What We Love

  • Sunsets over Gilkey Harbor
  • Carefully considered seating areas offer special places for quiet contemplation and appreciation of the area’s scenic beauty
  • Preserved historic details
  • Complete privacy within Dark Harbor
  • Boating in Gilkey Harbor and throughout nearby islands

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 estate also includes several additional buildings: a guest cottage with four-car garage, a carriage house / stable, a billiard house, a reading room, and a substantial deep-water dock with floats. The residence is characteristic of the Renaissance Revival Style with its stucco facade and long, rectangular two-story building with hip roof and sun porch to the south end, and ell to the north. 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.

The home was commissioned in 1907 by Richard D. Sears of Boston, a member of a prominent Boston family who later earned a name for himself playing lawn tennis, even being the first American finalist at Wimbledon in the 1880s. The current stewardship was responsible for the thoughtful restoration of the classic period character which meet the demands of a modern vacation residence with ease and grace.

  • Spacious living and dining areas accommodate large groups, while more intimate areas—indoors and outside—invite quiet conversation or time with a good book
  • Fine craftsmanship with custom moldings and woodwork throughout
  • Breathtaking water views from almost every room
  • Nine bedrooms and nine baths
  • Eleven wood-burning fireplaces with beautiful original details
  • Guest cottage with four-car garage
  • Charming billiard house features a grand, original stone fireplace
  • Original carriage house / stable serves multiple functions
  • Private reading room overlooking the water

Property Details


Interior (More Info)

Select a Point of Interest and Radius from the form above.