Oldest I have (though it looks like it's leaving after 25 years in the parents garage).

Schwinn Triplet Town n' Country - 1949




Oldest I have in my house and that I ride

1973 Raleigh International - city build



Newest I have -

2010 Marnati, but the COlumbus MAX tubeset was NOS from the early 90s. It has a 2010 SR group, record hubs, but also some vintage flourishes...Cinelli bars/stem and a Campy C-record non-aero post