Refine Search
Map
Sort by
$450,000
3 Beds ⋅ 2 Baths ⋅ 1680222 MLS
OPEN HOUSE - Sunday, September 13, 2026, 11:00am - 1:00pm. 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
$349,000
3 Beds ⋅ 2 Baths ⋅ 1680130 MLS
Nestled on the peaceful outskirts of Westport Island, this beautifully maintained 3-bedroom, 2-bath single-level home offers easy living in a wonderfully private setting. Set on 2 acres, the property is surrounded by established gardens, mature plantings and natural beauty, creating a welcoming haven for both people and wildlife. Enjoy morning coffee or evening gatherings from the decks while watching birds and other wildlife move through the landscape. A detached garage provides excellent storage and workspace, while the thoughtfully cared-for grounds offer plenty of room for gardening, relaxing and enjoying the outdoors. Conveniently located close to town yet feeling worlds away, this property offers the best of both worlds—peace, privacy and a strong connection to nature, with everyday amenities within easy reach. A special opportunity to enjoy the quiet beauty of Westport Island with comfortable, single-story living.

9 Hidden Rd, Westport Island

Listing courtesy of Blue Lobster Real Estate.

$549,900
3 Beds ⋅ 2 Baths ⋅ 1679234 MLS
Beautiful, Cape offering 3 bedrooms, 2 bathrooms, and over 1,700 square feet of living space on 5.7 private acres. This inviting island home features a spacious 3-bay garage with additional storage, a 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 Island living has to showcase

42 Bakers Rd, Westport Island

Listing courtesy of Tim Dunham Realty. 207-729-7297
$2,299,000
3 Beds ⋅ 3 Baths ⋅ 1676463 MLS
Down a quiet lane, a short distance from where the Sheepscot River meets the ocean, lies this property which the Westport Island History Committee refers to as ''a historic treasure''. Located on private waterfront where lobster and sail boats cruise past, the smell of Bayberry scents the air, bald eagles, ospreys and seals play: this property is sure to evoke favorite childhood memories of Maine. Believed to have been built in 1798, careful restoration indicates that much of the current structure likely dates to the early 1800s. The house was built by John M. Parsons, who founded a mill on the property at Rum Cove during the same time period. The house has been carefully returned to its original footprint by removing late additions. Throughout the property period details have been preserved or replicated using custom millwork, fine craftsmanship and historically accurate materials. Guided by the oldest known photographs of the house, the windows, unique eight-panel doors, fireplaces, clapboards and cedar-shingle roof have all been beautifully restored. The most dramatic update is the renovation of the kitchen ell, which replaces an outdated previous renovation with a design that well suits the age of the house. Features include new plumbing and electrical systems, custom cabinets, a soapstone sink and countertops, modern appliances and the opportunity to retain owner-procured antiques creating a timeless kitchen. Here you can prepare meals while looking out over the kitchen garden, past the ''Fish House'' and on to the water just as owners have stood for over 200 years. The house is situated on 6.4 private acres with 850' of waterfront, a private dock, a two-car detached garage and the antique Fish House, a small outbuilding ready for your renovation vision. Here is your Maine House and an opportunity to own a piece of Maine history.

44 Eloise Dr, Westport Island

Listing courtesy of Dwelling In Maine.

$1,450,000
3 Beds ⋅ 3 Baths ⋅ 1676015 MLS
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.

$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.

$499,999
4 Beds ⋅ 4 Baths ⋅ 1675201 MLS
Set on 5.8 private acres on beautiful Westport Island, this thoughtfully renovated home offers the perfect blend of comfort, privacy, and peaceful Maine living. Surrounded by rolling hills and overlooking its own pond, the property feels like a true retreat while still offering plenty of space for everyday life. Inside, the open and inviting main level is designed for both gathering and relaxing. The well-appointed kitchen features stainless steel appliances, generous workspace, and a large pantry, flowing easily into the dining and living areas. A mudroom and half bath add everyday convenience. Year-round comfort comes from efficient heat pumps providing both heating and cooling, while the wood stove adds warmth and cozy Maine charm on chilly evenings. Upstairs, you'll find three bedrooms, including a spacious primary suite, along with convenient second-floor laundry and a versatile flex space that's perfect for a home office, reading nook, or quiet retreat. Outside, there are plenty of ways to enjoy the peaceful setting. Settle onto the farmer's porch for a cozy evening, entertain on the large back deck overlooking the pond and rolling hills, or simply enjoy the privacy and natural beauty of nearly six acres. A two-car garage provides additional storage and functionality. Tucked away on scenic Westport Island, you'll enjoy a peaceful island setting while remaining within easy reach of some of Midcoast Maine's favorite destinations, including the Coastal Maine Botanical Gardens, area beaches, charming coastal villages, restaurants, shopping, and all that Boothbay and Wiscasset have to enjoy.

1479 Main Rd, Westport Island

Listing courtesy of Keller Williams Realty.

$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
$599,900
3 Beds ⋅ 3 Baths ⋅ 1674926 MLS
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
$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.

$579,000
3 Beds ⋅ 2 Baths ⋅ 1669543 MLS
Welcome to the community of Westport Island! This well maintained home is ready for the next new beginning with its new owner. New kitchen and roof with a stone fireplace in the living room ready for the upcoming months. Set back from a quiet paved road the home offers a 3 season sunroom, breakfast nook off kitchen and oversized 2 bay garage ready to stock your toys and tools. The backyard setting offers views ( but no frontage) offer a wildlife migratory bird pond which makes sitting by the outside firepit an absolute peaceful time. The trails that the current owner has trimmed into the 9 acres is great for year round treks. Easy to see , easy to close!

27 Doggett Rd, Westport Island

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

$3,950,000
3 Beds ⋅ 3 Baths ⋅ 1666204 MLS
Available for the first time in a quarter century, this rare coastal retreat encompasses 51 private acres with nearly a mile of frontage along the Sheepscot River. Step back in time as the meandering dirt drive, lined with mature oak trees and vintage stone walls, draws you to the meadow's edge and sweeping views of the river. Over 40 acres of your own private, magical wooded trails wander down the peninsula to a rocky point where seals frolic offshore and bald eagles perch above the water. Heading toward the water, you will pass the writing cottage, saltwater pool, and pool house. Next is the 3-bedroom, 3-bath antique Cape house from the 1800s, thoughtfully updated to honor its heritage while providing modern amenities. Exercising judicious design restraint, the owners added a new kitchen, upgraded the pantry, and refreshed all three bathrooms. The new heated saltwater pool and its pine-scented pool house offer hours of entertainment for all ages. The second writing studio, designed by Snyder and Cheng, sits at the water's edge, offering a quiet space for music, writing, storage, or creative retreat. The deepwater dock, a coveted feature for boaters, offers 8 to 9 feet of depth at mean low water and will welcome most boats. Vessels requiring more depth can swing on the mooring at 28 feet. The protected waterfront also invites quieter days on the water, offering easy access for kayaking, canoeing, and exploring the Sheepscot River at your own pace. Boaters can enjoy a remarkable network of rivers, coves, and island passages, with easy access to open water and the sea beyond. A true legacy offering with thoughtful conservation easements to ensure its quality for generations. The current owners chose understated simplicity, allowing the natural setting to remain the defining luxury: woods, wildlife, salt air, and the ever changing tides of the saltwater river. This coastal sanctuary is just an hour from the Portland, Maine airport and 2.5 hours from B

45 Bradley Rd, Westport Island

Listing courtesy of Vitalius Real Estate Group.

$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.

$699,900
2 Beds ⋅ 1 Baths ⋅ 1656387 MLS
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
$799,000
2 Beds ⋅ 1 Baths ⋅ 1656631 MLS
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
$329,000
3 Beds ⋅ 1 Baths ⋅ 1650674 MLS
Experience the quintessential Maine lifestyle in this beautifully renovated ranch, perfectly positioned on a spacious two-acre lot on Westport Island. This single-floor home features an expansive open-concept layout where the sun-filled living room flows seamlessly into a large dining area and kitchen, creating an ideal environment for entertaining and daily living. With three comfortable bedrooms and a full bathroom, the interior feels fresh and modern following a complete top-to-bottom renovation. Peace of mind comes standard with recent upgrades including a brand-new metal roof designed for longevity and low maintenance. Outside, the property offers two level acres with ample room for gardening, outdoor recreation, or simply enjoying the coastal air. Located just a few hundred yards from the Back River, this home provides easy access to the water for kayaking, beachcombing, and sunset strolls. Whether you are looking for a year-round residence or a peaceful island retreat, this property combines modern comfort with the natural beauty of the Midcoast region.

575 Main Rd, Westport Island

Listing courtesy of Coldwell Banker Realty.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Listing data is derived in whole or in part from the Maine IDX and is for consumers' personal,noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved.

This information is provided exclusively for consumers' personal, non-commerical use and may not be used for any purpose other than to identify prospective properties consumers may be intrested in purchasing.

Privacy Policy

Your privacy on the Internet is important to us. This Privacy Statement is to inform you that we will not provide your personal information to any third parties except as required by law or expressly authorized by you. We do not sell, trade, barter, or share information obtained from use of this site with any other businesses or people. All information gathered from a visitor to this web site is used solely by this office and/or its affiliated licensee(s). For additional information, please contact this office.