The Caretaker's House might have been built sometime before 1861. However, the exact date is unknown because the home has conflicting architectural designs that span decades and there is scant information about a home being located at the current site. However, in 1861 a property appraisal indicates a small dwelling in the area of the Caretaker's House. The building might have originally been an outbuilding that was moved to the current location and amended to include a cellar and a chimney at a later date. An 1861 probate inventory of Lewis Beers' estate lists a "carriage house" as one of several buildings that comprised his farm complex. Although the inventory does not specify a location, current research indicates this carriage house was associated with the Caretaker's House on the east side of Nod Hill Road.
The Caretaker's House was in visible disrepair in 1883, when Julian Alden Weir acquired the 153-acre farm from Erwin Davis. An August 1883 letter from John Ferguson Weir to his brother, Julian Alden Weir, John recommends that Julian improve the small dwelling and offer the home to the first caretaker, William Holsten. The renovations probably used scrap material from the renovations to the Weir House. From that point the structure would undergo five alterations including; the removal of the southern lean-to, replacing the original chimney, altering the roof, creating a lean-to on the east, and covering the cellar. This is where Julian Alden Weir's many caretakers would live, including Paul Remy the caretaker during the 1890s.
Dorothy Weir Young added interior plumbing around 1927, while electricity was added to the home in 1931. This addition would coincide with the installation of electricity to the rest of the buildings on the Weir Complex. During the early 1930s the Bass family, living at the Caretaker's House, added a three-car garage to the north of the carriage house. The three bays formed a rectangular structure, one story high, that was topped with a saltbox roof.
Sperry Andrews would include the Caretaker's House in oil paintings created from the Woodland Area and from the driveway of the Caretaker's House. Based on a review of aerial photographs, the carriage house was demolished between 1970 and 1975. The three-bay garage remained as a freestanding structure and by the mid-1990s, was in poor condition with a bowed ridgeline and failing exterior cladding.
The Caretaker's House and rehabilitated garage support the park's artist-in-residence program. The park began restoration in 2005, and by 2009 completed the rehabilitation of Caretaker's Garage. The 3PM ranger-led introductory tour includes a visit to the artist-in-residence studio.