Most Expensive Home in Massachusetts

Woodland Manor looks about as classic as it gets. Located just five miles outside of Boston in the ritzy village of Chestnut Hill, it’s a sprawling 27,000-square-foot home that sits on over seven acres of land. The limestone façade and Georgian architectural features give the home a stately look, an aesthetic that fills the bright interiors, too. Most notable is the gorgeous wrap-around staircase in the entryway, which, with its brass handrail and oversized rotunda, looks as though it was made for royalty. That’s likely not too far off from the design inspiration, as the neighborhood was once home to football royalty, at least: The home is a hop, skip and a jump from Tom Brady and Gisele Bündchen’s old place, which was last listed for $39 million.