Woodside Homes with Mediterranean Style

Welcome to Woodside, California—a hidden gem nestled in the heart of San Mateo County. Known for its breathtaking natural beauty and serene atmosphere, Woodside is a quintessential blend of rural charm and upscale living. With its rolling hills, majestic redwoods, and picturesque landscapes, this enchanting town offers a peaceful retreat just minutes away from the bustling Silicon Valley.

One of the most alluring features of Woodside is its stunning Mediterranean-style homes. These architectural masterpieces are characterized by their warm, earthy tones, terracotta roofs, and elegant arches, creating a timeless aesthetic that harmonizes beautifully with the surrounding nature. Many of these homes boast expansive outdoor spaces, perfect for entertaining or simply soaking in the tranquil views. Imagine sipping your morning coffee on a sun-drenched patio or hosting gatherings in a lush garden oasis—this is the lifestyle that Woodside offers.

The charm of Woodside extends beyond its homes. The community is known for its commitment to preserving the environment, with numerous parks and trails that invite residents to explore the great outdoors. Whether you’re hiking through the scenic trails of the nearby Huddart Park or enjoying a leisurely bike ride along the picturesque roads, there’s no shortage of ways to enjoy the natural beauty that surrounds you.

With its idyllic setting, exquisite Mediterranean-style homes, and a close-knit community, Woodside is not just a place to live—it’s a place to thrive. Discover the allure of this enchanting town and make it your home today!

Newest Woodside Homes with Mediterranean Style

$34,995,000

6 Beds ⋅ 5 Baths ⋅ ML82038776 MLS

One of Woodside's premier estates, encompassing nearly 10,000 square feet across all structures, this property offers exceptional scale, quality, and lifestyle, highlighted by a classically styled main residence and a brand-new guest house crafted with authentic European detail. The main home is luxuriously appointed across two levels, with nearly every room opening to the outdoors. A state-of-the-art theatre and a temperature-controlled wine cellar are just two of many standout features. The newly completed guest house pairs handmade roof tiles and Genoise eaves inspired by the South of France with state-of-the-art smart home technology. Designed for entertaining, the guest house opens to a new saltwater pool and spa and expansive limestone terrace with a full outdoor kitchen and easy catering access. A 310-vine Cabernet vineyard anchors the south-facing gardens, while heritage olive trees and oaks, a fragrant parterre rose garden, bountiful orchard, and raised vegetable beds enhance the estates agrarian beauty. The result is a property where timeless elegance and refined European living are masterfully expressed in an extraordinary private setting of more than 3 acres with western hill views. Main Residence 6,485 | Guest House 1,505 | Garage One 560 | Garage Two 520 | Gym 560

307 Olive Hill Lane, Woodside

Listing courtesy of from Compass. 650-888-0860

$2,999,000

4 Beds ⋅ 8 Baths ⋅ ML82017325 MLS

*NOW REDUCED FOR SALE* SKY VILLA: RE-IMAGINE ROYALTY IN THE WOODS. Sky Villa is an opportunity to dream big with unmatched grandeur & privacy. This is a bank-owned, non-livable development opportunity, approximately 70% complete, with expired permits. Buyer to verify with County of San Mateo the existence and status of any past permits and the ability to resume construction towards completion. Grand scale luxury features such as: 2-Story Lobby with Imperial Staircase | 4 levels of destinations inspire your finishing details | Library off the lobby | Two Enormous Primary Suites (one main level, one upstairs) | Multiple Offices | Immense walk-in closets | Unfinished lower levels of Rec Room, Wine Vault, Grand Loggia, & dreamy Mezzanine facing majestic Sequoia Forest | Flat rear grounds inspire a future pool & ADU | Off-street parking for the most grand events, plus 2 separate attached garages: a daily 3-car at the motor court, plus a lower level 2-car attached garage | Long the bastion for Silicon Valley founders and CEO's, Woodside blurs the line between timeless province and epicenter of wealth and innovation. SKY VILLA, prepare to take flight in one of California's most prestigious communities.

1 Reids Roost Road, Woodside

Listing courtesy of Geoffrey Nelson from Coldwell Banker Realty. 650-455-3735

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