Casselberry's housing stock is anchored by established single-family neighborhoods, with much of the city built out during the 1970s and 1980s. Ranch-style homes are common, and mature trees shade many of the streets. Because the city contains more than two dozen lakes, a notable share of homes sit on or near waterfront, offering lake views and private access. In addition to the older single-family inventory, the city includes newer townhomes and apartments, particularly along major corridors, which broaden the range of housing types. The mix of eras and styles, combined with widespread lake access, draws first-time buyers, families, and those seeking lakefront living within the Orlando metro.

Casselberry's neighborhoods are largely established, tree-shaded residential areas clustered around the city's many lakes. Homes near Lake Griffin, Lake Lotus, and the other lakes in the city's network offer water views and, in some cases, private docks or lake access. The older sections developed during the city's mid-century growth feature ranch-style homes on generous lots, while newer townhome and apartment communities have appeared along the U.S. 17-92 and Red Bug Lake Road corridors. The city's compact size means most neighborhoods are within a short drive of its parks and commercial areas. The overall pattern is a leafy, lake-oriented suburb with a mix of home eras and types rather than a single uniform development style.

Casselberry offers a relaxed, community-minded lifestyle with a strong emphasis on the outdoors and the arts. Lake Concord Park functions as the city's cultural heart, with art installations, an amphitheater, and a calendar of community events, festivals, and live performances. Secret Lake Park and the city's other parks provide lakefront green space for walking, picnicking, and kayaking. Residents are minutes from the shopping and dining of Altamonte Springs and Winter Park, and about twenty minutes from downtown Orlando's employment and entertainment. The city's proximity to Wekiwa Springs State Park and the Wekiva River adds a natural escape close to home. Casselberry suits those who want lake-centered living and community culture near the heart of the Orlando metro.

Casselberry is served by Seminole County Public Schools, a well-regarded district in the Orlando region. Casselberry Elementary School, located in the city, serves students in pre-kindergarten through fifth grade, and other district elementary, middle, and high schools serve the surrounding area. Seminole County Public Schools is known for strong academic performance and a range of magnet, career, and advanced coursework options. The city's location also puts families within reach of private schools and, for higher education, Seminole State College and the University of Central Florida, both short drives away. The presence of quality public schools is a key draw for families relocating to Casselberry.

Casselberry's location makes commuting across the Orlando metro straightforward. Interstate 4 is about five minutes from most parts of the city, providing direct access to downtown Orlando, roughly twenty minutes to the south, and to the attractions and employment centers of the region. Orlando International Airport is about thirty to thirty-five minutes away. U.S. 17-92 and Red Bug Lake Road serve as the city's main local corridors, connecting to neighboring Altamonte Springs, Longwood, Winter Springs, and Winter Park. SunRail commuter rail stations in nearby Longwood, Altamonte Springs, and Winter Park offer a rail alternative for downtown Orlando commuters, while LYNX bus routes serve the area.

Casselberry maintains seventeen parks, and water is central to its recreation. Lake Concord Park anchors the city's public life with its amphitheater, art installations, fountains, and event lawn, while Secret Lake Park offers a lakeside setting formed by three connected lakes. The city's many lakes support kayaking, fishing, and shoreline walking, and its trail network links neighborhoods to green space. Just a short drive away, Wekiwa Springs State Park and the Lower Wekiva River Preserve offer spring swimming, hiking, and paddling. The city's event calendar, from arts festivals to concerts at the Lake Concord amphitheater, keeps the parks lively throughout the year.