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$885,000
3 Beds ⋅ 2 Baths ⋅ 1675383 MLS
Perched high above the shores of Hockomock Bay, this 12-acre waterfront property captures the quiet beauty of Westport Island with its stunning westerly views and unforgettable sunsets. Offering approximately 550 feet of deep-water frontage on Back Door Passage, the setting is both peaceful and inspiring, with an expansive deck perfectly positioned to take in the ever-changing waterfront landscape. The log home features three bedrooms, one-and-a-half baths, and embraces the warmth and character of classic Maine craftsmanship. Ready for your thoughtful personal touches, the home's authentic rustic appeal provides an inviting canvas for creating a truly exceptional waterfront getaway or year-round residence. Surrounded by mature woods and offering privacy, the property is part of a welcoming island community and is close to acres of conserved lands, providing easy access to boating, kayaking, fishing, hiking, and the natural beauty that defines the coast of Maine. Whether you preserve its timeless log home character or thoughtfully update it for the next generation, properties with this combination of acreage, privacy, extensive deep-water frontage, and spectacular sunset views are increasingly rare, so don't let this opportunity pass you by. Schedule your private showing today!

39 Plummer Rd, Westport Island

Listing courtesy of Vitalius Real Estate Group, LLC.

$549,000
3 Beds ⋅ 1 Baths ⋅ 1674951 MLS
Some places simply call for you to slow down, and this is one of them. Tucked away at the end of a long private driveway, this charming cottage takes you down memory lane to another era. Its sweet 1970s vintage character evokes memories of simpler times, inviting you to relax, unwind, and appreciate the peaceful beauty of life along the shores of Montsweag Bay. Step onto the spacious wraparound deck, where gentle breezes drift in from the water and the rhythm of the tides sets the pace of the day. A wall of glass welcomes you as you enter the home, filling the rooms with natural light and ever-changing views. Each evening, the western sky takes center stage. As the sun slowly sinks beyond the bay, the water becomes a canvas of colors, delivering a sunset performance you'll never tire of watching. Follow the meandering staircase to the riverside deck, where a dock once welcomed boats and kayaks. Today, it remains a magical place to cast a line, launch a kayak, sip your morning coffee, or simply watch osprey soar overhead as the river quietly flows by. Whether you envision restoring waterfront access or simply embracing the tranquil setting, this special spot provides options. Are you looking for a year-round residence or a waterfront getaway? This enchanting cottage is ready for its next chapter --with you!

81 Bay Shore Rd, Westport Island

Listing courtesy of Tim Dunham Realty. 207-882-5020
$1,495,000
3 Baths ⋅ 1672860 MLS
Remarkable Waterfront Estate featuring two Distinct Residences and a Deep Water Dock. Ideal for Multi-Generational Living or Exceptional Rental Income Opportunity! Nestled along the picturesque Sheepscot, this unique Waterfront Estate offers a rare blend of refined country living, natural beauty, and seclusion. The 3-Bedroom, 2-Bath Primary Residence with an expansive deck, presents sweeping water views and the ideal perch from which to view soaring eagles. From the spacious living area, to the vaulted ceilings, to the breakfast nook, to the remodeled bathroom w/ bidet, the home includes thoughtful features throughout. The 2-car garage includes a handy work room and spacious 2nd floor storage. A separate Guest Cottage, rebuilt from the frame, offers additional year-round comfort & privacy, complete with its own deck & garage. (Rental Income history available). The property features a private Deep-Water Dock w/ an impressive stairway to the water, providing direct access to Boothbay Harbor, Wiscasset, & the Atlantic -- ideal for boating enthusiasts and Coastal adventurers alike. The low-maintenance landscaped grounds have been cultivated over time to create a seasonal paradise, bursting with color through the seasons. Outdoor living is elevated with a Bocce Court, Fire Pit, & Swing Chair. Automatic Generator serves both the House and Cottage. 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 special place to call home. From this sanctuary, you feel a world away, yet mere minutes to local restaurants & shopping. (Primary Residence expanded in 2000, renovations to 2023. Guest House renovated in 2015. Main House 2,445 sq ft; Guest House 1,180 sq ft. Bdrm/ Bath count includes House (3/2) & Cottage (3/1). 4-Bdrm Septic.) Ideal Multi-Family property. Westport Island includes exceptional benefits of School Choice & low Property Tax rate. *

33 30 Taylor Rd, Westport Island

Listing courtesy of Engel & Volkers Casco Bay.

$695,000
1 Beds ⋅ 1 Baths ⋅ 1669798 MLS
It's all here! Beautiful coastal land, charming cottage, garage, stunning, sparkling water views. Don't miss this opportunity to own a year round waterfront property with potential for so much more! 150 feet of frontage on the Back River, 1.5 acres of developed land with driveway, well, septic all in place. Come sit on the deck and feel the ocean breezes, enjoy total privacy and open water views. Looking due west for spectacular sunsets. Use as your getaway or the ultimate guest house for your new build on this stunning stie. This home features an open floor plan, a wall of windows overlooking the bay, warm wood floors, and exposed beams that create a classic Maine cottage feel. The main level offers a full bath with tiled shower and laundry, while the loft-style second floor provides flexible space for sleeping, a home office, or reading nook with elevated water views. A full basement offers ample storage, and the oversized detached garage with loft provides additional space for vehicles, hobbies, or a workshop. Conveniently located near beaches, state parks, nature preserves, and a public boat launch, this move-in-ready property is the perfect Midcoast retreat.

91 Bay Shore Rd, Westport Island

Listing courtesy of Vitalius Real Estate Group.

$1,495,000
6 Beds ⋅ 3 Baths ⋅ 1667936 MLS
Remarkable Waterfront Estate featuring two Distinct Residences and a Deep Water Dock. Ideal for Multi-Generational Living or Exceptional Rental Income Opportunity! Nestled along the picturesque Sheepscot, this unique Waterfront Estate offers a rare blend of refined country living, natural beauty, and seclusion. The 3-Bedroom, 2-Bath Primary Residence with an expansive deck, presents sweeping water views and the ideal perch from which to view soaring eagles. From the spacious living area, to the vaulted ceilings, to the breakfast nook, to the remodeled bathroom w/ bidet, the home includes thoughtful features throughout. The 2-car garage includes a handy work room and spacious 2nd floor storage. A separate Guest Cottage, rebuilt from the frame, offers additional year-round comfort & privacy, complete with its own deck & garage. (Rental Income history available). The property features a private Deep-Water Dock w/ an impressive stairway to the water, providing direct access to Boothbay Harbor, Wiscasset, & the Atlantic -- ideal for boating enthusiasts and Coastal adventurers alike. The low-maintenance landscaped grounds have been cultivated over time to create a seasonal paradise, bursting with color through the seasons. Outdoor living is elevated with a Bocce Court, Fire Pit, & Swing Chair. Automatic Generator serves both the House and Cottage. 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 special place to call home. From this sanctuary, you feel a world away, yet mere minutes to local restaurants & shopping. (Primary Residence expanded in 2000, renovations to 2023. Guest House renovated in 2015. Main House 2,445 sq ft; Guest House 1,180 sq ft. Bdrm/ Bath count includes House (3/2) & Cottage (3/1). 4-Bdrm Septic.) Ideal Multi-Family property. Westport Island includes exceptional benefits of School Choice & low Property Tax rate. *

33 30 Taylor Rd, Westport Island

Listing courtesy of Engel & Volkers Casco Bay.

$335,000
2 Beds ⋅ 1 Baths ⋅ 1657772 MLS
Join the nationwide Arched home community by owning this lovely, unique year-round Arched home. Sustainable. Modern. Turnkey. Experience this high-performance, all-electric year-round retreat on Westport Island, Maine. Architecturally distinct for its unique round design, this 2-bedroom, 1-bathroom home is ideal for energy efficiency and low-maintenance ownership. This camp or vacation home features an open-concept main level with a private bedroom and a versatile, light-filled second-story loft. Easy to maintain with high-end heat pumps and two infrared fireplaces. No oil or propane, no hassle. Recent upgrades include new high-end wood laminate and carpet flooring, new kitchen cabinets, and quartz countertops to complement the energy-efficient appliances. Enjoy the quiet evenings outside by the fire or relax inside with all the natural light pouring in. The seller is conveying most furniture and a generator, which could make it an immediate-start short-term rental. Located near Boothbay, Maine, and Wiscasset, Maine, you and your guests will love the proximity to Casco Bay. The property is conveniently located near the Westport Island boat launch and Clough land preserve.

35 Bayview Dr, Westport Island

Listing courtesy of Keller Williams Realty.

$1,100,000
2 Beds ⋅ 3 Baths ⋅ 1639704 MLS
''Eagle's Nest''. Nestled on its ideally elevated perch above the Sheepscot, with sweeping views of the sea life, this classic 3-Bedroom, 2 1/2-Bath Coastal Home offers breathtaking elevated views, deep- water frontage, and the peaceful rhythm of the tides. Situated on a private road in historic Squam Heights, on the northern tip of Westport Island, this property delivers unmatched serenity with panoramic water vistas from nearly every room. Designed to showcase its stunning waterfront setting, the home features a bright, open layout ideal for entertaining or quiet reflection. The spectacular Great Room -- with vaulted ceilings, a custom fireplace, and expansive windows -- opens directly onto a spacious waterside deck, perfect for viewing boats sailing past or dining under the stars. Enjoy the ease of optional single-floor living, an attached garage, and meticulous upkeep throughout. With its elevated position above the shoreline, this unique property also offers rare potential for a deep-water dock--an exceptional opportunity for boating enthusiasts. While blissfully secluded, you are just a few minutes to Wiscasset or Bath and the many attractions of Midcoast Maine. On-island adventures include kayaking, hiking, yoga, and visits to a local farm, organic brewery with outdoor summer events, a historic inn, and a vibrant community association. Furnishings are negotiable, making this a perfect turn-key coastal escape or year-round residence. Residents also benefit from School Choice and Westport Island's low property tax rate. Don't miss your chance to own a slice of classic Maine waterfront living on sought-after Westport Island. Come for a Visit, Stay for a Lifetime...

3 Rocky Rd, Westport Island

Listing courtesy of Engel & Volkers Casco Bay.

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