An enchanting coastal retreat! Set alongside the Pleasant Bay estuary in one of Orleans most private & naturally beautiful enclaves, this striking 5BR/5BA custom home blends relaxed coastal living with creative design & impeccable craftsmanship.Nestled among pines, rhododendrons, and roses, the residence offers expansive water views and exceptional privacy, while just minutes from world-class beaches, golf, dining, shopping, and the villages of Chatham, Orleans, and beyond.Enjoy a private beach, deep-water mooring (pending harbormaster approval), & shoreline perfect for kayaking, paddleboarding, sailing, or deep-sea fishing in one of the East Coasts premier marine playgrounds: Pleasant Bay and the Atlantic Ocean.The main residence spans 3 finished levels, with thoughtfully designed living areas, flexible spaces, and sweeping water views throughout. Burnished hardwood floors and freshly painted white shiplap walls & cabinetry enhance the coastal aesthetic. The open-concept main floor is ideal for both entertaining and everyday living. A sunlit living room with a wall of windows frames stunning water views and centers around a wood-burning fireplace. The adjoining dining area offers exquisite views and opens to multi-level mahogany decks. With built-in seating and custom cabinetry, the space is perfect for intimate dinners or larger gatherings. The kitchen features new appliances, gleaming wood floors, and quartz countertops that transition seamlessly into the dining space ideal for casual meals or serving guests. A sunny, sheltered side deck makes a delightful spot for morning coffee or al fresco dining when the coastal breeze picks up. To the west, a flexible bonus room serves perfectly as a media room, library, or extra sleeping area. To the east, the spacious primary suite offers water views, luxurious private bath, custom built-ins, and generous closet. A laundry room and powder room complete this level. Upstairs, the tower room offers a private BR suite with serene views and ensuite bath. The finished lower level includes a large BR with water views and private outdoor access, a cozy childrens room, full bath, and a flexible space with laundry hook-up and utility sink. Outside, the multi-level mahogany decks provide space for lounging, grilling, and entertaining. The expansive yard offers excellent potential for a pool, barn, or sport court enhancing both lifestyle and property value. A fully heated guest cottage featuring vaulted ceilings, paneled walls, a full bath, and water views is ideal as a studio, home office, overflow space, or potential ADU. Whether swimming at sunrise, sailing Pleasant Bay, or hosting a sunset dinner on the deck, this property is a rare combination of natural beauty, stylish comfort, and pure Cape Cod joy. Let the enchantment begin! NOTE: A large addition and home renovations have been done to the home, alterations not yet reflected in public records, assessments, and estimated valuation.