10 Most Expensive U.S. Retirement Communities

Naples, retirement communities
Naples, Fla., is well-represented on the Topretirements.com list of most expensive retirement communities

10 Most Expensive U.S. Retirement Communities

There’s no shortage of lists for best or worst places to retire, domestically or internationally, by state or by town, or even by retirement community.

That’s the focus of the latest list, and it’s aimed directly at the super-wealthy, who can afford to retire wherever they want.

To help those who like to dream big, Topretirements.com developed a “just for fun” list of the 10 most luxurious places to retire—communities where there are options like the beach club, marina, golf course, high-rise penthouses or even taking the plane out for a flight via the community’s private airstrip.

Editor’s Note: This portion on this page originally appeared on 401(k) Specialist in June 2019.

This list contains a range of 55+, all ages, active adult, lifecare, and CCRC (Continuing Care Retirement Communities) developments. In actuality, most of the residents of these communities are 55+, even if there is no requirement. But what they have in common is how expensive it is to buy into these places and pay their associated fees.

Topretirements.com readily admits the list is by no means complete (and is quite Florida-centric), but it nevertheless provides an interesting assortment of super-exclusive retirement communities.

Without further ado, the list (in no particular order):

    • Ocean Reef Club, Key Largo, Fla. This is a private community of more than 2,500 acres with over 1,700 condos, villas, townhomes, single family residences and marina slips. Members of the community enjoy two golf courses, a tennis center, marina, trails, and its own medical center. When a community has its own airport, like this one does, you know you have arrived. Ocean Reef Club is made up of several different neighborhoods, with homes priced from the $200,000s for a condo, to waterfront homes in the millions. There is currently a 4-bedroom/6-bath on the market here for $22 million.
Sailfish Point
Sailfish Point
    • Sailfish Point, Stuart, Fla. You cannot even get to this exclusive enclave on Hutchinson Island near Stuart unless you live here or have an appointment. There is a Jack Nicklaus-designed golf course, great beaches on the ocean, private docks, and amazing facilities. The 532-acre sea island community of 520 homes, many with price tags from $475,000 to $5 million or more.
    • White Sands at La Jolla, La Jolla, Calif. This luxurious Continuing Care Retirement Community (CCRC) on the beach in La Jolla has a newly expanded campus with $50 million worth of comforts and pleasures. The Residents Council leads 45 committees. There are oceanfront apartments to studios. Assisted or independent living, memory unit, skilled nursing. It can cost up to $1.5 million for the entrance fee, or less depending on other factors, plus monthly fees up to $7,000. There are similar communities in the area such as Vi at LaJolla Village.
Isleworth
Isleworth
    • Isleworth, Windemere, Fla. There is exclusive, and then there is Isleworth, home to many of America’s richest (retirees and people of all ages). Looking to spend from $4 million to $11 million and get 15,000 square feet of luxury home near Orlando? Here you go. Arnold Palmer designed the golf course. The community boasts art by Henry Moore and Salvador Dali.
    • The Clare, Chicago. The Clare gives city-loving retirees independent living residences and a range of assisted living programs within a high-rise building. With the city outside residents’ front door, the community offers transportation services, complimentary breakfast, a pool and 24-hour security service. Prices, which depend on the number of rooms and the quality of the view, can range from $300,000 to $1.5 million.
    • The Ritz-Carlton, Chicago. Here is luxury living at its easiest. Live in a big city hotel with an amazing array of amenities, and get your meals prepared by the hotel chefs. Actually the Ritz has residences for sale in a number of its biggest hotels across the country, and there are 89 ultra-luxurious residences in the “Magnificent Mile” downtown Chicago property. One of the special features is the Landmark Club, a full-floor private club for residents and their guests. One residence is 6,500 square feet; prices seem to range from the low millions to $8 million.
Spruce Creek Fly-In
    • Spruce Creek Fly-In Community, Port Orange, Fla. The world’s most famous residential airpark has a 4,000-foot lighted runway and a GPS approach. Its private airport, the center of the community, can accommodate anything from a Stearman to a Gulfstream. There are almost 5,000 residents, 1,300 homes and 700 hangars who share a unique life in this private gated village. There is a championship golf course and home prices range from a $165,000 condo to multi-million-dollar hangar mansions. A similar community that is even more expensive is Antiquers Aerodrome in Delray Beach.
    • Mediterra, Bonita Springs, Fla. Located near Naples, this huge development is beautiful and maintained to a tee. There are new pickleball courts, the giant clubhouse is being expanded, and there are two Tom Fazio golf courses in pristine condition. A separate beach club on the gulf offers dining and the Gulf of Mexico for entertainment. Homes range from about $500,000 for a townhome to over $7 million. Bonita Bay is just one similar competitor in the area.
    • Promontory Club, Park City, Utah. If you are looking for a place in the mountains where the grandchildren can’t wait to visit you, this might be the one. That is, if you can swing the price of admission in this all-ages community. There is the skiing, the Pete Dye golf, the hiking, the lake, and many more activities such as equestrian. Homes seem to range from the low millions to over $12 million.
Grey Oaks and Estuary
Grey Oaks and Estuary
  • Grey Oaks and Estuary, Naples, Fla. The real estate in Naples is known to be pricey, but this one seems like the top of the line. Established in 1983 and open to all ages, it is actually two different communities located near the center of town and beaches. There are two golf courses and many other amenities, with the centerpiece being a giant 62,000 square foot social center. Many homes in this exclusive development are on the market for $6 million or more.
Brian Anderson Editor
Editor-in-Chief at  | banderson@401kspecialist.com | + posts

Veteran financial services industry journalist Brian Anderson joined 401(k) Specialist as Managing Editor in January 2019. He has led editorial content for a variety of well-known properties including Insurance Forums, Life Insurance Selling, National Underwriter Life & Health, and Senior Market Advisor. He has always maintained a focus on providing readers with timely, useful information intended to help them build their business.

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