According to McDonald Group Realtors:

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The first residents of the Brentwood Darlington area were single-family homesteads in 1882, which divided the streets into a grid pattern of long blocks. Settlers Henry and Mary Ann Miller took advantage of the Donation Land Act of 1850, and along with George Wills, a baptist preacher and farmer, eventually owned most of the land in the area. By the 1930’s, residents of Brentwood-Darlington could catch the electric streetcar and go downtown for dinner and a movie, though for most of the neighborhood’s existence, roads led primarily to Milwaukie rather than Portland. World War II brought an influx of people into the Portland area, causing the rapid growth of Southeast Portland.

The area is defined by several strong geographical features, including Johnson Creek, tall Douglas Fir trees, and the soaring bluff along Flavel Drive. Commercial areas developed along SE 52nd Avenue, SE Flavel Street, and SE 72nd Avenue, along with the largely commercial thoroughfare, SE 82nd, which forms the neighborhood’s eastern border.

Brentwood-Darlington has been an officially designated neighborhood since 1974, though it was called Errol Heights at the time. The overall boundaries have remained constant, incorporating the smaller neighborhoods of Errol Heights, Brentwood, Darlington, Harney Park, Woodmere, and Crystal Springs into one neighborhood in 1996.