Housing in Jennings consists of modest single-family homes on small-town lots, along with scattered rural properties and acreage in the surrounding Pawnee County countryside. The town's history as a railroad and oil community is reflected in its older homes, and there has been little large-scale subdivision development. Buyers drawn to Jennings are typically looking for an affordable small-town property or rural land, with the convenience of the Cimarron Turnpike for commutes toward Stillwater and Tulsa.

Jennings is a compact town with no large planned subdivisions. Homes and a few local businesses cluster near the school and the main roads, with farmland and ranch land extending in all directions. The community's small footprint means most properties are within easy walking or driving distance of the school and the center of town, and the character is defined more by the surrounding rural landscape than by distinct neighborhoods.

Jennings offers a quiet, small-town way of life in the ranch and farm country of north-central Oklahoma. The community revolves around its school, churches, and the surrounding countryside, with a pace that has changed little since its boom years ended. Because the town is small, residents handle shopping, dining, and services in nearby Stillwater or Tulsa, both within a convenient drive, while enjoying the lower cost and open space of a rural community in between. It suits people who want a small-town address with access to the employment and amenities of two larger cities.

Jennings Public Schools serves the town's students from pre-kindergarten through eighth grade, keeping the elementary and middle grades close to home. The district is small, and its Oklahoma School Report Card grades have traditionally ranked among the better ones in the area. Because Jennings does not operate a high school, older students attend neighboring districts in the region, continuing their education outside the town while remaining part of its tight-knit community.

Jennings sits near the Cimarron Turnpike, the toll road that connects the Stillwater and Tulsa areas with Interstate 35 to the west, giving residents quick highway access in both directions. The nearest turnpike interchange is at Hallett, a short distance from town. There is no local transit, so commuting is done by private vehicle, with Stillwater and Tulsa serving as the primary employment destinations for the large majority of the town's working residents.

Recreation around Jennings is largely a matter of the surrounding countryside—rural roads, farmland, and open space characteristic of north-central Oklahoma. For lakes, parks, organized sports, and cultural events, residents look to nearby Stillwater, home to Oklahoma State University, and to the Tulsa metro area. The town's own pace is quiet, with school and community events forming the core of local social life.