ADAPTIVE REUSE PROJECTS OFTEN bring with them a fair amount of headaches. Historic designations, layers of municipal approvals, and constrained construction sites are just a few of the concerns that builders and developers often have to juggle with these kinds of endeavors. But adapting a building for a new use while retaining its historic features—the generally accepted definition of adaptive reuse—can have a big payoff if it's done right. Buyers just plain love saying they live in a former church or an old brewery. Or, in the case of these three projects, on top of an old Sears building, in a former plantation's rice mill, or, believe it or not, inside a prison that was once home to Nicola Sacco and Bartolomeo Vanzetti, infamous for their murder trial and execution in the 1920s.

  • Above The StoreIn Washington,what was once a tired old Sears store is now home to two vibrant retailers—and the building pad for more than 200 condominiums on top.

  • Antebellum Beauty On a former plantation in Richmond Hill, Ga., a building with an eclectic pedigree finds a home.

  • Captive AudienceIn Dedham, Mass., a former jail—once home to Sacco and Vanzetti—gets new life as a luxury condominium building.