In the heart of Silicon Valley, well-off baby boomers enjoy meals of porchetta and cheesy polenta, prepared with herbs plucked from the community garden. Thirty-foot-tall windows offer a view on a quiet creek winding along manicured grounds.

Spending later years at this community, Vi at Palo Alto, comes with a price tag that starts with an upfront payment that can range from $1.17 million for a one-bedroom apartment and up to $7.3 million for a three-bedroom unit. Ongoing monthly fees up to $13,800 cover services such as housekeeping and valet parking, and amenities. Residents can attend lectures by professors of nearby Stanford University or a performance by opera singers.

For wealthier Americans, greater options exist for how to spend their later years. A growing crop of high-end communities, called life plan communities, allow residents to start in an apartment and then move to more nursing-like […]