$5,750,000
6 Beds
7.5 Baths
9,449 sqft (on 5.25 acres)
866 Pendleton Point Road, Islesboro, ME 04848
Est. Mortgage $34,446/mo*
Get Pre-QualifiedWe estimate this home will sell faster than 96% nearby.
Home Highlights
Property Type
Single-Family Home
Year Built
2000
Lot Size
5.25 acres
Price/Sqft
$609
Parking
Attached Garage
Local Information
- Map ViewExplore the area around 866 Pendleton Point Road.
- Schools1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Last check for updates: about 11 hours ago
Listing courtesy of Legacy Properties Sotheby's International Realty
Source: Maine Listings, MLS#1667521
Also Listed on Maine Listings.
About this House
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.
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.
We estimate this home will sell faster than 96% nearby.
Home Details for 866 Pendleton Point Road
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MLS Status: Active |
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Interior Details Basement: Bulkhead,Interior Entry,Crawl Space,Finished,Full,Partial,UnfinishedNumber of Rooms: 19Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Bedroom 6, Dining Room, Exercise Room, Great Room, Kitchen, Laundry, Library, Living Room, Office, Other Room, Other Room 2, Other Room 3 |
Beds & Baths Number of Bedrooms: 6Number of Bathrooms: 9Number of Bathrooms (full): 6Number of Bathrooms (half): 3 |
Dimensions and Layout Living Area: 9449 Square Feet |
Appliances & Utilities Appliances: Dishwasher, Dryer, Microwave, Electric Range, Gas Range, Refrigerator, Wall Oven, Washer, OtherDishwasherDryerMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Forced Air,Heat Pump,Hot Water,ZonedHas CoolingAir Conditioning: Heat PumpHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa Number of Fireplaces: 4Has a Fireplace |
Gas & Electric Electric: Circuit Breakers |
Windows, Doors, Floors & Walls Flooring: Carpet, Tile, Wood |
Levels, Entrance, & Accessibility Floors: Carpet, Tile, Wood |
View Has a ViewView: Scenic |
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Exterior Home Features Roof: ShingleFoundation: Poured ConcreteHas a Private Pool |
Parking & Garage Has a CarportNo GarageHas an Attached GarageParking: Gravel,5 - 10 Spaces,Carport |
Pool Pool |
Frontage WaterfrontOn Waterfront |
Water & Sewer Sewer: Private SewerWater Body: Penobscot Bay, Ocean |
Farm & Range Frontage Length: Waterfrontage: 429, Waterfrontage Owned: 429 |
Finished Area Finished Area (above surface): 8696 Square FeetFinished Area (below surface): 753 Square Feet |
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Days on Market: 76 |
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Year Built Year Built: 2000 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Shingle |
Building Construction Materials: Wood Frame, Wood Siding |
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Price List Price: $5,750,000Price Per Sqft: $609 |
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Direction & Address City: Islesboro |
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Listing Agent Listing ID: 1667521 |
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Building Area Building Area: 9449 Square Feet |
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Lot Area: 5.25 Acres |
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BasementMls Number: 1667521Above Grade Unfinished Area: 8696 |
Around this home
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.
What Locals Say about Islesboro
At least 2 Trulia users voted on each feature.
100 % Say parking is easy
100 % Say it's dog friendly
100 % Say kids play outside
100 % Say people would walk alone at night
100 % Say yards are well-kept
100 % Say it's quiet
100 % Say there's wildlife
100 % Say car is needed
83 % Say neighbors are friendly
50 % Say there's holiday spirit
50 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
Market trends in Islesboro
Last updated July 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
31
4MoM
Home Value
Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
1.51 | Single-Family Home | $345,000 | 05/28/26 | 4 | 1.5 | 2,200 | |
2.23 | Single-Family Home | $515,000 | 06/01/26 | 2 | 1.5 | 1,463 | |
3.54 | Single-Family Home | $1,325,000 | 09/23/25 | 3 | 2.5 | 3,714 | |
3.31 | Single-Family Home | $430,000 | 09/09/25 | 3 | 2 | 2,400 | |
3.25 | Single-Family Home | $500,000 | 02/02/26 | 2 | 1.5 | 825 | |
3.10 | Single-Family Home | $348,936 | 12/30/25 | - | - | ||
4.23 | Single-Family Home | $835,000 | 10/31/25 | 4 | 2 | 2,258 | |
4.46 | Single-Family Home | $425,000 | 06/03/26 | 5 | 1.5 | 2,409 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.79 | $7,734,400 | 15 | 16.5 | 13,200 | Off Market | |
1.43 | - | 7 | 4.5 | 4,131 | Off Market | |
1.51 | $345,000 | 4 | 1.5 | 2,200 | Recently Sold |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Jun 16, 2026 Source: Maine Listings #1667521 | Listed For Sale | $5,750,000 |
Jan 1, 2026 Source: Maine Listings #1631135 | ListingRemoved | $6,750,000 |
Jul 19, 2025 Source: Maine Listings #1631135 | Listed For Sale | $6,750,000 |
Jul 14, 2022 Source: Maine Listings #1523560 | Sold | $4,500,000 |
Jun 21, 2022 Source: Maine Listings #1523560 | Pending | $4,850,000 |
Jun 21, 2022 Source: Maine Listings #1523560 | Contingent | $4,850,000 |
Apr 18, 2022 Source: Maine Listings #1523560 | Listed For Sale | $4,850,000 |
Jun 30, 2018 Source: Agent Provided | ListingRemoved | $4,875,000 |
Aug 12, 2017 Source: Agent Provided | Listed For Sale | $4,875,000 |
Nov 20, 2010 Source: Agent Provided | ListingRemoved | $2,500,000 |
Jul 15, 2010 Source: Agent Provided | Listed For Sale | $2,500,000 |
Jun 11, 2009 Source: Agent Provided | ListingRemoved | $2,750,000 |
May 22, 2009 Source: Agent Provided | Listed For Sale | $2,750,000 |
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Legacy Properties Sotheby's International Realty
Listing data is derived in whole or in part from Maine Real Estate Information System, Inc. (d/b/a Maine Listings) 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. Equal Housing Opportunity.
Zillow Inc. 415 Congress St #202 Portland, ME 04101 206-424-8443
Zillow Inc. 415 Congress St #202 Portland, ME 04101 206-424-8443
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Frequently asked questions about 866 Pendleton Point Road
- What is the estimated monthly payment for 866 Pendleton Point Road?Based on a $5,750,000 list price with 20% down at today's rates, the estimated monthly payment for 866 Pendleton Point Road in Islesboro, ME is approximately $35,666 (about $30,416 principal & interest, $5,175 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- What are the closest schools to 866 Pendleton Point Road?The closest schools to 866 Pendleton Point Road in Islesboro, ME are Islesboro Central School (Elementary/Middle/High, rated 9/10).
- Does 866 Pendleton Point Road have air conditioning?Yes, 866 Pendleton Point Road in Islesboro, ME has air conditioning.
- Does 866 Pendleton Point Road have a pool?Yes, 866 Pendleton Point Road in Islesboro, ME has a pool.
- Does 866 Pendleton Point Road have laundry facilities?Yes, 866 Pendleton Point Road in Islesboro, ME has in-unit laundry.
- How big is the lot at 866 Pendleton Point Road?The lot at 866 Pendleton Point Road in Islesboro, ME is about 5.3 acres.
866 Pendleton Point Road, Islesboro, ME 04848 is a 6 bedroom, 9 bathroom, 9,449 sqft single-family home built in 2000. This property is currently available for sale and was listed by Maine Listings on Jun 16, 2026. The MLS # for this home is MLS# 1667521.