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The Best in Real Estate, From a Portugal Palace to the Woolworth Building’s $79 Million Penthouse

As homeowners seek more spacious abodes with luxe amenities, these ritzy estates and condos have tons to offer.

Real Estate Illustration Shout

In prosperous eras of the past, sprawling estates embellished with long, winding driveways, guest cottages and amenities were built and handed down through the generations. Some, like a 1920s “castle” in San Diego or Linden Hill, a property nearly the size of a French village along Philadelphia’s Main Line, were designed by celebrated architects of their time. Rarely have these legacy homes come on the market—until now.

While the residences’ vast acreage and square footage were initially considered assets, in recent decades many homeowners with smaller families didn’t necessarily need the space or want to maintain such grand holdings. But Covid-19 changed some clients’ cravings, says Sean Matthews of Compass Real Estate in Santa Barbara. “That level of buyer is now looking strategically for a property that suits those pandemic-generated needs for privacy and safety.” One of his listings, the $109 million Rancho Cariñoso owned by the descendants of an oil tycoon, is zoned to stable horses, something that is hard to come by with a new build.

But it’s not just the shift in mindset that’s influencing purchasers’ desires this past year. “Inflation is definitely a driving factor in today’s luxury market. Sophisticated, ultrahigh-net-worth buyers understand that real estate is still one of the best hedges against rising inflation,” Matthews says. And “zoning changes, stricter building regulations, mixed with supply-chain issues lead to rising building costs. The more expensive it is for developers to build, the higher the price tag. That’s what makes these large legacy estates so special—whether it’s the amount of land, the exclusive location, multiple structures or the rare amenities, in most cases, these properties could never be duplicated again.”

However, some sellers, such as Linden Hill’s owners—who purchased the magnificent estate built by the heirs to the Campbell Soup fortune—are getting creative. They’re keeping the main house on one $8.5 million parcel and selling the substantial surrounding acreage off as four other individual lots, using zoning revisions to their advantage. A smart legacy.

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