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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.
Property Listed by: Legacy Properties Sotheby's International Realty
Exceptional piece of land located in a quiet and secluded gated community in a quaint little oceanside town. Great place to build your primary residence or construct a second home and enjoy all four seasons that Maine has to offer.
Property Listed by: Your Home Sold Guaranteed Realty
This modernized home has seen extensive upgrades over the past couple of years including, siding, roofing, kitchen, bathroom, electrical, plumbing, and many others!! Plenty of space with a great layout with a large dining and living area are a couple of the great features you will find inside this home! There is a 27x30 slab prepared and ready for a new garage.
Property Listed by: Amero Realty
This property features two very nice apartments, both offering a bright and airy feel throughout. The top unit boasts beautiful cathedral ceilings that add a sense of space and charm, while both apartments enjoy plenty of natural light. Conveniently located just a short drive to town, the property includes a one-car garage in the basement—perfect for either parking or additional storage. An extra outbuilding on the property also provides ample room for storing tools, bikes, or seasonal items. Whether you're looking to live in one and rent the other, or add to your investment portfolio, this setup checks all the boxes.
Property Listed by: Lone Pine Real Estate Company
Great opportunity to run the only store on the island, The Island Market & Supply, known as TIMS, is searching for a new owner. Its current owners of ten years are selling so that they may focus on their second business, Swan's Island Freight. The store is small but compact with all the necessities that people are looking for on the island and a great chance to have a very important role in the community. TIMS offers pantry staples, baked goods and beverages, fresh produce, meats and seafood, dairy and ice cream, specialty cured meats and cheeses, and prepared meals. Daily lunch specials and pizzas made to order on evenings are prepared in a concession trailer with a commercial kitchen. Turnkey operation, Real Estate, FF&E, inventory, and a propane filling station included in sale. Strong numbers and the owners will help with the transition.
Property Listed by: Better Homes & Gardens Real Estate/The Masiello Group
Great Opportunity! Discover the perfect opportunity to own your slice of Down East Maine with these four beautiful subdivided lots nestled in the serene town of Addison. Located in a subdivision close to beaches, nature trails, and local amenities. Power available at the road. Lots have been surveyed.
Property Listed by: Better Homes & Gardens Real Estate/The Masiello Group
This beautiful 15.4 acres lot of land is located in Monson, ME, just over the Abbot line. The lot has lots of tree cover and is currently off grid. Power has come in the road but poles will be needed to get to this lot. There are lots of berry bushes and a couple of streams on the land. There are also meandering paths through the woods to enjoy. There is also a water spring on the land that runs most of the year. The land owners in this subdivision are starting to form a road association and will continue to work on this to care for the road that is need of some work. Monson is a town that is situated perfectly between outdoor amenities such as hiking, boating, fishing, swimming and more. This lot is right near the ITS trail system and has access. The lot is currently in tree growth and the owners are working with the town to remove one lot from tree growth. This lot is part of the Winter Hill Subdivision and a soil test was taken on the corner of this lot when the subdivision was formed. The owner does not have that paperwork. There is a 12 X 24 shed that will be included in the sale. This is a beautiful lot, ready for you to enjoy!
Property Listed by: NextHome Experience
Raw land opportunity with this 24-acre parcel of land in Waterford situated on a hill leaving a vision for clearing and views. There is a driveway that is currently used by an abutter as a right of way and this property. It has been many years since the lot was last cleared, and it is overgrown. Seller states there were views last time the land was cleared at the top and there could be value in the wood, a buyer is responsible for due diligence to determine. The property features 300ft of road frontage based on town tax maps. Located on a town-maintained road with power nearby if you build close to Temple Hill Rd. Near Harrison & Waterford amenities, Crystal, Long, & Keoka Lakes are all within 10 -15 minutes away. Mt. Tirem for hiking is also close by. Bring your visions!
Property Listed by: Kezar Realty
Build your dream retreat on this surveyed 14.8-acre parcel with 480' of frontage on the Carrabassett River. Perfect for swimming, kayaking, canoeing, or simply enjoying the peaceful river views. In spring, enjoy harvesting wild fiddleheads along the water's edge. Direct access to ITS 84 makes this a snowmobiler's paradise in winter. Whitewater rafting on the Kennebec and world-class skiing at Sugarloaf are just 35 minutes away. Located off a private, gated road for added seclusion in a beautiful rural setting.
Property Listed by: EXP Realty
Opportunity awaits! This property offers a large home with 5 bedrooms including a primary on the first floor with a full bathroom. Along with a spacious home comes a great 2 bedroom apartment with a separate entrance! This two bedroom apartment is registered with the town, is cute and charming. It is just the right size for a rental or owner occupied with easy heat pump heating and cooling! Many important updates have been to the structure within the last 10 years including the roof, heating system, plumbing, electrical, flooring and the addition of a pool space! With great proximity to Baxter State Park, Katahdin Woods & Water Monument & The Penobscot River Trails rental possibilities are knocking! 18 Beech Street is an available lot that is being sold as part of this transaction. The lot can be built resold, built on for a single family home or a large garage. More income possibilities can be imagined. Schedule a showing today and enjoy all the area has to offer for the upcoming seasons!
Property Listed by: Portside Real Estate Group
Listing data is derived in whole or in part from the Maine IDX and is for consumers' personal, non-commercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved.
