Woodside Hills Homes for Sale

Welcome to Woodside Hills, a hidden gem nestled in the heart of San Mateo County, California. This enchanting neighborhood is a harmonious blend of natural beauty and refined living, making it an ideal destination for those seeking a serene escape from the hustle and bustle of city life. With its lush, rolling hills and majestic redwood trees, Woodside Hills offers residents a picturesque backdrop that is both tranquil and invigorating.

The community is known for its spacious estates and luxurious homes, each boasting unique architectural styles that reflect the area’s upscale charm. Whether you’re in search of a modern masterpiece or a classic ranch-style home, the real estate market in Woodside Hills has something to suit every taste. Many properties feature expansive lots, private gardens, and stunning views, providing an idyllic setting for families and individuals alike.

Woodside Hills is not just about beautiful homes; it’s also about a lifestyle enriched by nature and community. Residents enjoy access to a variety of outdoor activities, from hiking and horseback riding in the nearby parks to leisurely strolls through the quaint local shops and eateries. The neighborhood is renowned for its top-rated schools, making it a perfect choice for families looking to provide their children with an exceptional education.

If you’re considering a move to Woodside Hills, you’ll find a welcoming community that values privacy and tranquility, all while being just a short drive away from the vibrant culture of nearby cities like Palo Alto and Menlo Park. Explore the homes for sale in this captivating neighborhood and discover the perfect place to call home in Woodside Hills!

Newest Woodside Hills Homes for Sale

$4,750,000

4 Beds ⋅ 5 Baths ⋅ BE41140473 MLS

Tucked at the end of a peaceful cul-de-sac in Woodside Hills, this beautifully reimagined single-level retreat pairs timeless ranch design with an unbeatable connection to nature. Panoramic views stretch across Hoover Tower, Moffett Field, the Dish, and Mount Hamilton - a backdrop that changes with the light throughout the day. Set on a full acre with a creekside property line, the grounds feel like a private nature escape. Deer and songbirds pass through regularly, while four terraced garden beds await your green thumb. Outdoor living is at the heart of this property, with a spacious private deck, a bocce ball court, horseshoes, a swing set, and even a chicken coop - space to entertain, play, and unwind in equal measure. A large paved driveway offers ample parking for hosting guests with ease. Inside, the open floor plan is anchored by a custom kitchen featuring a large center island, stainless steel appliances, and timeless leathered granite countertops, prized for their easy maintenance, complete with a pantry for extra storage - all flowing seamlessly into the home's entertaining spaces. The thoughtfully remodeled layout (2013) also offers true separation between private and social areas. Two en-suite bedrooms and a Jack-and-Jill bath provide flexibility for family or guests,

140 Sheridan Way, Woodside

Listed by Ella Naylor, (650) 520-9864 from Compass
(If provided) CoList: Daniel Boot from Compass

$4,788,000

4 Beds ⋅ 4 Baths ⋅ ML82050181 MLS

Nestled among majestic oak trees on nearly 1.2 acres in Woodside Hills, this home is set well back from the street via a long paver driveway. Spanning 4,150 SF, the interiors feature wide-plank hardwood floors, soaring ceilings, and refined finishes that create a light-filled, airy atmosphere in harmony with its natural surroundings. Expansive formal rooms are complemented by multiple fireplaces, a well-appointed kitchen, and a walk-out family room that opens to the outdoors. The four-bedroom layout includes a primary suite with a spa-inspired bathroom designed for comfort and retreat. Outdoor living is equally compelling, with a generous deck and patio featuring an outdoor kitchen, all framed by a verdant, oak-studded backdrop that emphasizes the home's connection to nature. A three-car garage completes the property, while the setting balances privacy with convenience, just minutes to downtown Redwood City, nearby nature preserves and trailheads, and easy access to Highway 280.

61 Oak Haven WAY, Woodside

Listed by DeLeon Team, 650-407-0160 from Deleon Realty
(If provided) CoList: from

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The data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListingsTM MLS system. Real estate listings held by brokerage firms other than RE/MAX CAPITAL are marked with the Internet Data Exchange and detailed information about them includes the names of the listing brokers and listing agents.
Based on information from MLSListings MLS as of . All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.