# 866 Pendleton Point Road, Islesboro, ME 04848 > **TL;DR:** 6bd/9ba single family, $5,750,000 ($609/sqft), built 2000, 9,449 sqft. > Fireplace, Waterfront, A/C. Est. $30,752/mo. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $5,750,000 | | Price/sqft | $609 | | Bedrooms | 6 | | Bathrooms | 6 full, 3 half | | Square Feet | 9,449 | | Year Built | 2000 | | Lot Size | 228,690 sqft (5.25 acres) | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 0 | ## Why This Home Stands Out - **Waterfront** - Waterfront location listed ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $29,075 | | Estimated Insurance | $1,677 | | **Total** | **$30,752** | ## Key Amenities - Fireplace - Waterfront - A/C ## Property Highlights - Built in 2000 - 5.25 acre lot - Fireplace - Waterfront ## Description ### Agent 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 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. ## Location - **Address:** 866 Pendleton Point Road, Islesboro, ME 04848 - **County:** Waldo - **Coordinates:** 44.239332, -68.922017 - **Google Maps:** https://www.google.com/maps?q=44.239332,-68.922017 ## Listing Agent - **Name:** Michael Lynch - **Brokerage:** Legacy Properties Sotheby's International Realty - **Phone:** 2075583131 - **Broker Phone:** (207) 780-8900 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/866-Pendleton-Point-Rd_Islesboro_ME_04848_M47785-48537?f=listhub&s=MREISME&m=1667521&c=propsimple) ## Photos ![866 Pendleton Point Road - Photo 1](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f820420773r.jpg) ![866 Pendleton Point Road - Photo 2](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f2114180903r.jpg) ![866 Pendleton Point Road - Photo 3](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f3923009906r.jpg) ![866 Pendleton Point Road - Photo 4](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f3359020066r.jpg) ![866 Pendleton Point Road - Photo 5](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f3375704836r.jpg) ![866 Pendleton Point Road - Photo 6](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f255873898r.jpg) ![866 Pendleton Point Road - Photo 7](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f3667180391r.jpg) ![866 Pendleton Point Road - Photo 8](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f313823404r.jpg) ![866 Pendleton Point Road - Photo 9](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f987674953r.jpg) ![866 Pendleton Point Road - Photo 10](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f1851558473r.jpg) ![866 Pendleton Point Road - Photo 11](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f881516774r.jpg) ![866 Pendleton Point Road - Photo 12](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f395650142r.jpg) ![866 Pendleton Point Road - Photo 13](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f1361145783r.jpg) ![866 Pendleton Point Road - Photo 14](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f2895489660r.jpg) ![866 Pendleton Point Road - Photo 15](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f1326641810r.jpg) ![866 Pendleton Point Road - Photo 16](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f600770438r.jpg) ![866 Pendleton Point Road - Photo 17](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f3915400174r.jpg) ![866 Pendleton Point Road - Photo 18](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f4194391877r.jpg) ![866 Pendleton Point Road - Photo 19](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f129986190r.jpg) ![866 Pendleton Point Road - Photo 20](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f2225343936r.jpg) ![866 Pendleton Point Road - Photo 21](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f2511012276r.jpg) ![866 Pendleton Point Road - Photo 22](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f3085255537r.jpg) ![866 Pendleton Point Road - Photo 23](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f185896961r.jpg) ![866 Pendleton Point Road - Photo 24](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f1117277245r.jpg) ![866 Pendleton Point Road - Photo 25](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f3968989549r.jpg) ![866 Pendleton Point Road - Photo 26](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f1681886335r.jpg) ![866 Pendleton Point Road - Photo 27](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f3347466385r.jpg) ![866 Pendleton Point Road - Photo 28](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f949725290r.jpg) ![866 Pendleton Point Road - Photo 29](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f1869613828r.jpg) ![866 Pendleton Point Road - Photo 30](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f2809323125r.jpg) ![866 Pendleton Point Road - Photo 31](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f682156763r.jpg) ![866 Pendleton Point Road - Photo 32](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f1182183535r.jpg) ![866 Pendleton Point Road - Photo 33](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f2600808069r.jpg) ![866 Pendleton Point Road - Photo 34](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f4124009005r.jpg) ![866 Pendleton Point Road - Photo 35](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f1618642253r.jpg) ![866 Pendleton Point Road - Photo 36](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f2174537577r.jpg) ![866 Pendleton Point Road - Photo 37](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f1429309734r.jpg) ![866 Pendleton Point Road - Photo 38](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f3025502778r.jpg) ![866 Pendleton Point Road - Photo 39](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f4026159275r.jpg) ![866 Pendleton Point Road - Photo 40](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f3450965708r.jpg) ![866 Pendleton Point Road - Photo 41](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f1459361318r.jpg) ![866 Pendleton Point Road - Photo 42](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f3360261466r.jpg) ![866 Pendleton Point Road - Photo 43](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f4072925810r.jpg) ![866 Pendleton Point Road - Photo 44](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f157515372r.jpg) ![866 Pendleton Point Road - Photo 45](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f760441877r.jpg) ![866 Pendleton Point Road - Photo 46](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f746236445r.jpg) ![866 Pendleton Point Road - Photo 47](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f1390847247r.jpg) ![866 Pendleton Point Road - Photo 48](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f2800652218r.jpg) ![866 Pendleton Point Road - Photo 49](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f3753815513r.jpg) ![866 Pendleton Point Road - Photo 50](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f1769902201r.jpg) ![866 Pendleton Point Road - Photo 51](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f4165642818r.jpg) ![866 Pendleton Point Road - Photo 52](http://lh.rdcpix.com/0335bea178b7add094fe8c07fcb34b3al-f48748891r.jpg) --- **MLS#:** 1667521 | **Updated:** 2026-09-14 **Source:** listhub *Copyright © 2026 Maine Listings. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/866-pendleton-point-road-islesboro-me-04848-1667521) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/866-pendleton-point-road-islesboro-me-04848-1667521#listing", "url": "https://www.propertysimple.ai/listing/866-pendleton-point-road-islesboro-me-04848-1667521", "name": "866 Pendleton Point Road, Islesboro, ME 04848", "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 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. 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