3819 WATERSIDE Drive **Brand-New Roof & No CDD Fees!** This executive brick home is nestled on a quiet cul-de-sac in the highly sought-after Ashebourne community just off Doctors Lake Drive. Offering 4 bedrooms, 3 bathrooms, and 3, 520 sq ft on nearly a 1/2-acre lot, this well-maintained home features a first-floor owner's suite with three additional bedrooms upstairs, soaring ceilings, beautiful hardwood flooring, formal living and dining rooms, a spacious family room, a cozy fireplace in the family room, and a stunning double-sided fireplace shared between the dining room and one of the sunrooms, creating warmth and character throughout the home. Designed for both everyday living and entertaining, the home also offers two separate sunrooms overlooking the pool, providing the perfect space for morning coffee, relaxing with a good book, or hosting family and friends year-round. Step outside to enjoy the in-ground pool, expansive pool deck, wood dock, and peaceful water views, creating an exceptional outdoor living experience. Major system updates include HVAC systems (2021 & 2019), water heaters (2023 & 2014), and pool equipment (pool pump 2023 and pool caretaker system rebuilt in 2026) for added peace of mind. Located in Flood Zone X and offering No CDD fees, this home checks many of the boxes today's buyers are looking for. Conveniently located near top-rated Clay County public schools, just 5 minutes from St. Johns Country Day School, and close to shopping, dining, medical facilities, and NAS Jacksonville, this is a rare opportunity to own an executive home in one of Orange Park's most established and desirable neighborhoods.