Webster's housing stock is modest and rural, dominated by single-family homes on larger lots, along with scattered mobile homes and acreage properties. The town's small scale means there are no large suburban subdivisions; instead, housing reflects its agricultural surroundings, with room for gardens, animals, and equipment. Many residents own their homes, and the area attracts a mix of long-time locals, farmers, and retirees drawn by the quiet setting and lower density. Proximity to The Villages and the U.S. 301 corridor brings some commuter interest, but the overall character remains small-town and unpretentious, with more land per home than is typical of Florida's larger retirement and suburban communities.

Webster offers a quiet, rural lifestyle with a notable weekly rhythm: every Monday, the Swap-O-Rama flea market transforms the town as thousands of shoppers and vendors arrive for one of Florida's largest open-air markets. The rest of the week is calm, centered on farming, family, and the local schools. Vegetable fields, cattle pasture, and small lakes define the landscape, and residents describe the feel as a suburban-rural mix with a strong sense of community. Nearby The Villages and the city of Bushnell provide larger retail and services, while the Withlacoochee State Forest offers year-round outdoor recreation. Webster suits those who want genuine country living with the convenience of central Florida's growing corridor nearby.

Webster is served by the Sumter County School District. Webster Elementary School is located in town, while older students attend middle and high school campuses in the broader Sumter County system, including South Sumter schools. The district is relatively small, reflecting the county's mix of rural communities and the large retirement population of The Villages. For higher education, Lake-Sumter State College has campuses in nearby Leesburg and Sumterville, and the University of Central Florida and other institutions are within commuting distance. Families in Webster benefit from a close-knit local elementary school and a straightforward path through the county system.

Webster sits along the U.S. 301 corridor, a major north-south route through central Florida, which connects the town to The Villages, Wildwood, and Bushnell, and links to Interstate 75 a short distance to the west. State Route 471 and other county roads provide access to the Withlacoochee State Forest and surrounding communities. Orlando and Tampa are each roughly an hour's drive, and the region's airports are reachable within that same range. There is no public transit in Webster itself, so residents rely on personal vehicles, with the Monday flea market drawing heavy traffic into town once a week and U.S. 301 serving as the area's main commuting and commercial artery.

The Withlacoochee State Forest is Webster's outdoor backyard, offering hiking, biking, horseback riding, paddling, and camping across thousands of acres, with the River Junction Campground located nearby. The 46-mile Withlacoochee State Trail, a paved rail-trail, runs through the surrounding countryside for cyclists, runners, and walkers. Gant Lake Recreation Area provides freshwater fishing, boating, and picnicking at a small lake just outside town. For a different kind of outing, the Monday Swap-O-Rama doubles as a weekly social and shopping event. The region's larger attractions, including The Villages and the lakes of central Florida, are within a short drive.