Friends meadow or Wynsiges clearing
Winsley is an English habitational surname derived from Old English. It combines a personal name, such as Wine (meaning friend) or Wynsige (meaning joy-victory), with the suffix 'leah', referring to a meadow, clearing, or wood.
Less common today
Winsley isn't in the latest US Top 1000. It last peaked at #1,832 in 2025.
US births per 5-year period, 1990βpresent (SSA data).