866 Pendleton Point Road, Islesboro, ME 04848

$6,750,000
Property Type: Residential Bedrooms: 6 Baths: 9 Square Footage: 9,449 Lot Size (sq. ft.): 228,690 Status: Active
Current Price: $6,750,000 List Date: 7/19/2025 Last Modified: 9/24/2025

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 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.

Supplements: ********

More Information MLS# 1631135

Property Sub-Type

Property Sub-Type: Single Family Residence

Location Information

Book: 4820 Leased Land: No Page: 172 Map: 6 Lot: 6 Zoning Overlay: Unknown Association: No Tree Growth Y/N: No Street #: 866 Street Name: Pendleton Point Street Type: Road County: Waldo Town: Islesboro State/Province: ME Zip Code: 04848 Zip +4: 5159 Zoning: Shoreland Res Full Tax Amount $: 44550 Tax Year: 2024 Geo Lat: 44.239334 Geo Lon: -68.922012

Property Information

Surveyed: Unknown Seasonal: No Lot Size Acres +/-: 5.25 # Rooms: 19 Total Baths: 9 Total Half Baths: 3 Road Frontage: No # Fireplaces: 4 SqFt Finished Above Grade: 8696 SqFt Finished Below Grade: 753 SqFt Source: Other Other Source of Square Footage: Floor Plans Garage: No Garage Spaces: 0 # Bedrooms: 6 Total Full Baths: 6 Year Built: 2000 SqFt Finished Total: 9449 Source of Acreage: Public Records

Site

Level: 1 Open: 1 Rolling/Sloping: 1 Well Landscaped: 1

Location

Other Location: 1

Roads

Private Road: 1 Public: 1

Water Info

Water Frontage: Yes Waterfront Amount: 429 Water Frontage Owned: 429 Water Frontage Shared: 0 Water View: Yes Water Body Name: Penobscot Bay

Source of Water Frontage

Public Records: 1

Water Body Type

Bay: 1 Ocean: 1

Construction

Wood Frame: 1

Basement

Crawl Space: 1 Finished: 1 Full: 1 Partial: 1 Unfinished: 1

View

Scenic: 1

Foundation Materials

Poured Concrete: 1

Exterior

Wood Siding: 1

Roof

Shingle: 1

Heat System

Forced Air: 1 Heat Pump: 1 Hot Water: 1

Heat Fuel

Oil: 1 Propane: 1

Cooling

Heat Pump: 1

Floors

Carpet: 1 Tile: 1 Wood: 1

Parking

5 - 10 Spaces: 1

Style

Shingle: 1

Electric

Circuit Breakers: 1 Underground: 1

Gas

Bottled: 1

Sewer

Private Sewer: 1 Septic Tank: 1

Bedroom 2

Bedroom 2: 1 Bedroom 2 Level: Second

Water

Private: 1 Well: 1

Bedroom Amenities 2

Closet: 1 Full Bath: 1

Bedroom 3

Bedroom 3: 1 Bedroom 3 Level: Second

Bedroom Amenities 3

Closet: 1 Full Bath: 1

Bedroom 4

Bedroom 4: 1 Bedroom 4 Level: Second

Bedroom Amenities 4

Closet: 1 Full Bath: 1

Bedroom 5

Bedroom 5: 1 Bedroom 5 Level: Second

Bedroom Amenities 5

Closet: 1 Full Bath: 1

Bedroom 6

Bedroom 6: 1 Bedroom 6 Level: Second

Bedroom Amenities 6

Closet: 1 Full Bath: 1

Driveway

Gravel: 1

Basement Entry

Bulkhead: 1 Interior: 1

Water Heater

Off Heating System: 1

Amenities

1st Floor Primary Bedroom w/Bath: 1 Bathtub: 1 Irrigation System: 1 Laundry - 1st Floor: 1 Laundry - 2nd Floor: 1 Other Amenities: 1 Pool-In Ground: 1 Primary Bedroom w/Bath: 1 Shower: 1 Storage: 1 Walk-in Closets: 1

Equipment

Generator: 1 Other Equipment: 1

Vehicle Storage

1 Car: 1 Carport: 1 Attached: 1

Dining Room

Dining Room: 1 Dining Room Level: First

Dining Room Amenities

Wood Burning Fireplace: 1

Exercise Room

Exercise Room: 1 Exercise Room Level: Basement

Great Room

Great Room: 1 Great Room Level: Second

Great Room Amenities

Vaulted Ceiling: 1 Wood Burning Fireplace: 1

Kitchen

Kitchen: 1 Kitchen Level: First

Kitchen Amenities

Eat-in Kitchen: 1

Laundry Room

Laundry: 1 Laundry Room Level: First

Library

Library: 1 Library Level: First

Library Amenities

Wood Burning Fireplace: 1

Living Room

Living Room: 1 Living Room Level: First

Living Room Amenities

Built-Ins: 1 Vaulted Ceiling: 1 Wood Burning Fireplace: 1

Primary Bedroom

Primary Bedroom: 1 Primary Bedroom Level: First

Primary Bedroom Amenities

Closet: 1 Double Vanities: 1 Full Bath: 1 Separate Shower: 1 Suite: 1

Office

Office: 1 Office Level: First

Office Amenities

Heat Stove Hookup: 1

Other Room 1

Other Room 1: 1 Other Room 1 Level: First

Other Room 2

Other Room 2: 1 Other Room 2 Level: Basement

Other Room 3

Other Room 3: 1 Other Room 3 Level: Basement

Room Features

Built-Ins: 1 Closet: 1 Double Vanity: 1 Eat-in Kitchen: 1 Full Bath: 1 Heat Stove Hookup: 1 Separate Shower: 1 Storage: 1 Suite: 1 Vaulted Ceiling(s): 1 Wood Burning Fireplace: 1

Contract Information

Status: Active Original List Price: 6750000 List Price: $6,750,000 Current Price: $6,750,000

Property Features

Site: Level; Open; Rolling/Sloping; Well Landscaped Location: Other Location Roads: Private Road; Public Source of Water Frontage: Public Records Water Body Type: Bay; Ocean View: Scenic Style: Shingle Construction: Wood Frame Basement: Crawl Space; Finished; Full; Partial; Unfinished Basement Entry: Bulkhead; Interior Foundation Materials: Poured Concrete Roof: Shingle Exterior: Wood Siding Heat System: Forced Air; Heat Pump; Hot Water Heat Fuel: Oil; Propane Water Heater: Off Heating System Cooling: Heat Pump Floors: Carpet; Tile; Wood Amenities: 1st Floor Primary Bedroom w/Bath; Bathtub; Irrigation System; Laundry - 1st Floor; Laundry - 2nd Floor; Other Amenities; Pool-In Ground; Primary Bedroom w/Bath; Shower; Storage; Walk-in Closets Equipment: Generator; Other Equipment Driveway: Gravel Parking: 5 - 10 Spaces Vehicle Storage: 1 Car; Carport Electric: Circuit Breakers; Underground Gas: Bottled Sewer: Private Sewer; Septic Tank Water: Private; Well

Room Information

Primary Bedroom Level: First Bedroom 2 Level: Second Bedroom 3 Level: Second Bedroom 4 Level: Second Bedroom 5 Level: Second Bedroom 6 Level: Second Other Room Level: First Library Level: First Living Room Level: First Dining Room Level: First Kitchen Level: First Office Level: First Great Room Level: Second Office Level: Second Laundry Level: First Office Level: First Exercise Room Level: Basement Other Room 3 Level: Basement Other Room 2 Level: Basement

Documents

Listing Office: Legacy Properties Sotheby's International Realty
IDX
Last Updated: September - 24 - 2025
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