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San Mateo

Welcome to
San Mateo

The Perfect Balance of Nature and City Life

Nestled between San Francisco and Silicon Valley, San Mateo offers the best of both worlds—bustling tech energy and peaceful suburban charm. From its waterfront trails to vibrant downtown streets, this city blends natural beauty, excellent schools, and career opportunities, making it one of the Bay Area’s most sought-after places to live.

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Properties

The Green Gables Estate, in its entirety, is a 74 acre, spectacular, one of a kind, multi-generation oasis situated within walking distance from the Woodside Town Center. The estate is currently comprised of seven homes and 10 separate lots, featuring significant additional build out potential and may be purchased as a whole or in 6 potential lot combinations (see MLS listings for suggested lot combinations with Albion addresses 329-A, 329-AA, 329-C, 331, 333). The complete estates homes currently include 34 bedrooms, 26 bathrooms across approx. 23,900 existing square feet, with numerous options for expansion and/or redevelopment. The vast landscape includes world class gardens, magnificent vistas of the Western hills, its own large reservoir, three swimming pools, a tennis court and a breathtaking 100-yard Roman pool. Situated in the heart of Silicon Valley at the epicenter of venture capital, technology, and renowned educational institutions, the estates elegant blend of English and Italian design offers a bounty of elegant spaces to host retreats, social events, and cultural gatherings or to simply be a world class refuge from the pressure of the outside world. Green Gables is a truly remarkable estate and welcomes its next owner to the latest chapter of its amazing legacy. $125,000,000 Active

329 Albion Avenue Woodside, California

34 Beds 26 Baths 23,900 SqFt 74.04 Acres

Villa del Prato is a singular gem among Silicon Valley estates. Nestled in the woodlands of Portola Valley on nearly 12 acres of tranquil, private, flat land, the estate comprises three structures: a main house (12,000 sf); an entertainment or business building (6,500 sf); and a pool house (2,000 sf). Inspired by classic Palladian Italian architecture, each structure is reminiscent of a Tuscan villa, featuring soaring arches, 20-foot ceilings, dramatic skylights, solid stone columns direct from Italy, and the finest-quality finishes. The main home, built on two levels, features a one-of-a-kind 900-square-foot dressing suite that doubles as a safe room. Unseen are advanced systems for the comfort and security of residents and guests. The entertainment/business building provides an opportunity for customization. With its towering columns, airy loggia, and spacious ballroom, it could be utilized for entertaining, as a home office, conference center, staff housing, or a home for your next startup. Electrical, plumbing, HVAC, and other key systems are fully fitted out. This grand estate is centrally located close to Hwy 280 mid-way between San Francisco and San Jose, with easy access to major airports and technology and business centers. (All sf info per plans). $85,000,000 Active

20 Meadow Lane Portola Valley, California

6 Beds 13 Baths 12,305 SqFt 11.8 Acres

Known as The Main House and Historic Gardens, representing the magnificent central, architectural jewel of the entire estate. The main home and gardens, situated on approx.11.7 acres, were designed by renowned Craftsman era architects Greene & Greene and include a two-story English-inspired existing. 9,890 sf home (with additional lower-level square footage), and an estimated 11,945 potential future total square footage, extraordinary lawns, trees and gardens, all of which overlook the stunning 100 yard long Roman Pool which beautifully frames the spectacular views of the Western Hills. The homes beautiful motor court is connected to the wonderfully situated large free form swimming pool with lovely oak trees and vistas along with three bath houses, as well as separate barbecue and kitchen areas. $55,000,000 Active

329-AA Albion Avenue Woodside, California

10 Beds 8 Baths 9,890 SqFt 11.69 Acres

A private estate in the highly coveted Lower North Hillsborough, this trophy property spans 5.36 acres across four separate parcels, offering exceptional privacy, expansion potential, and investment value. Designed by renowned architects John Bakewell Jr. & Ernest Weihe, this French chateau-style masterpiece became home to Hollywood legend Bing Crosby. With ties to the legendary racehorse Seabiscuit and antique elements sourced from the Hearst Collection, this estate is truly one-of-a-kind. The residence includes 11 bedrooms, 10 full bathrooms, and 5 half bathrooms across four levels. A family-friendly floor plan, designed for both comfortable living and grand entertaining, includes multiple salons, a formal dining room, a paneled library, a private office, and a separate guest wing. Stunning architectural details include Rococo plasterwork, intricate millwork, and imported European antiques many hand-selected by Bing Crosby himself. The expansive estate grounds once housed Seabiscuit's stables and now feature lush gardens, serene walking paths, and endless opportunities for outdoor entertaining. With rare historical significance, unparalleled elegance, and extraordinary scale, this is a legacy estate a once-in-a-lifetime opportunity to own a piece of Californias Golden Era. $40,000,000 Active

1200 Jackling Drive Hillsborough, California

11 Beds 15 Baths 18,535 SqFt 5.355 Acres

This engineering and architectural masterpiece is a one-of-a-kind residence made from the highest level of architectural formed concrete, glass, and steel. Built in 2017, the home comprises two L shaped forms that balance on top of one another, creating courts and overhangs that define the indoor and outdoor spaces with bridges and two floating cantilevers, each spanning 23 feet. Designed as much for the terrain as for privacy, the walls facing the street are primarily solid with strategically placed glass, allowing natural light to brighten the space. On the sides away from the street, the walls are made entirely of glass, offering maximum enjoyment of the far-reaching views out to the San Francisco skyline. There are 16,000 total square feet, with a three-level main residence plus two separate buildings, each with a full kitchen, with flexibility for guests, office, and/or poolside entertaining needs. Behind the scenes, everything needed for comfort and convenience is found with wiring for home automation, solar panels for electricity, and multiple car charging stations. Added amenities include such luxuries as a 7-hole putting green with bunker, golf simulation screen, theater, and a design for elevator, if desired. $38,600,000 Active

96 Ridge View Drive Atherton, California

6 Beds 7 Baths 13,849 SqFt 1.627 Acres

Known as the Olive Orchard home, combined with the contiguous Olive Hill East and West lots, this fabulous combination of three parcels totaling just over 23.5 acres, currently includes two homes, one with approx. 3,345 sf and four bedrooms and the other with 1,755 sf with three bedrooms (the Estate Manager's home), each of which present a series of upgrade or redevelopment options. The parcels also include a beautiful vegetable and flower garden, the iconic Greene & Greene designed Tea and Dairy House, as well as a large barn and storage facility, both of which can be expanded and repurposed. The lot combination features fabulous vistas and a variety of development options, including the potential for relocating and expanding the homes as well as adding accessory structures and swimming pools. $34,500,000 Active

329-C Albion Avenue Woodside, California

4 Beds 4 Baths 3,345 SqFt 23.59 Acres

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San Mateo
Main Attractions

Must-See Spots in San Mateo

Coyote Point Recreation Area

A favorite for families and outdoor lovers, this waterfront park offers beaches, picnic areas, biking trails, and scenic views of the Bay. It’s also home to the beloved CuriOdyssey science museum and zoo.

Downtown San Mateo

Bustling with culture, food, and flair—downtown San Mateo is packed with award-winning restaurants, boutique shopping, historic buildings, and a lively nightlife scene. It’s the heart of the city’s social and cultural life.

Central Park & Japanese Garden

This urban oasis features lush green spaces, a mini train for kids, and a serene Japanese Tea Garden with koi ponds and waterfalls. It’s a peaceful spot perfect for afternoon strolls or community events.

Hillsdale Shopping Center

A modern mall experience with high-end retailers, local brands, and delicious dining options. Hillsdale is more than shopping—it’s a social hub with events, open-air lounging, and family-friendly activities year-round.

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Thinking of calling San Mateo home? Whether you’re buying, selling, or investing, we’re here to help you navigate the market with confidence. Let our local expertise and personalized support turn your real estate goals into reality.

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