Taylor Swift’s real estate moves may not get as much attention as her music or her romances, but her taste in homes has always generated buzz. It’s easy to see why. Since purchasing her first property in 2009, the 33-year-old superstar has amassed a portfolio of homes valued at $150 million, according to the Wall Street Journal.
To celebrate Taylor’s 2023 Eras tour, we’re taking a walk down memory lane of the performer’s greatest real estate hits, sorting each property into one of three eras marked by memorable music and high-profile relationships. After all, as the lyrics to some of her songs prove, for Taylor, romance and real estate are often intertwined.
Nashville Roots: 2009-2011
Albums: Taylor Swift, Fearless, Speak Now
Boyfriends: Joe Jonas, Lucas Till, Taylor Lautner, John Mayer, Jake Gyllenhaal
Even in the early days of her career, Taylor had her mind set on real estate. At this point, she stuck close to home—her first two major purchases were in Nashville, where Taylor’s family moved when she was a teenager so she could pursue music. It was a good move (pun intended).
Adelicia Penthouse, Nashville
In 2009, Taylor made her first real estate purchase, buying a three-bedroom penthouse in Nashville’s Adelicia condo right next to Music Row. That same year, she bought an additional one-bedroom unit right below hers. Taylor still owns this property today, and you can even be her neighbor: there are two units for sale in the building right now, each a cool $2.995 million.
Northumberland Estate, Nashville
By 2011, Taylor was ready for more space. She added Northumberland Estate, a 7,700-square-foot Greek Revival mansion built in 1934, to her fledgling collection. The property sits on six acres of what was once a horse farm. As with her Adelicia apartment, Taylor still owns this house today.
The Coast-to-Coast Expansion, 2011-2015
Albums: Red, 1989, Reputation
Boyfriends: Connor Kennedy, Harry Styles, Calvin Harris, Tom Hiddleston
As Taylor’s career continued to blossom, so did her real estate portfolio. The singer became a true bicoastal queen, first snatching up multiple properties in Beverly Hills, then two New England coastal manses, and, finally creating a compound in Tribeca, New York.
Dual Four-Bedroom Homes, Beverly Hills
Taylor’s first purchase in Beverly Hills was a four-bedroom, East Coast–style house in 2011, which she quickly followed up with a four-bedroom, midcentury-style home the next year. Taylor reportedly used the second home as a guesthouse. In 2018, she sold both. Bye-bye, Beverly Hills!
The Kennedy-Adjacent Manse, Hyannis Port, Mass.
For a brief spell between 2012 and 2013, Taylor owned a quaint little mansion next to the famous Kennedy compound on Massachusetts’ Cape Cod. At the time, Swift was dating Conor Kennedy—she sold the home after their split. When she bought the seven-bedroom house, she paid just shy of $5 million. A few months later, she sold it for $5.675 million a few months later, once again exhibiting her skill at spinning break-ups into gold.
High Watch, Westerly, R.I
In 2013, Taylor bought what might be one of her most famous and recognizable homes, a historic hilltop estate in the tony Watch Hill neighborhood of Westerly, R.I. High Watch, as the house is known, is an 11,700-square-foot Colonial-style manse built in the 1930s. When she first owned the property, Taylor threw grand Fourth of July parties here. Those fêtes seem to be in the past, but the home remains in her real estate stable—and has even made it into her discography. High Watch was once the Holiday Home (its official name at the time) of heiress, socialite, and ballet patron Rebekah Harkness, the subject of Swift’s “Last Great American Dynasty.” A verse of the song goes, “Holiday House sat quietly on that beach/Free of women with madness, their men and bad habits/And then it was bought by me.”
The Goldwyn Estate, Beverly Hills
In 2015 Taylor paid $25 million for the former home of legendary Hollywood producer Samuel Goldwyn. (Yes, he’s the reason there’s a G in MGM.) Built for Goldwyn in 1934, the house spans 11,000 square feet and sits on two acres. After restoring the home, Taylor had it designated a historic landmark, and she still owns it today. The home is still making history; Swift recorded her album “Folklore” here during the pandemic.
The Tribeca Sugar Loaf Compound, New York
Taylor has purchased not one, not two, but three units in Tribeca’s Sugar Loaf building, as well as an adjacent townhome. She bought the first two units in 2014, then added the second apartment, and the townhome, in 2017. The main purpose of the second unit, according to WSJ, was to create a private garage. Through renovations, Taylor will reportedly connect the townhome and its private garage to her third Sugar Loaf unit, meaning she’ll be able to get from her apartment to her garage without going outside.
Transatlantic Rentals: 2016—2023
Albums: Lover, Folklore, Evermore, Midnights
Boyfriend: Joe Alwyn
Though Taylor’s long-term relationship with Joe Alwyn has recently come to an end, the six-plus years in which they dated can be defined, at least in real estate terms, by two rental properties: one in New York, and one in London, where Alwyn is from.
23 Cornelia Street, New York
As is well-known to anyone who has heard her song “Cornelia Street,” while Taylor was renovating her Tribeca apartments, she rented a four-bedroom home at 23 Cornelia Street in the West Village. The property, which was listed at $45,000 a month last year, was where the singer lived when she met Aldwyn. The song begins with real estate and romance: “We were in the backseat/Drunk on something stronger than the drinks in the bar/”I rent a place on Cornelia Street”/I say casually in the car.” Don’t look for Taylor to return to the scene of happy memories, though. Another verse promises: “And I hope I never lose you, hope it never ends/I’d never walk Cornelia Street again/That’s the kind of heartbreak time could never mend/I’d never walk Cornelia Street again.”
Primrose Hill, London
Primrose Hill Townhome, London
In 2021, The Daily Mail broke the news that the couple had moved into a six-bedroom townhome in London’s Primrose Hill rented by Taylor—prior to that, they had been sharing Aldwyn’s flat. There’s not much known about the property, other than it’s valued at about $8.6 million (£7 million). Post-breakup, will Taylor hang onto her London address? Given her history on Cape Cod—and the tried-and-true adage “home is where the heart is,”—we’re thinking she’ll sell and move on to make new memories, new music, and more smart real estate decisions.
The full story of Holiday House is featured in season 3 of House Beautiful’s haunted house podcast, Dark House. You can listen to the full episode on Spotify.
Contributing Writer
Stefanie Waldek is a Brooklyn-based writer covering architecture, design, and travel. She’s worked on staff at Architectural Digest, ARTnews, and Oyster.com, a TripAdvisor company, and has contributed to Condé Nast Traveler, The Washington Post, Design Milk, and Hunker, among others. When she’s not dreaming about midcentury chairs, you can find her re-watching The X-Files, likely in an airport lounge or on a plane.