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3 Jolly Roger Rd, Harpswell
$340,000
2 Beds ⋅ 1 Baths ⋅ 1684122 MLS
Welcome to 3 Jolly Roger Road, a unique opportunity to create your own place in a wonderful island community. Set on 1.68 acres, this 1940s-era home offers 2 bedrooms, 1 bath, a beautiful lot, and glimpses of the water, along with plenty of potential for someone ready to bring new life to the property. The existing home could be a rewarding renovation project, or the property may appeal to someone looking for the perfect setting to build their future island home. The lot offers space, privacy, and flexibility, with an additional outbuilding that could make a terrific art studio, woodworking shop, workshop, or storage space. With its attractive acreage, island setting, water views, and range of possibilities, 3 Jolly Roger Road is a property where vision can truly make a difference. Renovate the existing home, reimagine the space, or start fresh and build the island home you've been dreaming of!

3 Jolly Roger Rd, Harpswell

Listing courtesy of Rob Williams Real Estate Brokers.

49 Garrison Cove Rd, Harpswell
$765,000
3 Beds ⋅ 2 Baths ⋅ 1683250 MLS
Experience the beauty of coastal Maine from this charming 3-bedroom waterfront cottage on Bailey Island, where spectacular sunset views stretch across Harpswell Sound. Set along the water with steps leading down to a tidal beach and natural ledges, this special property offers an idyllic setting for relaxing, entertaining, and enjoying the ever-changing rhythm of the coast. Inside, the well-built and inviting cottage offers a cozy retreat with thoughtful details throughout. The kitchen features granite countertops, while the upstairs bathroom offers a classic clawfoot soaking tub and separate shower. Wake up to incredible water views from the primary bedroom, complete with its own deck and balcony—perfect for enjoying those westerly views over the Sound. The living room opens to a large covered deck, creating an effortless connection between indoor and outdoor living. Beautifully landscaped grounds feature a stone patio overlooking the waterfront, where you can spend hours watching boats pass, taking in the activity of the working waterfront, or simply listening to the sounds of the tide. Beyond the property, Bailey Island's beloved local restaurants, shops, the iconic Cribstone Bridge, and the public landing and boat launch at Garrison Cove are all within walking distance. Whether you're seeking a peaceful summer retreat, a place to gather with family and friends, or a quintessential Maine coastal escape, this waterfront cottage captures the charm and beauty of island living.

49 Garrison Cove Rd, Harpswell

Listing courtesy of Roxanne York Real Estate.

66 Holbrook St, Harpswell
$625,000
3 Beds ⋅ 1 Baths ⋅ 1681579 MLS
Experience the quintessential charm of coastal Maine from this year-round 3-bedroom, 1-bath cottage overlooking the New Meadows River and the picturesque working waterfront of Cundy's Harbor. With sweeping water views with sunny first-floor spaces, this property offers a front-row seat to spectacular sunrises, highlighted by the sights and rhythms of a classic Maine fishing village. A spacious seaside deck provides the perfect spot for morning coffee, afternoon gatherings, or simply taking in the ever-changing waterfront scenery. The back lawn offers additional outdoor space for gardening or entertaining. Inside, the cottage has been used as-is yet offers an exciting opportunity for those with a creative vision. The home is a true canvas for an industrious person looking to renovate, refresh, and create a personalized coastal retreat. The first floor includes convenient laundry and inviting sun-filled spaces, while three bedrooms upstairs take advantage of the home's elevated water views. Whether you're searching for a year-round residence, a Maine getaway, or a property with renovation potential in an iconic coastal setting, this Cundy's Harbor cottage offers an opportunity to create something truly special along the New Meadows River.

66 Holbrook St, Harpswell

Listing courtesy of Roxanne York Real Estate.

117 Starboard Ln, Harpswell
$8,500,000
7 Beds ⋅ 7 Baths ⋅ 1680258 MLS
Encompassed by more than one mile of shoreline along Casco Bay, Dingley Island is an extraordinary coastal estate with 27± acres, a shingle-style residence, deepwater dock, and exceptional privacy. With open lawns for gathering, mature woodlands to explore, and secluded stretches of rugged shoreline, the property's diverse landscape & immense privacy create a timeless setting & true sense of exclusivity along the coveted Maine coast. Set on the point of the peninsula, the main residence faces east, west, and south, beautifully capturing panoramic water views from sunrise to sunset. The shingle-style home is distinguished by its architecture, fine craftsmanship, and effortless connection between its living spaces & the surrounding landscape. The well-appointed home features 6 bedrooms, 5.5 baths, and 5,805± SF of living space with soaring ceilings, high-end finishes, and abundant natural light. An impressive double-sided Maine granite fireplace anchors the dining & living rooms, creating warm & inviting spaces suitable for quiet moments, intimate gatherings, and entertaining. A separate garage with a 948± SF, 1-bedroom, 1-bath apartment provides added space for guests. Throughout the grounds, exceptional stonework—including walls, grass-lined steps, and several patios—creates a natural progression of outdoor spaces, each thoughtfully designed for dining, enjoyment, and being immersed in the waterfront setting. A private tennis court invites recreation, while a custom-built treehouse adds whimsy & adventure. Down at the shore, the deepwater dock is safely tucked away on a protected cove, creating a serene vantage point to view local lobster boats working the bay. A true wildlife paradise, enjoy seal colonies sunbathing on nearby rock ledges, daily sightings of bald eagles & porpoises, and an array of migrating seabirds moving through the pristine landscape. More than a coastal residence, Dingley Island is a legacy estate designed to be enjoyed for generations.

117 Starboard Ln, Harpswell

Listing courtesy of LandVest, Inc..

81 Lowells Cove Rd, Harpswell
$490,000
3 Beds ⋅ 2 Baths ⋅ 1679904 MLS
Set in the sought-after Lowell Cove area of Orr's Island, this charming 3-bedroom, 2-bath seaside cottage offers a wonderful blend of historic character, coastal views, and thoughtful modern updates. Originally built in 1880, the home retains its timeless cottage charm while offering the comfort and functionality needed for today's island living. Perched on a gradual slope overlooking Lowell Cove, the property enjoys peaceful water views and a setting that invites you to slow down and savor the best of coastal Maine. Quiet back roads wind through the neighborhood, offering beautiful ocean vistas and ideal walking routes right outside your door. Numerous updates provide peace of mind, including a kitchen renovation in 2020, a remote-control awning added in 2022, a new water softener in 2024, and a new hybrid water heater, relocated electrical panel, and replacement deck in 2025. Whether you're looking for a summer escape, an investment property, or a year-round island home, this special Lowell Cove property offers an inviting opportunity to enjoy the beauty, tranquility, and character of Orr's Island.

81 Lowells Cove Rd, Harpswell

Listing courtesy of Roxanne York Real Estate.

12 Graveyard Point Rd, Harpswell
$795,000
3 Beds ⋅ 2 Baths ⋅ 1679210 MLS
A charming antique Cape filled with character and warmth, beautifully positioned to capture gorgeous, long southerly views from nearly every room. Sunlight pours in throughout the day, creating a wonderfully inviting setting and a constant connection to the ocean. Lovingly updated throughout, this special home is ready to move in and enjoy. Easy first-floor living opens to a sunny, south-facing deck overlooking the water—a perfect spot for morning coffee, afternoon relaxation, or simply taking in the ever-changing coastal views. Set on a level, sunny lot with plenty of room to expand if desired, the property offers both immediate enjoyment and exciting possibilities for the future. The spacious third bedroom is tucked away upstairs and features its own elevated deck, offering a wonderful vantage point for taking in the beautiful ocean views. Just a one-minute stroll to the beach and boat launch, the location is ideal for embracing the very best of coastal Maine living. Enjoy easy access to local restaurants, scenic trails, shops, galleries, and the ever-popular Dolphin Marina. Launch a kayak, head out for a day on the water, explore the shoreline, or simply settle in and enjoy the salty air and beautiful surroundings. Located at the southern tip of Harpswell Neck, this is a place where the pace is relaxed, the scenery is spectacular, and the simple pleasures of coastal living are right outside your door. A truly inviting Maine home where antique charm, thoughtful updates, sunshine, and spectacular southerly views come together—vintage coastal Maine at its finest.

12 Graveyard Point Rd, Harpswell

Listing courtesy of Roxanne York Real Estate.

54 Indian Rest Rd, Harpswell
$414,000
2 Beds ⋅ 1 Baths ⋅ 1676979 MLS
Discover the beauty of coastal living in Harpswell's desirable Indian Rest community. This inviting two-bedroom (possibility of expansion to 3 bedrooms), one-bath raised ranch offers an open concept eat-in kitchen and comfortable living room with a heat pump providing both heating and air conditioning. The large unfinished basement features a brick hearth for a wood stove with an exterior metal chimney, offering potential for additional living or recreational space. Step outside onto the 200-square-foot elevated deck and enjoy peaceful views of the wooded backyard. Residents enjoy the unique lifestyle offered by association-owned waterfront land, including a deep-water dock, protected mooring opportunities, and scenic woodland trails. The property also benefits from abutting an expansive fifty-six acres of neighborhood common land, providing a sense of privacy and protected surroundings. Enjoy easy access to leisurely morning walks, refreshing swims, kayaking, boating, and the natural beauty of the Maine coast. Just 10 minutes from Brunswick's shops, restaurants, and services, this home also offers convenient access to Harpswell's beaches, trails, boating, and seaside dining, while providing a peaceful lifestyle in a welcoming coastal community.

54 Indian Rest Rd, Harpswell

Listing courtesy of Rob Williams Real Estate Brokers.

154 Indian Rest Rd, Harpswell
$415,000
1 Beds ⋅ 1 Baths ⋅ 1672469 MLS
Charming Maine cottage nestled in the highly desirable Indian Rest neighborhood, where coastal living and community amenities come together. Residents enjoy access to association-owned waterfront land featuring a deep-water dock, excellent protected mooring opportunities, and scenic walking trails that wind through the woods to the shore. Lovingly enjoyed by the same family for more than 20 years, this inviting year round cottage has been thoughtfully updated with a new furnace, newer windows, and updated flooring while preserving its original Maine charm and character. Designed for making memories, the spacious kitchen and dining area naturally flow to a large sun-filled deck and beautiful stone patio--perfect for summer gatherings, cookouts, and relaxing evenings. The living room easily accommodated overnight guests with a futon, making it a welcoming retreat for family and friends. The generous backyard offers plenty of room for games, gardening, or simply enjoying the peaceful setting. Beyond the lawn, wooded trails lead directly to the waterfront, where morning walks, swimming, kayaking, boating, and the beauty of the Maine coast become part of everyday life. Just 10 minutes to Brunswick for Shopping while enjoying all the beaches, trails, boating and seaside restaurants Harpswell has to offer!

154 Indian Rest Rd, Harpswell

Listing courtesy of Roxanne York Real Estate.

30 Driftwood Tide Ln, Harpswell
$1,925,000
4 Beds ⋅ 4 Baths ⋅ 1648682 MLS
A new oceanfront home in the charming Driftwood Tide neighborhood. The last of only four custom homes built by John Libby Construction. This rare offering features 204 feet of pristine ocean frontage along the protected waters of the Ewing Narrows. A to-be-built custom residence designed for refined coastal living showcases fine woodwork and sun-filled open spaces. Warm hardwood floors, and a ''must have'' pantry and mudroom. Summer dining on the screened porch and cozy winter days by the gas fireplace. All while enjoying the gorgeous, long ocean views from almost every room in the house! The home offers four bedrooms, choose from 1st or 2nd floor suites, a library, and spacious decking running from one side to the other. Energy-efficient systems, and an oversized two-car attached garage. A newer deep-water dock with mooring potential invites effortless boating, kayaking, swimming, and fishing. Just 15 minutes from Brunswick. Enjoy Harpswell's incredible oceanfront lifestyle--trails, beaches, dining, boating, and low taxes. A truly exceptional opportunity. (All photos are similar to be built)

30 Driftwood Tide Ln, Harpswell

Listing courtesy of Roxanne York Real Estate.

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