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The Best Cities for Boomers To Retire in Luxury

After decades of hard work, many retirees dream of living out their golden years in luxury—and with proper financial planning, a high-end home in a top market could be within their reach.

Every retiree has a reason for choosing where to retire. Some prefer the four seasons, others year-round warm weather, or family may be a big influence.

TOP 1: Anna Maria, FL
Median population age: 67.6
2024 median sale price: $2,067,842

Anna Maria is a 7-mile-long barrier island on the Gulf Coast, west of Bradenton. The luxury real estate appeal of this picturesque place is evident with 61% more homes listed for $1 million or greater. The area took a direct beating, though, when Hurricane Milton swept through in October 2024. Homes and businesses were left devastated, but the beach community is bouncing back and rebuilding. Beaches are back open to the public, and many iconic locations are being carefully restored.

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