Over the 50 years since the first issue of Unique Homes rolled off the presses, countless estates have graced our cover. Hundreds have captured a top position on Ultimate Homes’ list of the most expensive, but only a very few are real estate legends. Trackback through record-setting sales and property listings, and a handful of properties filter to the top, including an equally select cadre of real estate agents.

What destines a property for legendary status? Rarity, provenance, architecture, land and location all play a role. “We have represented and sold many properties that are above and beyond, but what makes them legendary is the architecture and the history of the property, including notable prior owners, location, and the property amenities that set the bar for other luxury properties,” explains Judy Zeder, a member of the Jills Zeder Group (along with Jill Eber and Jill Hertzberg) with Coldwell Banker Realty in Miami.

“What truly makes an incredible luxury property is that it’s something that someone else would never have. It’s not just another house with a different material feature,” shares Shari Chase, founder of Chase International Real Estate in the Lake Tahoe/Reno region. “Rarity is huge,” she says, as is “not being bumper to bumper with a lot of mega mansions that are exactly the same.”

Owlwood, Pickfair, Le Belvedere, Greenacres and Chartwell: the list of legendary properties that Joyce Rey, who heads Coldwell Banker Global Luxury’s division for Southern California, has sold is only surpassed by the number of accolades she has received over her more than 40-year career. Her sales have achieved price records multiple times, sometimes for the same property. In 1976, she sold the Sonny and Cher mansion for $1.2 million, a record at the time. Two years later, she sold it again for $4.2 million, which surpassed all other prices, setting a new high in the U.S. and worldwide. “It was a really big deal,” she says. “It changed the marketplace.”

The storied history of this property, which was renamed Owlwood to honor owls living in the estate’s towering trees, continues to the present day. The acquisition of neighboring properties and additional acreage over the years enhanced the value. Last offered for sale well above $100 million, it appeared on Unique Homes’ Ultimate list last year at $115 million. It sold in December in an off-market transaction for a reported $88 million.

Once dubbed “the Crown Jewel of Beverly Hills,” Owlwood’s resume includes a number of other high-profile names and celebrities, including Marilyn Monroe.

Ultimate Manhattan? The Tommy Hilfiger penthouse at The Plaza in New York City graced the cover of Ultimate Homes in 2014.

When it came on the market, the Playboy Mansion received lots of media coverage. Still, when Jade Mills, who represented the buyer, initially saw the property, she wasn’t expecting to find a zoo. The property had “been talked about, but not really the zoo and the peacocks and everything that was there,” she says.

“When I first went there, there were all of the animals, monkeys, peacocks were all over the property — I just thought that it was so amazing that right in the middle of Holmby Hills, you had all those fabulous animals. So, it was just fun to see, and to see the grotto.”

Gold says the number of birds increased over time as local avians decided it was a great place to call home and joined the menagerie.

Another interesting tidbit was an abundance of pushbuttons in this home, sort of a smart home before the era of home tech. For example, push a button and the bed would turn around. The grotto had an array of buttons, all glowing red, and a phone from which you could dial up whatever music you wanted

Foundation of Value

But for legends, it is the amount of land or an impossible-to-replicate location that usually sets them apart. A majority occupy sizable parcels, whether it’s hundreds of acres like Tranquility in Tahoe, or a dozen or less in Bel Air or Holmby Hills. The exception are places such as Malibu, where a setting on the beach is more prized and rarer than acreage.

“Regardless of the condition — like new, falling down or anything in between — each owner puts their heart and soul into these homes,” shares Robert Kinlin, co-owner of Robert Paul Properties, who works with some of the most expensive in Boston and on the Cape. “But a lot of times, people are buying the land and the feeling it evokes when they’re outside walking the property, because you can’t change the land, but you can change the house.”

“The biggest thing you can have with a beautiful estate is Mother Nature,” adds Shari Chase.

When Chase founded her brokerage in 1986, the word “luxury” really wasn’t part of the vocabulary. Instead, she says, “we talked about estates and extraordinary estates, and her tagline was Exceptional Properties for Exceptional People. “I wasn’t going to bother with just any kind of real estate. I only wanted the best, and whether I had one or two or three sales a year, it didn’t matter. I mean, as long as they were fantastic. I think the very first sale was lakefront.” Early on, Chase was involved in what she describes as “the most extraordinary sale we ever had at Tahoe,” the Thunderbird Lodge at a record $50 million. “It held the price record in the entire nation for over 8 years.”

Not often are newly constructed homes destined to become legendary, but Le Belvedere, sited on over 2 acres in Bel Air overlooking the city with a romantic landscape that includes a swan pond, rose gardens and a 280-degree panorama of city lights, is the exception. Over-the-top features such as opulent materials, a ballroom seating 200, a media room seating 50, and a 500-bottle wine cellar, were exceptional when it came on the market in 2009, but the way every detail is executed, the stateliness of the architecture and the sense of harmony from all facets working in perfect sync pushes it from a “stellar property” to a legendary estate.

Le Belvedere, like Tranquility, is also exceptional for its amenities. At that time, shares Rey, “people weren’t building so many of those major theaters. Before that, only those in the industry had large screening rooms.

Rey was involved in the sale of Le Belvedere for $50 million — the highest in the U.S. in 2010 –— and again in 2018 for $56 million.

Amenity Wars

In recent years, there have been a number of newly built for-sale trophy homes, some with list prices stretching current benchmarks. What sets these properties apart is the number of over-the-top features, including curated art installations, stocked wine bars, car collections, an onsite staff and even a helipad. The objective — to include everything someone might want in a home — is aligned with the motives behind the inclusion of extensive amenities in classic estates.