The original Henry Street Settlement buildings stand on a street first laid out on the Henry Rutgers farmland. The three c. 1830 Federal style row houses were built as stylish private homes for local merchants. During the first half of the 19th century, as the streets north of Franklin Square (now the site of the Brooklyn Bridge approach) were being developed, this was a prosperous neighborhood. Shopkeepers and workers from the nearby shipyards along the East River and ship captains from the thriving South Street Seaport area lived in these large and elegant homes.

The Settlement traces its beginnings to just after this period when, in 1893, a young nurse named Lillian Wald was called upon to visit an ill woman in her Lower East Side tenement. The squalid conditions she encountered there made a profound impression on her and, within the space of the visit, forged a commitment to serve the immigrant population of the Lower East Side. She established a non-sectarian community nursing service. The initial funders were Mrs. Solomon (Betty) Loeb, her son-in-law, banker and philanthropist Jacob Schiff. Schiff, who became Lillian Wald’s lifelong friend and benefactor, purchased 265 Henry Street in 1895, and gave the young Wald and her nurses a house on Henry Street to serve as their headquarters.

The c. 1827 building at 265 Henry Street is a modest three-story Federal style building. Initially a two-story structure, the third level was added well before its purchase for Lillian Wald. The front façade, composed of red-orange brick with a parged and painted fieldstone base, still has much of its original ornamentation. The entrance, complete with the eight-panel wood door framed by wooden ionic columns, lead glass sidelights and transom, is original to the building. The lintels and sills are original on all levels, and although early, all of the windows are replacements.

Its neighbor to the west, 263 Henry Street, was also built c. 1827 and is a modified four-story Federal town house with a red-orange brick façade and a parged and painted fieldstone base. Like No. 265, it was originally a two-story house, and evidence indicates that the two top floors were added at the same time as the third story was added to No. 265. However, unlike No. 265, substantial changes were made to No. 263. The door was narrowed to the existing width, and the carved stone decorative window and door lintels were replaced in the late 1870s with both the then fashionable Neo-Greco Style and with traces of the oncoming Queen Anne Style of the 1880s. This can be seen in the lintel panel and sunburst over the front door, and the heavy cornice at the top. Both are of the same period. The structure still retains some fine Federal details such as the stair rails and the decorative cast iron pineapple finial found on the front entrance hand-hammered wrought iron newel post. During the period, the pineapple was a welcoming symbol of hospitality that the Settlement still extends to this day.

Standing to the east is 267 Henry Street, which was built c. 1834 and is a handsome Georgian Eclectic three-story townhouse with basement. It is a fine example of this style, which was very popular in the early 1900s when the building underwent a major renovation by Buchanan & Fox Architects. Changes to the façade made during the renovation included the removal of the front stoop and relocation of the main entrance to the original service entrance on the basement level. The original door opening was replaced with a third window on the first level. The limestone door hood, lintels and pressed metal cornice were also added at that time. Distinctive characteristics of the façade include ornamental limestone flat arches with keystones and voussoirs, limestone sills at every level and stringcourses at the first floor sill and lintel levels and third floor sill level.

Although the buildings still maintain their separate facades, as each was acquired their interior walls were broken through to create a more usable space. In the early years, the nurses lived in small bedrooms on the top floors with offices on the middle floors, while the ground floor housed clinics and meeting rooms. The dining room of No. 267 became a reception and gathering place for both residents of the community and visitors. Among the distinguished guests who visited this room were Eleanor Roosevelt, Jane Addams, Herbert Lehman, Felix Warburg, Jacob Riis, Theodore Roosevelt and British Prime Minister Ramsay MacDonald. More than any other in the three buildings, this room retains the grand feeling of the houses’ former splendor. Its Greek Revival interior still has most of its original decoration including early raised door and window surrounds complete with corner blocks, as well as plaster ceiling medallions, ionic pilasters, fluted ionic columns, and two black with gold vein marble fireplace mantels.

On the basement level, the original early-1800s cooking hearth with the bake oven and clean-out was discovered and restored during a major preservation project (1993-1996) under the direction of J. Lawrence Jones & Associates Architects. Another unexpected find was the discovery of the building’s original masonry cistern, which was uncovered during stabilization of the rear foundation wall. The cistern is a masonry tank used for storing rainwater for household use. The rainwater collected in the roof gutters is led to the cistern through connections to the downspouts. In-ground cisterns provided the best protection against freezing, kept water at a constant cool temperature and minimized damage from leaks. The project addressed many of the historically significant elements of both the exterior and the interior including the dining room, and received the Municipal Arts Society award for Preservation in 1996.

These buildings that now serve as the Henry Street Settlement’s executive and administrative offices are designated with the New York City Landmarks Commission and listed on the National Register of Historic Places. They are also included in the Lower East Side Historic District. In 2018, the Settlement opened The House on Henry Street, a permanent exhibit detailing the Settlement’s history located in the headquarters.