The Massachusetts Cultural Resource Information System (MACRIS) is a really swell website for looking up the way back history of your home or a home you might be thinking of buying in town. The system also has historical info on neighborhoods and other structures in Wellesley.
My introduction to MACRIS came while researching town sites on the National Register of Historic Places website, which is in the process of digitizing material and is pretty tough to navigate. Members of the Wellesley Historical Commission pointed me to MACRIS (thank you!).
You can search Wellesley for properties and objects (including things like the giant world globe and Ominous Icon Sculpture at Babson College, the latter of which is shown below) by sections of Wellesley, such as Babson Park, Lower Falls, Wellesley Farms, Wellesley Hills and the Fells.
Results will include documents in PDF format with all sorts of handwritten details about the place or object, including who built a home, who sold it, resold it, etc. Some results also include digital images.
I learned, for instance, that the Fells section of town off Weston Road was called the Wellesley Gardens — Sunny Acres area (former farm land) , and was known for its bungalows built in the 1920s.
Warning: If you do look up your house or neighborhood, be sure to be sitting down when you see how much some of this property originally cost vs. how much it goes for today.