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$865,000
3 Beds ⋅ 2 Baths ⋅ TB8539707 MLS ⋅ Windwards/8 BLDG.
Virtually Staged. Virtually Staged. Welcome to an extraordinary opportunity to own a slice of paradise at the prestigious Windwards at Harbourside Building 8, Penthouse Unit 804. This meticulously updated, 1,915 sq. ft. penthouse is a rare find, being one of only a few located on the island, offering unparalleled resort-style living in South Pasadena FL. Key Residence Features includes Luxurious Interiors: Step inside to a magnificent tiled floor featuring a centered marble compass, guiding you through this expansive residence with crown molding and plantation shutters on every window. The entire condo has been freshly painted in "White Cloud" to match the pristine flooring and countertops. Spacious Living: The flexible floor plan includes a large, Waterview 14x13 room perfect for a den or third bedroom, and a 28x14 living room that can be configured into distinct conversation and media areas. Gourmet Kitchen & Dining: The renovated kitchen boasts newer cabinets and appliances, multiple pantries, a dedicated laundry room with a sink, and a dining area offering stunning views of the Gulf and intracoastal waterway. Master Suite Retreat: The master bedroom features an ensuite bathroom with a luxurious Jacuzzi tub, separate shower, and powder room. Premium Upgrades: Enjoy peace of mind with two A/C units (master bedroom 2025 and kitchen 2026), a tankless water heater, a whole-house water filtration system (2023), new sliders and windows installed 2026, and hurricane shutters on the balcony, bedrooms and den. Abundant Storage & Parking: The unit includes a storage unit on the balcony and another large one on the same floor (#804). Two parking spaces are provided: under Building 134 and Car Port #89. Harbourside Amenities & Community: Harbourside is renowned for its solid steel-reinforced concrete construction and an extensive array of amenities that cater to a vibrant, active lifestyle: Pools & Fitness: Access to six swimming pools (including one specific to the Windward building plus the main clubhouse pool), two fitness centers, separate men's and women's gyms, Jacuzzi, saunas, and three car wash stations. Sports & Recreation: Three tennis courts, three pickleball courts, shuffleboard, and a 1.5-mile walking trail around the island, perfect for exercise or walking your pet (Windward Building allows one pet under 20 pounds) Hobbies & Social: Enjoy a woodworking shop, library, card room, billiard room, outdoor grilling areas, car charging stations, and a clubhouse with a full social agenda. Waterfront Living: The community features a marina with three docks and 87 deeded slips (slips are available to rent or purchase from other owners), and two kayak racks with 50 spaces each. Experience resort-style living at its finest in this magnificent penthouse. Close to downtown, shopping, medical and walking distance to the BEACH!

7932 Sailboat Key Boulevard S Unit 804, South Pasadena
$555,000
2 Beds ⋅ 2 Baths ⋅ TB8528836 MLS ⋅ Beachwalker 2 BLDG.
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, South Pasadena
$523,900
2 Beds ⋅ 2 Baths ⋅ TB8528609 MLS ⋅ Beach Walker BLDG.
****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, South Pasadena
$675,000
3 Beds ⋅ 2 Baths ⋅ GC541644 MLS ⋅ Sunrise/11 BLDG.
Resort-Style Waterfront Living at Its Finest! Experience luxury coastal living in this beautifully updated 3-bedroom, 2-bath condominium offering approximately 1,300 square feet of elegant living space with breathtaking, unobstructed water views. From the moment you enter, you’ll appreciate the quality upgrades throughout, including high-impact windows and sliding glass doors, beautiful high-end laminate flooring, crown molding, chair rail accents, and Miami shutters. The spacious living and dining room combination provides the perfect setting for entertaining while taking in the spectacular waterfront scenery. The beautifully renovated kitchen features premium cabinetry, upgraded countertops, Frigidaire and GE stainless steel appliances, abundant cabinet storage, and a cozy breakfast nook. An inside laundry room with an LG stackable washer and dryer adds everyday convenience. The spacious primary suite offers stunning water views, private access to the rear balcony through impact sliding doors, a walk-in closet, and an updated bath with a walk-in shower. The guest bath also features a walk-in shower. The third bedroom, currently used as a home office, is complete with attractive French doors, making it a flexible space for work or guests. Enjoy true Florida living with two private balconies—one located just off the kitchen and a second expansive balcony accessible from both the living room and primary bedroom. The rear balcony features new tile flooring and panoramic water views. Storm shutters provide additional peace of mind on select windows, including both rear sliding doors. Additional features include ceiling fans throughout, under-building assigned parking, and abundant guest parking. The resort-style community offers an incredible list of amenities, including six swimming pools, pickleball courts, tennis courts, shuffleboard, electric vehicle charging stations, car wash stations, fitness center, and a beautifully renovated clubhouse featuring a library, card room, billiards room, and woodworking shop. Residents also enjoy yoga classes, water exercise programs, and a scenic 1.5-mile waterfront walking trail that winds throughout the community. Located just a short bike ride from some of Florida’s most beautiful beaches, popular waterfront restaurants, charming cafés, and lively beachside pubs, this exceptional condo offers the perfect combination of luxury, convenience, and the Florida lifestyle you’ve been dreaming of. Marina with several docks and many boat slips that are first-come first-serve. Some owners also offer available slips for rent. Come experience waterfront resort living every day!

7979 Sailboat Key Boulevard S Unit 101, South Pasadena
$819,000
3 Beds ⋅ 2 Baths ⋅ TB8523943 MLS ⋅ Baywatch 2/ 7872 BLDG.
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 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
$789,900
2 Beds ⋅ 2 Baths ⋅ TB8513430 MLS ⋅ Windwards / 8 BLDG.
Step into your personal "Palace in the Sky." From the moment you cross the threshold of this stunning 2-bedroom, 2-bathroom condo, your eyes are immediately drawn to the panoramic water views that stretch across the horizon. As a coveted end unit, the home is wrapped in extra windows that pull in an abundance of natural light, making the entire space feel airy and ethereal. It’s the kind of backdrop that makes every sunset feel like a private event and every morning coffee feel like a vacation. The interior has been thoughtfully refreshed to match the beauty outside, featuring brand-new luxury vinyl plank flooring and a crisp, modern paint palette that glows under the constant stream of sunshine. The smart, split-bedroom floor plan ensures maximum privacy for you and your guests, while a versatile bonus room offers the perfect footprint for a quiet home office, a private yoga studio, or a creative space. Life here feels like a permanent stay at a high-end resort. Located in a premier, gated waterfront community with a 24/7 guard, you’ll have access to an incredible suite of amenities designed for ultimate convenience and recreation. Take a dip in the sparkling pools, challenge a neighbor to a match on the tennis courts, or hit the fitness center. For the water enthusiasts, the on-site marina offers boat slips available for sale or rent, putting your days on the Gulf right at your doorstep. The community even takes care of the practical details—keep your vehicle pristine at the dedicated car wash and vacuuming stations, and take advantage of the on-site electric charging stations. Lush walking trails and a vibrant clubhouse are perfect for socializing, and best of all, this community is not age-restricted. You’re just minutes away from pristine beaches, boutique shopping, and the area's best dining. This isn't just a home; it’s the elevated waterfront lifestyle you’ve been waiting for.

7932 Sailboat Key Boulevard S Unit 701, South Pasadena
$649,000
3 Beds ⋅ 2 Baths ⋅ TB8497954 MLS ⋅ Windwards/8 BLDG.
Excellent location!!! This 1st floor corner unit has beautiful wide water views of Boca Ciega Bay. A blank slate, all the demolition has been done. Remodel to your own taste. It’s uncommon for these end units with the large balconies to come up for purchase. The building is offset, which maximizes the water views from your living room, dining room, and balcony. Both front and rear balconies. All fire sprinkler heads have been replaced. The unit also features Hurricane Shutters on every opening and Hurricane Impact sliders and windows. The building features a new roof. Reserved parking space under the building, #158. Harbourside is a guard gated (24 hour) complex with many amenities including pool, his and hers fitness centers, shuffleboard, pickleball, tennis, hot tub, electric car charging stations, car wash stations, recently renovated 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.

7932 Sailboat Key Boulevard S Unit 101, South Pasadena
$450,000
2 Beds ⋅ 2 Baths ⋅ TB8494579 MLS ⋅ Sunrise Bldg 12 BLDG.
Welcome to Sunrise at Harbourside! Experience waterfront living at its finest in this stunning 3rd-floor, 2-bedroom, 2-bathroom condo overlooking the serene Boca Ciega Bay. This unit perfectly blends peace of mind with an active resort lifestyle, featuring brand-new high-impact windows and sliding doors that frame beautiful water views from your private balcony. The interior is finished with sleek, uniform tile flooring throughout. Updates include a 2016 Trane AC and hot water heater is 2009. For added convenience, the unit comes with a dedicated under-building parking space (#107), keeping your vehicle..cool and protected. There are two storage units, one on the balcony and the other near the elevator. Located in a premier island community, the amenities are unmatched: A scenic 1.5-mile walking trail encircles the island, complemented by 5 tennis courts and a dedicated pickleball courts. Choose from 6 swimming pools, unwind in the hot tubs or sauna, and stay active in multiple on-site gyms. When Constructing Harbourside, JMC the contractor used Solid Steel reinforced concrete construction rather than hollow concrete blocks. Amenities include 6 swimming pools, 5 tennis courts with Pickle ball courts, 2 fitness centers, Men and Women's Gyms, Jacuzzi, saunas, shuffleboard, multiple outdoor gas grills, Wood Working shop, Library, Card Room, Billiard room, 3 car wash station with vacuum & air, 4 Car Charging stations, Marina with 3 docks and 87 deeded slips. There is no deeded slip to this unit but there are slips available to rent or purchase from other owners. A Clubhouse with a full social agenda and a 1.5 mile walking trail around the island to exercise or walk your pet. Sun Rise allows owners one pet under 20 pounds. Come and enjoy Resort style living at it's best. Whether you're looking for a year-round residence or a vacation getaway, this condo offers the perfect coastal retreat. Furniture and furnishing's include

7979 Sailboat Key Boulevard S Unit 306, South Pasadena
$475,000
2 Beds ⋅ 2 Baths ⋅ TB8490345 MLS ⋅ Bldg 11 BLDG.
Live the Florida lifestyle at an exceptional value in Harbourside Resort! This beautifully maintained, furnished 2-bedroom, 2-bath condo offers stunning views of Boca Ciega Bay and is your perfect gateway to Paradise. Located in the highly sought-after Harbourside gated community, this residence combines comfort, convenience, and resort-style living. Inside, you’ll find a spacious, well-designed layout featuring an updated kitchen with elegant cabinetry, striking granite countertops, stainless steel appliances and abundant storage. Luxury vinyl plank flooring flows throughout most of the home, adding a modern touch. The split-bedroom floor plan ensures privacy for guests, while both the main living area and primary suite open to a generous 15-foot balcony—ideal for relaxing and taking in breathtaking water views, marine life, and coastal bird activity. Additional highlights include in-unit laundry, assigned covered parking (#152), and convenient same-floor storage. The Sunrise Building #11 features a new roof (2024) and benefits from low HOA fees. Harbourside is a true waterfront oasis, surrounded by Boca Ciega Bay and designed for an active, coastal lifestyle. Residents enjoy a 1.5-mile waterfront walking trail, 86-slip full-service marina (slips may be available for sale or lease), fishing pier, and kayak storage—perfect for boating and nature enthusiasts alike. Resort-style amenities include a beautiful clubhouse with a large room for social gatherings and events, billiards, library, card and craft rooms, his and hers fitness centers with saunas, and heated pool & spa. In addition, there are 5 tennis courts, 2 pickleball courts, shuffleboard, multiple pools throughout the community, kayak storage, 24-hour guard-gated scurity, EV charging stations, car washing areas, picnic areas with grills and more! The Sunrise complex residents also enjoy their own private pool. Ideally located just minutes from the beaches, Corey Avenue, and vibrant downtown St. Petersburg—home to acclaimed dining, breweries, museums, and art galleries—and within 30 minutes of two international airports. Pet-friendly with 3-month minimum rentals allowed, this is an outstanding opportunity for a primary residence or seasonal retreat. Don’t miss your chance to own a slice of waterfront paradise and live the Florida lifestyle to the fullest!

7979 Sailboat Key Boulevard S Unit 205, South Pasadena
$675,000
2 Beds ⋅ 2 Baths ⋅ TB8488896 MLS ⋅ Sunrise/11 BLDG.
Imagine waking up every morning to sparkling water views, sipping your coffee on a private balcony, enjoying the early morning breezes of Boca Ciega Bay. This stunning waterfront residence delivers the lifestyle you've been dreaming of. Beautifully updated and truly move-in ready, this exceptional home features an open, light-filled floor plan, an elegant chef-inspired kitchen with quality finishes, spacious living and dining areas, and serene water views that make every moment feel like a vacation. Located in the 24 hour guard-gated Harbourside community, you'll enjoy resort-style amenities including pool and spa, fitness centers (His and Hers), tennis and pickleball courts, private marina access, scenic walking paths, clubhouse activities, shuffleboard, car wash stations, electric car charging stations and so much more. Whether you're searching for your forever home, a seasonal escape, or a luxurious waterfront retreat, this is a rare opportunity to own a true piece of paradise on Florida's Gulf Coast. Luxury Living! Resort-Style Waterfront Lifestyle! A Home You'll Never Want to Leave. Schedule your private showing today and experience why this could be the perfect place to begin your next chapter in paradise. The complex was developed by award winning JMC Communities. This desirable corner unit comes with two spacious balconies. The living room has unobstructed wide water views. This is a two bedroom, two bath unit with a den/office/bonus room. The primary bathroom is spectacular and all the backsplash is stone and glass, also granite counters. The guest bathroom has quartz counters, seashells in the backsplash and new shower tile. Both bathrooms have shower towers. The condo has 9' ceilings throughout. Indoor laundry with full sized washer and dryer is in the hall. The primary bedroom has an ensuite bath and walk in closet. The building passed the milestone inspection. The roof on the building was replaced in 2024. If interested, furnishings can be included. This unit has a reserved under-building parking space (#127). Also, the fact that this unit (bldg) doesn't get direct sun, the electric bills are considerably lower in the summer months. Come see what resort living in Florida is all about.

7979 Sailboat Key Boulevard S Unit 208, South Pasadena
$799,000
2 Beds ⋅ 2 Baths ⋅ TB8487704 MLS ⋅ 7862 BLDG.
Come see this beautifully updated end unit condo in the highly desired HarbourSide waterfront community! This spacious 2-bedroom, 2-bath home with a den has been completely remodeled, including a reimagined kitchen that truly sets this condo apart. Enjoy elegant crown molding, wood floors, a wet bar, water softener, storm shutters, and an expanded den perfect for extra living or office space. This end unit has two spacious balconies, you have the front one for the sunrises and enjoy the sunsets from the back one. This unit also comes with an assigned under-building parking spot #146. HarbourSide offers resort-style living just minutes from St. Pete Beach. This gated community features 6 pools, a marina with 87 deeded slips (slips available for purchase or lease) not one with this unit, tennis/pickleball courts, shuffleboard, his & hers fitness centers with saunas, clubhouse with heated pool/spa, library, craft room, billiards room, outdoor grilling areas, car wash station, and a lively social calendar. Enjoy peaceful walks along the 1.5-mile waterfront path that surrounds the island. You would be hard presses to find a community with more amenities for your enjoyment. Live the Florida dream in this exceptional home!

7862 Sailboat Key Boulevard S Unit 506, South Pasadena