THE GOODS: Marblehead was defined by a sudden building boom in the years following World War II as it became an attractive bedroom community for Boston commuters looking to live near the ocean. The boom ended just as abruptly in 1970, when Marblehead was almost entirely built out. The town got its start as a hardscrabble fishing village, and evolved into a favorite base for privateers raiding European ships. Now it is a well-off bedroom community with a quaint downtown, stunning oceanfront, and pleasant streets. The restaurant scene is stacked here, from the trendy Euro scene to the traditional seafood houses, and the local arts scene remains reliably strong. Marblehead, though, is ultimately defined by water, with a busy yachting scene and a protected anchorage that is the envy of sailors along the Northeast coast.
PROS: Despite the density, most of Marblehead's houses are picturesque, and many are situated on decent-sized lots. The charming town center, coupled with hilly pockets of older and historical homes have, in many ways, made Marblehead the quintessential North Shore town. The model shows up in the work of filmmakers and authors trying to capture the essence of the region, with Marblehead serving as the basis for fictional towns in the writings of H.P. Lovecraft and Robert B. Parker. For those with the money, Marblehead Neck is simply some of the loveliest seaside real estate in Massachusetts. And despite its reputation as an enclave for the rich, Marblehead still offers a more than decent amount of homes priced under $400,000.
CONS: Without direct access to major highways, commuting from Marblehead into Boston can be onerous. There is, though, a commuter rail station in neighboring Swampscott. Meantime, the town remains divided on efforts to build more affordable housing, with proposals for apartments and starter-priced condominiums a flashpoint at planning commission meetings in recent years. While some progress has been made by affordable housing advocates, the market still largely favors single-family homebuyers.