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The Midpeninsula is home to some of Silicon Valley’s most distinctive real estate. From family wineries and historic estates to modern mountain retreats, these properties stand out for their price, design or history. Each month, we spotlight a handful of these not-so-ordinary homes, whether newly listed or recently sold. This week, we look at four Midpeninsula homes listed at $25 million and see what that kind of money buys you in Atherton, Palo Alto, Los Altos and Woodside.
Condo with rooftop garden, private car elevator
Palo Alto
Located on University Avenue in downtown Palo Alto directly across from the Caltrain station, this 17,000-plus-square-foot ultra-modern residence is a collection of three condominiums featuring six bedrooms, nine bathrooms, three kitchens and 4,000 square feet of outdoor space, including two balconies and three rooftop gardens with a 360-degree view of the Bay Area. A private seven-car underground garage that also includes multiple storage rooms and other flexible spaces is accessed by what the listing calls a “Batman-like vehicular elevator.” The residence spans the entire basement garage, the entire third and fourth floors and three rooftop gardens.
Designed and built in 2011 by Palo Alto architect Joseph Bellomo, the residence has served as his family home for more than a decade. The property is on the market for $24.5 million.
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2 vacant lots near Menlo Circus Club
Atherton
For $25.5 million, Atherton buyers can get two vacant lots just steps from the town’s historic Menlo Circus Club. According to the listing, the property comes with 2.5 level acres that have been subdivided into two parcels, enabling buyers to build one large estate or two separate residences.
The property was listed for $32.8 million in May. Its price dropped by $7.1 million in November. “Recently refined pricing further elevates the appeal of this remarkable offering,” according to the listing.
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Vineyard home with its own wine-storage building
Woodside
Located off Mountain Home Road in Central Woodside, this 4.4-acre estate features a 7,930-square-foot main residence with six en suite bedrooms, an elevator, a library and a primary suite beneath a retractable skylight. The property includes a pinot noir vineyard, an olive orchard, a one-bedroom poolside guesthouse with a kitchen and sauna. A separate temperature-controlled building is dedicated solely to wine storage. Designed by Atelier Ugo Sap and completed in 1997, the estate also produces small batches of wine, jam, honey and olive oil.
The estate first hit the market for $38 million in April 2024 before being relisted for $25 million — about $3,153 per square foot — in June. For an additional $10 million, buyers also can get the 3-acre parcel adjacent to the estate.
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1.8 acres of waterfalls, palm trees, lush landscaping
Los Altos Hills
A $25-million price tag in Los Altos Hills will get you a gated home with expansive glass walls, limestone terraces and broad balconies overlooking 1.8 acres of lush grounds featuring more than 20 palm trees, tropical landscaping and cascading waterfalls. The main residence includes eight bedrooms and 11 bathrooms, plus a guesthouse with its own kitchen, living room and private entrance. Entertainment areas range from a 16-seat home theater to a wine cellar and fully equipped gym, all linked by an elevator. Outside, an infinity pool and sports court anchor the grounds. There’s also five garage spaces with EV charging. The property went on the market in March for $25 million, or $2,479 a square foot.
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