Woodside estate from 1920s hits market for $22M

A nearly 4-acre Woodside estate less than a mile from Oracle co-founder Larry Ellison’s longtime abode has hit the market for $22 million, more than four times the typical single-family home value in the wealthy San Mateo County enclave.

The property at 205 Winding Way includes four bedrooms and bathrooms split between its main ranch home and a caretaker cottage, which combined total 1,640 square feet of living space. Other features include a swimming pool and tennis and sports courts, according to its online listing that went live Aug. 28.

The estate was completed in 1920 and has been owned by the same family for more than 65 years, the listing says.

Yet the site’s real value lies not with its existing improvements but rather the land underlying them, listing agent Scott Dancer of Compass said in an interview. He said he expects whoever acquires the property will raze it to build a high-end home.

Compass’ Scott Dancer (Compass)

Only a few single-family estates that rival 205 Winding Way in terms of location have sold for around its asking price, Dancer said. Title service records show it’s owned by the Fay family. While Dancer didn’t divulge the family’s identity, he said it used the estate as a summer home but doesn’t do so anymore. A recent death in the family also factored into its decision to sell, Dancer said.

Public records indicate that the deceased is Anita Fay, who died in January at age 97. Her predeceased husband Paul was a close friend of John F. Kennedy and former Navy undersecretary in the Kennedy and Johnson administrations, according to his obituary.

If the Winding Way estate were to sell at its asking price, it would be this year’s fourth-priciest sale in Woodside, a town of about 5,100 people where the typical single-family home value is $5 million, according to Zillow and U.S. Census data.

Whether the estate sells at or near its ask and the time it spends on the market will help gauge the temperature of the Bay Area’s high-end home market, which is cooling amid rising interest rates and an uncertain economic climate.

The six new single-family listings in Woodside last month were a third of the June total, according to MLSListings data. Meantime, average days on the market for the town’s single-family home inventory increased by about 67 percent from June to July, the data show. The downward trend could indicate a typical late summer slowdown or the beginning of a bear market for upscale residences.

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