866 Pendleton Point Road
Islesboro, ME 04848
6 Beds
7.5 Baths
9,449 sqft (on 5.25 acres)
$5,750,000
$5,750,000
6 Beds
7.5 Baths
9,449 sqft
(on 5.25 acres)
We estimate this home will sell faster than 96% nearby.
Local Information
- Map ViewExplore the area around 866 Pendleton Point Road.
- Schools1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Last check for updates: 43 minutes ago
Listing courtesy of Legacy Properties Sotheby's International Realty
Source: Maine Listings, MLS#1667521
Also Listed on Maine Listings.
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.
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.
We estimate this home will sell faster than 96% nearby.
Home Highlights
Parking
Attached Garage
Outdoor
Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
$609
Listed
29 days ago
Home Details for 866 Pendleton Point Road
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MLS Status: Active |
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Interior Details Basement: Bulkhead,Interior Entry,Crawl Space,Finished,Full,Partial,UnfinishedNumber of Rooms: 19Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Bedroom 6, Dining Room, Exercise Room, Great Room, Kitchen, Laundry, Library, Living Room, Office, Other Room, Other Room 2, Other Room 3 |
Beds & Baths Number of Bedrooms: 6Number of Bathrooms: 9Number of Bathrooms (full): 6Number of Bathrooms (half): 3 |
Dimensions and Layout Living Area: 9449 Square Feet |
Appliances & Utilities Appliances: Dishwasher, Dryer, Microwave, Electric Range, Gas Range, Refrigerator, Wall Oven, Washer, OtherDishwasherDryerMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Forced Air,Heat Pump,Hot Water,ZonedHas CoolingAir Conditioning: Heat PumpHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa Number of Fireplaces: 4Has a Fireplace |
Gas & Electric Electric: Circuit Breakers |
Windows, Doors, Floors & Walls Flooring: Carpet, Tile, Wood |
Levels, Entrance, & Accessibility Floors: Carpet, Tile, Wood |
View Has a ViewView: Scenic |
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Exterior Home Features Roof: ShingleFoundation: Poured ConcreteHas a Private Pool |
Parking & Garage Has a CarportNo GarageHas an Attached GarageParking: Gravel,5 - 10 Spaces,Carport |
Pool Pool |
Frontage WaterfrontOn Waterfront |
Water & Sewer Sewer: Private SewerWater Body: Penobscot Bay, Ocean |
Farm & Range Frontage Length: Waterfrontage: 429, Waterfrontage Owned: 429 |
Finished Area Finished Area (above surface): 8696 Square FeetFinished Area (below surface): 753 Square Feet |
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Days on Market: 29 |
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Year Built Year Built: 2000 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Shingle |
Building Construction Materials: Wood Frame, Wood Siding |
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Price List Price: $5,750,000Price Per Sqft: $609 |
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Direction & Address City: Islesboro |
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Listing Agent Listing ID: 1667521 |
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Building Area Building Area: 9449 Square Feet |
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Lot Area: 5.25 Acres |
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BasementMls Number: 1667521Above Grade Unfinished Area: 8696 |
Market trends in Islesboro
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
26
Price History for 866 Pendleton Point Road
| Date | Price | Event | Source |
|---|---|---|---|
| 06/16/2026 | $5,750,000 | Listed For Sale | Maine Listings #1667521 |
| 01/01/2026 | $6,750,000 | ListingRemoved | Maine Listings #1631135 |
| 07/19/2025 | $6,750,000 | Listed For Sale | Maine Listings #1631135 |
| 07/14/2022 | $4,500,000 | Sold | Maine Listings #1523560 |
| 06/21/2022 | $4,850,000 | Pending | Maine Listings #1523560 |
| 06/21/2022 | $4,850,000 | Contingent | Maine Listings #1523560 |
| 04/18/2022 | $4,850,000 | Listed For Sale | Maine Listings #1523560 |
| 06/30/2018 | $4,875,000 | ListingRemoved | Agent Provided |
| 08/12/2017 | $4,875,000 | Listed For Sale | Agent Provided |
| 11/20/2010 | $2,500,000 | ListingRemoved | Agent Provided |
| 07/15/2010 | $2,500,000 | Listed For Sale | Agent Provided |
| 06/11/2009 | $2,750,000 | ListingRemoved | Agent Provided |
| 05/22/2009 | $2,750,000 | Listed For Sale | Agent Provided |
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New Listings near 866 Pendleton Point Road
Comparable Sales for 866 Pendleton Point Road
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
1.51 | Single-Family Home | $345,000 | 05/28/26 | 4 | 1.5 | 2,200 | |
2.23 | Single-Family Home | $515,000 | 06/01/26 | 2 | 1.5 | 1,463 | |
3.54 | Single-Family Home | $1,325,000 | 09/23/25 | 3 | 2.5 | 3,714 | |
3.31 | Single-Family Home | $430,000 | 09/09/25 | 3 | 2 | 2,400 | |
3.25 | Single-Family Home | $500,000 | 02/02/26 | 2 | 1.5 | 825 | |
3.10 | Single-Family Home | $348,936 | 12/30/25 | - | - | ||
4.23 | Single-Family Home | $835,000 | 10/31/25 | 4 | 2 | 2,258 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETLegacy Properties Sotheby's International Realty, Closed
OFF MARKETLegacy Properties Sotheby's International Realty, Closed
SOLDMAY 28, 2026Legacy Properties Sotheby's International Realty, Closed
Assigned Schools
These are the assigned schools for 866 Pendleton Point Road.
- Islesboro Central School
- K-12
- Public
- 64 Students
9/10GreatSchools RatingParent Rating Average
No reviews available for this school. 
Check out schools near 866 Pendleton Point Road.
What Locals Say about Islesboro
At least 2 Trulia users voted on each feature.
100 % Say parking is easy
100 % Say it's dog friendly
100 % Say kids play outside
100 % Say people would walk alone at night
100 % Say yards are well-kept
100 % Say it's quiet
100 % Say there's wildlife
100 % Say car is needed
83 % Say neighbors are friendly
50 % Say there's holiday spirit
50 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Legacy Properties Sotheby's International Realty
Listing data is derived in whole or in part from Maine Real Estate Information System, Inc. (d/b/a Maine Listings) and 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. Equal Housing Opportunity.
Zillow Inc. 415 Congress St #202 Portland, ME 04101 206-424-8443
Zillow Inc. 415 Congress St #202 Portland, ME 04101 206-424-8443
866 Pendleton Point Road, Islesboro, ME 04848 is a 6 bedroom, 9 bathroom, 9,449 sqft single-family home built in 2000. This property is currently available for sale and was listed by Maine Listings on Jun 16, 2026. The MLS # for this home is MLS# 1667521.