Come and vacation here now and retire here later! Three-bedroom year-round home on 2.4+/- pleasantly wooded acres with 200+/- feet of tidal frontage (gorgeous sunsets!) ...

Set in Pripet on idyllic Islesboro, the Abbey at Farrow Farm offers many possibilities for island life! Currently used as a residence & retreat center, the 2 flexible use...

This year round home sits on 2+ acres, has 210+/- feet of shorefront, remarkable western views, and the island's ferry is so close - just a 1/2 mile - you may walk to it!...

This elegant 5+ bedroom Victorian Cottage has been carefully restored and renovated to highlight the natural charm and character of the home while integrating sophisticat...

Roughly 9,024 acres to explore, 600 friendly year round home owners and 3,600 summer visitors a year, this charming little community is where it's at. Airbnb opportunitie...

1848 Cape, four bedrooms, pleasant corner lot, sun and shade, next to library on quiet side road. Mature hardwood, established perennials. Fresh interior paint, new sep...

Stunning Maine waterfront property. Private 70 acre peninsula includes over 8,600 feet of water frontage on both the West and East shores of Islesboro. Spectacular views,...

An Islesboro classic, ''The Bluffs House'' is a rambling 1830 oceanfront home sited on 17+ acres of meadow and woods with long views of Hutchins Island and East Penobscot...

Exquisite Islesboro home with all the charm and detail that you've been looking for. First floor features cooks kitchen, with pantry, sub zero fridge, viking range, and l...

Charming cottage on 2.3 acres +/- of privacy with beach and mooring await you for summer fun on beautiful easterly facing oceanfront and sweeping great lawn in Dark Harbo...

Ferry Road Cedar Shingle Cape, Sunset Waterview. Well-crafted 3-bedroom, 3-bath home situated perched on a hillside. Convenience, privacy, master bedroom en suite, first ...

Encompassing 9+/- acres with a point of land and 490+/- feet of shorefront, this property offers a private setting with an attractive residence and spectacular western vi...

Formerly the famous (or infamous) Island Pub in Dark Harbor Village, building was moved and totally renovated in 1998. First floor currently rented to Artisan Books, but...

Beautiful oceanfront with 400 ft of frontage with amazing views of Penobscot Bay. Pebbly beach and turtle rock. House sits on the hill with 3 bedrooms, 2 baths and a sepe...

This island home has what everyone is looking for; three bedrooms, 2.5 baths on a private waterfront lot with a gorgeous sunset view and beach all nestled in an evergreen...

Stunning panoramic waterviews from this gracious Gilkey Harbor cedar shingle three-bedroom waterfront cottage. Crisp interior finishes; living room, dining room, gourmet...

Elegant Yearround Rebel Hill Cottage Reminiscent of gracious turn of the century Dark Harbor summer homes, this luxurious open concept three bedroom home features large ...

Located on the eastern shore of Islesboro, this is a fantastic opportunity to own one of the most beautiful private peninsulas in Midcoast Maine, with total privacy and b...

Fabulous property in exclusive Dark Harbor location. Turn key vacation or retirement living at its best. Top-of-the line building and landscaping throughout. Three bedroo...

This year-round post and beam home is nestled in Islesboro's sought after Dark Harbor neighborhood. Privately set amongst the trees and rock croppings with beautiful pere...

Enjoy the peaceful setting of this sweet three bedroom one bath New Englander of Long Ledge Cove, just three minutes from the ferry terminal. This home offers great possi...

Splendid Turtle Head Sunsets from this 1960's contemporary three-bedroom year round home on bold shore front and beach on the calm end of the island. Back on the market ...

Conveniently located right in the heart of Dark Harbor Village, this 100+/- year-old Victorian house is in exceptionally good condition and very tastefully decorated. Wit...

This picturesque, year-round waterfront home is nestled on the sought after island of Islesboro. It is privately set on 7+ acres, w/ 650 ft. of varied shorefront, a deep ...

This private oceanfront Shingle-style cottage enjoys spectacular western views across Penobscot Bay to the Camden Hills. Built in 1993, the elegant three-bedroom residenc...

Over 9 acres with 321 feet of gorgeous beach frontage! A gentle step onto the beach with views all the way from Castine down the Bay. Extremely private and cozy living wi...

Cozy 3-bedroom, 2-1/2 bath cape on 11+/- acres of field centrally located mid-island. About 10 Acres of field suitable for equestrian activities. First floor master bedro...

Classic old Maine Farmhouse with 560 ft of East Penobscot waterfront and 6+ acres of open and wooded land sloping gently towards the water to the beach. Captivating views...

Prominently sited on 21+/- acres with 1,110+/- feet of varied shorefront on Gilkey Harbor and stunning views to the west, the Sears Cottage is one of the grand historic I...

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Impeccable waterfront property in small, sought after, charming neighborhood. Includes dock and float as well as a guest cottage across the road with unattached garage a...

An inviting yearround home, truly in the heart of Dark Harbor Village, just steps from summer shops. Built in 1920 and completely renovated in 1978. Open floor plan kitch...

Located on the eastern shore of Islesboro, Northeast Point is a spectacular 74+/- acre oceanfront property with over 6,800 feet of frontage on Penobscot Bay. This is a fa...

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 gener...

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 f...

Waterfront compound of 3 buildings, main house (2005); studio & guest apartment (2007); 3rd building /garage + 24 x 24 activity room (2009). Architect designed & built sp...

Pristine, seasonal Cedar log cabin with detached workshop/tractor shed. Fully furnished cottage contains 3 BR's, 2 full Baths, screened porch, paved driveway, car port, B...

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 d...

Oceanfront cedar-shingled year-round three-bedroom home, two bath, quaint and cozy wooded location. Refurbished kitchen. Great views, beach, deck.

Sherman Dodge Home on the way to Dark Harbor. Carefully constructed in 1912, by island builder Frederick Lee, this three-bedroom house is being sold 'as is' with all fix...