To date, the band have released six studio albums: Real Estate (2009), Days (2011), Atlas (2014), In Mind (2017), The Main Thing (2020) and Daniel (2024).

From there, Courtney became acquainted with Mondanile and his friends, and even auditioned to join the latter's band as a bass player before being rejected in favor of an older kid who had a car.

[11] The band also had the idea of working for Courtney's parents' real estate agency in case their music career didn't achieve success.

[13] After issuing singles on the Underwater Peoples and Woodsist labels, the band's 2009 self-titled debut received critical acclaim, including an 8.5 rating and Best New Music tag from Pitchfork Media.

After initial recording sessions and prior to signing the deal, the band parted ways with Duguay, not wanting to be legally-bound to the drummer due to his unreliability.

[17] Subsequently, the second album, Days, features one song with Duguay, "Out of Tune," while the rest of the drum tracks were performed by Courtney, Mondanile and Samuel Franklin.

For live shows, the band recruited drummer Jackson Pollis, formerly of Tiny Masters of Today, and keyboardist Jonah Maurer, a friend of Mondanile's at Buxton boarding school in Massachusetts.

[28] Shortly before recording of the album commenced, the band decided to add keyboard parts that were more advanced than they were capable of themselves, and so they recruited Matt Kallman, formerly of Girls.

[31] After Mondanile's exit, the band considered recording their fourth album as a four-piece, with an additional guitarist brought in for live shows.

After Courtney consulted with Bleeker and gained the latter's approval, Lynch officially joined and participated in writing and recording the band's fourth album.

"[34] During the band's Fall 2016 tour, Lynch was unable to participate due to a five-month visit to India from September to February with the purpose of research for his Ph.D dissertation in ethnomusicology.

[35][36] The band recruited Doug Keith, who had played guitar on tour for Courtney's solo album Many Moons,[37] to fill in until Lynch's return.

[43] On October 4, 2017, the band announced the postponement of a fall tour "for a mix of unforeseen reasons both personal and professional," with the cancelled dates being rescheduled for February 2018.

[46] Three days later, an article elaborating on the allegations was published in Spin, where the band added that they had not gone public sooner with details regarding Mondanile's dismissal because "the women concerned requested privacy and we honored their wishes.

"[48] In January 2018, Mondanile further elaborated on his firing from Real Estate, stating that a disagreement over the inclusion of one of his songs on Atlas led to a falling out with Courtney, and he wanted to record the next album with Courtney and Bleeker at the new studio he had set up in Los Angeles without Jackson Pollis whom he felt uncomfortable working with due to Pollis' dislike towards him over his behavior with women.

Ultimately, Courtney and Bleeker told Mondanile that they didn't want to record with him due to his unwillingness to tour, the distance of their living situations, and his treatment of women.

[49] On November 16, 2017, it was reported that Real Estate would be contributing original songs for the upcoming romantic comedy Plus One starring Jack Quaid and Maya Erskine.