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Scroll down to view currently listed condos and single family homes for sale in Islesboro, Maine. If you have any questions or would like to schedule a tour, contact our team. You can also create an account with our site to save your favorite listings, and you can get email updates when new properties match your search criteria.
This magnificent peninsula encompasses 76.29 acres with 6878 feet of waterfront and a renovated historic residence and guest cottage on the point. The property offers a deepwater dock and several excellent building sites. Also offered in smaller configu
East Bay is a beautifully designed and skillfully crafted home built in the tradition of the grand estates of coastal Maine. The residence is open and inviting with generous living spaces, high ceilings, fireplaces and exposed beams. Privately located on 4.2± acres with 390'± of rocky beach shore, the broad views encompass all the islands of the eastern bay, North Haven and the open ocean. Extensive landscaping combines formal gardens with fields of wildflowers firmly anchoring the residence in its setting.
Prominently sited on a scenic knoll surrounded by a multitude of gardens, the centrally located Dark Harbor House is a stunning example of Colonial Revival architecture designed by Fred Savage and built in 1896. In 2011/12 the current owners commissioned a complete restoration/renovation starting with a new foundation and ending with top period furnishings and landscaping. There are eastern views over the Dark Harbor Pool and 196 feet of tidal shorefront on Ames Cove with a kayak launch and gravel beach.
Rare opportunity to own an island compound as your private estate and/or investment property. Steeped in time & tradition this Dark Harbor property sits at one of the highest points on the island with commanding sunrise & sunset views, and includes two well appointed French Country designed cottages set at the water's edge. Opportunity for expansion on this property's sprawling 4.2± acre parcel with 380'± of accessible shoreline. Fully furnished. Rental history. Additional waterfront land may be available.
Listed by Legacy Properties Sotheby's International Realty
This year round 4+ bedroom home is on the rocky coastline of Charlotte's Cove. The open floor plan opens to a wrap around deck allowing one to take in the sweeping views of the bay and distant islands while observing the wildlife and sailing life this location offers. With 20+ acres, 1000 feet of frontage, and a small beach, this property can be expanded for a family compound (there are conservation easements on some parts) or used as a private retreat. Great light and nice flow for entertaining and family.
Architectural gem in the perfect Dark Harbor location! Views of East Penobscot Bay. Within walking distance of all activities. Updated and ready for immediate occupancy. Additional land with prime East Penobscot Bay shore frontage available.
Privacy accompanied by breathtaking ocean views are only some of the many features this Island retreat offers! Enjoy this custom built home with 3 bedrooms, 1.5 baths, cherry floors, stained glass windows and private decks with a great outdoor shower! Tons of character that needs to be seen! This 6.5 acre property boasts 438 ft of deepwater ocean frontage. Come and enjoy peaceful island life! Home has great rental income potential as well!
Waterfront compound of 3 buildings, main house (2005); studio & guest apartment (2007); garage + 24 x 24 activity room (2009). Architect designed & built for his personal home. Restored antique light fixtures throughout. Fantastic beach. Broker related.
Listed by Home Town Real Estate & Property Management
Privacy, privacy, privacy! This oceanfront home featuring almost 300' of frontage on Sprague Cove is the perfect island retreat with spectacular views over Penobscot Bay and the Camden Hills. Property has several outbuildings, separate workshop, and two moorings located just off shore in a protected cove. The two adjacent lots have 450' building setbacks and 100' "undisturbed buffer" from shore ensuring privacy.
Listed by Legacy Properties Sotheby's International Realty
The main house, built in 1997, has living room with fireplace, dining area, kitchen, breakfast area, two bedrooms, bath, laundry, and bonus room on the first floor. Attached 2-car garage. Second floor is insulated and framed for 3 more bedrooms and bath. French doors lead to fabulous porch. Wide wooden steps lead to 355 feet of beach frontage.
Entirely self-sufficient two-bedroom guest cottage with brand new kitchen, deck overlooking large yard and water. Perfect for guest overflow or rental income.
Classic Maine Farmhouse with 560 ft of East Penobscot waterfront and 6+ acres of open and wooded land sloping gently towards the private shorefront. Captivating views of Cape Rosier and points beyond. Other building sites possible.
Listed by Legacy Properties Sotheby's International Realty
Over 9 acres with 321 feet of gorgeous beach frontage! A gentle step onto the beach with views all the way from Castine to North Haven! Built in 1998, house is small and cozy with room for expansion. Master bedroom on 1st floor and extra sleeping room in the air-conditioned loft. Large storage shed, great fire pit, tent platform (with electricity) for when lots of guests visit. This is real Maine Living!
This tasteful custom designed Maine cottage is westerly oriented to capture sunsets over the Camden Hills on Islesboro's bay side. Live the endless summer you've longed for ... exploring 255 ft. of private shoreline, puttering in the garden, finding refuge on covered porch reading or napping in sun-drenched Adirondack chairs. Architect Chris Glass created an open concept perfect for entertaining or quiet retreats. The wooded 2.8 acres offer tremendous privacy while being only half-mile from Ferry Terminal.
Enjoy sweeping easterly views of East Penobscot Bay with 450 feet +/- of direct frontage. Dark Harbor, Islesboro. Sited on a private 2.3 acres +/-. this charming cottage offers a great lawn to the gravel beach moorage and natural surroundings. A separate 2 bedroom 1 bath guest cottage enhances this special offering. Amenities of Islesboro include transportational access by scheduled car ferry and public airstrip.
Situated in the midst of a 9 acre evergreen forest, this custom built cedar log home has 400+ ft of ocean frontage on protected Sprague Cove. The open floor plan features a central stone fireplace and a wall of windows facing the sunny deck and a captivating water view. Two bedrooms and a full bath are on the main level with additional sleeping space in the 450sq ft loft area. There is well protected moorage in the Cove and potential for a dock on the private shore front.
Listed by Legacy Properties Sotheby's International Realty
This nearly new contemporary 3500+ s.f. Dutch Colonial home is set on 4 private acres with a water view of East Penobscot Bay. Wrap-around porch, 2 decks, 3 BR, 3 baths, stone fireplace, viking stove, soapstone sink. All with lots of windows to enjoy the water & woods views.
Listed by Legacy Properties Sotheby's International Realty
150 Feet of Sandy, Pebble Beachfront, Think about walking the beach while enjoying the westerly views of the Camden Hills and Lincolnville across Penobscot Bay. Sit on your private covered porch and smell the salt air and listen to the sounds of island living. Enjoy a gourmet kitchen, lined with Cherry cabinets and a wonderful island opened to the window lined dining room. Warm up by the fireplace in a wonderful living room.Large deck and yard, great for making family memories.
This one bedroom dwelling sits on 3.7 ac +/- with 266' of shore frontage on Crow Cove facing the West Penobscot Bay. Possible dock and larger residence may be constructed. Dwelling has a newly constructed deck as well.
Listed by Legacy Properties Sotheby's International Realty
If waterfront, nature and simplicity is what you are seeking then this Islesboro home on Ryder Cove is for you. This furnished three bedroom A-frame with additional 3rd floor loft offers its' owners and guests a relaxing home-away-from-home. The living area has vaulted ceilings and an inviting wood stove. Great rental history and guests remark that this home offers the serenity they are seeking. Head down to the path to the 168' of waterfront and you are greeted with a beach with long Penobscot Bay views.
Cozy 3-bedroom, 2½ bath cape on 11± acres of field centrally located mid-island. First floor master bedroom and bath, kitchen, living room with fireplace, dining room. Large back deck overlooking a lovely, private yard with pond.
Historic building in Dark Harbor Village renovated in 1998 including mechanical and electrical systems, windows and baseboard heating. Existing first floor commercial space with established retail traffic, close to shops and amenities, offering ample parking; 2nd floor has full kitchen, living, dining and two bedrooms with full bath. Deck overlooking pond. 3rd floor Master Bedroom with full bath, skylight and beautiful view of the pond. All ready to go! Move in!
Listed by Legacy Properties Sotheby's International Realty
Warm, inviting, and impeccably kept island property. Three bedrooms, two full baths, two living rooms (one with fieldstone fireplace), dining room, attached barn with enormous work space plus studio and second floor dormitory. Beautifully landscaped with apple, plum, pear, crab apple, beechnut trees, and grape arbor. Spacious garden shed and deck overlooking it all. This circa 1895 house has been lovingly restored with far too many features to mention here. And all at an exceptionally reasonable price!
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