299 Drexel Lane, Islesboro, ME, 04848

299 Drexel Lane, Islesboro, ME, 04848

30 rooms

20 beds

7 Full / 1 Half baths


Cottage, Shingle Style

10,830 sqft

As featured in Architectural Digest, this classic shingle style home has been beautifully maintained and totally redecorated by the current owner. Set privately at the north end of Islesboro island, this remarkable home was built in 1903 and is made up of 4 lots and over 48 total acres of spectacular oceanfront land including a private dock on Sabbathday Harbor. The land, which is partially in conservation with the Islesboro Island Trust, includes wonderful open fields with ocean views, walking paths through the woods down to the shorefront, beach and open ocean access, garden areas, and a majestic approach up a tree covered winding gravel road. The house is perfectly designed to accommodate large groups, but cozy enough for single family living. There are great entertaining spaces including a large fieldstone fireplace in the living room, a fantastic custom built bar area, a great dining room with a fireplace, a large and well equipped kitchen with a walk in refrigerator and fabulous pantry area. There is also a large office and laundry room on the first floor. The second floor features the primary bedroom suite with its own private sun porch, and full bathroom with a claw foot tub and separate shower, as well as 5 additional bedrooms on one end of the home, and a separate guest wing with a number of additional smaller bedrooms. The entire third floor of the home is a magical play space complete with four separate themed bedrooms and a full bathroom, a school house, a library, a diner, and a performing stage for endless entertainment. There are two large sun porches, and a sunny back deck overlooking an in ground swimming pool. There is also a detached barn for car storage. This is a one of a kind property.




Single-family residential




Barn, Detached


Baseboard, Hot Air, Hot Water, Multi-Zones


A/C Units


Partial, Unfinished, Walkout Access


11 - 20 Spaces



Est. Taxes:


Lot Description:

Level,Open,Pasture/Field,Rolling/Sloping,Well Landscaped,Wooded


Attic, Bathtub, Deck, Laundry - 1st Floor, Out Building, Pantry, Pool-In Ground, Porch-Screened, Primary Bedroom w/Bath, Storage




Dryer, Gas Range, Refrigerator, Washer

MLS #:


Community Info

School Info

Adams School

Enrollment: 55

Distance: 5.21 Miles

Community Rating:

Edna Drinkwater School

Enrollment: 81

Distance: 5.48 Miles

Islesboro Central School

Enrollment: 94

Distance: 5.54 Miles

Brooksville Elementary School

Enrollment: 58

Distance: 6.94 Miles

Walk Score

Mass Transit


Listing courtesy of Legacy Properties Sotheby's International Realty