Islesboro, ME Homes for Sale under $500,000

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

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 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

Make summer memories at this seasonal cottage overlooking an expansive 1000+/- feet of waterfront along the East Penobscot Bay and with views extending towards Castine and Cape Rosier. The property includes a main cottage and a guest cottage that can also function as a boathouse. As if taken right off a sailing yacht, the open timber frame main cottage is efficient, comfortable, tastefully

Virginia Hess Cates Real Estate

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 side

John Oldham Island Property

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

Discover the opportunity to create your mountain sanctuary on this impressive 30.5-acre lush woodland, which offers a harmonious mix of elevated terrain and extraordinary privacy. Right across the street, seclusion is protected with almost 100 acres of land owned by Coastal Mountain Land Trust. Just a short stroll from your future property, Knights Pond invites you to enjoy kayaking, swimming,

Hanna Steinberg Camden Coast 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 established Ash and Oak trees, a private gravel beach and a bubbling brook. Part of the

Virginia Hess Cates Real Estate

Settle into a well-established subdivision, the former Grace Estate, on a four acre lot with deeded view easement to West Penobscot Bay. Magnificent hard and soft woods, dappled with lush ferns and ledge outcroppings. Access drive completed. Building site and view will need clearing once you've selected your preferred location. All this, on a quiet peninsula of Islesboro ensured with the

John Oldham Island Property

Woody Point. Cherished Ryder Cove Enclave Classic 1890's Clapboard Five-Bedroom Waterfront Home. It's seen glorious days from the covered porch on Sabbathday Harbor. Newer roof. Well worth the work to restore. 141 feet of beach and ledge. Large apple trees. Entry, kitchen, dining room with stamped tin ceiling, living room, bedroom down, four up and full bath, utility room. Great family home at

John Oldham Island Property

Step into history with this remarkable property, originally the Pendleton School, Islesboro's main elementary school during the 1800's until the early 1950s. This former schoolhouse has plenty of potential. Currently operating as the Double Door Gallery during the summer months, showcasing local and regional artists, the property boasts two large open rooms on the first floor, featuring curved

Virginia Hess Cates Real Estate

Set within the desirable Highfields at Catching Cove subdivision, this surveyed 1.38-acre ocean-view lot offers a rare opportunity to build in a thoughtfully planned coastal neighborhood. Residents enjoy access to shared amenities, including a 2-acre common area, a tennis court, and a deep-water dock with access to Penobscot Bay. Carefully maintained neighborhood standards help preserve the

Jack Uhll Legacy Properties Sotheby's International Realty

This thoughtfully transformed and rebuilt four-bedroom home offers modern comfort in an exceptional Midcoast location just minutes from beaches, Bayside Village, Belfast, and a short drive to Camden. Every major system and finish--inside and out--has been renewed, creating a move-in-ready home designed for long-term peace of mind. The main level provides true single-level living with an eat-in

Alyssa Parker Portside Real Estate Group

Tucked into a private, wooded Northport neighborhood, this flexible home is equally suited as a year-round family base or a low-maintenance coastal getaway minutes from the water. Room to Grow: Two bedrooms upstairs plus a finished, flexible lower level with a half bath sleep 4-6 comfortably -- ideal for a young family or hosting guests. Residents have access to any of the local schools,

Hanna Steinberg Camden Coast Real Estate

38-Acre Wooded Lot with Route 1 Address — Northport, Maine A rare opportunity to own 38 acres of unspoiled woodland in Northport with a Route 1 address and access via a deeded right-of-way. This expansive, undeveloped parcel has not been harvested in several years, offering a mature forest setting and a true blank canvas for your vision—whether residential, recreational, or investment. An

Rachael Umstead Lone Pine Real Estate Company

Beautiful 1.16-acre building lot in Northport's desirable Ocean Ridge Subdivision, offering an elevated setting with gorgeous sunrises and lovely, distant views of Penobscot Bay, Islesboro, and the islands beyond. Cleared, surveyed, and soils-tested, the property offers a wonderful opportunity to design and build a coastal Maine home surrounded by natural beauty. Underground power is in place,

Marjorie Crowley CoastWise Realty

Sterling View Farm. Cunning Three-Bedroom Cedar Shingle Home located mid-island handy to town and ferry. Many fine finishing details, wainscoting, exposed beams, wood flooring and widow's walk. Guest cottage all on idyllic 2.3 acre meadow with sunsets and waterview.

John Oldham Island Property

Deep Cove Lane. Southwesterly water views from this four acre wooded hillside parcel, 365 feet of gravel beach on Sabbathday Harbor. Soils tested. End of the private lane. You'll want to check the price twice.

John Oldham Island Property

Conveniently located off Beech Hill Road in Northport, this spectacular undeveloped land parcel offers lovely, elevated views. Set on 4.63± acres, this versatile property offers a unique opportunity to build or develop a private retreat tailored to your vision, along with the potential for views of Penobscot Bay. The serene landscape features blueberry fields and a beautiful mix of mature trees,

Joseph Sortwell LandVest, Inc.