This property was once owned by Rufus Caldwell and was part of his 75 acre farm. His house was located east of Boston Rd. between So. Main St. His estate was auctioned off after his death in October 1891. The property was purchased by Brooks F. Holt for $1500. Brooks F. home was on South Main St. and he was an Ice Dealer in town. Brooks later sold his business and began selling off parcel of the former Caldwell farm.

This lot was sold to Sophie & Thomas Doucette on July 22, 1915 for $200. Four years later the property was sold to Freeman & Kate Doucette on Jan. 25, 1919 for $400. The Andover Valuation Schedule 1920 lists Freeman & Kate Doucette - Main St. - South District - House $500. 2 acres land $150 = $650 assessment. Their home is the house located at 12 Boston Rd.

Freeman Doucette was a carpenter and most likely built this home. The property was sold to Edward A. & Marguerite Donahue on Apr. 6, 1946. The property was sold three months later to Robert W. & Delores M. Carter on July 8, 1946. Robert b. 1925 worked for the Tyer Rubber Company. Delores b. 1925 was a housewife. The Carter family owned for 66 years selling to Derek Oleary on Sept. 27, 2012.