In the premiere episode of the second season of Million Dollar Listing, Josh tries to persuade his pal, Dr. Sam, to buy a fixer-upper with huge profit potential, but it puts a strain on their friendship. Chad is dealing with a temperamental client who wants to sell his million-dollar condo in a not-so-million-dollar neighborhood. Meanwhile, Chad's girlfriend, Victoria, springs some surprising news on him. Madison's assistant leaves him in a bind, just as he secures one of the biggest listings of his career.

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Josh tries to make things right with Dr. Sam by finding him the perfect condo, but the listing belongs to his biggest rival, Chad. Chad is struggling with family issues while trying to sell a pair of condos for yet another demanding client. The pressure heats up for Madison, who is missing an assistant and is left in a tight situation on a high-end deal.

Josh thinks he finally found the perfect house for his client - a high-strung doctor and his spoiled daughter - but this dream house might be too good to be true. The rich widow of a famous businessman impatiently demands that Chad find her a beach house in the most exclusive part of Malibu. Madison lists his own home on the market, and then goes on a mystery blind date.

Josh's business-savvy grandmother finds him an "obituary listing," but when he ends up representing both the buyer and the seller he has to find a way to delicately negotiate. Chad tries to score a listing with an NBA star for a rental property in Las Vegas, but finds himself clashing with the star's bossy manager. Madison finds himself confused by unrequited feelings for his ex-girlfriend while house inspections reveal unexpected issues for one of his buyers.

While dealing with the erratic demands of an arrogant client, Josh questions whether real estate is really the right path for him. Just as Chad is about to strike a deal for his NBA star seller, an unexpected setback threatens the deal. A Texas tycoon expects Madison to find an ocean-view home for his college-age son at Texas prices.

As Josh copes with suffering from a "quarter-life" crisis, he strives to find the perfect piece of land for a designer's multi-million dollar fantasy compound. Chad battles over negotiations with a seller while shepherding a longtime family friend through the process of buying her dream home. Madison reaches a career milestone with his first double-digit listing, and attempts to make a buyer - a picky client of Josh's - fall in love with the property. Meanwhile, conflict between Josh and Chad explodes.