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Betsy Carson
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866 Pendleton Point Road, Islesboro, ME 04848

$5,750,000
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BEDS6 BATHS6 full 3 partial SQUARE FEET9,449 MLS#1667521
STATUSActive PROPERTY TYPEResidential - Single Family

Property Description

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.

866 Pendleton Point Road | MLS# 1667521

This single family home located at 866 Pendleton Point Road, Islesboro, ME 04848 is currently listed for sale with an asking price of $5,750,000. This property was built in 2000 and has 6 bedrooms and 6 full and 3 partial baths with 9449 sq. ft. Search Islesboro real estate on betsycarson.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Bulkhead, Interior Entry, Crawl Space, Finished, Full, Partial, Unfinished
Basement: Yes
Cooling: Heat Pump
Heating: Oil, Propane, Forced Air, Heat Pump, Hot Water, Zoned
Home Style: Shingle
Lot Size: 5.25 Acres
Roof Type: Shingle
Taxes: $47,732
Year Built: 2000

Feature Descriptions

Amenities: 1st Floor Primary Bedroom w/Bath, Bathtub, Irrigation System, Main Level, Upper Level, Other Amenities, In Ground, Shower, Storage, Walk-in Closets, Primary Bedroom w/Bath
Appliances: Dishwasher, Dryer, Microwave, Electric Range, Gas Range, Refrigerator, Wall Oven, Washer, Other
Electric: Circuit Breakers
Equipment: Generator, Internet Access Available
Exterior: Wood Frame, Wood Siding
Flooring: Carpet, Tile, Wood
Foundation: Poured Concrete
Lot: Irrigation System, Near Country Club, Near Golf Course, Near Public Beach, Other, Level, Open Lot, Rolling Slope, Landscaped
Parking: Gravel,5 - 10 Spaces, Carport
Sewer: Private Sewer
Special View Info: Scenic
SQ FT Above Grade: 8696
SQ FT Below Grade: 753
Swimming Pool: Yes
Total Rooms: 19
Water: Private, Well
Water Body Name: Penobscot Bay, Ocean

Listed By / Shown By

Listed By

Agency Name: Legacy Properties Sotheby's International Realty
Agent Name: Michael Lynch
Agency Phone: 207-230-1003

Shown By

Agent Name: Betsy Carson
Agent Phone:
Agency Title: Better Homes and Gardens Real Estate The Masiello Group

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Estimated Payment

$ 18,451.76 per month $12,797.01 Principal & Interest $3,977.67 Property Tax $1,677.08 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 07/22/2026. The listing information on this page last changed on 07/22/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 07/22/2026 12:01:21 AM EST) or MLSPIN MLS (last updated Tue 07/21/2026 11:38:24 PM EST) or Prime MLS (last updated Tue 07/21/2026 11:33:17 PM EST) or MREIS (last updated Tue 07/21/2026 11:55:21 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.



Listing data is derived in whole or in part from the Maine IDX & is for consumers' personal, noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified.© 2026 Maine Real Estate Information System, Inc. All Rights Reserved.

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Agency License Information: Better Homes and Gardens® and the Better Homes and Gardens Real Estate Logo are registered service marks owned by Meredith Corporation and licensed to Better Homes and Gardens Real Estate LLC. The Masiello Group Limited fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each franchise is independently owned and operated. Any services or products provided by independently owned and operated franchisees are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC nor any of its affiliated companies.


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