Bennington's housing stock reflects its small-town, agricultural character. The town contains a mix of older frame and brick single-family homes on modest in-town lots, along with mobile homes and larger homesteads on acreage in the surrounding countryside. Much of the surrounding land remains in pasture and cropland, giving many rural properties a sense of space and privacy. The market is modest and locally oriented, serving families, retirees, and those employed in the surrounding agricultural economy, with prices far below those of the larger Durant and Texoma markets.

Bennington is organized around a compact town grid centered on its main streets, where the school, churches, and remaining local businesses cluster. Older homes line the in-town streets, while the surrounding township consists of rural homesteads, farms, and ranch properties spread across the eastern Bryan County countryside. There are no large suburban subdivisions; instead, the community's residential pattern is defined by the small-town core and a dispersed network of county roads leading to agricultural properties.

Life in Bennington is quiet, rural, and close-knit. Residents know their neighbors, and community activity revolves around the school, churches, and local events. Fishing, hunting, and time outdoors are common pastimes, with the Blue River and the surrounding countryside providing year-round opportunities. For shopping, dining, and entertainment, residents make the roughly 20-mile drive to Durant, which offers the amenities of the Choctaw Nation's headquarters community and the broader Texoma region, while returning home to a much slower pace.

Bennington is served by Bennington Public Schools, a small public school district based in the town. The district operates two campuses serving roughly 270 students, combining elementary and secondary education within a close-knit setting. Its small size allows for individualized attention, and the district is a central institution in the community. For specialized programs, higher-level coursework, and additional activities, families can draw on resources in Durant and the surrounding Bryan County area.

Bennington sits near U.S. Highway 70, the principal east-west route through Bryan County, placing the town roughly 20 miles east of Durant and providing a direct connection to the county's commercial center. The highway network also links Bennington to the Texoma region and, farther afield, to the Dallas-Fort Worth metropolitan area via the broader Oklahoma and Texas highway systems. Personal vehicles are essential, and commuting patterns generally center on Durant, with some residents traveling to larger regional employers.

The Blue River is the signature outdoor destination for the Bennington area. This clear, spring-fed stream flows through Bryan County and is managed in part for public recreation, supporting trout, bass, crappie, and catfish fishing along with seasonal floating. Its accessible stretches and state-managed areas draw anglers from across southeastern Oklahoma. The surrounding rural landscape offers hunting and open-space recreation, while Lake Texoma, one of the region's largest reservoirs, is within reach for boating and fishing farther south along the Oklahoma-Texas border.