East Bay is a lovely coastal estate, an ideal summer retreat and

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Home For Sale

866 Pendleton Point Road

Islesboro, Maine 04848

Waldo County

Waterfront: Yes

Community: 

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$6,750,000 6 br, 0.0 bath 9449 sq. ft. 5.250 acres

East Bay is a lovely coastal estate, an ideal summer retreat and a serene sanctuary for year-round living. Privately sited on 5 plus acres with 430 feet of accessible, pristine waterfront, the property is gracefully perched above a scenic pristine shoreline, where lush gardens and thoughtful landscaping frame cinematic views of Penobscot Bay and the islands. The residence unfolds along a gently sloping bluff, capturing sweeping vistas from nearly every room and outdoor space. Originally constructed as a post-and-beam home circa 2000, East Bay has since undergone a series of thoughtful transformations. Its final form, guided by the timeless coastal architecture of Royal Barry Wills, seamlessly blends classic character with understated luxury. Gracious indoor and outdoor living spaces are designed for both grand entertaining and intimate gatherings, offering a harmonious balance of formal and informal areas. Highlights include a first-floor primary suite with private sitting room and office, multiple guest suites, sitting rooms, library, offices, a wine cellar, exercise room, updated systems, air conditioning, generator, and carport. The grounds are equally compelling: a heated pool, hot tub, and wood-fired sauna are thoughtfully positioned to take full advantage of the views, while a custom-built staircase provides direct access to the private beachfront. The result is a property that evokes the spirit of Islesboro's historic Summer Cottages. Located just south of the island's storied Dark Harbor Village, East Bay is a true legacy estate, an extraordinary fusion of Maine's rugged coastal beauty and enduring craftsmanship. View our 3D Tour and Floor Plans for a fully immersive experience.

Interior:
  • Bedrooms: 6
  • Baths: 0.0
  • Sq Ft: 9449
  • Year Built: 2000
  • Utilities: 
  • Fireplaces: Has Fireplace
  • Stories: 
  • Heat/AC: Hot Water(Heating), Heat Pump (Heating), Forced Air
  • Garage: Carport
Exterior:
  • Lot Size: 5.250 acre
  • Lot Dimensions: 
  • Waterfront: Yes
  • View Types: 
  • Yard: 
  • Siding: Wood Siding, Wood Frame
  • Roof: Shingle
  • MLS #: 1631135
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Contact Information:
Beach Home For Sale in Islesboro, Maine
Listing Agent: Michael Lynch, Legacy Properties Sotheby's International Realty, 207-558-3131, 207-230-1003 Listing Site, Listing Status: Active
Copyright © 2025 Maine Real Estate Information System, Inc.. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Ad Number: 6433295
Viewed 79 times.
Updated: Jul 19, 2025

This property is a Home located at 866 Pendleton Point Road, Islesboro, Maine 04848, and is currently For Sale at $6,750,000. This Home has 6 bedrooms, 0.0 baths, 9449 sq ft.