Under contract-accepting backup offers. 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!