luxury seaside houses for sale Waldo County, United States

An Island Life with Room to Create | Come to Islesboro and live a little differently. Long known for its thriving arts community, the island offers a blend of creative energy, natural beauty, and a welcoming spirit. This historic three-bedroom Maine sea captain's house features wood floors, abundant natural light, and views toward Mill Creek Cove and Gilkey's Harbor. Open living, kitchen, and dining spaces flow to a screened porch, while the kitchen features cherry countertops and a handcrafted Maine Monson slate sink. A first-floor primary suite opens to the deck. Outside, more than 60 heirloom fruit trees surround a fenced garden, spring-fed pond, firepit, and outdoor shower. Stairs lead to the shore of Mill Creek Cove, providing direct access for launching a kayak or paddleboard. A separate artist studio with electricity and loft space overlooks the pond, offering a peaceful setting for inspiration and creativity. A lovely deck extends to the water's edge, perfect for morning coffee or a quiet moment of reflection. A historic former village post office serves as a seasonal guest cottage or flexible retreat, with a full bath and screened porch. The property borders acres of undisturbed wilderness, creating a wonderful sense of privacy and connection to nature. Golf, trails, the ferry, island market, community center, seasonal farmers market, bakery, and other island amenities are all nearby. Ideal for seasonal living, with potential for year-round use with additional improvements, this is a distinctive island property with room to create, garden, gather, and enjoy life on Islesboro.

TWO HOMES-ONE OCEANFRONT PROPERTY: Set along the shores of beautiful Searsport Harbor, this timeless seasonal cottage offers the kind of coastal experience that feels increasingly difficult to find. For generations, it has quietly stood watch over family gatherings, beach picnics, sunrise coffees, and long summer evenings spent listening to the tide roll in. Rooted in simplicity and connection, it is a place where memories have been made for decades and where the pace of life naturally slows. Inside, the home features 5 bedrooms and 2 baths, with warm old-growth wood interiors that immediately transport you to another era. The spaces feel authentic and unpretentious, shaped more by laughter, storytelling, and salt air than by trends. Every room carries a sense of history and comfort, inviting time together after long days spent outdoors. The ever-changing beachfront offers a rare and treasured stretch of shoreline, perfect for swimming, launching kayaks, searching for shells, or simply sitting quietly by the water's edge as boats pass through the harbor. More than just a cottage, this is a true generational retreat; a place to reconnect with family, with nature, and with the enduring rhythm of the Maine coast. Included with this remarkable property is a newer 3-bedroom, 3-bath contemporary home offering open, airy living spaces filled with natural light and a sense of volume throughout. Two of the three bedrooms feature ensuite baths, adding comfort and flexibility for guests or multi-generational living. Designed with adaptability in mind, the layout easily suits a variety of lifestyles. The spacious lower level can serve as an in-law suite, exercise or artist studio, media room, or additional living space. A separate bonus room provides the perfect setting for a workshop or hobby area. Energy-conscious features include solar panels for low monthly electric costs and a 2-car attached garage with EV charging station. Modern, versatile, and filled with possibility.

On an island in Maine sits this sweet cottage with room to expand or build on the elevated point looking West over Penobscot Bay. Explore 14 acres and 1,288 feet of shore front and beach.

Rarely does a property like this become available in Islesboro's storied and much-loved summer colony, Sabbathday Harbor. Perfectly sited, up high on the shores of East Penobscot Bay, this classic cottage offers sweeping easterly water views extending to Cape Rosier and approximately 100 feet of bold, accessible shoreline. The first floor features a living room with a wood stove and doors that open to a spacious water view deck, a functional galley kitchen, and a full bath. The generous wrap-around deck provides the perfect vantage point for sunrise coffee, afternoon reading, or evening gatherings with the bay as your backdrop. Upstairs, three charming bedrooms capture the light and sea breezes. A separate simple structure could make for a fun getaway space. Steeped in tradition and rich in natural beauty, this property invites you to create lasting memories for generations to come in one of Maine's most cherished summer enclaves.

Discover an exceptional coastal compound on the peaceful north end of Islesboro, where expansive acreage, shoreline access, and privacy come together in a truly uncommon offering. Spanning 13 acres with approximately 514 feet of open waterfront, the property provides direct, easy access to the beach without stairs. Abutting conservation land and reached by a long private drive, the setting feels secluded and removed from the everyday. At the heart of the compound is a beautifully threebedroom crafted log-style residence completed in 2025. The approximately 2,200-square-foot home combines rustic warmth with a bright, contemporary layout. Adding another dimension to the property is the original 1968 residence, a comfortable fourbedroom, two-bath home designed for year-round use. All of the living space is conveniently located on a single floor, and the home retains plenty of character. There is a separate two-car garage provides ample room for vehicles, equipment, and storage, as well as a boat house. Outdoor living is an integral part of the compound. A covered porch and waterside fire pit provide inviting places to gather, unwind, and enjoy the shoreline. Both residences have fenced yards with gated paths leading directly to the beach. For those interested in gardening or a more self sufficient lifestyle, the property also includes a newly installed greenhouse and 10 young fruit trees. With two distinct homes, substantial acreage, protected surroundings, and rare open waterfront, this Islesboro compound offers remarkable versatility for extended family, private retreats, and generations of shared summers. Offered separately. See MLS 1679400 & 1679401.

East Bay is an exceptional coastal estate offering the perfect blend of a private summer retreat and a tranquil year-round residence. Set on more than five secluded acres with 430 feet of pristine, accessible waterfront, the property enjoys an elevated position above the scenic shoreline, where beautifully curated gardens and mature landscaping frame sweeping views across Penobscot Bay and its islands.The residence unfolds along a gently sloping bluff, capturing spectacular water vistas from nearly every room and outdoor living space. Originally built as a post-and-beam home around 2000, East Bay has been thoughtfully transformed over time. Its current design, inspired by the timeless coastal architecture of Royal Barry Wills, combines classic New England character with understated sophistication.Designed for both elegant entertaining and comfortable everyday living, the home offers a seamless balance of formal and informal spaces. Highlights include a first-floor primary suite with a private sitting room and office, multiple guest suites, inviting sitting rooms, a library, additional office spaces, a wine cellar, exercise room, updated mechanical systems, air conditioning, a generator, and a carport.The outdoor amenities are equally impressive. A heated swimming pool, hot tub, and sauna are perfectly positioned to maximize the breathtaking waterfront setting and views, while a custom-built staircase provides direct access to the property's private beach.Evoking the charm and grandeur of Islesboro's historic summer cottages, East Bay is a rare legacy property--an extraordinary expression of Maine's rugged coastal beauty, enduring craftsmanship, and timeless elegance.Explore the 3D tour and floor plans for a fully immersive experience of this remarkable estate.

Experience the magic of coastal living at this seasonal camp, set on 7 acres of level land and offering 1,400 feet of accessible shoreline and beach. Whether you choose to enjoy the camp as it is or build your dream retreat, this property provides the ideal setting to enjoy island life. Imagine long summer days filled with swimming, boating, and beach combing, capped off by breathtaking sunsets over the water. When you're ready to explore, take a stroll up the beach to Islesboro Island Trust's Turtle Head Preserve, where rocky cliffs, panoramic views, and fascinating geological history await. Or head out to explore all the island has to offer. The property is being offered as is.

TWO HOMES-ONE OCEANFRONT PROPERTY: Set along the shores of beautiful Searsport Harbor, this rare oceanfront offering includes two distinct homes on a single waterfront parcel, creating exceptional flexibility for personal enjoyment, multi-generational living, guest accommodations, or income-producing opportunities.The original seasonal cottage has been part of the same family's summer traditions for generations. With 5 bedrooms, 2 baths, warm old-growth wood interiors, and a timeless coastal character, it captures the essence of classic Maine waterfront living. Days here are spent enjoying the private beachfront, launching kayaks, gathering for meals with family and friends, and watching boats pass through the harbor. Authentic and unpretentious, the cottage offers the kind of coastal experience that is increasingly difficult to find.Complementing the cottage is a newer 3-bedroom, 3-bath contemporary home designed for year-round comfort and versatility. Open living spaces, abundant natural light, and two ensuite bedrooms create a welcoming environment for owners and guests alike. The spacious lower level offers flexibility for additional living space, a media room, studio, exercise area, or in-law suite, while a separate bonus room is ideal for hobbies or workshop use. Solar panels help keep operating costs low, and the attached 2-car garage includes an EV charging station.Whether utilized as a private family compound, a combination of owner occupancy and seasonal rental income, or a property shared across generations, the possibilities are extensive. With two homes, a private beach, and a coveted Searsport Harbor setting, this is a rare opportunity to enjoy the Maine coast while benefiting from the flexibility and income potential that few waterfront properties can offer.

Discover a private coastal escape on the quieter northern end of Islesboro, where expansive acreage, immediate waterfront access, and new construction come together in an exceptional setting. The property encompasses eleven acres with approximately 260 feet of shoreline, offering the rare convenience of level access to the beach directly from the groundsno stairs or difficult terrain required. Completed in 2025, the 2,200-square-foot log-style residence was designed to make the most of its natural surroundings. The heart of the home is an airy kitchen and living space defined by soaring cathedral ceilings and a broad expanse of windows that captures abundant daylight and views toward the water. A covered rear porch extends the living area outdoors, providing an inviting place to gather while overlooking the shoreline. Two bedrooms are located on the main level, including a generous primary suite with a walk-in closet and direct access to a screened porch. Upstairs, a spacious third bedroom and private bath provide comfortable accommodations for visitors or family members. Privacy is a defining feature of the property. The home is reached by a lengthy private drive, creating a peaceful sense of separation from the surrounding island community. A recently completed detached garage with room for two vehicles adds valuable storage and everyday functionality. Offered as a move-in-ready waterfront property, this Islesboro retreat combines contemporary comfort with the timeless appeal of island living. An expanded 13-acre purchase is also available for those interested in creating a larger family compound or multi-generational estate. That offering includes an additional four-bedroom, year-round residence, providing an uncommon opportunity to establish a substantial private coastal property.

Set on two private acres on the northeast side of Islesboro, this thoughtfully updated coastal retreat offers an idyllic setting overlooking East Penobscot Bay. Originally conceived as a classic Maine camp, the property has evolved into a comfortable four season home that combines its original character with the conveniences of modern island living. The single-story interior is designed for easy everyday living, centered around an inviting open living space and framed by a dramatic glass enclosed entry. Beyond, a covered porch provides an exceptional spot to take in the water views and enjoy the changing landscape throughout the seasons. The home includes four bedrooms, including a bright built-in bunk room, along with two full bathrooms. Practical updates include a new washer and dryer and 1GB high-speed internet. The waterfront setting is equally appealing. A gradual path leads toward the shore, creating an easy place to launch a kayak, swim, or simply spend time beside the bay. Above the approximately 120+/- foot long seawall, a stone terrace and fire pit provide a natural gathering place for long afternoons, evening fires, and waterfront dinners featuring lobster from the local fleet. The grounds have been designed with both recreation and privacy in mind, including a fenced area. Just across the driveway, a substantial boathouse and workshop offer ample room for equipment and storage, with ceiling mounted hoists making it convenient to store kayaks and smaller boats. Additional improvements include a recent property survey along with enhancements to the easement and driveway. Located on peaceful Pripet Woods Lane, the property enjoys a quiet, low-traffic setting with nearby access to Islesboro Island Trust trails. Private, waterfront, and surrounded by the natural beauty of coastal Maine, this is an inviting island escape with the flexibility to serve as a seasonal getaway or a year-round home. Septic not designed for 4 bedrooms.

The Bluff House is a gracious 19th Century Greek Revival ship captain's house, set high on the north end of the island with inviting views over its nearly 18 private and mostly wooded acres with trails leading to over 700 feet of sandy beach on the eastern shore of Islesboro. As the back of this stately home opens to a sprawling lawn with the views over tree tops east to Penobscot Bay, the Bluff House's privacy, quiet neighborhood, and bucolic feel beckon a time long ago. Set up island, this home is in close proximity to the island's community center, places of interest, and activities. This 1800's, 4 bedroom, 3 bath property has many renovations and updates complete with new engineered European White Oak flooring, new structural support system under the kitchen, new lighting in the kitchen and bathrooms, and new plumbing stubbed and ready to go. Currently the kitchen and two of the bathrooms are ready for your own touch and completion! There are generous yet comfortable spaces to enjoy - family room, living room, dining room, library/study - at the Bluff House with its architectural elements echoing an age of simplicity and elegance, while its systems and structures have been updated during thoughtful and meticulous renovation creating a distinguished, historic home of notable character with modern convenience, including a two car garage - with sub flooring in place and could be finished as an office, studio, or other space -, 10kw generator, and high speed internet. A perfect island home ready for year round living or seasonal retreat.