If you bought a home out there 20 years ago then you are likely talking about a different situation than today.
That place reeks of money and leftism.
Don't know how familiar you are with the Boston area (I've lived here all my life) but Weston has *always* been the richest town in the area,so he probably paid very serious $$$ for his house when measured by the price of real estate at the particular time that he bought it.