866 Pendleton Point Rd

Islesboro, ME 04848

$5,750,000
Price
6
Beds
9,449 Sq. Ft.
$609 / Sq. Ft.
9,449
Sq. Ft.
$609
per Sq. Ft.
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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...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.

Property Details for 866 Pendleton Point Road

Architectural Style
Shingle
View
Scenic
Has Waterfront
Yes
Zoning
Shoreland Res
LISTING UPDATED: 06/16/2026 11:19 PM

Property Details for 866 Pendleton Point Road

StatusActive
MLS #1667521
Days on Market20
Taxes$47,732 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built2000
Lot Size5.25 AC / 228,690 SF
CountyWaldo County
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Location

Listing Courtesy of Legacy Properties Sotheby's International Realty
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Building Information for 866 Pendleton Point Road

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

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$32,631 per month

30 year fixed, 6.36% Interest

Principal and Interest

$28,653

Property Taxes

$3,978

HOA Dues

$0

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Property Information for 866 Pendleton Point Road

Summary
Location and General Information
  • Water View: Yes
  • Page: 172
  • Latitude: 44.239332
  • Longitude: -$68.92
  • Water Frontage Owned: 429.0
  • Source of Water Frontage: Public Records
  • Waterfront Amount: $429.00
  • Water Body Type: Bay, Ocean
  • Water Body Name: Penobscot Bay, Ocean
Taxes and HOA
  • Association: No
  • Parcel Number: ISBR-000006-000000-000006-C000000
  • Tax Lot: 6
  • Tax Book Number: 4820
  • Tax Map Number: 6
  • Tax Year: 2025
  • Tax Annual Amount: $47,732.00
Parking
  • Parking Features: Gravel, 5 - 10 Spaces, Carport
  • Vehicle Storage: 1 Car, Attached, Carport
  • Has Attached Garage: Yes
  • Has Garage: No
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Property
Lot Information
  • Lot Features: Irrigation System, Near Country Club, Near Golf Course, Near Public Beach, Other, Level, Open Lot, Rolling Slope, Landscaped
  • Lot Size Acres: 5.25
  • Lot Size Area: 5.25
  • Lot Size Source: Public Records
  • Lot Size Square Feet: 228690.0
  • Lot Size Units: Acres
  • Other Source of Square Footage: Matterport Floor Plans, Estimated
  • Roads: Public
  • Road Frontage: false
  • Tree Growth: false
Property and Assessments
  • Above Grade Finished Area: 8696.0
  • Below Grade Finished Area: 753.0
  • Building Area Source: Other
  • Building Area Total: 9449.0
  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Year Built: 2000
Building Features
  • Foundation Details: Poured Concrete
  • Construction Materials: Wood Frame, Wood Siding
Financial Information
  • List Price/SqFt: $661.22
Green Features
  • HERS Certified: No
Utilities
  • Electric: Circuit Breakers
  • Gas: Bottled
  • Sewer: Private Sewer
  • Water Source: Private, Well
  • Water Heater: Off Heating System
Interior and Exterior Features
Exterior Features
  • Pool Features: In Ground
  • Roof: Shingle
Interior Features
  • Amenities: 1st Floor Primary Bedroom w/Bath, Bathtub, Irrigation System, Laundry - 1st Floor, Laundry - 2nd Floor, Other, Pool-In Ground, Shower, Storage, Walk-in Closets, Primary Bedroom w/Bath
  • Appliances: Dishwasher, Dryer, Microwave, Electric Range, Gas Range, Refrigerator, Wall Oven, Washer, Other
  • Other Appliances: See listing remarks
  • Bathrooms Full: 6
  • Bathrooms Half: 3
  • Bathrooms Total Decimal: 7.5
  • Bathrooms Total Integer: 9
  • Bedrooms Total: 6
  • Equipment: Generator, Internet Access Available
  • Fireplaces Total: 4
  • Laundry Features: Main Level, Upper Level
  • Other Equipment: Generator, Internet Access Available
  • # Full Baths Level 1: 1
  • # Full Baths Level 2: 5
  • # Half Baths Level 1: 3
  • Rooms Total: 19
  • Basement: Bulkhead, Interior Entry, Crawl Space, Finished, Full, Partial, Unfinished
  • Has Fireplace: Yes
  • Cooling: Heat Pump
  • Has Cooling: Yes
  • Heating: Oil, Propane, Forced Air, Heat Pump, Hot Water, Zoned
  • Has Heating: Yes
  • Flooring: Carpet, Tile, Wood
  • Interior Features: 1st Floor Primary Bedroom w/Bath, Bathtub, Other, Shower, Storage, Walk-In Closet(s), Primary Bedroom w/Bath
  • Room Features: Exercise Room
Room Information
Primary Bedroom
  • Primary Bedroom: Primary Bedroom
  • Primary Bedroom Level: First
  • Primary Bedroom Amenities: Closet, Double Vanities, Full Bath, Separate Shower, Soaking Tub, Suite, Sunken/Raised, Walk-in Closet
Bedroom 2
  • Bedroom 2: Bedroom 2
  • Bedroom 2 Level: Second
  • Bedroom Amenities 2: Closet, Full Bath
Bedroom 3
  • Bedroom 3: Bedroom 3
  • Bedroom 3 Level: Second
  • Bedroom Amenities 3: Closet, Full Bath
Bedroom 4
  • Bedroom 4: Bedroom 4
  • Bedroom 4 Level: Second
  • Bedroom Amenities 4: Closet, Full Bath
Bedroom 5
  • Bedroom 5: Bedroom 5
  • Bedroom 5 Level: Second
  • Bedroom Amenities 5: Closet, Full Bath
Bedroom 6
  • Bedroom 6: Bedroom 6
  • Bedroom 6 Level: Second
  • Bedroom Amenities 6: Closet, Full Bath
Dining Room
  • Dining Room: Dining Room
  • Dining Room Level: First
  • Dining Room Amenities: Wood Burning Fireplace
Exercise Room
  • Exercise Room: Exercise Room
  • Exercise Room Level: Basement
Great Room
  • Great Room: Great Room
  • Great Room Level: Second
  • Great Room Amenities: Vaulted Ceiling, Wood Burning Fireplace
Kitchen
  • Kitchen: Kitchen
  • Kitchen Level: First
  • Kitchen Amenities: Eat-in Kitchen
Laundry
  • Laundry Room: Laundry
  • Laundry Room Level: First
  • Laundry Room Amenities: Main Level, Upper Level
Library
  • Library: Library
  • Library Level: First
  • Library Amenities: Wood Burning Fireplace
Living Room
  • Living Room: Living Room
  • Living Room Level: First
  • Living Room Amenities: Built-Ins, Vaulted Ceiling, Wood Burning Fireplace
Other Room 1
  • Other Room 1: Other Room 1
  • Other Room 1 Level: First
Other Room 2
  • Other Room 2: Other Room 2
  • Other Room 2 Level: Basement
Other Room 3
  • Other Room 3: Other Room 3
  • Other Room 3 Level: Basement
Office Room
  • Office: Office
  • Office Level: First
  • Office Amenities: Heat Stove Hookup
Rental
Rent Information
  • Land Lease: No

Property History for 866 Pendleton Point Road

DateEvent & SourcePriceAppreciation
Jun 16, 2026

Listed (Active)

Maine Listings #1667521

$5,750,000—
Dec 31, 2025

Expired

Maine Listings #1631135

$6,750,000—
Jul 15, 2025

Listed (Active)

Maine Listings #1631135

$6,750,000—
DateEvent & SourcePrice
06/16/2026

Listed (Active)

Maine Listings #1667521

$5,750,000
12/31/2025

Expired

Maine Listings #1631135

$6,750,000
07/15/2025

Listed (Active)

Maine Listings #1631135

$6,750,000

For completeness, we 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 Record2025$47,732 ($3,978 / 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 June 16, 2026 by Legacy Properties Sotheby's International Realty, it's currently listed at $5,750,000. It has been on the market for a total of 20 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 any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make 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. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved.