1. Every Vincent Chase House in Entourage

Series: Entourage
Various spots in Los Angeles, CA

On the real, Entourage could take up about a fifth of this list. Vince and the boys from Queens were already ballin when we met them and their bread only got longer with each passing season. A brief history, as correlated in the pictures:

S1 - Typical Hollywood spanish-style house.
S2 - Vince bets everything on Aquaman just so he can move into a mansion previously owned by Marlon Brando and Johnny Depp.
S2 - Gang relocates to Jessica Alba's Malibu crib while Vince films Aquaman. 
S4 - The gang returns from filming Medellin, briefly crowding into Drama's Beverly Hills condo before leasing a new place up in the Hills.
S6 - After experiencing a temporary fall from grace and bank in season five, Vince repurchases the season one crib. Eric finally moves out.
S7 - The gang upgrades to a Tuscan villa, which remains through season eight until Turtle burns it down while smoking at Vince's welcome home party.