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6 Beds
9 Baths
9,449 sqft

$5,750,000

866 Pendleton Point Road, Islesboro ME, 04848

Price per sqft$608.53
Built in2000
Property size9,449 sqft
Property typeResidential

Overview

Active

Listed Jun 16, 2026

Updated Jun 25

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.

$38,255/mo

Est. mortgage payment based on a $5,750,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
1667521
Available since
June 16, 2026

Interior Features

Bedrooms
6
Bathrooms
9
Basement
No

Other Property Details

Taxes
$47,732
Tax Frequency
Annually

 Courtesy of Michael Lynch | Legacy Properties Sotheby's International Realty

Based on information from DASH - Sotheby's International Realty (SIR) as of 6/25/2026. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. The display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent. 

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Data last updated 5:17 PM UTC, 6/25/2026

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