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Set on three acres near the south end of Westport Island, this distinctive property offers views toward Goose Rock Passage and the surrounding waters of the Sheepscot River. The land has been in the same family since the 1760s, while the home was built in 2011, connecting generations of family history with newer construction. Quiet and private, the property features open fields, abundant bird and wildlife activity, and access to nearby trails and coastal waters. The home was built with a remarkable connection to the land. Trees used for the framing, flooring, interior finish, cabinetry and doors were harvested from the property and milled for its construction. Nine-foot ceilings and oversized windows complement a design influenced by traditional coastal Maine architecture. Designed for first-floor living, the primary bedroom, bath, laundry, kitchen and main living spaces are all on the first level. The kitchen features custom cabinetry, granite countertops, a Wolf range and Bosch dishwasher. A 12' x 12' three-season room and 16' x 27' deck extend the living space. The well-insulated home offers three heat pumps, a Rinnai propane heater and wood heat. A full basement with approximately nine-foot ceilings provides substantial storage and workshop space. A significant feature is the 30-foot-wide shared easement providing shore access and a potential dock area, with water even at low tide. From here, explore the protected waters surrounding Westport Island or head toward the open coast and Boothbay Harbor. Approximately 25-30 minutes from Bath and just over an hour from Portland, this property brings together acreage, craftsmanship, water access and generations of family history on the Maine coast.

3 Beds ⋅ 3 Baths

Set on three acres near the south end of Westport Island, this distinctive property offers views toward Goose Rock Passage and the surrounding waters of the Sheepscot River. The land has been in the same family since the 1760s, while the home was built in 2011, connecting generations of family history with newer construction. Quiet and private, the property features open fields, abundant bird and wildlife activity, and access to nearby trails and coastal waters. The home was built with a remarkable connection to the land. Trees used for the framing, flooring, interior finish, cabinetry and doors were harvested from the property and milled for its construction. Nine-foot ceilings and oversized windows complement a design influenced by traditional coastal Maine architecture. Designed for first-floor living, the primary bedroom, bath, laundry, kitchen and main living spaces are all on the first level. The kitchen features custom cabinetry, granite countertops, a Wolf range and Bosch dishwasher. A 12' x 12' three-season room and 16' x 27' deck extend the living space. The well-insulated home offers three heat pumps, a Rinnai propane heater and wood heat. A full basement with approximately nine-foot ceilings provides substantial storage and workshop space. A significant feature is the 30-foot-wide shared easement providing shore access and a potential dock area, with water even at low tide. From here, explore the protected waters surrounding Westport Island or head toward the open coast and Boothbay Harbor. Approximately 25-30 minutes from Bath and just over an hour from Portland, this property brings together acreage, craftsmanship, water access and generations of family history on the Maine coast.

1851 Main Rd, Westport Island

Listing courtesy of Real Broker.

$450,000

An exciting new and affordable opportunity on coveted Westport Island! This wonderful family home has 3 bedrooms (office and/or craft rooms), 2 full baths, a spacious kitchen with direct access to outside screened porch, dining/den area, large living room and entertaining space with bar on the lower level. Outside decks surround the home and include the covered screened porch for relaxing in a very quiet private setting. The detached garage is oversized with a large workshop and storage above. The property is wooded with plenty of outdoor space to explore and enjoy. In addition to being very well maintained, this home has multiple heat sources, including two energy efficient electric heat pumps, monitor 41, wood and pellet stoves, a whole house Generac generator, and benefits from very attractive real estate taxes! In this highly priced market, this home has a lot and certainly deserves a close look!

3 Beds ⋅ 2 Baths

An exciting new and affordable opportunity on coveted Westport Island! This wonderful family home has 3 bedrooms (office and/or craft rooms), 2 full baths, a spacious kitchen with direct access to outside screened porch, dining/den area, large living room and entertaining space with bar on the lower level. Outside decks surround the home and include the covered screened porch for relaxing in a very quiet private setting. The detached garage is oversized with a large workshop and storage above. The property is wooded with plenty of outdoor space to explore and enjoy. In addition to being very well maintained, this home has multiple heat sources, including two energy efficient electric heat pumps, monitor 41, wood and pellet stoves, a whole house Generac generator, and benefits from very attractive real estate taxes! In this highly priced market, this home has a lot and certainly deserves a close look!

17 Cromwell Rd, Westport Island

Listing courtesy of Coldwell Banker Realty. 207-773-1990

$529,900

3 bedrooms, 2 bathrooms, and over 1,700 square feet of living space on 5.7 private acres. This inviting Cape features a spacious 3-bay garage with additional storage, convenient loop driveway, and a walkout basement with both interior and exterior access. Enjoy peaceful surroundings and beautiful Maine views from the deck, with plenty of space for outdoor living, entertaining, and recreation. Easy access to nearby Wright Landing Boat Launch provides convenient access to the water and all that Westport living has to showcase!

3 Beds ⋅ 2 Baths

3 bedrooms, 2 bathrooms, and over 1,700 square feet of living space on 5.7 private acres. This inviting Cape features a spacious 3-bay garage with additional storage, convenient loop driveway, and a walkout basement with both interior and exterior access. Enjoy peaceful surroundings and beautiful Maine views from the deck, with plenty of space for outdoor living, entertaining, and recreation. Easy access to nearby Wright Landing Boat Launch provides convenient access to the water and all that Westport living has to showcase!

42 Bakers Rd, Westport Island

Listing courtesy of Tim Dunham Realty. 207-729-7297

$1,450,000

Discover a truly remarkable 73-acre estate on picturesque Westport Island, Maine, where history, craftsmanship, and thoughtful stewardship come together in perfect harmony. Lovingly cared for by the same family for 53 years. At the heart of the estate is a classic Cape Cod-style farmhouse, originally built in 1800 and seamlessly expanded in 1995 to provide modern comfort without compromising its timeless appeal. Throughout the home, all plumbing and electrical systems have been completely updated while rooftop solar panels provide energy-efficient electricity and hot water. Inside the home you'll find three beautifully restored, fully functioning fireplaces. One features a traditional brick bake oven, offering the unique opportunity to cook as generations past once did. The primary suite is located upstairs and includes a private ensuite bath, creating a peaceful retreat overlooking the surrounding landscape. Attached to the home is a handsome timber-frame barn offering convenient vehicle storage, while a charming guest cottage tucked just behind the house provides comfortable accommodations for family and friends. The grounds are equally extraordinary. Owners have thoughtfully created a 3.2-mile private trail system winding throughout the property's 73 acres, inviting year-round exploration by foot, snowshoe, or cross-country skis. Much of the acreage is enrolled in Maine's Tree Growth Tax Program. Some of the adjacent lands are owned by the Kennebec Estuary Land Trust, which protects and conserves undeveloped lands. Whether you're seeking a private family estate, recreational retreat, or legacy property to pass on for generations, this well built and well-maintained home combines historic charm and modern efficiency into one unforgettable property.

3 Beds ⋅ 3 Baths

Discover a truly remarkable 73-acre estate on picturesque Westport Island, Maine, where history, craftsmanship, and thoughtful stewardship come together in perfect harmony. Lovingly cared for by the same family for 53 years. At the heart of the estate is a classic Cape Cod-style farmhouse, originally built in 1800 and seamlessly expanded in 1995 to provide modern comfort without compromising its timeless appeal. Throughout the home, all plumbing and electrical systems have been completely updated while rooftop solar panels provide energy-efficient electricity and hot water. Inside the home you'll find three beautifully restored, fully functioning fireplaces. One features a traditional brick bake oven, offering the unique opportunity to cook as generations past once did. The primary suite is located upstairs and includes a private ensuite bath, creating a peaceful retreat overlooking the surrounding landscape. Attached to the home is a handsome timber-frame barn offering convenient vehicle storage, while a charming guest cottage tucked just behind the house provides comfortable accommodations for family and friends. The grounds are equally extraordinary. Owners have thoughtfully created a 3.2-mile private trail system winding throughout the property's 73 acres, inviting year-round exploration by foot, snowshoe, or cross-country skis. Much of the acreage is enrolled in Maine's Tree Growth Tax Program. Some of the adjacent lands are owned by the Kennebec Estuary Land Trust, which protects and conserves undeveloped lands. Whether you're seeking a private family estate, recreational retreat, or legacy property to pass on for generations, this well built and well-maintained home combines historic charm and modern efficiency into one unforgettable property.

75 Post Office Rd, Westport Island

Listing courtesy of Sprague & Curtis Real Estate.

$840,000

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!

3 Beds ⋅ 2 Baths

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

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!

3 Beds ⋅ 1 Baths

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

$599,900

Set on 1.5± acres in a peaceful Westport Island setting, this expanded Cape blends classic Maine character with rare flexibility for modern living. Stone walkways, mature gardens, and a broad deck create an inviting arrival, while the interior offers warm wood floors, natural light, and comfortable gathering spaces. The kitchen opens easily to everyday living and entertaining, and the home is best marketed as 3 bedrooms plus bonus/flex space, with 2.5 baths and an attached 2-car garage. A standout feature is the finished family room over the garage with vaulted ceilings, built-ins, an arched window, a private exterior entrance, and a half bath--ideal as a studio, office, guest retreat, recreation room, or possible future ADU/guest-suite conversion. Surrounded by woods and close to the Sheepscot River coastline with seasonal views, this property offers privacy without isolation and convenient access to Wiscasset, Bath, Boothbay, and Midcoast amenities. A distinctive Westport Island home with room to gather, create, garden, and unwind.

3 Beds ⋅ 3 Baths

Set on 1.5± acres in a peaceful Westport Island setting, this expanded Cape blends classic Maine character with rare flexibility for modern living. Stone walkways, mature gardens, and a broad deck create an inviting arrival, while the interior offers warm wood floors, natural light, and comfortable gathering spaces. The kitchen opens easily to everyday living and entertaining, and the home is best marketed as 3 bedrooms plus bonus/flex space, with 2.5 baths and an attached 2-car garage. A standout feature is the finished family room over the garage with vaulted ceilings, built-ins, an arched window, a private exterior entrance, and a half bath--ideal as a studio, office, guest retreat, recreation room, or possible future ADU/guest-suite conversion. Surrounded by woods and close to the Sheepscot River coastline with seasonal views, this property offers privacy without isolation and convenient access to Wiscasset, Bath, Boothbay, and Midcoast amenities. A distinctive Westport Island home with room to gather, create, garden, and unwind.

280 W Shore Rd, Westport Island

Listing courtesy of Tim Dunham Realty. 207-729-7297

$1,495,000

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. *

3 Baths

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.

$1,495,000

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. *

6 Beds ⋅ 3 Baths

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.

$648,000

NEW ROOF in fall of 2025!!! Charming home along the shores of the Sheepscot River offering deep water frontage for those boating enthusiasts. Roof was re-shingled in the late fall of 2025. Hardwood floors, deck for waterfront enjoyment in the summer months. Watch the boating activity from your perch with the morning coffee or watch the sunrise. Walkout daylight basement, two wells and a great set back from the public road along with plenty of space for addition and garage.

2 Beds ⋅ 1 Baths

NEW ROOF in fall of 2025!!! Charming home along the shores of the Sheepscot River offering deep water frontage for those boating enthusiasts. Roof was re-shingled in the late fall of 2025. Hardwood floors, deck for waterfront enjoyment in the summer months. Watch the boating activity from your perch with the morning coffee or watch the sunrise. Walkout daylight basement, two wells and a great set back from the public road along with plenty of space for addition and garage.

124 Main Rd, Westport Island

Listing courtesy of Cromwell Coastal Properties. (207)208-9311

$782,000

PLEASE NO DRIVE-BY or WALKING property without an Appointment - Owner and Dog occupy home . Deep water ready for your new dock system! The waterfront is stunning and the home has been a comfortable place to relax for decades. Now it is time for someone to bring their new ideas and make it their own. One may finish the second level into a stunning primary suite with additional bedrooms and bathrooms. Attached and detached garage, plenty of storage in the full basement or finish off the area intended to be an exercise room.

2 Beds ⋅ 1 Baths

PLEASE NO DRIVE-BY or WALKING property without an Appointment - Owner and Dog occupy home . Deep water ready for your new dock system! The waterfront is stunning and the home has been a comfortable place to relax for decades. Now it is time for someone to bring their new ideas and make it their own. One may finish the second level into a stunning primary suite with additional bedrooms and bathrooms. Attached and detached garage, plenty of storage in the full basement or finish off the area intended to be an exercise room.

15 Lewis Rd, Westport Island

Listing courtesy of Cromwell Coastal Properties. (207)208-9311

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