David Sears, one of the wealthiest property owners in Boston, recognized the potential for development of this marshy area of Brookline due to its close proximity to the city. Although he purchased the property in the 1820s, the configuration of streets and squares was not finalized until 1849 after he had given lots to his children to build houses. He chose the name Longwood and modeled it on English precedents in urban planning. With the construction of Beacon Street as a continuation of Mill Dam Road in Boston, Sears established three squares and the Longwood Mall in Brookline and a fourth square across the Muddy River in Roxbury. The portion of Longwood south of the Muddy River in Boston has not survived as a residential area, but most of the land in Brookline is extant and follows the Sears plan. The premier park is Longwood Mall, which is still graced by the magnificent beech trees that Sears imported from France in the 1840s.
Near the Longwood Mall, Sears erected the block of four houses on Hawes Street and the church on Colchester Street. The residential block, originally known as the Searston Charter House (1856, 5–11 Hawes Street, NRD), was financially endowed for widows and families in reduced circumstances. The choice of the Jacobean style is unusual and may have been based on the model housing by Henry Roberts erected for the Great Exhibition in London in 1851, which Sears may have seen when he traveled in Europe at that time. In 1901–1902, George Wightman erected a large French Renaissance mansion (43 Hawes Street) opposite Longwood Mall to designs by Shepley, Rutan and Coolidge and the Olmsted Brothers.
In close proximity stands Christ's Church (1860, NRD) at 70 Colchester Street, erected as a non-denominational union church and commonly known as Sears Chapel. Perhaps the nonsectarian basis of Christ's Church encouraged Arthur Gilman to design a building in the Romanesque rather than the Gothic Revival, boasting a square tower. Neighbor Amos A. Lawrence was not pleased with the church and hired Alexander Esty to design a stone Gothic Revival Episcopal Church, the Church of Our Saviour (NRD), in 1867–1868 at the corner of Carlton and Monmouth streets.