866 Pendleton Point Road

Islesboro, ME 04848

East Bay is an exceptional coastal estate offering the perfect blend of a private summer retreat and a tranquil year-round residence. Set on more than five secluded acres with 430 feet of pristine, accessible waterfront, the property enjoys an elevated position above the scenic shoreline, where beautifully curated gardens and mature landscaping frame sweeping views across Penobscot Bay and its islands. The residence unfolds along a gently sloping bluff, capturing spectacular water vistas from nearly every room and outdoor living space. Originally built as a post-and-beam home around 2000, East Bay has been thoughtfully transformed over time. Its current design, inspired by the timeless coastal architecture of Royal Barry Wills, combines classic New England character with understated sophistication. Designed for both elegant entertaining and comfortable everyday living, the home offers a seamless balance of formal and informal spaces. Highlights include a first-floor primary suite with a private sitting room and office, multiple guest suites, inviting sitting rooms, a library, additional office spaces, a wine cellar, exercise room, updated mechanical systems, air conditioning, a generator, and a carport. The outdoor amenities are equally impressive. A heated swimming pool, hot tub, and sauna are perfectly positioned to maximize the breathtaking waterfront setting and views, while a custom-built staircase provides direct access to the property's private beach. Evoking the charm and grandeur of Islesboro's historic summer cottages, East Bay is a rare legacy property--an extraordinary expression of Maine's rugged coastal beauty, enduring craftsmanship, and timeless elegance. Explore the 3D tour and floor plans for a fully immersive experience of this remarkable estate.

Listing courtesy of of Legacy Properties Sotheby's International Realty Bought with of



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Last checked 2026-06-23 07:56 PM UTC