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 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 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 1426982

• Residential
• Bedrooms 6
• Bathroom 5
• Rooms 15
• Acreage 7.22

This iconic property is prominently sited on 7.22 acres on the highly desirable West Bay Road with stunning views of West Penobscot Bay and the Camden hills, and 500 +/- feet of beach frontage. There are two properties with this listing, the main residence at 400 West Bay Rd. and the cottage at 391 West Bay Rd., both year round structures. The main house is a beautiful example of New England architecture and has changed ownership only twice in almost a century and it has been impeccably restored and renovated by the current owner. The 6 bedroom main home has a formal dining room with a fire place, a chef's kitchen, a spectacular wood paneled great room with fireplace, a conservatory, and lovely grounds. The shingle style guest cottage at 391 West Bay Road was built in 2009 to the highest standards and includes one bedroom, a full bath, a large living room/office with wood burning fireplace, and an expansive covered deck with breathtaking views of Penobscot Bay and great shore access

Listed by Legacy Properties Sotheby's International Realty

MLS Number 1435709

• Residential
• Address 1228 Main Road
• Bedrooms 3
• Bathroom 2
• Rooms 9

Charming 150 year old 1 1/2 story Cape Farmhouse situated on a high level knoll overlooking the East Penobscot Bay, the entrance for all vessels sailing or motoring their was ''Down East''. With views of the many inlets, islands, Cape Rosier, Castine, and Hutchin's Island. Perfect glorious morning sunrises! Across the road is protected land owned by the Islesboro Islands Trust so your view will never be obscured as it has been designated as a blueberry farmland! The property has manicured fields full of blueberries, extensive vegetable and herb gardens with a waterfall, tunnel covered with grape vines, pergola, fruit trees mostly fenced. A 30 x 60 Pole Barn with large doors that open for equipment or any other storage. Workshop, heated exercise room, and 2-car garage.

Listed by Legacy Properties Sotheby's International Realty

MLS Number 1434977

• Residential
• Address 435 Ferry Road
• Bedrooms 3
• Bathroom 4
• Rooms 8

Mainestay, located on the sought after island of Islesboro, is a private property well suited for Summer vacations and year round living.Nestled in privacy on 9+/- well established and landscaped acres, this property boasts stunning westerly views of Penobscot Bay and the Camden Hills, a well maintained and an easy house to live in, substantial and versatile boat barn with workshop, deep water dock, and 490+/- feet of sand and pebble beach.This contemporary style home offers fabulous sunsets from almost every window. Open concept living on the first floor with a master suite, screened in porch and expansive deck overlooking the water, powder room, and 2 car garage. The second floor provides another master suite, bedroom with deck, full bathroom, spacious artist studio/office with the potential to be a fourth bedroom.

Listed by Legacy Properties Sotheby's International Realty

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. There is frontage on Dark Harbor swimming pool and you are around the corner from the Tarratine Yacht Club. If you need to work while away, there is Broadband internet service; allowing you access the internet easily.

Listed by Camden Real Estate Company

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, full bath, and a powder room. 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 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 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 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 1425651

• Residential
• Bedrooms 2
• Bathroom 3
• Rooms 7
• Acreage 5.23

Heavenly Daze. Well-crafted, fully furnished yearround home perched on rugged ledges in an enchanting woodland setting. Completely renovated. Large open floor plan living and dining and full cathedral ceiling, AC. Garage apartment. Glorious sunsets, simple and inviting gardens, footpaths. Just steps to the beach.

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 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 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 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

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 1318590

• Residential
• Address 1071 Deep Cove Lane
• Location Rural
• Bedrooms 3
• Bathroom 1

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.

Listed by Dwelling In Maine

MLS Number 1426296

• Residential
• Address 243 Main Road
• Bedrooms 3
• Bathroom 3
• Rooms 8

Cozy 3-bedroom, 21/2 bath antique cape on 11+/- acres of field centrally located mid-island. About 10 acres of field suitable for equestrian activities. First floor master bedroom and bath, kitchen, living room with fireplace, dining room. Large back deck overlooking a lovely, private yard with pond.

Listed by Warren Realty

MLS Number 1420331

• Residential
• Address 1081 Deep Cove Lane
• Bedrooms 3
• Bathroom 1
• Rooms 6

180' Of tidal frontage on 1.9 acres overlooking scenic Ryder's Cove on the East Penobscot Bay with an excellent view of the Camden Hills in the background. Look down the length of the East Penobscot Bay as the myriad of boats pass by. Two bedroom home on a high bluff away from it all. Wooded and sloping to the shore.

Listed by Legacy Properties Sotheby's International Realty

MLS Number 1407706

• Residential
• Address 111 Derby Road
• Bedrooms 3
• Bathroom 3
• Rooms 7

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 could be re-purposed as new retail space or additional living space. Second floor has living and dining room, full kitchen, 2 bedrooms, 1 bath. Third floor contains master bedroom w/full bath. Second floor deck overlooks peaceful pond

Listed by Warren Realty