Remarkable Waterfront Estate featuring 2 Distinct Residences and a Deep Water Dock. Ideal for Multi-Generational Living or Exceptional Rental Income Opportunity! Nestled along the picturesque Sheepscot, this unique Waterfront Estate offers a rare blend of refined country living, natural beauty, and seclusion. The 3-Bedroom, 2-Bath Primary Residence, with an expansive deck, presents sweeping water views, as well as the ideal perch from which to view soaring eagles & osprey. From the spacious living area, to the vaulted ceilings, to the breakfast nook and beyond, the home includes thoughtful features throughout. The 2-car garage includes a handy work room and spacious 2nd floor storage. A separate Guest Cottage, rebuilt from the frame in 2015, offers additional year-round comfort & privacy, complete with its own deck & 2-car garage. (Rental Income history available). The property features a private Deep-Water Dock w/ an impressive stairway to the water, providing direct access to Boothbay Harbor, Wiscasset, & the Atlantic -- ideal for boating enthusiasts and Coastal adventurers alike. The low-maintenance landscaped grounds have been cultivated over time to create a seasonal paradise, bursting with color thru the seasons. Outdoor living is elevated with a Bocce Court, Fire Pit, & water-side lawn. Automatic Generator serves both the House and Cottage. Whether enjoying quiet mornings on the deck, launching a kayak or boat from your dock, or entertaining guests in a setting of timeless coastal charm, this estate is a special place to call home. From this sanctuary, you feel a world away, yet mere minutes to local restaurants & shopping. (Primary Residence expanded in 2000, renovations to 2023. Guest House renovated in 2015. Main House 2,445 sq ft; Guest House 1,180 sq ft. Bdrm/ Bath count includes House (3/2) & Cottage (3/1). 4-Bdrm Septic. Ideal Multi-Family property. Westport Island includes exceptional benefits of School Choice & low Property Tax rate.