"To each according to their need/desire" seems to be the guiding principle here. Peoples' needs naturally change over time, so there'd still be a housing market, it just wouldn't require tens of thousands of dollars per month in rent to live in a bachelor's apartment in Toronto.
Picard has a family (of sorts, made up of two Romulans, a pitbull, and possibly his sister-in-law who lives elsewhere) and a business that requires a fairly large land allotment, so he needs the Chateau and its vinyard.
Dahj was apparently living alone (there's no sign that her boyfriend was cohabiting) and appears to have been early in her career (she had just been accepted for a position at the Daystrom Institute, so she probably would've been moving soon); she probably didn't
need more than an apartment at this point in her life.
The Riker-Trois were living in a house big enough for four (Thaddeus' room was still there), but they decide to move away in S3; they'll probably "sell" the house (whatever process that entails), then move to a smaller place in a city. Once Kestra is old enough to want her own home, she'll probably start in an apartment (or just go to the Academy and live in the dorm), and Will & Deanna may move again.
Raffi was living alone in the equivalent of a trailer, so when she returned to the fleet she sold either the building or the land (it looks like her house was all pre-fab, so it could probably just be dismantled and either disposed of or moved to wherever the new owner wants it).
Rios, of course, was living on his own ship, which he then gave to Seven, who gave it to Raffi (who uses it as part of Starfleet Intelligence-sanctioned operations, so I guess it's now
technically part of SI's "motor pool" or whatever.