Prominently sited on 18.5± acres with 955± 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 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 estate also includes a carriage house with stables, a reading room, and there is a substantial deep-water dock with ramp and floats on Gilkey Harbor.

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
• Original carriage house / stable serves multiple functions
• Private reading room overlooking the water