Chatham Borough's housing stock is dominated by older, established single-family homes — Colonials, Victorians, and early-20th-century foursquares on tree-lined streets — many within walking distance of the downtown and station. The borough is largely built out, so turnover is the primary path to ownership, and newer construction or large-lot properties are more common in Chatham Township than in the borough itself. Homes tend to command a premium relative to the broader county, reflecting the schools, the rail commute, and the scarcity of walkable inventory. Buyers here are typically trading lot size for location, walkability, and proximity to the train.

Chatham's lifestyle centers on its walkable downtown, where residents can stroll from the train station to Main Street's shops, cafes, and restaurants, or gather at the borough's library and municipal green. The community is active and family-oriented, with youth sports, civic organizations, and a busy calendar of school and town events. The Passaic River and its parks provide a green edge to daily life, and the short rail ride into Manhattan puts city culture and employment within easy reach. It is a refined but unpretentious suburb where the daily rhythm is set by the train schedule and the school calendar.

Chatham is served by the School District of the Chathams, a unified district shared by Chatham Borough and Chatham Township since the two communities merged their school systems in the 1980s. The district operates elementary schools in both municipalities and a single middle and high school serving the combined community. Its strong reputation is one of the central reasons families choose Chatham, and the shared district reinforces the sense that borough and township function as one community. Families confirm specific school assignment by address within the two municipalities.

Chatham's transportation story begins at its train station, located in the heart of the borough on NJ Transit's Gladstone Branch. The line offers Midtown Direct service into New York Penn Station, with a typical trip of under an hour, and connections to Hoboken and the PATH. By road, the borough is served by New Jersey Route 24, Interstate 287, and Interstate 78, providing access across Morris County and toward Newark and the Holland Tunnel. Newark Liberty International Airport is roughly 20 minutes away. The station's central location makes Chatham one of the region's most convenient walk-to-rail suburbs.

Recreation in Chatham is anchored by its parks and the Passaic River, which runs along the borough and provides walking paths and green space. The borough maintains neighborhood parks, playgrounds, and athletic fields, and the nearby Great Swamp National Wildlife Refuge and the Watchung Reservation offer larger tracts of preserved land for hiking and nature within a short drive. Youth sports, particularly through the recreation programs shared with Chatham Township, are a major part of community life. For culture and entertainment, residents can reach the venues of Manhattan by rail or the theaters and restaurants of Morristown and Summit in minutes.