Islesboro Maine Homes for Sale

MLS Number 1452405

• Residential
• MLS Status Active
• Address 135 Shore Drive
• Location Intown
• Bedrooms 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
• MLS Status Active
• Location Other Location
• Bedrooms 6
• Bathroom 9

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
• MLS Status Active
• Address 117 Jetty Road
• Bedrooms 9
• Bathroom 10

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
• MLS Status Active
• Address 134 Big Tree Lane
• Bedrooms 5
• Bathroom 5

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 1435709

• Residential
• MLS Status Active
• Address 1228 Main Road
• Bedrooms 3
• Bathroom 2

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 1365192

• Residential
• MLS Status Active
• Address 577 Ferry Road
• Location Near Country Club
• Bedrooms 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 1415287

• Residential
• MLS Status Active
• Bedrooms 5
• Bathroom 4
• Rooms 18

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.New boiler. ' COVID-19: By scheduling a showing, you are acknowledging that neither you, your client or anyone in your party exhibits any cold or flu-like symptoms or meets any of the criteria for self-quarantine mandated by Maine Centers for Disease Control & Prevention. Buyers and their agents are required to wear face masks, shoe coverings and gloves for showings'.

Listed by Camden Real Estate Company

MLS Number 1459026

• Residential
• MLS Status Active
• Address 119 DErby Road
• Bedrooms 7
• Bathroom 7

Great 4-season home right in the heart of Dark Harbor Village. Entirely renovated with particular attention to detail and an entirely new kitchen. Includes a fully equipped post-and-beam apartment on the second floor.

Listed by Warren Realty

MLS Number 1445143

• Residential
• MLS Status Active
• Bedrooms 5
• Bathroom 5
• Rooms 12

On 6+/- acres of landscaped field, woods, and orchard, at the corner of Pendleton Point Road and Decker Road, sits this 11/2-story single-family winterized home with a detached studio, a detached garage, and a greenhouse and a gazebo. The interior contains 10 rooms (5 bedrooms and 41/2 baths) plus an enclosed porch and an open porch. The foundation has recently been rebuilt and the house is on the town sewer.$550,000

Listed by Warren Realty

MLS Number 1425651

• Residential
• MLS Status Active
• Bedrooms 2
• Bathroom 3
• Rooms 7

Heavenly Daze. Well-crafted, fully furnished year-round home perched on rugged ledges in an enchanting woodland setting. Completely renovated. Large open floor plan living and dining and full cathedral ceiling, high-efficiency heating and cooling mini split heat pump. Garage apartment. Glorious sunsets, simple and inviting gardens, footpaths. Just steps to the beach.

Listed by Island Property

MLS Number 1304129

• Residential
• MLS Status Active
• Location Near Public Beach
• Bedrooms 2
• Bathroom 2

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
• MLS Status Active
• Address 147 Jenny's Lane
• Bedrooms 3
• Bathroom 2

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 1437917

• Residential
• MLS Status Active
• Address 1159 Main Road
• Bedrooms 4
• Bathroom 3

1159 Main rdSpectacular ocean views abound at exceptional 17 acre oceanfront retreat ; private sandy beach,to launch kayaks or access Hutchin's Island.Stately 1830's iconic New England farmhousefeatures many original architectural details aswell as recent tasteful upgrades throughoutScenic location ; set on an island bluff,Enjoy amazing open water vistas- look outat sailing regattas and schooners on the bay.Sprawling, 4 season home; located in idyllic oceanfront enclave , features 2 bay garage with ocean view -upper floor- Ideal for potential studio, guest space , etcOffered turnkey; this rambling waterfront property with all the amenities; is in Move in Ready condition.

Listed by Warren Realty

MLS Number 1403988

• Residential
• MLS Status Active
• Address 135 Rebel Hill Road
• Bedrooms 3
• Bathroom 2

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 1443659

• Residential
• MLS Status Active
• Address 391 Main Road
• Location Rural
• Bedrooms 2

Contemporary Islesboro home with 400' East Shore Penobscot Bay waterfront.Enjoy the sunrise from your private rear deck. Home features a first flooropen concept kitchen dining area with brick fireplace and tile flooring, living room with built-ins, a full bath and mechanical room with laundry. Attached one car garage. Second floor features a huge den with wet bar, built-ins and hearth for woodstove as well as 2 bedrooms, one with direct access to a full bath. There is a detached two car garage with unfinished storage area above - perhaps for that hobby area. Natural landscaping with mixed water frontage with a beach area and rocky coastline. Use as your year round orseasonal home.

Listed by Coldwell Banker Rizzo Mattson

MLS Number 1318590

• Residential
• MLS Status Active
• Address 1071 Deep Cove Lane
• Location Rural
• Bedrooms 3

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 1448442

• Residential
• MLS Status Active
• Address 243 Main Road
• Bedrooms 3
• Bathroom 3

Cozy 3-bedroom, 21/2 bath 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 1455194

• Residential
• MLS Status Active
• Address 689 Main Road
• Location Neighborhood, Rural
• Bedrooms 3

Magnificent views of East Penobscot Bay from this 1870's Greek Revival year-round three-bedroom home centrally located just north of the Narrows on almost seven acres of open meadow abounding with lupine. Inviting path and foot bridge through the woods to 560 feet of smooth gently sloping beach. Kitchen, dining, living rooms, knotty pine sunporch, bath and half. Detached garage and shed. Many possibilities from this LOCATION! $379,000.

Listed by Island Property

MLS Number 1256431

• Residential
• MLS Status Active
• Location Rural, Subdivision
• Bedrooms 1
• Bathroom 1

This one bedroom dwelling sits on 3.7 ac +/- with 266' of shore frontage on Crow Cove facing the West Penobscot Bay. Crow Cove is very protected anchorage in all storms and contains deep water. Possible dock and larger residence may be constructed upon the property as well. Current dwelling is winterized with some sandy beach along the shoreline. We think it's perfect and one of the best parcels on the island. Price has been lowered.

Listed by Legacy Properties Sotheby's International Realty

MLS Number 1452713

• Residential
• MLS Status Active
• Bedrooms 4
• Bathroom 3
• Rooms 9

Charming classic village house featuring 9 rooms with three bedrooms, a nursery and 21/2 baths. Newer first floor bedroom with full bath overlooks a lovely and private courtyard. The light-filled kitchen has ample cupboards and storage. Separate laundry/pantry. Attached greenhouse has outside entry. Additional 500+/- sq. ft. is perfect for summer dinner parties.

Listed by Warren Realty

MLS Number 1339257

• Residential
• MLS Status Active
• Bedrooms 2
• Bathroom 3
• Rooms 8

Inviting yearround home, heart of Dark Harbor Village, just steps from summer shops. Built in 1920, completely renovated 1978. Open floor plan kitchen, new stainless steel appliances, dining room, two large living rooms, perfect for first floor bedroom with full bath, master bedroom and bath with jacuzzi, guest bedroom and bath. Gambrelled two story shop/barn. Delightful pond and ample acreage included behind the house for two homesites via neighboring right-of-way. Enjoy a glimpse of Dark Harbor Pool from your front porch wicker and life in a quaint historic island summer community. $300,000.

Listed by Island Property

MLS Number 1458764

• Residential
• MLS Status Active
• Address 1326 Main Road
• Bedrooms 3
• Bathroom 1

Historic Greek Revival island home built in 1860. Situated on the less trafficked end of North Islesboro on 2. 23 acres of open lawn and meadow with hardwood and apple trees and even a small pond, you'll find yourself settling into a relaxed pace with comfortable space inside and out. Kitchen island, first floor full bath, dining and living rooms plus three bedrooms upstairs. Great starter home or island getaway.

Listed by Island Property