These were the five highest-priced home sales reported in San Mateo Peninsula, California for the week ending October 25, 2026, and together they came to $43.855 million. Each sale was in a different city: Portola Valley, Hillsborough, Atherton, Redwood City and San Mateo.
The homes span almost nine decades of building, from 1917 to 2006, and range from a 3,380-square-foot home on just over a quarter acre to one with 8,170 square feet. One of the five sales had the same agent on both sides.
No. 1 — $14,850,000 · 155 Grove Dr, Portola Valley, California
The most expensive sale of the week was not a single home so much as a small compound. The property at 155 Grove Drive in central Portola Valley sits on 1.25 acres, the largest lot among the five, and has four separate structures: the main residence, a one-bedroom accessory dwelling unit, a detached studio or guest house, and a car barn built of heavy timber with a recreation lounge on its upper level.
The main home, built in 1950, is all on one level, with six bedrooms, six bathrooms and 5,195 square feet. Its rooms have vaulted ceilings, floors of European white oak and honed marble surfaces. The kitchen pairs custom cabinets with Moroccan tile. The primary suite has its own sitting area with a fireplace, and French doors lead out to a garden terrace; its bath has a deep soaking tub, a walk-in marble shower and radiant-heated floors of Belgian bluestone.
Places to entertain, dine and relax are set among mature redwoods, heritage oaks and perennial gardens, and the property also has a fire pit and a barbecue. It is a few minutes from Interstate 280, open space preserves and athletic clubs. The property last sold in 2019 for $8.5 million.
The home went under contract 15 days after it was listed and sold at its full asking price of $14,850,000. The Dreyfus Group of Golden Gate Sotheby’s International Realty was the listing agent, and Renee Daskalakis, also of Golden Gate Sotheby’s International Realty, represented the buyer.
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No. 2 — $8,250,000 · 701 Chester Way, Hillsborough, California
The oldest home in this week’s Top 5 is also the largest. Built in 1917, the Mediterranean-style home at 701 Chester Way in Lower Hillsborough has 8,170 square feet of living space, eight bedrooms and seven bathrooms, more of each than any other home on the list. It has four fireplaces, including ones in the living room, the family room and the primary bedroom, and a four-car garage.
The home stands on 0.92 acres of mostly level, gently sloping ground with a long private approach. The grounds include an in-ground swimming pool, a cabana and a squash court. The listing presents the property as a candidate for restoration or renovation and notes that the home has some deferred maintenance.
Jose Dos Ramos of Berkshire Hathaway HomeServices Drysdale Propertie was the listing agent, and Cullinan Luxury of KW Advisors represented the buyer.
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No. 3 — $8,100,000 · 98 Rebecca Ln, Atherton, California
In Atherton, 98 Rebecca Lane went under contract the same day it was listed and sold for $8,100,000, which was $600,000 above its $7.5 million asking price. Built in 1963, the home stands on a 0.90-acre lot on a quiet cul-de-sac lined with trees.
All five bedrooms, the primary suite among them, are on the upper floor. On the main level, French doors lead from the living and dining room to the backyard, and the family room has built-in shelves. The kitchen has been updated and has a center island with a cooktop, a breakfast bar and space to eat in. Also downstairs is a room that can serve as an office or a hobby room, along with the laundry and a bathroom that has been fully renovated. In all, the home has five bathrooms and 3,950 square feet, with fireplaces in the living room and the family room.
The landscaped backyard has a swimming pool with solar heat and a tiered fountain. Menlo Park schools serve the home, and downtown Palo Alto and Menlo Park, the train station and Highway 101 are all nearby.
Tom LeMieux and Alicia Young of Compass were the listing agents, and the DeLeon Team of Deleon Realty represented the buyer.
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No. 4 — $6,500,000 · 5 Colton Ct, Redwood City, California
Built in 2006, the custom Spanish-style home at 5 Colton Court in the Farm Hill neighborhood of Redwood City is the newest in this week’s group. Colton Court has no through traffic, and the listing places the home in the gated Parkwood Estates. The lot covers 0.47 acres, and Edgewood Park, hiking trails and Highway 280 are nearby.
The entry is a pair of arched double doors in glass and iron, opening onto a grand staircase with iron railings. Archways, custom millwork and ceilings with wood beams or coffers run through the formal living and dining rooms, the office and library, and a great room that has a fireplace, a wet bar and access to the grounds behind the home. The kitchen has an eight-burner Wolf range, a Gaggenau steam oven, double ovens, two dishwashers, two Sub-Zero refrigerators and a pair of copper sinks. A temperature-controlled wine cellar has room for about 1,200 bottles.
The home has five bedrooms, five bathrooms and 5,700 square feet. One bedroom and a full bath are on the main level. Upstairs, the primary suite has a fireplace, a balcony, a large closet and a spa-style bath. Out back are a paver patio, a lawn and landscaped grounds, and the home has a three-car garage. It last sold in 2016 for $3.675 million, ten years before this sale.
The home went under contract 12 days after it was listed and sold for $6,500,000, which was $1.502 million above its asking price of $4.998 million. Eleni Giotinis and Holly Noto of Coldwell Banker Realty were the listing agents, and Charles Holcomb of Compass represented the buyer.
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No. 5 — $6,155,000 · 342 Parrott Dr, San Mateo, California
The Baywood Knolls neighborhood of San Mateo produced the week’s fifth-highest sale, a 1927 Spanish-style home at 342 Parrott Drive with white stucco walls, a terracotta roof and black-framed windows. The living room is the centerpiece, with an 11-foot barrel-vaulted ceiling, arched windows, a gas fireplace and oak floors.
The main level also has a formal dining room, a kitchen with a breakfast area set in a bay window, a bedroom with its own bath, an office and a mudroom. French doors lead out to a patio laid in Arto tile and to the gardens. A family room with access to the yard and a powder room are on the garden level. On the upper floor, the primary suite has a steam shower, walk-in closets and a bonus room, and two more bedrooms share a hall bath. In all, the home has four bedrooms, four bathrooms and 3,380 square feet on a 0.28-acre lot, with a detached two-car garage and a motor court. San Mateo Central Park and downtown San Mateo are a few minutes away.
The property last sold in 2020 for $3.051 million. It went under contract seven days after it was listed and sold for $6,155,000, which was $1.156 million above its $4.999 million asking price. Jenn Gilson of Golden Gate Sotheby’s International Realty was the listing agent and also represented the buyer, so the same agent was on both sides of the sale. It was one of two Top 5 listings this week for Golden Gate Sotheby’s International Realty, which also listed the No. 1 sale in Portola Valley.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 25, 2026. The report may exclude private, off-market, delayed or nondisclosed transactions. Prices, property details and professional representation are reported as available at publication and may be updated following confirmation from transaction participants.
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