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Picking where to move is a deeply personal choice—after all, everyone has different priorities. The area you want to live in in your 20s is probably quite different from your dream neighborhood in your 40s. These differences are exactly what a new study from homes.com seeks to suss out. The report breaks down the best cities to live in according to generation… and we have to say, we didn’t see them coming.

Orlando, Miami, and Pittsburgh take home the top spots for millennials, Generation X, and baby boomers, respectively. If you, too, are a little surprised at Orlando’s win, the city is much more than just a tourist trap: Researchers looked at criteria like median home prices, number of entry-level jobs, and the number of millennials, and it turns out this Floridian city has it all in spades. The parameters for determining the top cities for Gen X-ers and baby boomers were similarly specific to each generation. Homes.com evaluated school quality and number of management-level jobs for the former, and healthcare availability and retiree tax-friendliness for the latter.

However, while the criteria for “best city” might differentiate by generation, a love for great design is universal. Each of the top three cities have proven themselves as either up-and-coming or established hubs for art and design, and if you’re considering a move to any of them, here are some spots worth checking out.


It’s admittedly not quite in the center of the city, but the Winter Park neighborhood in the Orlando metro area is a boutique-lined enclave perfect for an afternoon spent dipping into little shops and cafes. Flex your green thumb at botanical goods store Piante before hitting up New General, a combination coffee shop and boutique that’s the ideal place to reenergize.


While the Versace mansion (pictured above) is definitely on the opulent end of the Miami design scene, there’s more than enough attainable style to enjoy in the sunny city. For example, you can’t get more literal than the Design District. Home to most of the city’s interior design stores, art galleries, and showrooms, it’s a veritable mecca for those serious about style. Head to Swan, one of the district’s coolest new restaurants, to get a taste of Deco decor.


Leanne Ford calls Pittsburgh home—how’s that for a ringing design celeb endorsement? The city has definitely been going through a revival of sorts in recent years, and while newer additions like the Ace Hotel or the Schoolhouse store in the East Liberty neighborhood are definitely worth a visit, we’re equally enthralled by its older charms. Specifically, vintage. Head to nearby Shadyside to peruse a few of the city’s most beloved vintage shops; for a more robust experience, head to the Pittsburgh Vintage Mixer or the Neighborhood Flea.  

See more moving guides: Millennials Are Moving to These 2 Cities—and They’re Not New York or LA Hey, Recent College Grads: Study Says You Should Move Here Where to Move If You Want to Raise a Family