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Brookline, MA
Brookline is almost entirely surrounded by the city of Boston itself, an unusual geography that's left it as one of the largest incorporated towns in Massachusetts never to have been formally annexed into the city it borders on nearly every side — a distinction Brookline residents and town officials have actively defended across more than a century of periodic annexation proposals. John F. Kennedy was born in Brookline in 1917, and his childhood home on Beals Street has been preserved by the National Park Service as the John F. Kennedy National Historic Site, a modest suburban house that stands in deliberate contrast to the more famous Kennedy estates in Hyannis Port and elsewhere. Coolidge Corner, Brookline's best-known commercial district, centers on the historic Coolidge Corner Theatre, an art-house cinema operating continuously (aside from a brief 1980s closure) since 1933, anchoring a walkable strip of independent shops and restaurants that's kept the neighborhood one of the more urban-feeling suburban commercial districts in the entire Boston area. Served directly by the MBTA Green Line's C and D branches along with several bus routes, Brookline's combination of near-total encirclement by Boston proper, a genuine walkable town-center feel at Coolidge Corner, and a direct connection to Kennedy family history has made it one of the most distinctive and consistently sought-after close-in suburbs anywhere in the metro area.
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Wellesley, MA
Wellesley is best known nationally as the home of Wellesley College, a highly selective women's liberal arts college founded in 1870 whose alumnae include Hillary Clinton and Madeleine Albright, and the campus's lake-and-woodland setting has made it one of the more scenic private-college grounds in the entire Boston area, open to the public for walking and running along Lake Waban. The town sits along the Massachusetts Turnpike roughly twelve miles west of Boston, and both the Framingham/Worcester commuter rail line and highway access have made it a genuinely practical commute for residents working downtown, even as much of the town's character has stayed oriented around large, architecturally varied single-family homes on generous lots. Wellesley Square, the town's compact downtown commercial district built directly around the commuter rail station, has kept a concentration of independent boutiques and restaurants that's stood in deliberate contrast to the larger chain-retail shopping centers found in some neighboring suburbs. Wellesley's public schools have consistently ranked among the very highest performing in Massachusetts on state assessments, and that reputation, combined with the town's direct association with one of the country's most prestigious women's colleges, has made Wellesley one of the most consistently expensive and sought-after suburban housing markets west of Boston.
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