|Ability||Spirit possesses his house|
|Status||Dead † (partly alive by spirit)|
Nearly 3 decades ago Holloway brought his wife and daughters to Haven. He built a large house for his family, invested all he had in it. However, the man became so obsessed with the building that it triggered his trouble: he and the house became one. Initially his wife chose to stay with him and installed mirrors so Roland could see and intercoms so he could hear. When his wife and daughters attempted to leave him, Holloway kept them prisoner. In desperation Mrs. Holloway killed her daughters first, then herself. Lucy Ripley and James Cogan (the Colorado Kid) were too late to prevent the tragedy. When Lucy realized how crazed Holloway had become she opted not to help him and left Roland to rot.
Years later, Holloway finally got his chance at revenge. On Halloween he lured two teens, Teena and Chad, into the house and frightened them. He chased Teena out but kept Chad. Teena went to Audrey for help who decided to check things out. Audrey, accompanied by Duke and Tommy, followed Teena into the Holloway house. Suddenly, all of them were trapped inside and Audrey discovered Chad's mangled corpse; this caused Teena to flee only to be killed by Holloway soon after. The house then lured Nathan and Jordan into its clutches and tried to turn all present against each other. Because of the regressive hypnosis by Dr. Callahan, Audrey remembered how she (as Lucy) escaped before. Audrey and her friends destroy all mirrors and loudspeakers in the house and manage to escape. Afterwards they have Dwight blow the house to smithereens and put a "no trespassing" sign on the land. After everybody has left, the house starts to rebuild itself.
The Holloway Trouble is eventually passed to Laverne through Duke, as Wade Crocker killed one of the Holloways during his serial killing spree, and thus would have ended Roland's trouble, likely killing him for good.
Roland Holloway a refined yet bitter man who’s been trapped inside his house for more than 27 years and is bent on vengeance.