Here's a link to an old thread that should answer your question...
Age of the Diffrent Villages
From that thread, here is KayakerNC's list. Only need to add the newest Villages for 2009-2010. Pennecamp and Buttonwood with Tamarind Grove and St James to come north of 466A. Everything from about 2001 on is accurate. I see some Villages missing for prior to 2001 .... Glenbrook, Palo Alto, Polo Ridge, Hacienda, El Santiago, Santo Domingo. Stuff prior to '92 is CC Hills, Orange Blossom Hills, and Silver Lake
Kayaker's list:
This is NOT official, based on my research into the tax rolls, which may be not 100% accurate.
1992 Del Mar (Lake County)
1994 Rio Ponderosa
1995 Rio Grande
1996 de La Vista
1997 Alhambra
1997 Santo Domingo
1999 Santiago
2000 Belle Aire
2001 Springdale (Marion Cty)
2002 Chatham (Marion Cty)
2002 Piedmont (Marion Cty)
2003 Summerhill
2003 Bonnybrook
2003 Calumet Grove (Marion Cty)
2004 Lynnhaven
2004 Winifred
2004 Ashland
2004 Belvedere
2005 Liberty Park
2005 Sunset Pointe
2005 Tall Trees
2005 Poinciana
2005 Virginia Trace
2006 Caroline
2006 Sabal Chase
2006 Mallory Square
2006 Duval
2006 Largo
2007 Amelia
2007 Hadley
2008 Bonita
2008 Hemingway
2008 St Charles
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Maryland (DC Suburbs) - first 51 years

The Villages - next 51 years