The short version
Greenwich offers multiple village identities, more land at the upper end, and a premium address. Stamford offers the county’s most frequent rail service, real urban energy, and a much wider range of entry prices.
Do not compare medians alone
Greenwich ranges from denser Byram and Cos Cob to waterfront Old Greenwich and expansive backcountry. Stamford ranges from downtown towers and Harbor Point to wooded North Stamford. Neighborhood selection changes both budget and lifestyle.
The practical test
Spend a morning walking from each station, then repeat the trip from an actual listing. The towns are close on a map; the lived experience is not.
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.