The Real estate and housing series is arranged into five subseries: Flats; Citizens Housing Corporation (CHC); Brandywine Hundred; Parks; and Leases and deeds.

The Flats subseries includes applications for rental properties and responses from Woodlawn, data about rents, lists of expenses for each building; lists of bidding specifications; furnishings; information about construction, lists of tenants, Bancroft Parkway, and Wilmington ordinances. Also contains information about the construction, renovation, furnishings, supplies, and maintenance projects for houses in the "Flats" area of Wilmington. Oversize drawings and maps are arranged by date and placed as close as possible to the subjects of the construction and renovations.

Citizens Housing Corporation (CHC) subseries is comprised of records about the beginning of the CHC to provide low-cost housing in Wilmington's African American community. Major investors, financing, and all correspondence are included. In addition, there are descriptions of the types of houses owned by the CHC, lists of addresses and rents, expenses for maintaining the houses, information about repairs and heating of CHC houses, expense ledgers, check stubs, bills collected by Tatnall and Wensing, investment records, City and County tax statements, events leading up to Woodlawn's purchase of CHC assets, Wilmington historic district information, Kirkwood Properties Inc., and Park Theatre/Revival Fellowship Church property information.

Brandywine Hundred subseries include survey books and descriptions of farms. There are records indicating that in 1922 William Bancroft commissioned noted civil engineer, landscape designer, and urban planner Charles Wellford Leavitt to develop a master plan for future communities and thoroughfares in Brandywine Hundred. This subseries also includes lists of properties purchased, properties of interest, historic properties, Pennsylvania properties, properties no longer owned by Woodlawn, farmland assessments, expenses for construction and renovation, and communities later developed by the Woodlawn Trustees: Alapocas, Woodbrook, Edenridge, Tavistock, Sharpley, and Village of Rocky Run. Monies from property sales and rental fees were used to maintain and renovate the low-cost housing originally constructed in Wilmington's "Flats" area. Also contains files about property development and expansion, such as the development of the west side of Concord Pike, the Brandywine Commons Retail Center, and miscellaneous photographs and maps.

Parks subseries contains files about all parks developed in the City of Wilmington and New Castle County by William P. Bancroft, the Woodlawn Company, and the Woodlawn Trustees. This includes reports; studies; research papers; and information about Northern Delaware Greenways, Department of Natural Resources and Environmental Control, Division of Parks and Recreation, State Parks, Brandywine Creek State Park, New Castle County Parks, Delaware County Planning Department, and the Jessup Moore/St. Joe's Paper Company tract.

This subseries includes several reports and lists of the lands transferred to the City of Wilmington for parks beginning with the purchase of Brandywine Park in 1886 to 1887. There is evidence in Scharf's History of Delaware of an unsuccessful attempt to create a park in Wilmington earlier in 1868 when funds for a park were not a priority. Much information is included on the development of a park system during the subsequent ninety-three years in the city. Bancroft's creation of the Wilmington Board of Park Commissioners in 1883 is recorded, as well as his subsequent transfer of lands to Wilmington, followed by Woodlawn's later gifts. Also included is Woodlawn's donation in 1981 of 500 acres to the State of Delaware as an addition to the already existing Brandywine Creek State Park. Records are included about the dedication ceremony for BCSP and plans for developing greenways throughout New Castle County. There are records here also regarding park maintenance, funded by a trust fund in Wilmington created in 1935, and another trust fund for maintaining Brandywine Creek State Park.

Leases and deeds subseries include deeds written between 1862 and 1915, as well as deed restriction documents for the communities constructed in Brandywine Hundred. A Woodlawn lawyer later suggested the deed restrictions for communities constructed by Woodlawn for seventy-five years to be unenforceable once the properties were sold.