Known for its island dotted waters, working harbors, and scenic shoreline towns, Casco Bay is one of Maine’s most iconic and desirable coastal regions. At Legacy Properties Sotheby’s International Realty, we’re proud to present exceptional waterfront listings throughout Casco Bay. Featuring coastal homes from Cape Elizabeth to Harpswell, and island living on Great Diamond Island, these properties offer not only proximity to the water but also a front row seat to some of Maine’s most beautiful seascapes.
55 Zeb Cove Road, Cape Elizabeth, ME 04107
Offered at $15,000,000
Represented by Bill Gaynor and Sam Michaud
Welcome to SEASCAPE. This incomparable oceanfront estate awaits your consideration. Imagine, if you will, after a hectic day you arrive via a secluded tree lined pathway and ancient stonewalls to take in the unfolding grandeur of 7+ private acres of groomed fields and woods. Reminiscent of an English countryside setting, the site both embraces and excites as you suddenly glimpse the presence of the glittering Atlantic and 1184 feet of bold frontage. The majesty of the main house appears and is perfectly sited above the roaring waters looking out Eastward along the sweeping granite shoreline of genuine Maine. Time stands still. From nearly every room you will drink in dreamlike views of the sea spread out before you. The residence itself is a tour-de-force of craftsmanship and grand architecture. Every space and every surface reflects a merger of highly refined quality and casual comfort. Exquisite millwork and casework is evident throughout. Balconies, covered porches and a classic bluestone terrace invite relaxation and reflection. And it is all wrapped up with an internationally recognized pedigree. SEASCAPE is simply beyond extraordinary.
10 Cromwell Cove Road, Harpswell, ME 04079
Offered at $5,950,000
Represented by Elise Kiely and Sam Michaud
The most significant property to come to the Harpswell market in over two decades, this estate is set on almost 3 private acres with 315′ +\- of beachfront. Both the main and guest houses provide sweeping, uninterrupted views of Rogue Island and the Atlantic horizon beyond-evoking the timeless coastal scenes captured by Maine’s iconic artists. Designed by prominent architects, Will Winkelman and Rob Whitten of Whitten Architects. Every detail has been thoughtfully designed for beauty, comfort, and lasting quality. The home seamlessly blends a classic New England shingled exterior with a striking refined interior where clean lines, natural materials, and expansive glass invite the outdoors in.
23 Peabbles Cove Road, Cape Elizabeth, ME 04107
Offered at $3,295,000
Represented by Heather Shields
Tucked in the quaint seaside neighborhood of Peabbles Cove, this exceptional coastal residence is sited on 2 acres with sweeping water views and deed access to a private cove and long sandy beach. The setting provides a front-row seat to maritime life, framed by Portland Head Light and two additional historic lighthouses while overlooking Whaleback Rock and the dynamic channel into Portland Harbor. A wide wrap-around porch welcomes you into the home through elegant double front doors. Inside, timeless details meet coastal elegance shiplap walls, rich hardwood flooring, and sun-drenched rooms define the space. The mudroom offers practical charm with tile flooring and built-ins, while the open-concept living area is anchored by a gas fireplace with a textured stone surround. The adjacent sunroom, with vaulted shiplap ceiling and exposed beams, is a cozy retreat with tranquil views and access to the porch. The kitchen is as stylish as it is functional, featuring a large center island with a galley workstation, Wolf & Sub-Zero appliances, striking stone countertops, vibrant lower cabinetry, and a butler’s pantry. The dining room is wrapped in windows on three sides, showcasing ocean views. Upstairs, the primary suite is a sanctuary with vaulted ceilings, sitting area, water views, and an ensuite bath featuring a soaking tub, dual vanities, and a walk-in shower. Three additional bedrooms, a full bath w/ custom tile, and a separate laundry room with antique cabinetry complete the upper level. A spacious bonus room over the garage offers flexible space. A plumbed, daylight walk-out basement offers an exceptional opportunity to create a private in-law suite, guest quarters, or a potential income-generating Airbnb. Additional highlights include custom tilework, wallpaper and refined finishes throughout. Outside there are raised garden beds, a firepit, and a small outdoor building with garage bay door. This is Maine coastal living elevated, effortless, and unforgettable.
7 Dyer Lane, Cape Elizabeth, ME 04107
Offered at $2,985,000
Represented by Alexa Oestreicher
Stunning Oceanfront Views, Timelessly Elegant A dreamy coastal retreat! This beautifully renovated 1930’s seaside cottage offers a perfect blend of historic charm and modern amenities. Nestled in an iconic, picturesque location with bold, unobstructed ocean views, overlooking a dramatic rocky coast, it features a classic New England shingle-style cottage exterior with covered front porch. Inside and out, updates are showcased with designer colors that complement the natural elements of summer sea and sun! Features of the home include a native-rock stone fireplace that opens to the dining area and living room with multiple seating options – all with expansive, panoramic views! Additionally the first floor includes a reading room area, full bath with laundry, a beautiful custom kitchen with spacious cabinets, stainless steel appliances, center island and pantry. Upstairs the 2-3 bedrooms – are perfect for accommodating family and guests and each features a different dramatic view! The second floor bathroom has a generous soaking tub or if you’d like to take a cold plunge, you are just steps away from a dip in the tide pools, a perfect refreshing bath in nature’s own spa! Located on a quiet lane, this cottage is just a short stroll from two famous lighthouses, Crescent Beach State Park, Two Lights State Park and the beloved Lobster Shack restaurant, offering the best of coastal living with convenience and charm. Whether you’re seeking a permanent residence or a seasonal escape, this seaside gem is ready to welcome you home. Conveniently located 15 minutes to the International Jetport and downtown Portland, this is coastal Maine living at its best!
30 Barker Point Road, Harpswell, ME 04079
Offered at $2,850,000
Represented by Dennis Duggan
Welcome to 30 Barker Point Road, Harpswell. This property is the epitome of a ” Maine CoastalCottage”. Located on the granite shoreline of Bailey Island. Long offshore easterly views of islands and open ocean. A very sensory setting. Shingle sided, wraparound porches, fireplaces, large windows, – a real period feel. Originally built in the 1890s, but updated in every respect, – while still maintaining the presence of another time. Truly, a very rare and unique offering ! There are a total of five bedrooms, three baths, a large living room, den/library, and a turret room high above the main level. Spacious and suitable to easily accommodate a large group of family and friends. Conveniently located on Bailey Island. A classic Maine coastal community Enjoy low taxes and easy access to the surrounding Town of Brunswick. Home to Bowdoin College, and all the conveniences you would expect.
240 W Cundys Point, Harpswell, ME 04079
Offered at $2,795,000
Represented by Dennis Duggan
Welcome to 240 West Cundys Point Road in Harpswell. A truly notable property located in a highly desirable section of town. The site consists of 3.7 acres of wooded land with over 1,400 feet of water frontage. Commanding ocean views combine with serene privacy. The scene is long ocean views, offshore islands, and boats transiting the area. Classic Maine. A never ending changing panorama. In addition, enjoy low Harpswell taxes as well as a convenient location with easy access to the Town of Brunswick, and all that college town has to offer. The house is a contemporary design of some 4,263 square feet. Open concept, it takes full advantage of its location and the ever changing views. Sit in your living room and be mesmerized by the scene. There are two mini bedroom suites on the main level, Primary bedroom on the second level, as well as a Bunk Room with multiple beds. Could easily accommodate larger groups. There are four bathrooms as well as a Media Room. In addition to all of the above, it should be noted that the land area can accommodate a separate buildable lot that could be used to build a Guest House, or sold to recoup a portion of your investment. Survey data is available.
15 Myrtle Avenue, South Portland, ME 04106
Offered at $1,790,000
Represented by Anne Bosworth and Elizabeth Banwell
A Waterfront Retreat with Unmatched 180-Degree Ocean Views. Step into a world of tranquility and classic Maine beach living with this exceptional waterfront property, featuring breathtaking 180-degree views of the Portland Ship Channel, historic Fort Gorges, and Casco Bay. Nestled on a spacious lot, the property offers exclusive private access to desirable Willard Beach, a rare find in this coveted neighborhood.The existing 100 year old classic Cape-style home has been cherished by the same family for 50 years and offers four bedrooms and two full bathrooms. Picture yourself enjoying your morning coffee on the expansive deck, where panoramic ocean vistas create a stunning daily backdrop. Conveniently located just moments from Willard Square and vibrant downtown Portland, you’ll find yourself surrounded by fine dining, boutique shopping, and a variety of cultural attractions. This property presents a unique opportunity to embrace coastal living at its finest. Whether you choose to appreciate the charm of the current residence or envision building your dream home to fully capitalize on the spectacular views and special location, this is a truly remarkable offering.
30 Pleasant Cove Lane, Portland, ME 04109
Offered at $1,790,000
Represented by Amy Farrell
This impeccably maintained Maine island property on Great Diamond Island, provides a sense of warmth and place. The clapboard, coastal style 4 BR, 3.5 BA home, part of the Diamond Cove community, is sited on a rise overlooking Pleasant Cove Beach, affectionately known as Sea Glass Beach. The 2-acre site is a gardeners dream and includes several beautifully established flowerbeds, a renovated historic outbuilding for use as a garden shed, studio or bunk room, and glorious views of Casco Bay and Cow Island. Built in 2000, this 3-level home has been lovingly maintained by only one owner & provides many amenities that have been added over the years. Enjoy waterfront views from the elevated covered porch that runs the length of the home or bring a chair down to the beach that is just steps away. A stone patio is ideal for outdoor dining, and relax in front of the outdoor fireplace on chilly nights. Top it off with a soak in the hot tub as you watch the stars come out. Imagine having the ability to enjoy this lifestyle every day! Inside, the open floor plan allows for casual living, a nicely appointed kitchen with custom cherry cabinetry and large island makes it ideal for entertaining & showcases the breathtaking views of the ocean. If work calls, 2 private studies are available with reliable high-speed internet. The 2nd level includes 3 BR, 2 full BA, including a primary bedroom suite with a recently updated bathroom & large walk-in closet. Access the lower level from an interior staircase or ground level through a large screened-in porch that leads to the 4th BR, full BA, pantry, heated garage, and workshop. This island haven is an ideal location as it’s conveniently located only 30 minutes to Portland by ferry service that runs 10x per day, and close to airport, bus, and train. While on island, enjoy all the community amenities: pool, tennis, fitness gym, private beaches, walking trails, and dining. This property will provide you with Maine island living at its best!
1241 Harpswell Islands Road, Harpswell, ME 04079
Offered at $1,650,000
Represented by Dennis Duggan and Kaleb Swan
Nestled on Orr’s Island in Harpswell, Maine, the waterfront estate at 1241 Harpswell Island Road is a stunning coastal retreat and a versatile investment opportunity. Spanning 445 feet of diverse waterfront along Gun Point Cove, it features a deep-water dock, a protected tidal area, sandy shores at low tide, a boat mooring, and a private dock, ideal for capitalizing on Maine’s tourism and rental markets. This property offers multiple revenue streams, making it a gem in New England’s coastal market. The Dutch Colonial seaside cottage, a charming three-bedroom, 1.5-bath residence, exudes nostalgic allure with easterly water views, wide-plank wood floors, and vintage floral wallpaper. A proven Airbnb success, it draws guests for its authentic coastal experience and serene backyard, delivering consistent rental income. Built in 2009, the main house blends open-concept living with breathtaking easterly and southerly views of deep and shallow tidal waters. Large windows frame mature terraced gardens and a gently sloping lawn leading to the water’s edge. The second-story primary en-suite offers elevated water views and a versatile open space, perfect for additional bedrooms or a private retreat. A second-story, one-bedroom efficiency apartment with distant water views provides a quaint guest retreat. A separate studio, formerly an art gallery, now serves as prime retail space with an adaptable layout, ideal for a boutique or artisan shop, enhancing the property’s versatility. This estate’s investment potential shines through its diverse income sources, including three residential units for short- or long-term rentals and the retail space, perfect for tapping into Harpswell’s tourism and nearby Brunswick’s vibrant downtown. Capturing the essence of coastal Maine living, this property offers unparalleled water access, captivating views, and a rare opportunity to invest in a multifaceted revenue-generating estate.
6 Quartermaster Court, Portland, ME 04109
Offered at $895,000
Represented by Amy Farrell
Island living could not be easier! This year-round historic Quartermasters unit is located in the heart of the Diamond Cove community on Great Diamond Island. Beautifully appointed, this 3 bedroom, 2.5 bath includes a spacious 1st floor bedroom suite. Appreciate the historic charm including original hardwood floors throughout, exposed brick walls, wooden beams, steel girders, and wainscoting, while enjoying all the modern conveniences you’d expect. Stainless appliances, granite counters, soaring ceilings, and a private deck with ocean water views. This property is part of the Diamond Cove Homeowners Association and includes many amenities including heated pool, tennis, fitness center, historic bowling alley, hiking trails, marina, restaurants, and so much more. It’s also just a short walk to the ferry dock and marina, and only 2 miles by ferry or private boat to Portland, Maine’s largest city.
