866 Pendleton Point Rd

Islesboro, ME 04848

$6,750,000
Price
6
Beds
9,449 Sq. Ft.
$714 / Sq. Ft.
9,449
Sq. Ft.
$714
per Sq. Ft.
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Virtual Tour
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Description

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...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.

Property Details for 866 Pendleton Point Road

Waterfront
Yes
ArchitecturalStyle
Shingle
Garage Spaces
.00
Garage
No
Zoning
Shoreland Res
View
Scenic
LISTING UPDATED: 09/24/2025 10:00 AM

Property Details for 866 Pendleton Point Road

StatusActive
MLS #1631135
Days on Market158
Taxes$44,550 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built2000
Lot Size5.25 AC / 228,690 SF
CountyWaldo County

Location

Listing Courtesy of Legacy Properties Sotheby's International Realty
Add your commute

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Building Information for 866 Pendleton Point Road

Stories-Year Built2000Building Size-Lot Size5.25 AC / 228,690 SF

Payment Calculator

$37,067 per month

30 year fixed, 6.28% Interest

Principal and Interest

$33,354

Property Taxes

$3,713

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 866 Pendleton Point Road

Summary
Location and General Information
  • Water Body Name: Penobscot Bay
  • Zip Code: 5159
  • Directions: Pendleton Point Road. Stone pillars at entrance.
  • Town: Islesboro
  • State/Province: ME
  • Zip Code: 04848
  • County: Waldo
  • Geo Latitude: 44.239334
  • Geo Longitude: -68.922012
  • Road Frontage Type: Private Road
  • Tax Lot: 6
  • Site:Level: Yes
  • Site:Open: Yes
  • Site:Rolling/Sloping: Yes
  • Site:Well Landscaped: Yes
  • Location:Other Location: Yes
  • Water Info:Waterfront Amount +: 429.00
  • Water Info:Water Frontage Owned: 429.00
  • Water Info:Water Frontage Shared: .00
  • Source of Water Frontage:Public Records: Yes
Parking
  • Parking Features: 5 - 10 Spaces, Gravel, Carport
  • Attached Garage: Yes
Taxes and HOA Information
  • Tax Book Number: 4820
  • Tax Map Number: 6
  • Tax Year: 2024
  • Parcel Number: ISBR-000006-000000-000006-C000000
  • Location Information:Association Y/N: No
  • Tax Annual Amount: $44,550.00
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Property
Heating and Cooling
  • Water Heater:Off Heating System: Yes
Lot Information
  • SqFt Finished Below Grade: 753.0
  • SqFt Finished Above Grade: 8696.0
  • Lot Size Acres: 5.25
  • Source of Acreage: Public Records
  • Building Area Total: 9449.0
  • Lot Size Area: 5.25
  • Lot Size Units: Acres
  • Lot Size Square Feet: 228690.0
  • Bedrooms Total: 6
  • Bathrooms Full: 6
  • Bathrooms Half: 3
  • Street Number: 866
  • Property Information:Surveyed: Unknown
  • Property Information:Seasonal: No
  • Property Information:# Rooms: 19.00
  • Property Information:Total Half Baths: 3.00
  • Property Information:# Full Baths Basement: .00
  • Property Information:# Half Baths Basement: .00
  • Property Information:# Full Baths Level 1: 1.00
  • Property Information:# Half Baths Level 1: 3.00
  • Property Information:# Full Baths Level 2: 5.00
  • Property Information:Other Source of Square Footage: Floor Plans
  • Property Information:# Half Baths Level 2: .00
  • Property Information:# Full Baths Level 3: .00
  • Property Information:# Half Baths Level 3: .00
  • Property Information:# Full Baths Upper: .00
  • Property Information:# Half Baths Upper: .00
Parking
  • Driveway:Gravel: Yes
Property and Assessments
  • Leased Land: No
  • Property Type: Residential,Single Family Residence
  • Property Type Label: Residential
  • Property Sub-Type: Single Family Residence
  • Building Area Source: Other
  • Year Built: 2000
Utilities
  • Electric: Underground, Circuit Breakers
  • Sewer: Septic Tank, Private Sewer
  • Water Source: Well, Private
  • Other Equipment: Other Equipment, Generator
  • Gas:Bottled: Yes
Interior and Exterior Features
Exterior Features
  • Construction Materials: Wood Siding, Wood Frame
  • # Fireplaces: 4
  • Fireplace: Yes
  • Vehicle Storage:1 Car: Yes
  • Vehicle Storage:Carport: Yes
  • Roof: Shingle
Interior Features
  • Basement: Interior, Crawl Space, Finished, Full, Partial, Bulkhead, Unfinished
  • Flooring: Wood, Tile, Carpet
  • Interior Features: Walk-in Closets, 1st Floor Primary Bedroom w/Bath, Bathtub, Other, Shower, Storage, Primary Bedroom w/Bath
  • Cooling: Heat Pump
  • Heating: Hot Water, Heat Pump, Forced Air
  • Foundation Details: Concrete Perimeter
  • Laundry Features: Laundry - 1st Floor, Upper Level, Main Level
  • Room Total: 19
  • Bathrooms Total (Integer): 9
  • Bathrooms Total (Decimal): 7.50
  • Bathrooms Total (Notational): 6.30
  • Cooling YN: Yes
  • Heating YN: Yes
Room Information
Room 1
  • Room Type: Primary Bedroom
  • Room Level: First
Room 2
  • Room Type: Bedroom 2
  • Room Level: Second
Room 3
  • Room Type: Bedroom 3
  • Room Level: Second
Room 4
  • Room Type: Bedroom 4
  • Room Level: Second
Room 5
  • Room Type: Bedroom 5
  • Room Level: Second
Room 6
  • Room Type: Bedroom 6
  • Room Level: Second
Room 7
  • Room Type: Other Room
  • Room Level: First
Room 8
  • Room Type: Library
  • Room Level: First
Room 9
  • Room Type: Living Room
  • Room Level: First
Room 10
  • Room Type: Dining Room
  • Room Level: First
Room 11
  • Room Type: Kitchen
  • Room Level: First
Room 12
  • Room Type: Office
  • Room Level: First
Room 13
  • Room Type: Great Room
  • Room Level: Second
Room 14
  • Room Type: Office
  • Room Level: Second
Room 15
  • Room Type: Laundry
  • Room Level: First
Room 16
  • Room Type: Office
  • Room Level: First
Room 17
  • Room Type: Exercise Room
  • Room Level: Basement
Room 18
  • Room Type: Other Room 3
  • Room Level: Basement
Room 19
  • Room Type: Other Room 2
  • Room Level: Basement

Property History for 866 Pendleton Point Road

DateEvent & SourcePriceAppreciation
Jul 15, 2025

Listed (Active)

Maine Listings #1631135

$6,750,000—
Jul 14, 2022

Sold

Maine Listings #1523560

$4,500,000—
Jun 21, 2022

Pending

Maine Listings #1523560

—
Jun 19, 2022

Active Under Contract

Maine Listings #1523560

—
Mar 15, 2022

Listed (Active)

Maine Listings #1523560

$4,850,000—
Dec 31, 2021

Expired

Maine Listings #1483182

$4,495,000—
Jun 1, 2021

Expired

Maine Listings #1321528

$4,875,000—
Feb 23, 2021

Listed (Active)

Maine Listings #1483182

$4,495,000—
Aug 12, 2017

Listed (Active)

Maine Listings #1321528

$4,875,000—
Oct 31, 2010

Expired

Maine Listings #855223

$2,500,000—
Nov 14, 2007

Expired

Maine Listings #824153

$2,950,000—
Nov 14, 2007

Expired

Maine Listings #832587

$2,950,000—
Jun 28, 2007

Listed (Active)

Maine Listings #855223

$2,750,000—
Feb 8, 2007

Listed (Active)

Maine Listings #832587

$2,950,000—
Nov 15, 2006

Listed (Active)

Maine Listings #824153

$2,950,000—
Nov 3, 2006

Expired

Maine Listings #790049

$2,950,000—
Nov 3, 2006

Expired

Maine Listings #772419

$3,400,000—
Apr 8, 2006

Listed (Active)

Maine Listings #790049

$3,400,000—
Nov 4, 2005

Listed (Active)

Maine Listings #772419

$3,400,000—
Jun 16, 2005

Expired

Maine Listings #632069

$3,400,000—
Jun 17, 2003

Listed (Active)

Maine Listings #632069

$3,200,000—
DateEvent & SourcePrice
07/15/2025

Listed (Active)

Maine Listings #1631135

$6,750,000
07/14/2022

Sold

Maine Listings #1523560

$4,500,000
06/21/2022

Pending

Maine Listings #1523560

—
06/19/2022

Active Under Contract

Maine Listings #1523560

—
03/15/2022

Listed (Active)

Maine Listings #1523560

$4,850,000
12/31/2021

Expired

Maine Listings #1483182

$4,495,000
06/01/2021

Expired

Maine Listings #1321528

$4,875,000
02/23/2021

Listed (Active)

Maine Listings #1483182

$4,495,000
08/12/2017

Listed (Active)

Maine Listings #1321528

$4,875,000
10/31/2010

Expired

Maine Listings #855223

$2,500,000
11/14/2007

Expired

Maine Listings #824153

$2,950,000
11/14/2007

Expired

Maine Listings #832587

$2,950,000
06/28/2007

Listed (Active)

Maine Listings #855223

$2,750,000
02/08/2007

Listed (Active)

Maine Listings #832587

$2,950,000
11/15/2006

Listed (Active)

Maine Listings #824153

$2,950,000
11/03/2006

Expired

Maine Listings #790049

$2,950,000
11/03/2006

Expired

Maine Listings #772419

$3,400,000
04/08/2006

Listed (Active)

Maine Listings #790049

$3,400,000
11/04/2005

Listed (Active)

Maine Listings #772419

$3,400,000
06/16/2005

Expired

Maine Listings #632069

$3,400,000
06/17/2003

Listed (Active)

Maine Listings #632069

$3,200,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 866 Pendleton Point Road

Taxable ValueLand$844,500Additions$2,899,200Total$3,743,700
Tax Record2024$44,550 ($3,712 / month)
Home Facts
Beds0Total Finished SqFt7,852 SqFtAbove Grade Finished SqFt7,852 SqFtStories2Lot Size189,050 SqFtStyleSingle Family ResidenceYear Built1999CountyWALDOAPNISBR M:0006 L:0006-C

Schools near 866 Pendleton Point Road

This home is within Islesboro Public Schools.
Rating
School
Type
Grades
Distance
Islesboro Central School
Public - K to 12
Rating
School
Distance
Islesboro Central School
PublicK to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 866 Pendleton Point Road, Islesboro, ME 04848

866 Pendleton Point Road is a single family home for sale in Islesboro, ME 04848. This property was listed for sale on July 15, 2025 by Legacy Properties Sotheby's International Realty, it's currently listed at $6,750,000. It has been on the market for a total of 158 days and was last sold on July 14, 2022. This listing's school district is Islesboro Public Schools. Nearby schools include Islesboro Central School. 866 Pendleton Point Road is a 6-bed, 9-bath, 9,449 sqft single family home built in 2000.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Legacy Properties Sotheby's International Realty

Listing data is derived in whole or in part from the Maine IDX and is for consumers' personal, noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2022 Maine Real Estate Information System, Inc. All Rights Reserved.