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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.
…By Legacy Properties Sotheby's International Realty
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.
…By Legacy Properties Sotheby's International Realty
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.
…By Legacy Properties Sotheby's International Realty
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.
…By Legacy Properties Sotheby's International Realty
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.
…By Legacy Properties Sotheby's International Realty
There are properties that sit near the water, and then there are properties like this one. With 400+ feet of direct Penobscot Bay frontage, a private deepwater mooring, and a whole-house generator, 220 Shore Road is as complete a waterfront package as the mid-coast offers.Every room has been renovated with intention. The kitchen shines with butcher block counters, a hands-free faucet, new lighting, and custom storage. The living room anchors around a fireplace with built-in shelving. The primary suite features a custom window seat and a fully updated bath with new shower, flooring, and a statement Fandelier. Downstairs, a finished lower level delivers a custom built-in den, Whirlpool laundry, and a second fully renovated bath.Outside: fresh blacktop driveway, a cedar fence with solar lighting enclosing the entire yard, and a refinished deck with new railing and 180 degree views! Whole-house generator. Private mooring. Nothing left on the to-do list.
…By Legacy Properties Sotheby's International Realty
Nestled along the scenic coast of Belfast, this well-maintained 5-bedroom, 3.5-bath waterfront home offers spacious living, sweeping views, and the ease of a stand-alone residence within a quiet residential condominium community -complete with a deep-water dock for boating and kayaking on Penobscot Bay. Designed with flexibility and comfort in mind, the main level allows for true one-floor living with a sun-filled open layout, well-appointed kitchen, laundry, half bath, and a serene primary suite opening onto the deck. The generous water-facing deck extends the living space outdoors, ideal for entertaining or peaceful morning coffee. Upstairs are two additional bedrooms and a full bath - one of which lends itself perfectly to a bunk room, office, studio, or media room. The lower level offers a fantastic in-law or guest setup, with two bedrooms, full bath, spacious great room with kitchen, and easy walk-out access to a private patio and the beautifully landscaped grounds. Central air-conditioning keeps hot weather at bay, and the living room gas fireplace makes cooler days feel cozy. Sweeping ocean views grace nearly every room, and thoughtful touches throughout offer comfort, light, and versatility. Plenty of storage on each level and an oversized 2-car heated garage accommodates modern lifestyles with ease. Little to no work is required to maintain this beautiful property, thanks to the condominium association amenities. Furnishings could convey for an easy, turnkey move. Close to downtown Belfast for shopping, dining, and entertainment, only a short drive to Lincolnville Beach, Camden, and the Camden Hills State Park for hiking/biking trails. With its blend of privacy, coastal beauty, and community amenities, this is an exceptional opportunity to enjoy year-round living or seasonal retreat in one of mid-coast Maine's most desirable locations.
…By Legacy Properties Sotheby's International Realty
Discover a rare opportunity to own one of Brooksville's most historic waterfront properties. Known as the original Wasson's Wharf, this remarkable offering features approximately 254 feet of deep-water frontage on the Bagaduce River as it opens to Castine Harbor, where 23 clipper ships were launched during Brooksville's renowned shipbuilding era. At the water's edge sits the original boathouse, thoughtfully preserved and currently operating as a seasonal rental, providing immediate income potential while you plan your future waterfront home. Above the shore, a gently elevated homesite has been carefully positioned to capture breathtaking westerly sunsets across Castine Harbor with the Camden Hills rising in the distance. A 4-bedroom septic design has already been approved, making it easy to begin creating your dream coastal retreat. A sweeping meadow leads gracefully to the shoreline, offering a picturesque setting rich in natural beauty and maritime heritage. Whether enjoying the peaceful waterfront, launching a kayak, or simply watching boats navigate one of Maine's most scenic waterways, this property offers an exceptional connection to the coast. Brooksville's rich maritime history comes alive here, where shipbuilders, sailors, and merchants once helped shape Maine's seafaring legacy. Today, the property presents a unique opportunity to preserve that history while creating a legacy of your own. Ideally located just 20 minutes from the vibrant coastal village of Blue Hill, with its acclaimed restaurants, galleries, shops, and yacht club, and approximately one hour from Acadia National Park and Mount Desert Island, this extraordinary property offers the perfect balance of privacy, convenience, recreation, and history. Whether you envision a year-round waterfront residence, a seasonal retreat, or simply wish to own a remarkable piece of Maine's maritime past, Wasson's Wharf is truly a once-in-a-generation offering.
…By Legacy Properties Sotheby's International Realty
A rare opportunity in one of Midcoast Maine's most coveted settings. Privately situated on 4.52 acres, 15 Wildwood Lane is elevated above the surrounding landscape with sweeping views across Penobscot Bay to the lighthouse and islands beyond. Ever-changing coastal light, sea and sky become part of the experience. The 3,721-square-foot residence offers 5 bedrooms and 3.5 baths, with living spaces filled with natural sunlight and beautiful water views. The main living area features an open floor plan flowing effortlessly from formal to informal spaces, creating an inviting setting for entertaining and everyday living. A sizable kitchen with abundant storage is well connected to the heart of the home. The grounds are equally appealing, with lovely perennial gardens adding color and character throughout the seasons. A detached garage includes a workshop at the rear, while an additional outbuilding, once used for beermaking, offers intriguing possibilities as a studio, bunkhouse, artist's retreat, writer's getaway, or creative space. A 7-bedroom septic capacity provides valuable room for expansionan uncommon advantage for those envisioning additional living space or a more substantial residence. Whether reimagined, expanded, or enjoyed as it is, this property offers an extraordinary opportunity to create a home that reflects its owner's vision. The setting's privacy and natural beauty belie its exceptional convenience. Rockport, Camden, and Rockland are just minutes away, with picturesque harbors, fine dining, galleries, shopping, and vibrant year-round communities. The Pen Bay Medical Campus is nearby, while boating, hiking, biking, skiing, are readily accessible. With spectacular views, established gardens, versatile outbuildings, generous acreage, and an exceptional location, 15 Wildwood Lane is a distinctive Maine property with a wonderful sense of possibility - a beautiful blank canvas for creating an extraordinary coastal retreat.
…By Legacy Properties Sotheby's International Realty
This exceptional waterfront property showcases quality craftsmanship and thoughtful design throughout. Set along the shores of Penobscot Bay, the custom modern farmhouse is designed for convenient one-level living, featuring a first-floor primary bedroom and full bathroom. There is also an inviting loft, and a spacious finished lower-level. Distinctive interior details, beautiful sunlight filled living spaces, and sweeping ocean views from throughout. Architectural details include leaded-glass transom windows, a compass rose inlay, and custom built-ins. There is an attached and heated garage, and an additional detached and heated two-car garage featuring an indoor/outdoor kennel and a dedicated cat boarding area which could be easily adapted as a home-based business or workshop/ studio space. The landscape is equally inviting, with an expansive deck, backyard firepit, and shared access over an existing set of steps to the beach below, ideal for relaxing or entertaining. Set on approximately 2.8 acres with 350? feet of waterfrontage, the property features vibrant plantings, mature trees for privacy, and panoramic bay views. Conveniently located with great proximity to Camden, Belfast, Bangor, and the Acadia region.
…By Legacy Properties Sotheby's International Realty
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