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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New
New
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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.
  1. Listed by Michael Lynch • Legacy Properties Sotheby's International Realty

Property Details for 866 Pendleton Point Road

Waterfront
Yes
ArchitecturalStyle
Shingle
Garage Spaces
.00
Garage
No
Zoning
Shoreland Res
View
Scenic
LISTING UPDATED: 06/16/2026 10:06 PM

Property Details for 866 Pendleton Point Road

StatusActive
MLS #1667521
Days on Market1
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

Payment Calculator

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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 Body Name: Penobscot Bay, Ocean
  • Zip Code: 5159
  • Town: Islesboro
  • State/Province: ME
  • Zip Code: 04848
  • County: Waldo
  • Geo Latitude: 44.239332
  • Geo Longitude: -68.922017
  • Tax Lot: 6
  • Site:Level: Yes
  • Site:Open: Yes
  • Site:Other Site: Yes
  • Site:Rolling/Sloping: Yes
  • Site:Well Landscaped: Yes
  • Location:Near Country Club: Yes
  • Location:Near Golf Course: Yes
  • Location:Near Public Beach: 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
  • Construction: Wood Frame
  • Road Frontage: false
  • Water View2: Yes
  • Tree Growth YN2: false
Parking
  • Parking Features: Gravel, Carport, 5 - 10 Spaces
  • Attached Garage: Yes
  • Parking: 5 - 10 Spaces
Taxes and HOA Information
  • Tax Book Number: 4820
  • Tax Map Number: 6
  • Tax Year: 2025
  • Parcel Number: ISBR-000006-000000-000006-C000000
  • Location Information:Association Y/N: No
  • Tax Annual Amount: $47,732.00
Virtual Tour
Property
Green Features
  • HERS Certified: No
Heating and Cooling
  • Water Heater:Off Heating System: Yes
  • Heat Fuel: Oil, Propane
  • Heat System: Forced Air, Heat Pump, Hot Water, Multi-Zones
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: Matterport Floor Plans, Estimated
  • 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
  • Driveway: Gravel
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: Circuit Breakers
  • Sewer: Private Sewer
  • Water Source: Private, Well
  • Other Equipment: Internet Access Available, Generator
  • Appliances Included:Dishwasher: Yes
  • Appliances Included:Dryer: Yes
  • Appliances Included:Electric Range: Yes
  • Appliances Included:Gas Range: Yes
  • Appliances Included:Microwave: Yes
  • Appliances Included:Refrigerator: Yes
  • Appliances Included:Wall Oven: Yes
  • Appliances Included:Washer: Yes
  • Appliances Included:Other: Yes
  • Appliances Included:Other Appliances: See listing remarks
  • Gas:Bottled: Yes
  • Water Heater: Off Heating System
  • Appliances: Other, Washer, Wall Oven, Refrigerator, Microwave, Gas Range, Electric Range, Dryer, Dishwasher
  • Equipment: Generator, Internet Access Available
Interior and Exterior Features
Exterior Features
  • Construction Materials: Wood Frame, Wood Siding
  • # Fireplaces: 4
  • Fireplace: Yes
  • Vehicle Storage:1 Car: Yes
  • Vehicle Storage:Carport: Yes
  • Roof: Shingle
  • Vehicle Storage: 1 Car, Carport
  • Basement Entry: Bulkhead2, Interior
Interior Features
  • Basement: Crawl Space, Finished, Full, Partial, Unfinished
  • Flooring: Carpet, Tile, Wood
  • Interior Features: Other Amenities, Walk-in Closets, 1st Floor Primary Bedroom w/Bath, Bathtub, Shower, Storage, Primary Bedroom w/Bath
  • Cooling: Heat Pump
  • Heating: Oil, Propane, Forced Air, Heat Pump, Hot Water, Zoned
  • Foundation Details: Poured Concrete
  • Laundry Features: 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
  • Dining Room Amenities: Wood Burning Fireplace8
  • Amenities: 1st Floor Primary Bedroom wBath, Bathtub, Irrigation System, Laundry - 1st Floor, Laundry - 2nd Floor, Other Amenities, Pool-In Ground, Primary Bedroom wBath, Shower, Storage, Walk-in Closets
  • Great Room Amenities: Vaulted Ceiling11, Wood Burning Fireplace11
  • Kitchen Amenities: Eat-in Kitchen
  • Library Amenities: Wood Burning Fireplace13
  • Living Room Amenities: Built-Ins14, Vaulted Ceiling14, Wood Burning Fireplace14
  • Primary Bedroom Amenities: Closet7, Double Vanities6, Full Bath7, Separate Shower6, Soaking Tub6, Suite6, SunkenRaised15, Walk-in Closet6
Room Information
Room 1
  • Room Type: Primary Bedroom
  • Room Level: First
Room 2
  • Room Type: Bedroom 2
  • Room Level: Second
  • Bedroom Amenities 2: Closet2, Full Bath2
Room 3
  • Room Type: Bedroom 3
  • Room Level: Second
  • Bedroom Amenities 3: Closet3, Full Bath3
Room 4
  • Room Type: Bedroom 4
  • Room Level: Second
  • Bedroom Amenities 4: Closet4, Full Bath4
Room 5
  • Room Type: Bedroom 5
  • Room Level: Second
  • Bedroom Amenities 5: Closet5, Full Bath5
Room 6
  • Room Type: Bedroom 6
  • Room Level: Second
  • Bedroom Amenities 6: Closet10, Full Bath8
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
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 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.