The Best Cities for Boomers To Retire in Luxury

After decades of hard work, many retirees dream of spending their golden years in luxury. With careful financial planning, a high-end home in a top retirement market may be within reach. But where are the best places to enjoy a lavish retirement lifestyle?

Every retiree has unique reasons for choosing a retirement destination. Some seek the beauty of four distinct seasons, others prefer year-round warm weather, and many prioritize being close to family. For those with significant home equity and retirement savings, the idea of purchasing a luxury retirement home is especially appealing. "Households who have a sizable amount of existing home equity and retirement savings may find purchasing a luxury retirement home appealing," says Hannah Jones, senior economic research analyst at Realtor.com.

The Financial Landscape of Retirement

Beyond Social Security benefits, which average $1,975 per month in 2025, retirees often rely on a well-planned nest egg to support their desired lifestyle. Social Security benefits vary based on age, employment history, and earnings, with retirees eligible to start collecting as early as age 62. However, for those eyeing luxury retirement, private savings and investments play a crucial role.

Where Are Boomers Retiring in Luxury?

Economists at Realtor.com analyzed the top 10 luxury retirement markets, considering factors such as a median population age of 55-plus and year-over-year growth in $1 million-plus home sales. "The luxury market has been relatively active in recent months despite a challenging overall market," Jones explains. "There were roughly 15,000 more luxury homes for sale in January compared to one year prior, and these homes sold about two days slower."

Here are the top destinations where affluent retirees are choosing to settle:

1. Anna Maria, FL

• Median population age: 67.6
• 2024 median sale price: $2,067,842

A stunning Gulf Coast barrier island, Anna Maria has seen a 61% increase in $1 million-plus listings. Though it endured damage from Hurricane Milton in 2024, the resilient beach community is bouncing back, with restored beaches and revitalized landmarks.

2. Pleasanton, CA

• Median population age: 66
• 2024 median sale price: $1,650,167

This charming suburb east of San Francisco offers turn-of-the-century appeal with a high quality of life. The luxury real estate market has boomed, with 85.5% more homes listed above the $1 million mark.

3. Isle of Palms, SC

• Median population age: 58.2
• 2024 median sale price: $1,484,354

This East Coast barrier island, just 20 minutes from Charleston, features six miles of pristine beaches, golf courses, and a vibrant luxury housing market that grew by 77.3% last year.

4. Lawrence, NY

• Median population age: 57.6
• 2024 median sale price: $1,947,333

For those seeking an urban lifestyle, Lawrence on Long Island offers a mix of suburban charm and access to Manhattan's cultural and dining scene. Over 75% of homes here were listed for $1 million or more in 2024.

5. Weston, CT

• Median population age: 72.5
• 2024 median sale price: $1,274,284

This New York City suburb is known for its arts community and zoning regulations requiring residential properties to be at least two acres. In 2024, there was a 74.4% increase in $1 million-plus listings.

6. Jackson, WY

• Median population age: 57.1
• 2024 median sale price: $1,396,209

Nestled in the Jackson Hole valley, this destination offers retirees access to world-class skiing and national parks. The luxury market here remains strong, with 62.6% of homes listed above $1 million.

7. Avon, CO

• Median population age: 56.4
• 2024 median sale price: $1,366,859

A hub for year-round outdoor activities near Vail and Beaver Creek, Avon saw a 60.7% increase in $1 million-plus listings.

8. Hinsdale, IL

• Median population age: 58
• 2024 median sale price: $1,224,368

Just 20 miles west of Chicago, Hinsdale blends small-town charm with metropolitan convenience. "Of course retirees want Hinsdale's lifestyle, beautiful homes, clubs, arts, excellent dining, and health care facilities," says Dawn McKenna, a local luxury real estate broker.

9. Jamestown, RI

• Median population age: 62.5
• 2024 median sale price: $1,169,938

A historic coastal town, Jamestown boasts iconic lighthouses, scenic landscapes, and a rising luxury market, with 54.1% more homes listed above $1 million last year.

10. Cannon Beach, OR

• Median population age: 59.7
• 2024 median sale price: $1,259,395

Renowned for its breathtaking coastline and walkable downtown, Cannon Beach has become a favorite retirement destination, with 51.8% more homes listed above $1 million in 2024.

The Takeaway

"Ample luxury inventory and a stable market pace means that buyers will have ample options and enough time to decide before taking the leap," says Jones. Whether retirees seek coastal serenity, mountain adventure, or urban vibrancy, these luxury destinations offer a wealth of options for a fulfilling retirement.

This article is based on "The Best Cities for Boomers To Retire in Luxury" by Joy Dumandan, originally published on Realtor.com.