present owners Terry and Nancy Crossfield

8 Pleasant St. is at the intersection of High Plain Rd, Haggetts Pond Rd. and Pleasant Street, a West Andover area settled and farmed by the Flint and Boutwell families. According to Doris Newton and Steve Kearn, the Flints lived on the east side of Pleasant St. #22 (old house remained at #22 Pleasant St. 1993 ). Bailey, the other longtime family, is represented by the historic Bailey District School divisions and the neighboring Bailey Road. 47 Bailey Rd. original Bailey Schoolhouse built 1868.

This farm property was once part of the John Webster farm in the mid 1850s and was sold to James Selden Flint on April 4, 1891. The Webster - Flint homestead was located across from Boutwell Rd at 22 Pleasant St. The home was razed in 1995 for new construction. James S. Flint b. 1851, wife Mary b. 1854, and their children, Alice E. b. 1878, Edwin Miles b. 1881, Eleanor H. b. 1883 and Lucretia 1888 all lived in the homestead until their deaths. Son Edwin M. Flint continued the farm after his father's death in 1920. Prior to Edwin's death in Nov. 1959, the homestead lot was sub-divided off into a 2.2 acre parcel and the remaining 63.16 acres were sold to Fred W. Doyle for $19,000. on Aug. 29, 1959.

Doyle was a developer in town and also owner of Doyle Lumber Co. then on Chandler Rd. Doyle purchased additional parcels of farmland in the Bailey District. In Dec. 1972 Doyle sold off this portion of land to George Chongris. Chongris was a business partner with Evangelos A. & Ernest Theodore of the Theodore Realty Trust. Much of the farmland was divided up into house lots and sold off.

Richard D. Roper, a carpenter, purchased four lots 7, 9, 12, and 13 on Pleasant St for $46,000. This home on lot 12 now 8 Pleasant St. was built by Roper, A classic Cape style home, modified for 20th century living. The home was sold to Terry & Nancy Crossfield on Nov. 12, 1975 and continue their ownership in 2016.