Chester's housing market reflects its historic and rural character. The borough contains restored 18th- and 19th-century homes near the village center, including colonial and Victorian-era houses, while Chester Township offers larger lots, farm properties, and equestrian estates on rolling acreage. Newer construction is limited, preserving the area's low-density, historic feel. Buyers drawn to Chester typically seek older homes with character, spacious properties, and the rural ambiance that defines this corner of Morris County.

Chester's historic village center is its defining neighborhood, with preserved buildings, brick sidewalks, and the borough's boutique shopping district concentrated along Main Street and its side streets. Surrounding the village, residential streets and the rural expanse of Chester Township feature older farmhouses, equestrian properties, and wooded lots rather than conventional subdivisions. This blend of a walkable historic core and open countryside gives Chester a distinctive, unhurried residential character.

Chester's lifestyle centers on its small-town village atmosphere and outdoor surroundings. The downtown draws shoppers and diners to its boutique stores and eateries, and the community supports seasonal events, local farms, and equestrian activities that reflect its country heritage. Residents value the quiet, family-oriented pace, the strong schools, and easy access to Hacklebarney State Park and the Black River for fishing and hiking. It is a community oriented toward local traditions and preserved open space.

Chester's students are educated by two districts. The Chester School District serves both Chester Borough and Chester Township for pre-kindergarten through eighth grade, with Dickerson Elementary, Bragg Intermediate, and Black River Middle School. High school students attend West Morris Central High School, part of the highly regarded West Morris Regional High School District. The private Gill St. Bernard's School is nearby. These schools are a central draw for families moving to the area.

Chester sits at the crossroads of U.S. Route 206 and New Jersey Route 24, two regional arteries that connect the borough to Morristown, the surrounding Morris County towns, and the wider northern New Jersey highway network. Interstates 78 and 287 are within easy reach, and NJ Transit commuter rail service is available at stations in neighboring communities for travel toward New York City. The location offers a balance of rural seclusion and regional accessibility.

Hacklebarney State Park, with more than 700 acres in Chester Township, is the area's outdoor centerpiece. The Black River bisects the park, which is considered one of New Jersey's premier trout-fishing streams, and more than five miles of trails wind through its wooded glacial valley. Local parks and preserved farmland offer additional open space, while the surrounding horse country supports riding and other rural pastimes. The region's trails and waterways give residents year-round outdoor access close to home.