The Van der Woodsen penthouse, located at 300 East 55th Street as the Milan Condominiums, is not actually in the Upper East Side but is shown in the show as it is for the residence of the van der Woodsen family. The family moved back into the penthouse in season two, as it was undergoing renovations throughout the entire first season. The apartment was bought by CeCe Rhodes for Lily and William van der Woodsen when they were first married, for tax purposes.

Residents and OwnershipEdit


Current resident(s)Edit

Former resident(s)Edit

Season One Edit

The van der Woodsen penthouse is not shown in the first season, as Lily is having the place redecorated.

Season Two Edit

In the second season, the Bass and van der Woodsen family is still living in the penthouse. However, when Bart dies in a car accident, Chuck moves back to his suite at the Palace, leaving the grieving van der Woodsens by themselves, yet later returns after persuasion by Lily.

Season ThreeEdit

With Lily's marriage to Rufus, Rufus and his daughter, Jenny Humphrey, move into the penthouse. Serena moves out to supposedly attend Brown but instead stays with Chuck at the Palace. She eventually stays with Nate during their relationship once Chuck purchases the Empire Hotel. However, for a brief moment, Serena announces she wants to move back into the penthouse and kick Jenny out of her room. However, this never comes to fruition. Once Jenny is banished, she goes to live with her mom in Hudson.

Season Four Edit

Serena decides to move in with Blair Waldorf for college, leaving the penthouse occupied by Rufus, Lily, and Eric. When Jenny comes back for a brief visit, she stays at the penthouse with them before moving away for good. When Ivy Dickens, posing as Charlie Rhodes, comes in the second half of the season, she moves into Serena's room before going back to Florida. After Lily turns herself into the police for framing Ben Donovan, she is put on house arrest in the penthouse that lasts through the summer and Eric moves out to attend Sarah Lawrence College.

Season FiveEdit

When CeCe dies, the penthouse is among the possessions in CeCe's estate left to Ivy Dickens, the girl hired by Carol Rhodes to mime her daughter, Charlie. After learning of her proprietorship of the penthouse, Ivy evicts Lily and Rufus and claims it as her own. However, Ivy is soon tricked out of her inheritance by Lily, who then kicks Ivy onto the streets. With the revelation that Bart Bass is alive, Lily annuls her marriage to Rufus and he moves back to the loft in Brooklyn. Meanwhile, Blair kicks Serena out of her apartment and she moves back to Lily's.

Season SixEdit

When summer ends, Lily and Bart return to the penthouse to find it in disarray, as Serena moved out without telling anyone. However, she returns eventually and lets Dan Humphrey stay with her there when he has nowhere else to go.

In the series finale, New York, I Love You XOXO, Lily gets back together with her ex husband, William van der Woodsen, and it's assumed they still reside in the penthouse together.

Gallery Edit

Gossip1 rect540 via apartmenttherapy

Chuck's Bedroom