Tortured Poets or Real Estate Rock Stars? Taylor Swift's Past Boyfriends—and Their Incredible Homes – News

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You simply can’t check your phone these days without seeing a headline about Taylor Swift. The music megastar has achieved an unprecedented level of fame—and with the drop of “The Tortured Poets Department” album on Friday, she’s set to seize the celebrity gossip narrative for another few months still.
Swifties have been trying to decode the meaning behind the singer’s 11th studio album since she announced it at the 2024 Grammy Awards in February. Some have suggested that Taylor’s ex Joe Alwyn might have inspired the title, while others believe it could even include songs about her relationship with Matty Healy, The 1975 frontman.
While we’re eagerly awaiting the chance to decide for ourselves which past loves the lyrical legend is waxing poetic about, we got to wondering: Where are these dudes now? And, more specifically, what kinds of properties do they call home? (Can you blame us? We’re permanently in our real estate era, after all.)
From one Scottish boyfriend’s seriously stylish Beverly Hills, CA, mansion (which you can rent for $100,000 a month) to a chic Tribeca building where not one—but two—of her rumored exes have condos, we rounded up the real estate of Swift’s former romances.
If you were plugged in in 2008, then you remember that Joe Jonas dated Swift for a few months when they were teenagers—and that the former boy-band member famously broke up with the “Lover” singer in a 27-second phone call.
Dating life aside, Jonas’ real estate portfolio is punctuated by a string of recent purchases and sales.
In 2016, he bought a new Sherman Oaks, CA, farmhouse for $3,700,000. The four-bedroom home, nicknamed “Sutton House,” comes with a guesthouse and screening room. However, Jonas put the pad on the market in 2018 following his engagement to actress Sophie Turner.
That same year, Jonas and Turner bought a Manhattan condo in the city’s lively Nolita neighborhood for $5,600,000. The luxe unit features a 1,450-square-foot terrace and Miele appliances.
The couple eventually parted ways with the property last winter for $5,999,999.
In 2019, the couple snagged another new build: a 15,000-square-foot, $14.1 million Encino, CA, mansion. They didn’t live there long, selling it for $16,750,000 after just two years.
In 2021, Jonas decided to shake things up and move back to the East Coast, where he and Turner snagged an $11 million Miami mansion. The six-bedroom, Frank Lloyd Wright–inspired residence has floor-to-ceiling windows and 94 feet of water frontage.
Jonas sold this property for $15 million in 2023, after splitting from Turner.
If you’re a fan of Swift’s 2010 song “Back to December,” you already know that it’s rumored to be about “Twilight” star Taylor Lautner.
Swift and Lautner dated for about four months after meeting on the set of “Valentine’s Day” and remain friends today. We love to see it.
Lautner, a Michigan native, has a short yet intriguing real estate backstory. For one, he sold his four-bedroom Agoura Hills, CA, mansion to “Big Bang Theory” actress Kaley Cuoco in 2022 for $5,250,000.
After shedding that property, Lautner picked up another Agoura Hills abode for $3,900,000.
The incredible Mediterranean-style estate features stylish beamed ceilings, a 750-bottle wine room, and a greenhouse in the backyard.
Musician John Mayer and Swift were rumored to be dating in 2009. They even released a duet together, “Half of My Heart.”
Following vocal cord surgery in 2011, Mayer moved to Bozeman, MT, and bought a 15-acre property near the Yellowstone River.
He still maintains a beautiful Beverly Hills, CA, home that he picked up in 2018 from Maroon 5 singer Adam Levine for $13,500,000. It was Levine’s bachelor pad prior to his marriage to Behati Prinsloo—and it likely serves the perpetual bachelor Mayer just as well.
If you want a summary of Swift’s relationship with actor Jake Gyllenhaal, give a listen to the 10-minute version of “All Too Well.”
The hit song is widely speculated to be about the couple’s short-lived relationship: The two made headlines in 2010 after they were snapped together in New York City.
Three years after their highly publicized courtship, Gyllenhaal decided to sell his spacious Hollywood Hills, CA, home of 10 years.
In 2017, the actor dropped $8,630,000 on a high-end Tribeca condo at 443 Greenwich St. Gyllenhaal isn’t the only star at the supposedly paparazzi-proof address—Meg Ryan, Ryan Reynolds, and Swift pal Blake Lively also own units in the building.
After Gyllenhaal, Swift dated musician Harry Styles. Swift reportedly met the One Direction member backstage at an awards show in 2012.
Strangely enough, Styles purchased a unit in the same Tribeca building as Gyllenhaal in 2017, joining the long list of celebs who call the downtown Manhattan address home. The “Watermelon Sugar” singer paid $8,710,000 for his loft-style condo.
Previously, in 2016, Styles purchased a lavish Los Angeles residence for $6,870,000. He sold it at a loss for $6 million a year and a half later.
The U.K. native also owns several properties in London’s Hampstead Heath neighborhood.
After Styles, Swift and DJ Calvin Harris met through their mutual musician friend Ellie Goulding. The couple reportedly dated from winter 2015 to summer 2016, co-writing Rihanna‘s “This Is What You Came For.”
Harris picked up a $15 million Beverly Hills megamansion a year before he met Swift. The 10-bedroom, 12-bathroom property has a two-bedroom guesthouse and several recording studios.
The Scottish DJ tried to sell this property in 2022. It’s now available for rent for a whopping $100,000 per month.
In 2017—a year after his relationship with Swift ended—Harris snapped up a lavish 1940s estate in Hollywood from another famous music maker, Swedish House Mafias Steve Angello.
Harris sold the place for $5,750,000 in 2019.
British actor Tom Hiddleston and Swift became an item in 2016 after they were snapped dancing at the Met Gala. They were also spotted holding hands near Swift’s Rhode Island mansion. Then began a whirlwind summer romance.
Although Hiddleston spends time in the States, he did—and maybe still does—own a residence in Primrose Hill, a lovely London town steps from The Regent’s Park. The actor reportedly paid $6,750,000 for the luxury spot in 2011.
In 2016, Hiddleston moved to the equally luxe Belsize Park in London.
Speaking of Primrose Hill, Swift once rented a picture-perfect townhouse there with her ex Joe Alwyn.
Before that, the couple lived in Alwyn’s Crouch End apartment in North London.
The pair, who dated for six years, also briefly rented a renovated carriage house in New York City’s West Village neighborhood for  $38,000 a month. Swift’s 2019 song “Cornelia Street” was inspired by the elegant address.
The 1975 frontman Matty Healy and Swift made headlines last year with their relatively brief fling.
The two, who have known each other for nearly a decade, caused a media frenzy when they were photographed together in New York City.
As far as we can tell, Healy doesn’t have a place in the States. The British rocker does own a minimalist London home with concrete walls, arched doorways, and a pebbled courtyard.
Last but certainly not least is Swift’s current beau, NFL superstar Travis Kelce.
This past fall, the Kansas City Chiefs tight end picked up a 17,000-square-foot Lakewood, KS, mansion for $6,000,000. The mansion on a secluded 3-acre lot features a carved wood bar and a putting green.
Kelce also owns a four-bedroom home in Kansas City’s Briarcliff West neighborhood. It was apparently easily accessible for fans and papparazzi. As his celebrity rose, Kelce outgrew the Missouri home, which he purchased for $995,000 in 2019.
Brittany Natale is a writer based in New York City. Her work has appeared in i-D, Village Voice, Teen Vogue, Domino, and other publications.
Celebrity Real Estate
Celebrity Real Estate
Celebrity Real Estate



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