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.
Ownership and residentsEdit
- Bart Bass
- Chuck Bass
- Ivy Dickens
- Dan Humphrey
- Jenny Humphrey
- Rufus Humphrey
- Eric van der Woodsen
- Serena van der Woodsen
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.
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. Surrounded by the wealth of the van der Woodsens, Jenny grows accustomed to her new lifestyle and begins to solidify her place as Constance's new queen bee. 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. Meanwhile, Dan Humphrey decides to remain at the loft as he attends New York University.
In the fourth season, 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, comes in the second half of the season, she moves into Serena's room before moving back to Florida. After Lily turns herself into the police for framing Ben, she is put on house arrest in the penthouse that lasts through the summer and Eric moves to Sarah Lawrence College.
In season five, it is revealed that the van der Woodsen penthouse is owned by Lily's mother, CeCe Rhodes, who bought it for her daughter and then-son-in-law for tax purposes. 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 CeCe's real granddaughter. However, as the will dictated "Ivy Dickens" as CeCe's beneficiary, it is revealed that she was aware of Ivy's true identity.
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 Lily's former husband, Bart Bass, was alive, Lily and Rufus' marriage comes into question. Because of Rufus' kindness towards Ivy, his relationship with Lily had already become strained. With the annulment of their marriage, Rufus moves out and back into the loft with Dan while Bart moves back into the penthouse with Lily.
In season six, Lily and Bart travel for the summer and leave Serena to take care of the penthouse. Upon their return, Vonya tells them he hasn't seen Serena all summer.