A Trusted Friend in a Complicated World

The Best Cities in America for Each Generation

Home is where the heart is sure, but according to a new 2019 Homes.com study, it should also be determined on a variety of other factors and what those specific factors depend on what generation you're a part of. Here are the top ten American cities to live in for baby boomers, Generation X, and millennials according to the real estate site's data.

1 / 31
City streets at dusk as seen from above. Aerial photograph. Urban scene.

10 best cities for baby boomers

Boomers are defined as those born in the prosperous and inventive years following World War II, generally between 1946 and 1964. According to SeniorLiving.com, the first round of them turned 65 in 2011 and from then until 2030, 10,000 boomers will hit retirement age every day. Many of those will choose to stop working, start collecting social security, and enroll in Medicare. Thus, it’s no surprise that Homes.com determined the best places for that age group to live based on healthcare availability, retiree tax-friendliness, and the city’s population share that already falls in that generational category. City scores were calculated out of 25.0 and were based on weighted factor scores. After you figure out where to retire, check out these 13 retirement facts you need to take seriously.

2 / 31
Skyline of downtown Pittsburgh at twilight panorama

Boomers: Pittsburgh

Steel City, which earned a score of 19, sits securely in the top spot for baby boomers, most notably because there are almost 425 doctors per 100,000 people and an already high number of boomers residing there. U.S. News & World Report voted it the fifth best place to retire, mostly because it offers affordable housing, great healthcare, a high quality of life, and lots of cultural activities and sporting events like Steelers football, the Carnegie Museums, and The Andy Warhol Museum to fill that job-free calendar.

Psst! You might also be interested to learn which are the cleanest (and dirtiest) cities in America.

3 / 31
The historical Birmingham, Alabama Skyline Morning Daytime . View from railroad park. Sharp colors and very vibrant perspective.
IA Fillm Group/Shutterstock

Boomers: Birmingham, Alabama

Also earning a score of 19 was the most populous city in Alabama. More than 21 percent of that population is classified as boomers and 376 doctors serve every 100,000 folks. The retiree tax rules are also categorized as friendly. Like Pittsburgh, it is also a former industrial (steel and iron) town trying to reinvent itself as a cultural epicenter, according to U.S. News & World Report. The median home price is $171,450 and the cost of living is roughly equivalent to the national average, but everyday expenses including groceries and health care are generally lower than in other cities, which is helpful for those living on savings and fixed incomes.

4 / 31

Boomers: Miami

Coming in third was perennial retiree favorite Miami with a score of 18. Although there were only 247 doctors per 100,000 residents, a Kiplinger state-by-state study revealed Florida tax laws to be most friendly in regard to retirees. It was ranked 21ston a recent U.S. News & World Report Best Places To Retire list, earning a 6.3 out of ten for healthcare access and a 5.6 for housing affordability, although the median age of the Magic City’s population is 40.7.

5 / 31
Cleveland, Ohio in the United States. City skyline.

Boomers: Cleveland

Cleveland still rocks for this age group. Ranking fourth with 18 points, it offers the highest number of doctors (439.5 per 100,000 people) among the list’s top 11 cities for boomers. On the other hand, its retiree tax-friendliness level only earns mixed status. BestPlaces.Net reports that Cleveland’s cost of living falls far below the national average, mostly because the median home price is $54,200.

6 / 31

Boomers: New Orleans

The Crescent City earned 17 points thanks to Louisiana’s “friendly” tax situation regarding retirees and healthy healthcare status with 215 doctors to care for every 100,000 people. The median home price according to the millennial list is $216,000. SeniorHousingNet lists 67 assisted and independent living facilities in New Orleans aimed at seniors. Boomers, which make up less than 21 percent of the jazzy destination’s population, are outnumbered by both millennials and X-ers. Both of those groups account for more than a quarter of the population.

7 / 31
Panorama of Las Vegas, Nevada, USA

Boomers: Las Vegas

Boomers make up more than 20 percent of Sin City’s population and those willing to gamble on the good life there will benefit from Nevada’s tax laws and rates that Homes.com determined to be “most friendly to retirees.” But there’s also only 166 doctors per 100,000 residents. MoneyWise also warns the casino-crazy desert city’s livability for seniors might be a mirage. Summers are sweaty, traffic is awful, and the city seems to cater more to the transient tourist population than its permanent players. That site does admit that finding low-cost housing in Sin City and surrounding towns is pretty easy as the average monthly rent is under $1,000 and the median home sale price is $209,000. It was hit hard by the housing crash a decade ago but has been rebounding strongly over the last few years. Want to explore the globe? Check out these 15 best places around the globe to retire.

8 / 31
Richmond, Virginia cityscape skyline with blue sky and clouds on the James River.
vincent noel/Shutterstock

Boomers: Richmond, Virginia

Currently, boomers only make up 19.3 percent of the capital’s population, despite having friendly tax status for retirees. The number of doctors (281 per 100,000 people) was also a little low, especially when compared to Pittsburgh, Cleveland, and St. Louis. It also came in at No. 53 on U.S. News & World Report Best Places To Live list in 2019.

9 / 31
ST.Louis Missouri
Dietmar Rauscher/Shutterstock

Boomers: St. Louis

The Gateway to the West built up 16 points on the Homes.com boomer list despite being in a state with mixed retiree tax friendliness. Its overall tally was helped by 317 doctors to every 100,000 denizens, but MoneyWise also cautions against spending your post-work period in The Lou, noting its higher-than-average crime rate and low wages. Of course, that wouldn’t affect people who are no longer interested in holding down a job and who saved well for retirement.

10 / 31
Aerial view of Jacksonville skyline on a sunny day, Florida, USA.

Boomers: Jacksonville and Tampa, Florida

The Sunshine State made three appearances in the boomer top ten thanks to Jacksonville and Tampa earning 15 points each in the evaluation. Both benefit from most-friendly tax situations but Jacksonville boomers make up 20 percent of the population versus Tampa’s 18.6. But Tampa is light years ahead in the medical category with 204 docs per 100,000 people compared to Jacksonville’s measly 56.

11 / 31
Gustavo Frazao/Shutterstock

10 best cities for Generation X

The factors for Generation X—people who were born between 1965 and 1981 or as Pew Research called them in a 2014 report “America’s neglected ‘middle child'”—reflect the reality that most of its members have been out of college for more than a decade, are still working with many trying to climb the corporate ladder, and raising school-aged children. A CNBC leadership forecast published in 2018 found that 51 percent of global leadership roles are held by Gen X-ers. Homes.com rated each city on the quality of schools, Gen X population share, and the number of management-level jobs per 100,000 people. If you’re feeling old just reading this, see all the things you are best at when in your 30s and 40s.

12 / 31
Miami Florida
Richard Cavalleri/Shutterstock

Gen X: Miami

Maybe Ponce De Leon was on to something about Florida water as one of its cities grabs another top slot on these lists with a 21.5 rating. Miami is the best city for X-ers as it boasts an average number of management jobs, is home to high-quality schools, and has a strong representation (almost 30 percent) of Generation X individuals living there. It is, however, an expensive place to live according to USA Today. The newspaper reported the cost of living in Magic City to be 7.6 percent higher than the national average. The average family of four also incurs $7,081 in monthly living costs and $1,351 in monthly housing costs. Good thing more than 30 percent of adults there have at least a bachelor’s degree.

13 / 31
Stormy Atlanta Skies Georgia
Brett Barnhill/Shutterstock

Gen X: Atlanta

This 20.5 points-earning Georgia peach is the only city in the Gen-X top ten that tipped into the four-figure range in the management jobs category. There were 1,137 positions per 100,000 people. It also had the fourth highest school quality in the top ten. According to Moneywise, there are lots of verdant parks and downtown attractions to take your children to when you aren’t toiling away as a manager or wasting time stuck in the city’s problematic traffic. There’s also a growing culinary scene when you happen to remember to plan a date night. According to SmartAsset.com, the housing appreciation rates are trending upwards and owning your own home is a realistic goal as the National Association of Realtors reported the median sales price of a single-family home in the metro area to be $216,000.

14 / 31
San Francisco. Image of San Francisco skyline at sunset.
Rudy Balasko/Shutterstock

Gen X: San Francisco and San Jose, California

While we tend to associate digital know-how (and consequently dependence) on millennials and Generation Z/iGeneration/whatever we eventually decide to call them, a 2018 CNBC leadership forecast found that 54 percent of Gen X-ers (compared to 56 percent of millennials) believe themselves to be digitally savvy. This might contribute to the two tech hubs in California’s Bay Area grabbing the third and fourth positions with 19.5 and 19 points respectively. While San Francisco and San Jose both topped 24/7 Wall St./USA Today‘s list of America’s most expensive cities (24.7 percent and 27.1 percent more expensive cost of living than the national average respectively), Homes.com reported healthy job markets in both. San Francisco had 832 managerial positions per 100,000 people while the Silicon Valley hub had 479. Both also scored in the 80 percentile in terms of school quality. The 2017 Bankrate study placed SF in the top five for young professionals’ employment rate and salary level. San Jose was Bankrate’s number one city for career potential, based on regional job growth and GDP per capita.

15 / 31
View of Skyline downtown Louisville in Kentucky USA

Gen X: Louisville, Kentucky

As the home of the annual Derby, it makes sense that this Southern city, where Gen X-ers make up 28.9 percent of the population, placed in the top five with 19 points. There were 507 jobs per 100,000 people and school quality was ranked at 84.8. A Louisville Courier-Journal article reported that residents could easily live comfortably there if they used the “50-30-20 rule” where “50 percent of your income is used to pay for necessities, 30 percent covers the fun stuff, and 20 percent is set aside for savings each month.”

16 / 31
Charlotte, North Carolina, skyline in the afternoon sun.
Rose-Marie Henriksson/Shutterstock

Gen X: Charlotte, North Carolina

The Homes.com study assessed the Queen City with a 19 score. Charlotte gained two spots (from 22 to 20) from the 2018 U.S. News & World Report‘s 25 Best Places To Live in the U.S. list this year thanks to fast and sustained population growth (28.3 percent of which is X-aged) and a median salary of $50,150. About a quarter of Charlotte households include children under 18 so it’s important that it earned the second highest score in the Gen-X top 10 in the school quality category. Interestingly the only city that ranked higher in that category, Raleigh, is also found in the Tar Heel State.

17 / 31
Looking downtown at the Orlando skyline from Lake Lucerne

Gen X: Orlando, Florida

The best city for millennials, according to Homes.com, also has a lot to offer the generation ahead of them, which makes up 27.1 percent of Orlando’s population. It is the first of four cities on this list to accrue 18.5 points. It had the third-highest number of management jobs (861 per 100,000 people) in the top 16, only trailing behind Atlanta and D.C. And unlike Miami and West Palm Beach, it did not rate an entry on 24/7 Wall St./USA Today‘s America’s Most Expensive Cities list.

18 / 31
The skyline of Seattle on a bright sunny day
Darryl Brooks/Shutterstock

Gen X: Seattle

The generation that grew up with grunge is apparently pretty well suited to live in the birthplace of it. Amassing a score of 18.5, the Pacific Northwest powerhouse had 675 high-level jobs for every 100,000 locals, no doubt in part because of its ever-growing status as a tech hub, and offered good schools. And X-ers can take a trip down memory lane anytime at the Museum of Pop Culture, which currently offer exhibits on both Pearl Jam and Nirvana, and at concerts at the historic Showbox club, where the Foo Fighters and Soundgarden played some of their earliest shows. It was also tied for tenth on the best cities for millennials.

19 / 31
Cityscape of Tampa with tall buildings,photo taken from tall building
Peppermint Joe/Shutterstock

Gen X: Tampa, Florida

Making its second appearance on a Homes.com generational top ten, Tampa’s high number of upper management positions (665 per 100,000) and terrific quality of schools added up to a very healthy 18.5 overall score. And as the median age in town is 42, it should be easy to strike up conversations at the city’s many bars and restaurants as it’s a good chance most of the patrons will share the same pop culture touchstones. And lucky for X-ers, if they have already gotten settled in the oceanside hamlet before they reach 65 and say “sayonara” to slaving away, they won’t need to relocate for their twilight years as U.S. News & World Report ranked Tampa the 35thbest city to retire to in the states.

20 / 31
Raleigh downtown skyline in cloudy day

Gen X: Raleigh, North Carolina

Rounding out the top ten for Gen Xers is one of the towns that make up the tri-city triangle (Durham and Chapel Hill are the other points), an area known for college rivalries, strong job growth in the research, medical, and technological fields, a high quality of life, and friendly diverse educated citizens. It is the tenth best place to live and 15th best place to retire in 2019 according to U.S. News & World Report. It earned 18.5 points from Homes.com, just like the three cities that come before it on the list. It has far fewer management opportunities than those cities but the highest school quality of all the top ten urban centers.

21 / 31
Intersection traffic circle road with car and green tree look down view

10 best cities for millennials

Generational analysis is far from an exact science and who falls in what group often differs depending on who is doing the grouping. Nowhere is the cutoff more blurry or debated than between Gen X and millennials. There is often disagreement on where one ends and the other begins. Pew Research Center defines millennials, sometimes referred to as Generation Y, as anyone welcomed to the world between 1981 and 1996, whereas marketing specialists FutureCast argues that millennials started life from 1979 to 1995. They make up 25 percent of the U.S. population. For Homes.com’s report, the factors considered were a city’s median home price, its number of entry-level positions, and the population share that fell into the same age category. Only one in four millennials are currently parents, according to FutureCast, so the quality of educational institutions isn’t as important. Find out if not having that stressor in their lives is the reason they identify as the happiest generation.

22 / 31
Orlando aerial skyline along Lake Eola.

Millennials: Orlando, Florida

Florida earned the highest marks once again as the city of Orlando scored 22 points, making it the best U.S. city for millennials to put down roots. It boasts more than 500 entry-level jobs per 100,000 people and has a relatively low median home price of $266,000. And unlike Miami and West Palm Beach, it doesn’t appear on 24/7 Wall St./USA Today‘s America’s Most Expensive Cities list.

23 / 31
Minneapolis, Minnesota Skyline seen from above by Drone in Spring
Jacob Boomsma/Shutterstock

Millennials: Minneapolis

With almost 430 starter jobs per 100,000 people and a median home price of $274,500, the City of Lakes nabbed a 21.5. A 2018 WalletHub study found the highest millennial homeownership (nearly 50 percent) in Minnesota. A 2017 study by personal finance website Bankrate backs up the claim that the Twin Cities is a great place to call home as a young professional as a whopping 88 percent of people ages 22 to 26 were employed. Also, Bankrate noted, there were a high number of bars, which are great for networking and blowing off steam after a long day at work.

24 / 31
Downtown Salt Lake City skyline Utah in USA

Millennials: Salt Lake City

Homes.com gave SLC a 21.5 rating thanks to the median home price being $322,300 and there being 422 entry-level positions per 100,000 workers. WalletHub’s 2018 Best & Worst States for Millennials list ranked the Beehive State as the seventh best. U.S. News & World Report said SLC was overall one of the best 25 places to live in America in 2019 thanks to its strong job market, ability to attract new residents, and high quality of life. They also found that residents of the city only spend 22.14 percent of the median household income on housing costs. SLC also made our list of 15 best places to move before they get too crowded.

25 / 31
Skyline of Pittsburgh, Pennsylvania from Schenley Park
Christian Hinkle/Shutterstock

Millennials: Pittsburgh

Earning a rating of 21, the rust-belt city ranked high in affordability (median home price was only $200,000) and had 400 entry-level gigs for every 100,000 residents. The Bankrate study also ranked it fifth in the lifestyle category thanks to a wide variety of eating and drinking establishments, recreational and entertainment options, and arts activities. It made U.S. News & World Report‘s Best Places To Live list thanks to a rise in job opportunities with major tech and education companies setting up shop in town, a strong sense of community, and ample green spaces (city parks make up almost 2,000 acres of land).

26 / 31
Atlanta Georgia
Katherine Welles/Shutterstock

Millennials: Atlanta

Atlanta makes its second appearance on the Homes.com trio of lists. While not graded quite as high for millennials as it was for their generational predecessor (which maybe makes it perfect for members of the new micro-generation), Hotlanta still racked up 21 notches in the best places belt thanks to a well, hot, job market (487 starter jobs for every 100,000 people in town) and low housing costs ($224,100). And if you aren’t ready to settle into a permanent living situation, rent for a one-bedroom apartment will set you back $1,400 a month downtown, arguably the coolest place to live, and less than $1,000 in less in-demand neighborhoods according to MoneyWise. It should be easy to find roommates of a similar age as 30.1 percent of the population share is classified as millennial.

27 / 31
Boston skyline as seen from ferry.

Millennials: Boston

Although the 24/7 Wall St. ranked the larger Boston metropolitan area 16th on America’s 25 Most Expensive Cities list in 2019 thanks to the cost of living being 11.1 percent higher than the national average, Homes.com still feels it is a viable choice for this generation because the median home price is $491,400 (much lower than San Francisco, San Diego, Los Angeles, or Seattle) and there are 371 entry-level jobs per 100,000 people. Given that 24/7 Wall St. calculates the monthly living costs for a family of four as $9,463, perhaps Boston is still a good option because the U.S. Centers For Disease Control and Prevention reports that millennials are waiting longer to have children and because of this the birth rate fell to a record low in 2017. Maybe it’s a safety in numbers thing as millennials make up 34.6 percent of Beantown’s community, the highest share in all of the top ten cities.

28 / 31
Washington DC, skyline with federal government buildings and the Monument
Orhan Cam/Shutterstock

Millennials: Washington, D.C.

The nation’s capital has been an old boys’ club for decades, but the needle is moving. Homes.com says 31.4 percent of D.C.’s population falls under the millennial banner and there were 455.5 entry-level positions to every 100,000 residents. WalletHub’s 2018’s Best & Worst States for Millennials report found that millennials make up nearly 35 percent if the total workforce there and earn the most in monthly wages, pocketing approximately $5,000 each month, thus earning it the title of most livable area for the 18- to 35-year-old age group. D.C. is also home to one of the 20 most beautiful Main Streets in the United States.

29 / 31
Downtown Hartford, Connecticut Skyline seen in Summer by Drone
Jacob Boomsma/Shutterstock

Millennials: Hartford, Connecticut

The former hometown of Mark Twain and Harriet Beecher Stowe racked up 20 points with high marks in the entry-level jobs (557 per 100,000) and median house price ($244,200). It also successfully avoided being put on the 2019 list of America’s most expensive cities compiled by 24/7 Wall St. despite its neighbors Bridgeport, Stamford, Norwalk, New Haven, and Milford all making an appearance. It also nabbed the 47thslot on U.S. News & World Report‘s 2019 Best Places To Live list with an average annual salary of $60,040 and an average commute time of 24 minutes.

30 / 31
St. Louis
Frank Romeo/Shutterstock

Millennials: St. Louis

Just as the city’s slogan promises, there’s more to St. Louis than its iconic Arch for this age group that makes up 27.2 percent of its population. Earning 17 points, the Midwestern metropolis is extremely affordable. The median home price is $182,000. There’s also 392 entry-level gigs per 100,000 people according to Homes.com’s findings. However, a 2019 survey conducted by real estate site Apartment List warns it might not be the place to settle if you’re single as only 26 percent of St. Louis’ millennials were happy with the local dating scene. That result placed the metro area in the bottom five nationwide.

31 / 31
Shutterstock (2)

Millennials: Seattle and Providence, Rhode Island (tie)

Seattle had the highest median home price ($502,000) and the lowest number of starter jobs (261 per 100,000) of any city that made the top ten but still managed to score a 16.5. The arbiter of cool in the grunge ’90s, it has been bestowed several awards including fifth place on Expedia’s 2017 21 Super Cool U.S. Cities list and fifth place on Zagat’s Best Food City 2016. Many tech companies are headquartered there including Amazon and Microsoft and any free time can be filled with museums, outdoorsy activities like hiking and kayaking, or festivals like Bumbershoot. There’s also a thriving craft beer scene and legal marijuana.

On the other side of the country, the capital of Rhode Island tied for tenth place with 16.5 pints. Homes have a median price of $305,300 and there were 275 starting positions per 100,000 people. Almost 30 percent of the population is also made up of residents born during the millennial time period. But proceed with caution as a WalletHub study alleges Little Rhody has the fifth highest tax burden. Here’s more on the best—and absolute worst—states for taxes.

Carrie Bell
Carrie Bell brings more than 20 years of experience writing about entertainment, pop culture, travel and lifestyle topics for national magazines, newspapers and websites to RD.com, where her coverage runs the gamut from road trip guides to Star Wars locations you can visit in real life, best crime shows to infamous awards show scandals. She has a journalism degree, two spoiled cats, a wicked snow globe collection and a desire to visit all 50 U.S. states by age 50 (she just hit No. 41).