Henry and Jane move into a Manhattan apartment complex owned by Gavin and Olivia Dunn, as the new co-managers. Soon after moving in it becomes clear that not all is as it seems, as the building along with its tenants are possessed by a mysterious demonic force.
Jane makes a terrifying discovery about what lies behind the walls of The Drake as she begins to renovate Mr. Barlow's apartment. Meanwhile, Henry wrestles with whether he should tip Gavin off to inside information he has on one of his big projects, and lonely Drake resident Danielle Vincent gets a much needed assist from Gavin with a romantic tryst with a business associate of his. Finally, Brian struggles with his continuing temptation for Alexis, and Jane determines to continue her investigation of the mysterious door in the basement.
More mysteries begin to unfold at The Drake as Jane repeatedly glimpses a little girl - or an apparition? - who beckons her to a room with a strange suitcase. Meanwhile, Henry and Jane are drawn closer to the Dorans, Gavin manipulates a possible career change for Henry, and Olivia shares a painful secret with Jane about her daughter Sasha's death ten years ago. Finally, Gavin offers to help Annie Morgan, a budding young journalist residing at the Drake, who suddenly discovers that anything that she writes becomes the truth - with terrifying results.
Henry learns that Gavin is under investigation for questionable real estate transactions, and must choose between loyalty to his boss or his friendship with Gavin. Jane, unaware of Henry's dilemma, has her own decision to make after she discovers the identity of the thief at The Drake. Meanwhile, the eerie apparition of the little girl reappears with a warning about the contents of the suitcase Jane retrieved, and Nona is troubled by alarming visions of Henry's future. Finally, Annie begs for Gavin's help when her "creation" of Kandinsky goes awry, and he offers her a dangerous quid pro quo as a solution.
As Olivia works to put the finishing touches on the lobby for the annual Drake Halloween costume gala, it brings to mind another memorable Halloween night in 1929, when hug and mayhem reigned in the building. However, now it's Jane who finds herself in the crosshairs of the spirit from the suitcase. Meanwhile, Gavin receives cryptic texts from an unknown source threatening Olivia's safety, and Henry meets a media consultant interested in propelling his political career. A jealous Brian questions Louise about her rendezvous with Dr. Evans while she was recovering from her elevator accident, and one of Gavin's most crucial personal possessions is missing by the end of the evening.
The aftermath of the Dorans' Halloween party leaves everyone with an emotional and psychological hangover. Jane, traumatized by the terror she experienced, is even more devastated by the lack of support not only from the detectives investigating the case, but from Henry, leading to repercussions in their relationship. Meanwhile, Dr. Evans, who suffers from a gambling addiction, becomes beholden to Gavin in order to pay off a large debt. Finally, Gavin tracks down the person responsible for endangering Olivia and stealing his property, and is determined to end the trouble or risk losing The Drake and everything he owns. And in one horrifying moment, Jane pieces together how is she is connected to the history of the building.
Henry's political career continues to rise when he receives a special commendation from the Mayor for his heroic actions. However his exultation is tempered by Jane's ever-changing mood about staying at The Drake, where she no longer feels safe. Meanwhile, Jane discovers that both Nona and her missing grandmother, Lottie Clark, have mysterious connections to the building; Brian determines that Alexis has been duplicitous when it comes to Louise and her "affair" with Dr. Evans; and back at the hospital, the good doctor learns the unethical terms of his payback to Gavin in exchange for his help. Finally, Jane and Nona discover one of The Drake's ultimate secrets as they search for Lottie - a secret that will change Jane's life forever.
Jane disappears without a trace, forcing a despondent Henry to worry for her safety and sanity. When she suddenly pops up in the middle of Times Square dazed and confused and is taken to a hospital for observation, Jane discovers that a horrible fate may be waiting for her there. Meanwhile, Gavin has Victor Shaw held captive in The Drake's boiler room with Kandinsky torturing him to give up the location of the red box. Shaw, however, shockingly reveals to Gavin his knowledge of what really happened to his daughter, Sasha, and threatens to tell Olivia. Finally, to Brian's dismay, he discovers that unless he is with Alexis, his creativity vanishes.
Jane is hurled back in time to October 1927 by the mysterious Maris Elder, who hypnotizes her in an effort to find out where she disappeared down the spiral staircase. Her time travel adventures unlock secrets long hidden in Peter Kramer's apartment, where his wife was cuddled, and shows Jane that her family has a dark legacy that's tangled with The Drake's history. Meanwhile, Gavin talks to Henry about the possibility of becoming a city councilman, but his chances may be destroyed by the leak of some sensitive personal information. And in a shocking revelation, Sasha's identity is exposed.
Jane's disturbing dreams keep fusing with reality, but many Drake residents have reason to celebrate. Gavin and Olivia are thrilled and grateful that Sasha (a.k.a., Laurel Harris) has returned; Olivia connects Louise with a great opportunity to work for a top magazine, and Brian is close to making a deal with a producer for his play. Meanwhile, Alexis' overwhelming guilt over her indiscretion with Brian drives her to find an escape clause in her deal with Gavin. Finally, the Dorans plan a big kick-off fund raiser to introduce Henry into the political world, and Jane, propelled by her dreams, visits an ancient Harlan Moore to learn more about Peter Kramer's journal and The Drake's history.
Sasha/Laurel Harris lays out her plan to get Henry elected, which includes his speaking at the Dorans' local church. She secretly offers Father Douglas a disturbing arrangement to rid himself of the demons who have tormented him since being tempted to open Gavin's red box. Meanwhile an enigmatic new tenant who may have ulterior motives moves into the Drake. Brian is still upset with Louise for her relapse into substance abuse while, simultaneously, Alexis plots her revenge on Louise after she discovers they've crossed paths in the past. Finally, Sasha and her parents have a bizarre showdown.
Who or what is the 'conspiratii'? When Jane tries to crack the meaning of this mysterious word that keeps popping up in Peter Kramer's journal, a secretive Detective Cooper shockingly reveals his part in the shadowy group. Jane agrees to be their eyes and ears at The Drake, but Gavin is one step ahead of her. Meanwhile, Henry tries to track down Jane's estranged father to surprise her at a splashy engagement party Olivia is throwing them. Jane and Henry spend a magic night at the Dorans' party, while on another floor there is no love lost between Alexis and Louise when they have a final face-off and Louise learns the true depth of Alexis' hate for her.
Brian and Louise are discussing what to do with Alexis's body. Henry refuses to get into dirty politics. Jane's father returns to the Drake and tries to take her away at gunpoint.