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Land with Home for Sale in Islesboro, Maine

866 Pendleton Point Rd, Islesboro, ME 04848

$5,750,000
5.25 acres
Active sale
ago
Est $33,705/mo

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 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.

9,449
Sq feet
6
Beds
6
Full baths
3
1/2 baths
2000
Built

Location

Street address
866 Pendleton Point Rd
Zip code
04848
Elevation
59 feet
Coordinates
44.2393, -68.922

Property details

Acreage
5.25 acres
Zoning
Shoreland Res
MLS #
MREIS 1667521
Posted

Parcels

  • ISBR-000006-000000-000006-C000000

Details and features

Listing

Type
Residential
Subtype
Single Family Residence
Franchise
Sotheby's International Realty

Lot

Waterfront
Yes
Features
Irrigation System, Level, Near Country Club, Near Golf Course, Near Public Beach, Open, Rolling/Sloping, Well Landscaped

Exterior

Parking
Carport
Structures
Storage

Structure

Style
Shingle
Basement
Crawl Space, Finished, Full, Partial, Unfinished
Water
Private, Well
Sewer
Private Sewer
Heating
Forced Air, Heat Pump, Hot Water, Oil, Propane, Zoned
Materials
Wood Frame, Wood Siding

Interior

Room Count
19
Rooms
Basement, Bathroom x 9, Bedroom x 6, Dining Room, Exercise Room, Laundry Room x 2
Flooring
Carpet, Tile, Wood
Features
1st Floor Primary Bedroom w/ Bath, Bathtub, Primary Bedroom w/ Bath, Shower, Walk-In Closets

Property utilities

CategoryTypeStatus
GasPropaneConnected

Listing history

DateEventPriceChangeSource
June 16, 2026New listing$5,750,000MREIS
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This 5.25-acre property is located at 866 Pendleton Point Rd in Islesboro, ME 04848. The property is available for sale, priced at $5,750,000. It has a 9,449 square foot 6-bedroom, 7.5-bath house built in 2000.

Listed by Legacy Properties Sotheby's International Realty, (207) 780-8900

Checked 1 hour agoUpdated Source

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