Islesboro Maine Homes for Sale

MLS Number 1359132

• Residential
• Address 135 West Shore Drive
• Location Intown
• Bedrooms 9
• Bathroom 9

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 Islesboro estates constructed at the turn of the 20th century. The nine-bedroom, nine-bath home also includes staff quarters, a guest cottage with four-car garage, billiard house, carriage house / stable, reading room, and substantial deep-water dock with floats. The residence, characteristic of the Renaissance Revival Style, has been thoughtfully restored and retains many original details such as eleven wood-burning fireplaces and fine woodwork throughout. The grounds are those of a classic Maine summer estate: artfully landscaped with lawns, flowering shrubs, specimen trees, and both formal and informal gardens interspersed with natural Maine woods.

Listed by LandVest, Inc.

MLS Number 1411611

• Residential
• Address 562 Main Road
• Bedrooms 4
• Bathroom 4
• Rooms 12

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, protected cove, deep water dock and anchorage, accessible shore frontage, beaches, bold cliffs, and trails. A historic Cape Cod style home reroofed, resided, structural work completed, gutted to the studs and ready for your completion. A substantial post and beam barn, with improvements. Several additional, excellent building sites.

Listed by Legacy Properties Sotheby's International Realty

MLS Number 1321528

• Residential
• Location Other Location
• Bedrooms 6
• Bathroom 9
• Rooms 16

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.

Listed by LandVest, Inc.

MLS Number 1279536

• Residential
• Address 117 Jetty Road
• Bedrooms 9
• Bathroom 10
• Rooms 26

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 1885/86. In 2011/12 the current owners commissioned a complete restoration / renovation starting with a new foundation and ending with top period furnishings and landscaping. The commanding historic residence features views of the iconic Dark Harbor to the north, and to the west 196 feet of waterfront on Ames Cove includes a gravel beach and a six-kayak storage rack with custom launch system providing access to excellent kayaking in the picturesque Gilkey Harbor.

Listed by LandVest, Inc.

MLS Number 1337200

• Residential
• Address 565 Main Road
• Location Other Location
• Bedrooms 4
• Bathroom 4

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 fantastic opportunity to own one of the most beautiful private peninsulas in Midcoast Maine, with total privacy and bold ocean views. The property includes a fully furnished 4 bedroom shingle style home, a seasonal guest cottage, a deepwater dock and pier, a protected cove with great anchorage, and wonderfully accessible shore frontage with great walking trails and several beach areas. The property is an approved 13 lot subdivision, but available for purchase in its entirety giving the Buyer the unique opportunity to configure the property in a number of appealing ways.

Listed by Legacy Properties Sotheby's International Realty

MLS Number 1368551

• Residential
• Address 134 Big Tree Lane
• Bedrooms 5
• Bathroom 5
• Rooms 14

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 water dock in protected Seal Harbor, and thoughtful landscaping w/ views across Penobscot Bay to the Camden Hills. This home was custom-built to the highest standards, and exemplifies exquisite form and function, allowing for smooth transitions among the gracious formal and casual informal living and entertaining spaces, indoors and out. This home offers a generous master bedroom plus 4 additional bedrooms, some w/ windows seats, a sitting room w/ balcony, covered porch and screened porch, a greenhouse, sunroom, a library w/ wood burning fireplace and hand-built custom shelves and cabinets, living room w/ wood burning fireplace, a formal dining room w/ custom built-lighted shelving, and kitchen w/ an AGA stove. Additional amenities include home office, laundry room, radiant heat, whole-house generator and 2-car garage.

Listed by Legacy Properties Sotheby's International Realty

MLS Number 1376961

• Residential
• Address 565-1 Main Road
• Location Other Location
• Bedrooms 4
• Bathroom 4

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 bold ocean views. The property includes a furnished 4 bedroom shingle style home, a seasonal guest cottage, access to a shared deepwater dock and pier, a protected cove, and accessible shore frontage with several beach areas. Northeast Point is an undeveloped 13 lot subdivision and this is an opportunity to own 7 of the lots at the tip of the property including the main house and guest house as well as over 3,900 feet of spectacular private frontage on Penobscot Bay. The property is also being marketed in its entirety, and the Seller is also willing to explore re-configuring the property in a in a number of different ways to suit a Buyer's needs.

Listed by Legacy Properties Sotheby's International Realty

MLS Number 1408365

• Residential
• Address 435 Ferry Road
• Location Other Location
• Bedrooms 3
• Bathroom 4

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 views. The year-round home is located at the end of a winding drive through lovely wooded land, and the house is thoughtfully landscaped with native shrubs and perennials. There are three bedrooms, an extensive studio/office or potential fourth bedroom, three-and-a-half baths, and an open living room with access to the deck and screened porch. Well-maintained woods on the point provide privacy and a natural environment while allowing stunning views across Penobscot Bay and back to the Camden Hills. The property is conveniently located close to the ferry and includes an attached two-car garage, a large boat barn with workshop, pocket pebble beach, part of a larger pebble beach, and a well-built deep-water dock.

Listed by LandVest, Inc.

MLS Number 1365192

• Residential
• Address 577 Ferry Road
• Location Near Country Club
• Bedrooms 3
• Bathroom 3

This private oceanfront Shingle-style cottage enjoys spectacular western views across Penobscot Bay to the Camden Hills. Built in 1993, the elegant three-bedroom residence was designed by architect John Silverio and features a light-filled open floor plan centered around an impressive Russian brick fireplace. A classic wraparound porch, a rooftop widow's-walk, and impeccable craftsmanship are among its distinguished details. The surrounding 11.64+/- acres of wooded property includes 2,403+/- feet of shorefront on Penobscot Bay with a private sand and pebble beach and a deep-water mooring. In addition to the main residence, there is also a newly built guest cottage/studio affectionately known as Two Nights, with a one-bedroom apartment on the second level and a two-vehicle garage and large open studio below. Additional 3.58+/- acres of abutting land is being offered separately.

Listed by LandVest, Inc.

MLS Number 1377355

• Residential
• Address 161 Jetty Road
• Bedrooms 3
• Bathroom 3
• Rooms 10

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 bedrooms, 2-1/2 baths, huge kitchen and dining areas as well as living rooms. 1.7+/- acres with 260+/- feet of tidal frontage on Ames Cove.

Listed by Warren Realty

MLS Number 1410277

• Residential
• Address 317 Main Road
• Location Rural
• Bedrooms 5
• Bathroom 5

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 large island for entertaining. Double sided fireplace in the kitchen and sun-room, formal dining room, living room with fireplace, family room and library/den both have wood burning fireplaces too! Second floor features 5 bedrooms, and 3 bathrooms. 11 acres with stunning grounds, views of Islesboro Harbor, your own pond, two story 3 car garage/barn with attached greenhouse to start all your flowers and vegetables for your gardens.

Listed by Camden Real Estate Company

MLS Number 1415287

• Residential
• Bedrooms 5
• Bathroom 4
• Rooms 18
• Acreage 0.36

This elegant 5+ bedroom Victorian Cottage has been carefully restored and renovated to highlight the natural charm and character of the home while integrating sophisticated elements throughout. There is custom paneling in the formal dining room, and built-ins/shelving thoughtfully dispersed in the sitting area off the gourmet style kitchen, the formal dining room, and the comfortable; yet accommodating library. The gourmet kitchen with large island and granite counters; also includes the original butler pantry. Polished floors and custom draperies, throughout. The air conditioned, airy master suite has a lovely bathroom; along with customized shelving and drawers in the walk-in closet. The third floor has additional bright rooms for guests or additional storage. Whether it is sitting in the three season sunporch overlooking the Dark Harbor swimming pool, or taking a quick ride to the Tarratine Yacht Club, this property has everything you need to create everlasting memories.

Listed by Camden Real Estate Company

MLS Number 1405670

• Residential
• Bedrooms 3
• Bathroom 3
• Rooms 8
• Acreage 3.7

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 forest. Master bedroom en suite, cathedral ceiling living room with fireplace AND PRIVACY!Constructed in 1989 on 3.7 acres this yearround home is the keystone in a quiet subdivision in north Islesboro. Neighboring parcels have significant home site setbacks providing further insulation. Interior layout offers spacious common and private areas. Wood flooring and finishes throughout. Covered porches, detached workshop, gardens, landscaping and two moorings complete the picture.

Listed by Island Property

MLS Number 1370848

• Residential
• Address 147 Jenny's Lane
• Bedrooms 3
• Bathroom 2
• Rooms 10

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 perennial gardens, this home provides private outdoor spaces and immediate access to one of Maine's quintessential coastal beaches. Custom-built in 2002 with remarkable detail and to the highest standards by Maine's Shelter Institute, this home is filled with light and provides accommodating spaces for easy living and entertaining - a spacious dining room, living room and family room. Amenities include a gas burning fireplace and wood burning stove, home office, mud and laundry room, and a 2-car garage with partially finished space above. 3 vaulted ceiling bedrooms with shuttered windows and ceiling fans, 2 baths. Good opportunity as rental property or guest home too!

Listed by Legacy Properties Sotheby's International Realty

MLS Number 1365742

• Residential
• Location Rural, Subdivision
• Bedrooms 2
• Bathroom 1
• Rooms 5

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 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 truly real Maine vacation living!

Listed by Warren Realty

MLS Number 1304129

• Residential
• Location Near Public Beach
• Bedrooms 2
• Bathroom 2
• Rooms 6

Waterfront compound of 3 buildings, main house (2005); studio & guest apartment (2007); 3rd building /garage + 24 x 24 activity room (2009). Architect designed & built special for his personal home. Restored antique light fixtures throughout. Fantastic beach. Broker related.

Listed by Home Town Real Estate & Property Management

MLS Number 1273937

• Residential
• Address 431 Main Road
• Location Neighborhood, Rural
• Bedrooms 3
• Bathroom 2

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

Listed by Island Property

MLS Number 1411196

• Residential
• Address 1159 Main Road
• Bedrooms 5
• Bathroom 3
• Rooms 12

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 Bay and a path that leads to 400 feet of shore frontage and a private sandy beach. Thoughtfully and recently updated, this gracious, 12-room home combines historic charm with all the modern amenities. Best of all, it's being offered fully furnished and equipped with everything you need to move right in or start your own vacation rental venue. With 5 bedrooms, including a first-floor bedroom and a spacious master suite, 3 full baths, an elegant living and dining room, a library, an updated kitchen and butler's pantry, a newly renovated, 4-season sun room that leads to one of 2 decks and a 2-bay garage with unfinished space for a studio above, this home is an idyllic island retreat with an excellent vacation rental history.

Listed by CoastWise Realty

MLS Number 1368749

• Residential
• Bedrooms 6
• Bathroom 3
• Rooms 8
• Acreage 0.45

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. With 6 bedrooms, 2-1/2 baths and more sleeping space available on the third floor, the home has plenty of capacity for a large family or even a bed and breakfast. Amenities include first-floor master bedroom, two fireplaces, large living room, study and much more. Home is being offered partially furnished and ready to move into in time for next summer.

Listed by Warren Realty

MLS Number 1406984

• Residential
• Address 391 Main Road
• Location Near Town
• Bedrooms 3
• Bathroom 2

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 seperate 2 car garage with studio space above.

Listed by Better Homes & Gardens Real Estate/The Masiello Group

MLS Number 1359203

• Residential
• Address 689 Main Road
• Bedrooms 3
• Bathroom 2
• Rooms 7

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 of Cape Rosier, Castine, Isle au Haut and points beyond. Possible subdivision for family members or others. Needs some updating and repair, many possibilities. Price has been significantly reduced.

Listed by Legacy Properties Sotheby's International Realty

MLS Number 1409871

• Residential
• Address 244 East Shore Drive
• Bedrooms 1
• Bathroom 1
• Rooms 3

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 Harbor. The residence includes a separate 1 bedroom guest cottage. Amenities of Islesboro include transportation access by scheduled car ferry, water taxi, and public airstrip.

Listed by Town & Shore Associates LLC

MLS Number 1404999

• Residential
• Address 452 Ferry Road
• Location Neighborhood, Rural
• Bedrooms 3
• Bathroom 3

Stunning panoramic waterviews from this gracious Gilkey Harbor cedar shingle three-bedroom waterfront cottage. Crisp interior finishes; living room, dining room, gourmet kitchen, halfbath. Two bedrooms with vaulted ceilings and full bath up. Knotty pine guest annex across the covered breezeway with cathedral ceilinged large living/dining area and kitchenette, bedroom and full bath. Southerly harbor views from both porches overlooking five acres of lawn and meadow down to water and steps to the shore. Detached playhouse for recreation and boat storage. Now aggressively priced.

Listed by Island Property

MLS Number 1403988

• Residential
• Address 135 Rebel Hill Road
• Bedrooms 3
• Bathroom 2
• Rooms 7

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 living room with massive stone fireplace, dining room, state of the art kitchen, master bedroom en suite, two guest bedrooms and second full bath, and second floor family room to enjoy the horizon view of East Penobscot Bay. Radiant heat throughout, covered porches. Conveniently located to library, tennis courts, and town.

Listed by Island Property

MLS Number 1419020

• Residential
• Address 104 Dunn Lane
• Bedrooms 3
• Bathroom 3
• Rooms 9

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!) on Crow Cove. First floor has a very open floor plan with many built-ins, 1/2-bath and separate entrance to large home office space. Second floor contains three generous bedrooms and two full baths. Large deck and outbuilding for storage.

Listed by Warren Realty