Dennis Gleason

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Dennis Gleason

Real Estate Professional

As a decades-long resident of Boothbay Harbor, I have had a ringside seat to the transformative changes taking place on this special peninsula, including as a founding board member of the Opera House at Boothbay Harbor, saving the building from being razed; to two terms on the board of the Coastal Maine Botanical Garden, which has become among the most-visited attractions in northern New England and an economic driver for Midcoast Maine; and as a business owner for more than 25 years.


I have had a real estate license for over 20 years, and am honored to have been associated with Legacy Properties,Sotheby’s International Realty for the last 10 years, surely the most significant years for the real estate market in Maine.


In 1985, my wife Marty and I established what was to become Gleason Fine Art, one of the longest continually operating commercial galleries in the state. We have twice been recognized as the Best Art Gallery (2020 and 2021; and in the top five for 2022 and 2023) in Down East magazine’s annual Best of Maine competition. Our son Andrew has joined the business, and he will continue GFA’s active presence on Maine’s art scene.


I thoroughly enjoy introducing prospective Mainers to the many qualities of this corner of our state. Its long maritime legacy; its environmental profile with Bigelow Laboratories and the Department of Marine Resources. Our community hosts an active and well-funded YMCA; public trails offered by the Boothbay Region Land Trust, entertainment and cultural venues like the Opera House and Coastal Maine Botanical Gardens; and world-class boating from one of the best harbors on the coast.


If you are a buyer, let me show you around! If selling I will represent your property with enthusiasm and integrity to prospective buyers.

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