Experience elevated courtyard living in this beautifully enhanced residence within the prestigious, gated community of Gulf Harbour Yacht & Country Club. Designed for privacy, sophistication, and seamless indoor-outdoor living, the home gracefully wraps around an expansive central courtyard showcasing a sparkling pool, soothing spa, and fully equipped outdoor kitchen--creating a private retreat at the heart of the property. Significant recent improvements enhance both value and peace of mind, including a two-year-old roof, fresh interior and exterior paint, new awnings, retextured walls, all-new flooring, and updated baseboards. Ideally located within walking distance to the club's extensive amenities and situated on one of the quietest streets in the neighborhood, this home offers both convenience and tranquility. Inside, a completely remodeled kitchen makes a striking impression. Anchored by a dramatic waterfall-edge quartz island, the space features premium finishes, modern cabinetry, updated lighting, and sleek appliances, including a Monogram induction cooktop with pot filler. Porcelain tile flooring flows seamlessly throughout the main living areas, delivering a clean, cohesive aesthetic. Elegant French doors open to the formal dining room, while a stylish bar area with a temperature-controlled wine chiller provides the perfect setting for entertaining. The primary suite serves as a private sanctuary, featuring a luxurious bath with tumbled porcelain tile, a relaxing soaking tub, and a spacious shower that doubles as an impressive steam shower for a true spa-like experience. Additional guest bedrooms are positioned in the second-floor wing and connect to the casita via a charming upper-level lanai, offering privacy and a unique indoor-outdoor flow. The two-story casita is exceptionally appointed, complete with its own patio, a welcoming living area on the first floor, and a bedroom retreat upstairs. Equipped with a microwave, sink, refrigerator, and stackable washer and dryer, it is ideal for extended-stay guests, family members, or live-in support. An additional office off the main home provides a quiet, functional workspace for remote work or study. Two spacious two-car garages complete the property, offering abundant storage for vehicles, golf carts, bicycles, and more. Residents enjoy championship golf, a deep-water marina, tennis, a state-of-the-art fitness center, spa services, clubhouse dining, and an active social calendar. Select Golf and Sport Membership opportunities may be available, presenting a rare opportunity to embrace the full club lifestyle without the standard waitlist. 14540 Headwater Bay offers a distinctive blend of luxury, comfort, and architectural character--an exceptional courtyard residence designed for refined Florida living.