The short version
Fairfield is the broader-value choice with a walkable center and varied housing. Westport costs more but delivers a distinct arts-and-beach identity and a somewhat shorter ride from its western station.
Housing
Fairfield presents more attainable starting points and a wider mix of housing eras. Westport inventory is typically larger and more expensive, with premiums tied to beach access, schools, and location.
Try both stations
Each town has more than one rail station. Parking, train patterns, and the drive from a particular home can matter more than the town-level average.
Sources and verification
Transit context: MTA Metro-North schedules. Property-tax context: Connecticut OPM. Public-school information: Connecticut EdSight. Housing ranges are broad planning bands and must be replaced or verified with brokerage-approved licensed data before marketing launch.