Set against private garden views with tranquil eastern exposure, this beautifully appointed villa in Winding Cypress offers a peaceful retreat and effortless indoor-outdoor living. Featuring two bedrooms plus a den, two baths, and a two-car garage, this thoughtfully designed residence combines quiet luxury with meticulous updates in one of Naples' most dynamic lifestyle communities. The screened lanai is ideal for entertaining or unwinding, complete with brick paver flooring, a saltwater pool with waterfall feature, pool heater, and recent upgrades including a new salt generator and pool pump. A custom outdoor kitchen with a stainless steel gas grill with matching hood and sink further enhances the outdoor living experience. Electric hurricane shutters protect the lanai, while manual shutters cover the remainder of the home. Inside, tile flooring extends throughout, accented by crown molding, recessed lighting, and white plantation shutters. The living room opens to the lanai through expansive glass sliders, anchored by a modern ceiling fan. The kitchen features white Shaker-style cabinetry, quartz countertops, a tile backsplash, pantry, and stainless steel appliances including a gas range, refrigerator with icemaker, microwave, and dishwasher. A modern chandelier defines the dining area, which flows easily into the main living space. The primary suite is a private haven with a tray ceiling, garden views, custom closet, and a spa-inspired bath featuring dual quartz vanities, full-width mirrors, and a frameless glass walk-in shower. The second bedroom includes a walk-in closet and an adjacent bath with a shower-tub combination. A den with French doors offers flexible space for a home office or reading room. Additional highlights include a mini-split air conditioning system in the garage, a brand-new water heater, and recent property updates including a full exterior repaint (approximately two years ago) and interior paint touch-ups. Residents of Winding Cypress enjoy access to resort-style amenities including a pool, an attended fitness center, an on-site restaurant, five tennis courts, four bocce ball courts, four pickleball courts, a community garden, and a dog park. With a vibrant social calendar, low HOA fees, rental-friendly policies, and a prime location near Marco Island, downtown Naples, 5th Avenue, and I-75, this villa offers elevated living in a premier Naples community.