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
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. Copyright ©2022 Maine Real Estate Information System, Inc. All Rights Reserved. Equal Housing Opportunity.

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