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Last Updated: Thursday, October 1, 2026 at 05:43 PM
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Upmarket getaways for super-wealthy

In today’s red-hot real estate boom, the business of second homes — not investment properties, but vacation homes for the wealthy — is one of the fastest-growing segments. CNBC reports on some of the most expensive homes on the market.

In today’s red-hot real estate boom, the business of second homes — not investment properties, but vacation homes for the wealthy — is one of the fastest-growing segments.

Thanks to a strong appreciation in the value of their primary homes and a reluctance to invest in stocks, a growing number of boomers are investing their money in second homes as places to vacation and eventually retire.

From La Jolla, Calif., to Hilton Head Island, S.C., CNBC’s reporters fanned out to find the most amazing second homes just waiting for a buyer, in some cases with a few million to spare.

In Aspen, Colo., for example, multimillion-dollar homes are not going up fast enough to meet demand, while earlier this year rumors of a record $90 million home sale rocked the fashionable Hamptons area of Long Island, one of the nation’s fabled summer haunts. And on Hilton Head Island, S.C., even the elite are balking at a $14 million price tag for a second home that recently appeared on the market.

Click on the link below for a gallery of ritzy second homes.