I’m a Real Estate Agent: The Best 4 Cities for Middle-Class Retirees
Written by
Laura Bogart
Edited by
Molly Sullivan
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Planning your retirement involves a lot of decisions. For starters, there’s when you’ll collect Social Security or how you’ll diversify your portfolio. But on a more essential level, you’ve got to figure out where you’ll live. Affordability is understandably important. You’re also concerned about safety and access to healthcare — and you want a city where you can have a little fun.
It might seem like a tall order. However, according to the real estate experts GOBankingRates connected with, finding great cities that can give middle-class retirees everything they want isn’t as difficult as it sounds. Here are their suggestions for where to start looking.
Naples, Florida
This gorgeous Gulf Coast city has long been known as a haven for retirees — and for good reason, said Spencer Rigsby, a realtor with Premier Sotheby’s International Realty. Naples offers walkable communities, plenty of activities to suit many interests and a thriving restaurant scene.
“Retirees (both singles and couples) will find a welcoming environment with social clubs, golf leagues and various volunteer opportunities,” she said. “Families enjoy Naples for its small-town feel … and multigenerational recreation.”
In addition to beautiful beaches, championship golf courses and a robust arts scene, Naples also has nationally recognized hospitals — offering seniors peace of mind.
“Naples really does offer so much to everyone in each stage of life,” Rigsby said. “Current home values are now showing signs of improved affordability, with the July 2025 market report stating that the median closed price is $575,000.”
Wellen Park, Florida
Roberta Tengerdy, PA, with Premier Sotheby’s International Realty believes middle-class retirees could also enjoy another Florida hotspot: Wellen Park.
“For retirees, activities are plentiful — swimming pools, fitness centers, golf at places like Boca Royale, pickleball courts, and walking or biking trails,” she said. “There are also community events, nature preserves for birdwatching or kayaking nearby, and CoolToday Park for baseball fans.”
Tengerdy cited downtown Wellen Park as a particularly great place for retirees to spend time with family — it blends a waterfront vibe with family-friendly attractions like a play park and nature trails.
“It’s all walkable, blending retirement with that active, community feel not every spot offers,” she said.
Knoxville, Tennessee
Between its mild climate and the presence of six major hospital complexes — with expertise in areas like cardiology and stroke prevention — Knoxville, Tennessee, is another haven for active middle-class retirees.
Fred Loguidice, real estate expert and founder of Sell My House Fast Massachusetts and several other national brands, recalled taking one retiree on a tour of a bungalow in Knoxville.
“She looked over at me with a smile and said, ‘This already feels like home,'” he said. “That alone makes me believe Knoxville’s doing something right.”
There are a few other reasons Loguidice believes Knoxville is ideal for retirees, including a lower cost of living compared to the national average. He added that healthcare, utilities and housing costs are also below average.
“Of specific note for retirees is that Tennessee does not tax Social Security income, pensions or retirement funds,” he said.
Omaha, Nebraska
Loguidice also believes middle-class retirees could enjoy life in Omaha, Nebraska. With a robust cultural scene — including flourishing art and theater communities — and plenty of family-friendly activities, there’s a lot to love.
“I’ll never forget taking one retiree through the zoo — by the time we were exiting, she was chatting with families and children, exclaiming that she felt younger than she’d felt in years,” he said.
Calling Omaha “a winner for balancing affordability with easy access to quality services,” Loguidice noted that Nebraska does not tax Social Security income. Retirees can also benefit from lower housing prices and an overall cost of living that’s below the national average.
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