When it comes to forested hideaways near bustling urban centers, few are as refined as Woodside. This town of 5,500 in Northern California is a haven for the region’s innovators, creatives, and sportspeople: Its properties are secluded and serene, its landscape idyllic, and the economic engine of Palo Alto and the esteemed halls of Stanford University are all within reach. This is equestrian country on the cusp of the city, and the properties here feel like sanctuaries. Whether your days are spent recreating or ideating, Woodside offers private country living to the active and discerning buyer.

1. For the Equestrian...

The best of this destination town can be seen at this traditional Woodside estate. Thanks to the area’s temperate climate, the home provides a green getaway: cloaks of wisteria, stately hornbeams, and wild grasses surround the property, enhancing the sense of history and privacy. The vibrant hub of Silicon Valley is less than 15 minutes away—and, suitably, the property includes a separate 621-square-foot office for the enterprising professional.

The estate was bought by shipping magnate Captain William Matson in 1924, but it was his daughter, celebrated equestrian Lurline Matson Roth, who commissioned the world-class 2,897-square-foot stables and adjacent riding ring. This is a home that lends itself to health, wellness, and active living, as further evidenced by its fitness studio, tennis court, swimming pool, spa terrace, and abundance of trails and wildlife corridors.

2. The Vintner...

This Woodside vineyard estate is tailor-made for life in the sun, and is exceptional even by local standards. Situated in a neighborhood known for its large acreage, private properties, and secure setting, this is one of the few homes in the area that features its very own field of grafted aged vines; fittingly, its wide selection of amenities includes a wine room. Built for the active family, this home features an au pair suite, a separate entertainment pavilion, and a truly inspiring arboreal playground spanning three large trees.

The home has been remodeled twice since it was built in 2009, and its interiors are infused with an airy, modern simplicity. The contemporary details continue behind the scenes, in the buildings’ many technological features and sustainable LEED Platinum-certified design.

3. The Founder...

When it comes to spectacular architecture, this Woodside Italian villa is a timeless construction that unites classical Tuscan splendor with contemporary California style. When the original homeowners redeveloped the property, replacing the plot’s original Cliff May-designed ranch home, they preserved the building’s carved wood ceiling, crafted in Venice circa 1490; they knew this would be a showpiece for their new villa. They subsequently sourced and handpicked many of their materials in Italy—including wood beams, local stone, and 300-year-old terracotta roofing tiles—to build a home unlike any in the area.

The result is a stunning residence that evokes a rambling country estate. Nearly every room overlooks the gardens and the surrounding redwood forests; the central great room is notable for its 11-foot windows and latticed skylights. The master suite, with its signature Venetian plaster tray ceiling, boasts a bath that overlooks the meadow in the backyard, and a rooftop terrace with views of the lawns and outdoor pool.

4. The Family...

Entertaining guests is child’s play at this sophisticated family farmhouse that combines clean lines and futuristic tech to offer creative spaces and relaxation to visitors and residents alike. The bespoke architectural touches are truly one of a kind: 40-foot vaulted ceilings in the great room are bisected by a flying bridge connecting the second-story bedrooms. This open-concept approach continues out onto porches and patios, where the home’s state-of-the-art audiovisual systems controls music and lighting throughout the house and outdoor spaces.

For the growing household, that’s only half the fun. From the climbing gym and media room in the basement to the artist loft on the upper landing to the in-ground trampoline, skateboard ramp, and professional-grade putting green in the yard, this home offers unparalleled recreation opportunities for the whole family. And all of these outdoor amenities are laid out tastefully amid the property’s mature oaks and manzanita trees, staples of the iconic Woodside landscape.

Picturesque hills with towering redwood forests are yours in Woodside, where cycling paths and horse trails crisscross nature preserves and the Pacific Ocean is less than 20 miles away. With the central pillar of the world’s tech sector and some of the nation’s top schools on its doorstep, it’s no wonder artists, equestrians, and venture capitalists call this fashionable town home.