Westport Island, Maine listings for sale

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$3,995,000 - Westport Island, ME
92 Brooks Cove Road Westport Island, ME - Move quickly to see this luxury home with over a half-mile of waterfront enjoying protected deep water and stunning sunsets. A wonderland of luxurious privacy and immense opportunity awaits you at this peninsula estate overlooking Robinhood Cove, Knubble Bay, Goose Rock Passage, and the Little Sheepscot River. Boasting over 20 acres of prime west-facing waterfront, this property can easily support a sprawling family compound or additional waterfront lots. With 1000s of feet of sunlit shoreline, this is without doubt Maine's most epic deep water offering in decades. Enjoy sunrises over MacMahan Island while the granite patio beneath your feet gathers heat from the morning rays. Leave your phone behind and push off for a picnic out to Damariscove Island. Set sail on that classic sloop or chase tuna around Sheepscot Bay with the Hinckley, this epicenter of midcoast boating is the perfect departure point. Excellent small boating here, too! End your day at a fire ring with IPAs, local oysters, and captivating sunsets! This handsome shingle-style home newly built by Chartier Construction boasts an open floor plan, one floor living, and well-appointed guest accommodations on the second floor. Amenities are endless here, including a slate foyer, white oak flooring, custom tiles, and fine woodworking. A chef's kitchen awaits, boasting spacious areas for cooks and guests alike, with water views in nearly all directions. Whether it is a soaking tub, fireplace, or a protected deepwater dock that is at the top of your list, this property checks all the boxes. Explore development on this expansive private peninsula and cove or reserve for family and friends. This property has substantial capacity for whatever the future might bring. Rare end of the road location assures the highest level of privacy affordable without compromises -- proximate to Portland, Boothbay, Bath/Brunswick and more! Many restaurants are just a quick boat ride away.
2021 | 3 | 2 | 3,305 sqft.
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$1,800,000 - Westport Island, ME
33 & 30 Taylor Road Westport Island, ME - Exclusive Waterfront Estate. Nestled along the picturesque Sheepscot, this exceptional waterfront estate offers a rare blend of refined country living, natural beauty, and seclusion. The 3-Bdrm, 2-Bath Primary Residence with an expansive deck presents sweeping water views, as well as the ideal perch from which to view eagles & osprey soaring about the estate. From the spacious living area, to the vaulted ceilings, to the breakfast nook & beyond, the home includes thoughtful features throughout. The 2-car garage includes a handy work room, as well as spacious 2nd floor storage. A separate Guest Cottage - rebuilt from the frame in 2015 - offers additional comfort and privacy, complete with its own deck & 2-car garage. The Guest House also presents a compelling income opportunity (rental income history available). The property features a private Deep-Water Dock w/ an impressive stairway to the water, providing direct access south to Boothbay Harbor, Robinhood Marina, & the Ocean—ideal for boating enthusiasts and coastal adventurers alike. The professionally landscaped grounds have been cultivated over decades to create a seasonal paradise, bursting with color throughout the seasons. Outdoor living is elevated with a Bocce Court, fire pit, & park-like clearing In wooded areas—perfect for strolls or wildlife watching. Striking stone and wood sculptures mark the entrance to this unique property, offering a sense of arrival and artistry. Whether enjoying quiet mornings on the deck, launching a kayak or boat from your dock, or entertaining guests in a setting of timeless coastal charm, this estate is a truly special place to call home. From this estate, you feel you are a world away... Yet minutes to restaurants & shopping. Primary Residence expanded in 2000, renovations to 2023. Guest House renovated 2015. 4,380 sq ft = 3,200 (Primary Res) + 1,180 (Guest House). Westport Isl offers the exceptional benefit of School Choice & low Property Tax rate.
1974 | 6 | 3 | 4,380 sqft.
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$1,295,000 - Westport Island, ME
178 Main Road Westport Island, ME - BEAUTIFULLY RENOVATED Circa 1820s WESTPORT ISLAND FARMHOUSE This finely renovated Colonial style Farmhouse rests on 7.3+/- acres of deep-water frontage on the Sheepscot River, and is located on highly coveted Westport Island, Maine! This 3-story home features 3,346+/- sf of light airy living spaces and has been completely renovated with great attention to detail. The 1st floor includes a beautiful kitchen with exceptional views of the river with dining and living spaces and 1/2 bath. The 2nd floor includes several bedrooms, study/reading spaces and two full baths, and the ''attic'' space includes two more bedrooms and another full bath. From this home you can watch incredible sunrises directly over the Sheepscot River from your easterly facing rear porch and deck; then later in the day, enjoy exceptional sunsets from your west facing front porch and covered/converted greenhouse structure. Imagine for a moment taking your golf cart with fishing supplies in-hand down to the pier and dock to fish for the morning, or spending family time picnicking down by the river or enjoying an evening firepit in the vast open space, or even more exciting would be to imagine building a new home closer to the Sheepscot River and use the existing home as guest space creating a truly superb family compound or use it as an income producing vacation rental destination - so much room and so many possibilities! There is 15+/- feet of deep water at the float at mean low water and a riverside shed building for all your boating/fishing supplies and equipment. And if that is not enough, this impressive offering comes fully furnished with all furniture, kitchen dishware, pots and pans, and even the zero-turn mower!
1820 | 5 | 4 | 3,346 sqft.
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$1,150,000 - Westport Island, ME
51 Malone Road Westport Island, ME - Waterfront - Overlooking the Sheepscot (Back) River/Cowseagan Narrows, just a short distance to Wiscasset Harbor, Yacht Club & all its fine shops and restaurants, this exceptional Texas-style home was built in the early 1960s with the finest craftsmanship and materials of the day! Sitting on nearly 9 acres of land with 600+/- feet of water frontage, this unique 2-story home, barn and waterfront provide total privacy, yet located close to everything Mid-Coast Maine has to offer. This well-built and maintained home is super clean and features 2,604+/- sf of living space, including a fully applianced kitchen w/large walk-in pantry (floor to ceiling shelving) & brick charcoal BBQ grill vented directly to its own chimney flue. A further walk-through the home offers a formal dining room, large living room with brick fireplace, 4 bedrooms, including master suite w/full bath & large walk-in closet, library/media/music room w/its own fireplace, an office, a laundry room and 2.5 baths. Off the formal dining room is an elevated 3-season furnished screened porch excellent for entertaining guests. The open attic space above is full length w/lighting & built-in shelving providing huge amounts of additional storage. The heated 2-bay garage provides direct entry to living space, generator hook-up & heated project workshop. The separate barn has south-facing glass providing lots of natural light w/space for 2 more vehicles, landscaping tools/equipment and a full second floor for small projects and additional storage. From this home you will enjoy incredible natural light/sunrises coming up directly over the Sheepscot River from your easterly facing front yard, porch and café style dining table in the kitchen. Later in the day, this property provides exceptional sunsets from westerly facing spaces, screened porch & water's edge ramp and float. The grounds have beautiful rolling plush lawns, shade trees, well defined garden spaces, & mature plantings! High quality must see offering!
1960 | 4 | 2 | 2,604 sqft.
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$1,100,000 - Westport Island, ME
3 Rocky Road Westport Island, ME - Perched on an exclusive, private road on Westport Island, this classic 3-bedroom, 2 1/2-bath waterfront home offers unmatched tranquility and stunning elevated views of the Sheepscot. This updated, meticulously maintained home features a spacious open layout with optional one-floor living, spectacular great room with fireplace and custom chimney, an attached garage, and expansive water side decks ideal for relaxing or entertaining, as you take in the ever-changing tides and deep water vistas. Perched above the shoreline for added privacy and dramatic views, the property offers the rare potential for a deep-water dock—perfect for boating enthusiasts. Enjoy the peace and quiet of this secluded location while just a short drive from Wiscasset and Midcoast Maine amenities. Most furnishings are included, making this an ideal opportunity for a turn-key coastal retreat or year-round residence. Additionally, benefit from School Choice and low property tax rate on Westport Island! On-island activities include hiking, kayaking & boating, yoga, local produce farm, brewery w/outdoor summer activities, historic inn, community association, and more. Experience the best of Maine waterfront living on beautiful Westport Island...
1986 | 3 | 2 | 2,270 sqft.
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$985,000 - Westport Island, ME
49 Moose Walk Road Westport Island, ME - Tucked away on picturesque Westport Island—surrounded by the serene Sheepscot River to the east and the Sasanoa River to the west—this beautiful custom home is a balance of elegance, comfort, and classic Maine charm. With 3-4 bedrooms, 3.5 baths, and over 2,500 square feet of living space, the home is a retreat for those seeking privacy, beauty, and connection to the water. Built with enduring materials and an eye for detail, the open-concept layout is anchored by a striking Douglas Fir timber frame and a cathedral-ceilinged living room featuring a stone fireplace. The main level offers radiant heat beneath Douglas Fir floors, blending warmth with rustic sophistication. A screened porch with a tropical hardwood (Garapa) and deck beside the hot tub offer idyllic indoor-outdoor living. The kitchen is designed with cherry Durawood cabinetry, granite countertops, a large apron-front sink, oversized island with seating, induction cooktop, KitchenAid double wall oven, and pantry storage. Adjacent is a light-filled dining area beneath a soaring ceiling—perfect for hosting. The first-floor primary suite is a peaceful escape with patio doors opening to a private deck and hot tub. The ensuite bath features a glass shower, soaking tub and a walk-in closet for ample storage. The tiled entry/mudroom and laundry area with built-ins add everyday practicality. Upstairs, two spacious bedrooms (one with a private deck), a shared full bath with double vanity, and an office nook overlook the living space below. A large bonus room above the 3-car garage includes its own full bath—ideal for guests. Outdoor features include: a fenced-in yard, perennial gardens, potting shed, fieldstone walkways and fire pit. A deepwater dock opportunity adds appeal for boating enthusiasts. This is quintessential midcoast Maine living—private, peaceful, and perfectly designed for comfort and enjoyment.
2005 | 4 | 4 | 2,691 sqft.
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$975,000 - Westport Island, ME
15 Lewis Drive Westport Island, ME - Deepwater Front home with exceptional views on the Sheepscot River is now available. Full basement has exercise room and workshop areas , the partially unfinished second floor offers numerous possibilities added to the private setting with two locations that used to have the pier/runway /float make this a great spot for your next adventure . Whether you are year round or seasonal the local community will welcome you. A well rounded town with many services along with the services from the county and town of Wiscasset add to the comfort and peace of mind you will find here. If you are a boater or like to fish the Sheepscot can be your new paradise !
1960 | 2 | 1 | 1,414 sqft.
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$785,000 - Westport Island, ME
36 Hodgdon Road Westport Island, ME - Welcome to your private riverside retreat in Westport! This unique property boasts an impressive 443 feet of river frontage, including a charming 2-bedroom cabin and a spacious boathouse, all nestled on a sprawling 2.8-acre lot. Enjoy the luxury of having your own deep-water docks, perfectly situated to capture the stunning westerly views and breathtaking sunsets every evening. The cabin and boathouse are both equipped with their own private docks, ensuring easy access to the water for boating, fishing, or simply relaxing by the river. Imagine hosting gatherings or unwinding with loved ones against the picturesque backdrop. Whether you're seeking a tranquil getaway, a prime location for water activities, or an investment with endless potential, this very special property awaits your vision. Note: Sqft for cabin only. See floor plans for cabin and boathouse contained within listing documents for full sqft.
1979 | 2 | 2 | 1,012 sqft.