The town center of Chesterland is located at the intersection of U.S. Route 322 and State Route 306. The commercial district of Chesterland spans out from this intersection in all directions.
Chesterland is considered part of the Chagrin Valley area, which is defined by the cities and villages along the Chagrin River.
Chesterland lies entirely in the West Geauga school district, and shares this district with neighboring Russell Township. There are two elementary schools, one middle school, and one high school, West Geauga High School. Hawken Upper School also lies in Chesterland, although it has a Gates Mills address because its mailbox lies on the opposite side of County Line Road. A third elementary school, Chester Elementary, served the community for many years but closed in the 1980s.