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What do Katy Perry, Taylor Swift, Jennifer Aniston, Jessica Simpson and Jennifer Love Hewitt have in common?

The first commonality: dating singer John Mayer. The second: some major real estate flipping.

While Mayer tends to stay put when it comes to real estate, his girlfriends — past and present — are much more prone to shaking things up. And with his latest album, “Paradise Valley,” dropping this week, we thought now would be a great time to revisit the homes of his former leading ladies — and to determine who has the best digs.

Source: IMDb

Source: IMDb

Katy Perry

John Mayer status: Currently dating Mayer on and off

Perry bought her first home with ex-husband Russell Brand. While the two were married, they also picked up a New York penthouse and another home in Hollywood Hills, which is currently on the market.

The singer recently picked up a new property to call her own: a three-home Hollywood Hills compound that centers around a mid-century modern home. Newer relationship with Mayer, newer home and just recently, Perry added a new single to the mix as well, releasing “Roar” in mid-August.

Perry's new mid-century home.

Perry’s new mid-century home.

Source: IMDb

Source: IMDb

Taylor Swift

John Mayer status: Dated 2009-2010

True to form, Swift wrote a scathingly honest love song after her rumored fling with Mayer ended. Among the “Dear John” lyrics: an accusation of “Don’t you think I was too young to be messed with?”

While Swift most definitely moved on in her dating life — she was linked to Conor Kennedy and One Direction’s Harry Styles  — she also moved on real estate-wise, buying a Cape Cod-style home in Beverly Hills in 2011, buying and flipping a true Cape Cod near the Kennedy Compound in 2012 and most recently, picking up an oceanfront manse in Rhode Island.

Swift bought this home in April 2013.

Swift bought this home in April 2013.

Source: IMDb.com

Source: IMDb

Jennifer Aniston

John Mayer status: Dated 2008-2009

If the gossip magazines were to be believed, Aniston and Mayer’s relationship was the one that was supposed to last, but the couple reportedly broke up because Aniston didn’t understand Twitter.

Aniston was able to move on and then some, making a fresh start in New York City with a new penthouse, meeting and becoming engaged to actor Justin Theroux and buying an A. Quincy Jones-designed home in Bel-Air. The two have not set a date for their wedding, but they are overhauling their new home, including putting in chicken coops.

Aniston bought this home with fiance Theroux.

Aniston bought this home with fiance Theroux.

Source: IMDb

Source: IMDb

Jessica Simpson

John Mayer status: Dated 2006-2007

This was the relationship no one really understood, and it didn’t last long. Simpson and Mayer were spotted at a New Year’s event and then split up later in June 2007. Since then, Simpson has been lucky in love and real estate.

Currently she is the mother of two children with fiance Eric Johnson. Simpson listed her former “bachelorette” pad, and the two snagged Ozzy and Sharon Osbourne’s 11,000-square-foot designer abode in Hollywood Hills early this year.

Simpson bought the Osbournes' home this year.

Simpson bought the Osbournes’ home this year.

Source: IMDb

Source: IMDb

Jennifer Love Hewitt

John Mayer status: Dated in 2002

Hewitt was the first of Mayer’s famous girlfriends, and rumor has it that the curvaceous actress inspired Mayer’s hit “Your Body is a Wonderland,” although both parties deny it.

The “Party of Five” alum currently stars on Lifetime’s “The Client List” and is pregnant with her first child with fiance Brian Hallisay. She recently listed two of her homes — one for rent and one for sale — and bought a brand-new modern pad in Pacific Palisades.

Hewitt's new modern home.

Hewitt’s new modern home.

What does Mayer have to say about his list of exes? He was quoted recently as saying that he was a “jerk” in the past, and with a new album and a new relationship with Perry, he’s ready for a fresh start.

The real estate winner

While all have incredible digs — and Perry’s three-lot compound has quite the potential — we have to give the nod to Swift, who not only has a sprawling Beverly Hills home, but was able to buy and sell a home near the Kennedys and pick up the Rhode Island place, all in the span of a year. To top it off, she’s only 23.

Related: 

Erika Riggs, a real estate writer for Zillow Blog, covers celebrity real estate, unusual properties and home design trends. Read more of her work here.

About the Author

Erika Riggs, the Zillow Digs manager, covers home design and trends.

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