Amos A. Lawrence, head of one of Boston's most influential families, acquired land in this section of Brookline in 1850 for a country home with an easy commute to the city. He called his suburban retreat Cottage Farm and hired George Dexter to build a stone Gothic Revival residence (1851, 135 Ivy Street, NRD). Across the street Dexter built a smaller Gothic house for his daughter Emily and her husband, Thomas Hall (1851, 156 Ivy Street, NRD). Expressive of English architectural traditions other than the Gothic Revival popularized by Andrew Jackson Downing, both stone houses feature minimized exterior ornament. Dexter retired from practice after he completed these houses, perhaps his most important surviving commissions. Lawrence added a chapel wing to his house in 1865, commemorating the fall of Richmond and memorializing President Lincoln. Although the interior was remodeled in 1997, the exterior has been carefully restored, including the fence that dates from 1899 when the house was turned and moved east on its lot.

Nearby Frederick Sears erected a third stone cottage (25 Cottage Farm Road, NRD) in 1850–1851 on land given by his father, David Sears. No architect is known, but the house resembles the demolished David Sears House (1843) by Edward Shaw. Although also constructed of stone, the Frederick Sears House characterizes more fully the American interpretations of Gothic Revival.

Amos Lawrence built several brick single-family houses for rental purposes in the vicinity of his own house, such as the early example of the Mansard style at 96 Ivy Street (1853, NRD) and the Gothic Revival cottage at 89 Carlton Street (1855, NRD). After Lawrence's death in 1885, prominent turn-of-the-twentieth-century firms designed many houses in this neighborhood. An outstanding example is the French Renaissance–style house built in 1908 for oil company owner Bernard Jenny Jr. (132 Carlton Street, NRD), one of several in the Cottage Farm Historic District by Kilham and Hopkins.