, ballroom, marina and kayak launch. Historic Gulfport’s beach, Williams Pier, restaurants, colorful shops and live entertainment are only a few blocks away. The seller reports that this unit did not experience interior flooding during the 2024 hurricanes. Inside, white Shaker-style cabinetry, warm butcher-block countertops and stainless steel appliances give the updated kitchen a crisp coastal feel. The split-bedroom layout adds privacy, while the spacious primary suite offers an updated private bath and walk-in closet. A garden-view Florida room works beautifully as an office, reading room or morning-coffee retreat, and tile flooring keeps upkeep simple. Less upkeep, more Gulfport—and a first-floor corner unit worth seeing. All information to be verified with the HOA. Boat slips are available on a 1st come 1st serve basis.

2960 59th Street S Unit 101, Gulfport
$220,000
2 Beds ⋅ 2 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
Wake up to beautiful waterfront views from highly desirable Lancaster building in Town Shores. Watch the dolphins and manatees from your window in this 2 bedroom, 2 bath DELUXE unit. The kitchen offers newer stainless appliances (including a gas range!). Through the spacious living/dining room enter into into a light filled Florida room that overlooks Boca Ciega Bay. The large primary bedroom offers a walk in closet and ensuite bath. Town Shores offers a true resort-style lifestyle with exceptional amenities, including four heated pools, a fitness center, his-and-hers saunas, tennis and pickleball courts, shuffleboard courts, marina access, and beautifully maintained waterfront grounds. Ideally located just minutes from world renowned Gulf beaches, and of course shopping, restaurants and weekly markets in bustling downtown Gulfport. Whether you're looking for a full-time residence, seasonal retreat, or investment opportunity, this is your chance to own a slice of paradise. All information is deemed correct and should be verified by interested parties.

5925 Shore Boulevard S Unit 302, Gulfport
$245,000
1 Beds ⋅ 2 Baths ⋅ Bay Island Group 1 SubDv. ⋅ 33707 Zip Code
Beautiful 7th floor condo with views of Boca Ciega Bay from your spacious living room, dining room, and enclosed lanai/porch with tile floor. Large master suite provides a luxury feel with a large walk-in closet. This condo has been totally remodeled. The kitchen features new, shaker-style cabinets, granite countertops, butcher block island & stainless steel appliances. Luxury vinyl plank flooring throughout. Both bathrooms have been renovated. Amenities include a beautiful clubhouse, fitness center, sauna, tennis courts, swimming pools, hot tubs, shuffleboard, docks, and walking/jogging path encircling the complex. Convenient to shopping, medical complex, restaurants, and the sandy beaches of the Gulf of Mexico. If you are looking for your slice of paradise in a gated, waterfront, 55+ community, schedule your showing now!

7400 Sun Island Drive S Unit 709, South Pasadena
$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
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