Homes for Sale near Islesboro Central School

This property offering includes an historic Arts and Craftsman-style Foursquare house - thought to be one of the first houses built in Dark Harbor - set on a sunny and open lot, as well as an additional vacant wooded lot both, just a short walk from the charm and amenities of Dark Harbor Village, Gilkey Harbor, and scenic Kissel Point. Brimming with original character and island warmth, the

Michael Lynch Legacy Properties Sotheby's International Realty

This delightful cottage is set on a sunlit lot within walking distance of Dark Harbor Village, Gilkey Harbor, and scenic Kissel Point. Enjoy soaking up Summer days on the deck surrounded by honeysuckle, peonies, and mature rhododendrons and playing out on the lawn. Inside, are cozy living spaces with a bedroom tucked upstairs. A detached storage shed provides convenient space for garden tools and

Michael Lynch Legacy Properties Sotheby's International Realty

Plum Point Cottage: Contemporary Island Home set on a hill with Breathtaking Ocean Views. Wake up to island life at Plum Point Cottage, a coastal retreat designed by Architect Christopher Glass. With 400+/- feet of rocky waterfront, this contemporary island setting offers stunning sunrises over Bounty Cove and Penobscot Bay from your private deck. The first floor welcomes you with a small

Virginia Hess Cates Real Estate

The Farrow-Farnsworth Home is an historic gem on about 40 acres overlooking Broad Cove and Gilkey Harbor on Islesboro island in Penobscot Bay, one of Maine's top cruising grounds. Two distinct homes are joined together seamlessly. One is a lovingly restored 1790's home and the other a spacious 1970's house. The original house, built by Revolutionary War soldier Josiah Farrow and home to

Michael Lynch Legacy Properties Sotheby's International Realty

Little Broad Cove, Guinea, Islesboro. Easterly water views like you read about. Three bedroom yearround home with guest shore cottage across the road. Beautifully landscaped grounds, raised beds and sunny open yard with 138 feet of shorefront. Large living room and primary bedroom. Generous open decks. Both structures will need attention. Being sold ''as is''. Walk to the Historical

John Oldham Island Property

Oceanfront retreat includes 17 acres with incredible views and 700 feet of sandy beach! Once known as The Bluff House, a former Sea Captain's House. This 1800's, 4 bedroom, 3 bath property has many renovations and updates complete with new birch flooring, new structural support system under the kitchen, new lighting in the kitchen and bathrooms, and new plumbing stubbed and ready to go.

Nicole Emery Camden Coast Real Estate

292 + 300 Main Road are comprised of an elaborate, historical, federal style, island home and the former island schoolhouse that is currently used as an art gallery. The main house has an updated kitchen, a large dining room with original built-ins, a family room that could be a first floor bedroom, a formal living room with an ornate fireplace surround with a wood stove insert, a grand front

Rachael Umstead Lone Pine Real Estate Company

Prominently sited on 18.5± acres with 955± feet of varied shorefront on Gilkey Harbor and stunning views to the west, the Sears Cottage is one of the grand historic Islesboro estates constructed at the turn of the 20th century. The nine-bedroom, nine-bath home also includes staff quarters, a carriage house / stable, reading room, and substantial deep-water dock with floats. The residence,

Joseph Sortwell LandVest, Inc.

Located just moments from the Islesboro ferry terminal, this 4.43± acre undeveloped land parcel offers the opportunity to pursue your creative vision. The mostly wooded lot features an identified and partially cleared building site and sweeping water views. With approximately 1,064± feet of diverse shoreline—including stretches of sand and pebble beach mixed with gentle tidal pools—this property

Joseph Sortwell LandVest, Inc.

Improved and elevated 2.3+/- acre waterfront lot with 387+/- feet of shore front accessible by stairs. Existing on site is a gravel driveway, underground electricity and internet, well water with expansion tank, and septic system design. Shed pictured conveys.

Michael Lynch Legacy Properties Sotheby's International Realty

Deepwater access to Penobscot Bay from 2.5 acres of elevated, East facing, buildable land. A roadway has been cleared and a septic design is available.

Maggie McGaw Camden Real Estate Company

1588 Turtle Head Road is a premier waterfront retreat with stunning western views across Turtle Head Cove and Penobscot Bay, back towards Belfast and the Camden Hills. The property includes a beautifully renovated mid-century modern home with two bedrooms and a spacious, open floor plan designed to capture natural light and maximize the water views. There is also a versatile garage/barn with a

Joseph Sortwell LandVest, Inc.

East Shore Drive, Islesboro. Dark Harbor Village north along the shore dotted with grand waterfront summer cottages to your private haven. You will have your breath taken away as this stunning wildflower meadow reveals an unsurpassed view of the ocean and possibilities. 15 parkland acres edged with woods and 770 feet of bold shorefront and beach comprise commanding hillside building sites,

John Oldham Island Property

This parcel of waterfront land is perched up and out of the flood zone and has a westerly orientation looking out over the cove and bay. The property is set on Golf Club Road just a stroll to the Tarrantine Club's Golf Course. It is comprised of 1.9 acres and 320 feet along the accessible shore.

Michael Lynch Legacy Properties Sotheby's International Realty

Welcome to Maine summer living. This quintessential Maine summer cottage overlooks an expansive 1000+/- feet of waterfront along the East Penobscot Bay and with views extending towards Castine and Cape Rosier. It includes two buildings: a main cottage and a guest cottage that can also function as a boat house. As if taken right off a sailing yacht, the open timber frame main cottage is

Virginia Hess Cates Real Estate

Discover this beautiful 5.7+/-acre wooded lot on Seal Harbor, Islesboro. Enjoy 541+/- feet of waterfrontage with southern and southwestern views of the protected, public harbor with a public dock and float hosting sailing lessons, swimming, and fishing in warmer months. This unique property features numerous old Ash and Oak trees, a private gravel beach, a bubbling brook, and an old cellar hole.

Virginia Hess Cates Real Estate

Known as The Abbey, this truly unique property on a quintessentially Maine island began life as a residence and summer retreat for a local pastor. With numerous repairs, paint, holtz hausen wood piles, garden, and landscaping from the current owner, the property is ready for its next chapter. Sadly, the current owners have been called away from their island paradise, but a new owner now has the

Wendy Huntington Berkshire Hathaway HomeServices Northeast Real Estate

If waking up to the sunrise glimmering off of the Atlantic Ocean is how you want to start your days or are looking for a great investment, this waterfront property with elevated and easterly views of the Penobscot Bay located on the very desirable East Shore Dr. in Islesboro checks all the boxes! With a beautiful and modern Den Outpost cabin, this property is ready to put the final touches on.

Wendy Huntington Berkshire Hathaway HomeServices Northeast Real Estate

Welcome to 228 Gooseberry Point Road on the picturesque island of Islesboro. Located on over 5 private acres with 743 feet of frontage on West Penobscot Bay, the 4-bedroom house is in excellent condition with many recent upgrades, including newly landscaped, whole-house generator, hot tub, delightful patio just 75'± from the beach. Water view from every bedroom! Fully winterized, this home is

William Warren Warren Realty

Iconic and Historic Dark Harbor Village Prime Real Estate in the heart of summer community and activity. Peg's Giftshop with 1,700 sq ft of retail space and 2,800 sq ft of residential space upstairs with three bedrooms, kitchen, living/dining room, full bath and third level apartment with full bath, even a harborview from the widow's walk. Cedar shingles, apple and cherry trees, pleasant

John Oldham Island Property

Escape to the serenity of Islesboro, Maine, with this remarkable 10.9-acre parcel of undeveloped land offering privacy, natural beauty, and panoramic westward-facing views — perfect for taking in stunning sunsets over Penobscot Bay.This unique property features approximately 250 feet of dramatic, rocky shoreline, where the rugged coast meets open ocean vistas. A peaceful creek flows through the

Shelby Place Hoang Realty

Location, Location! Near Town Spacious Three-Bedroom Home. Walk to almost everything; store, community center, post office, town office, garage. Handy to ferry and Dark Harbor village shops and amenities, near golf course. Detached garage, shop, and office. Landscaped, wooded 1.74 acres with 425 feet of road frontage. Open concept living room, dining room, kitchen. Two full baths, laundry

John Oldham Island Property

The Artist Cottage is nestled unseen from the road on 1.5± acres with 150+/- feet of tidal waterfront on Islesboro Harbor offering stunning views of Islesboro Harbor, Bounty Cove and the narrows. This charming seasonal cottage is located in the desirable and seldom available mid-island neighborhood of Hewes Point, near Maddie Dodge Field, with tennis and pickleball courts at your disposal

Virginia Hess Cates Real Estate

This is a terrific opportunity to own a corner lot with views of the ocean from two sides. Rent out the house as an ADU and build your primary, summer, or investment residence in an open field, surrounded by apples tree and sweeping views of the Penobscot Bay and Broad Cove. Islesboro is only a 20-minute ferry ride from Lincolnville, close to Camden and Belfast, has a highly rated school,

Wendy Huntington Berkshire Hathaway HomeServices Northeast Real Estate

300 Main Rd is the former Island schoolhouse that is currently used as an art gallery. It is made up of two very large rooms - 858 and 528 square feet respectively. Both rooms have extremely high ceilings and windows almost as high that afford seasonal Atlantic Ocean views on the North side. There is a half bath on the first floor and a studio apartment with a full bathroom on the second floor

Rachael Umstead Lone Pine Real Estate Company

Welcome to 292 Main Road, Islesboro, ME—a large five-bedroom summer retreat perfect for those seeking a blend of comfort and charm. This spacious house boasts an elegant new kitchen equipped for culinary adventures, and electric baseboard heat to keep you cozy during the cooler months. Imagine sipping lemonade on the expansive front porch, watching the day unfold on your picturesque front lawn

Rachael Umstead Lone Pine Real Estate Company

292 + 300 Main Road are comprised of an elaborate, historical, federal style, island home and the former island schoolhouse that is currently used as an art gallery. The main house has an updated kitchen, a large dining room with original built-ins, a family room that could be a first floor bedroom, a formal living room with an ornate fireplace surround with a wood stove insert, a grand front

Rachael Umstead Lone Pine Real Estate Company

Improved Price! Westerly Horizon Turtle Head Waterfront Building Lot. Exceptional western water views of upper Penobscot Bay from 2.6 acres of mixed hard and soft wood and fern glades with 185 feet of bold water frontage and gravel beaches. Deep water access, suitable for a dock. Subdivision restrictions and green buffer easement assure quality, density, and privacy. Soils report available.

John Oldham Island Property

The Grace Cottage, Hermit's Point. This magnificent stuccoed Renaissance Revival cottage built in 1918 designed by noted Philadelphia architect, Wilson Eyre commands unsurpassed views from its 8.8 acre peninsular location and 3,570 feet of shore line. Eight bedrooms, seven fireplaces. Replete with all the requisite amenities for an elegant summer's stay including pool, dock and stone lodge.

John Oldham Island Property