Sarah Benson prefers traditional neighborhoods filled with early 20th-century houses and big trees and often surrounds herself with myriad connections to the past, from her collection of clown memorabilia to her grandmother’s Art Deco–era liquor cart, crafted from brass and turned wood. When she found a 1925 house in Portland’s Overlook neighborhood, she was charmed by the area’s curving streets, generous porches, tiny yards, one-car garages, and the occasional pocket park. Nestled against a bluff with a view of the Willamette River, the home was also conveniently located near a light rail that replaced a trolley that once ran two blocks away. But the property lacked one major element Sarah desired: a free-flowing, midcentury-style space.
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