Skywood Area Real Estate

Welcome to the enchanting Skywood Area, a hidden gem nestled within the serene landscape of Woodside, California. Located in the picturesque San Mateo County, this neighborhood is a perfect blend of nature's tranquility and suburban charm. Known for its lush greenery and breathtaking views, Skywood offers residents a peaceful retreat just a stone's throw from the vibrant heart of the Bay Area.

Skywood is characterized by its stunning homes, many of which are set on spacious lots surrounded by towering redwoods and mature oaks. The architecture varies from charming mid-century designs to modern masterpieces, ensuring there’s a perfect home for every taste. Residents here enjoy a close-knit community feel, where neighbors become friends and gatherings are common.

One of the highlights of living in Skywood is its proximity to outdoor activities. The area is crisscrossed with scenic trails, perfect for hiking, biking, and horseback riding. The nearby Huddart Park and Wunderlich Park provide ample opportunities for picnics and nature walks, making it an ideal spot for families and outdoor enthusiasts alike.

Skywood is also conveniently located near top-rated schools, making it an attractive choice for families seeking quality education for their children. With easy access to major highways, commuting to Silicon Valley or San Francisco is a breeze, allowing residents to enjoy the best of both worlds—peaceful living in a beautiful neighborhood, with the excitement of city life just a short drive away.

Discover the charm of Skywood Area, where nature meets community, and find your dream home in this idyllic enclave!

Newest Listings in Skywood Area

$4,295,000

4 Beds ⋅ 4 Baths ⋅ ML82037717 MLS

Stunning views of Stanford, San Francisco Bay, and the East Bay, just 10 minutes from downtown Woodside and 4 minutes to Alices Restaurant. Custom-built in 2004 on 1.4 acres with INCREDIBLE QUALITY AND SEISMIC INTEGRITY, this home exudes quality features including walnut floors, 12-foot ceilings, and fireplaces in the living and dining rooms. The large kitchen features Carrara marble and zinc countertops. Every bedroom and main living area opens to wraparound decks with sweeping views. Dedicated office for remote work, and a large 2-car garage. Level yard for entertaining, with room for pickle ball court, plus a sunny pool area. Direct walking distance access to scenic hiking on Mid-Pen Open Space trails. Convenient door-to-door bus to top-rated Portola Valley schools.

950 Espinosa RD, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: from

$1,100,000

ML82034086 MLS

Spacious lot with a view on beautiful Grandview in Woodside! Bring your contractor to build your dream home!

215 Grandview DR, Woodside

Listed by Costantini Team, 650-430-8425 from Compass
(If provided) CoList: from

$450,000

BE41106236 MLS

Tucked into the tranquil forested hills of Woodside, this serene 5.64-acre parcel offers an immersive escape into nature. Surrounded by mature trees, quiet trails, and peaceful open space, the property is perfect for those seeking solitude, fresh air, and natural beauty-just minutes from the 280 freeway and an easy route to Silicon Valley. Enjoy hiking, biking, or simply relaxing beneath the canopy in a setting that feels miles away from it all. This property is ideal for buyers who value privacy, recreation, and a deep connection to the outdoors. Adjacent 13.72-acre parcel also available (APN 075-220-280) offering a rare opportunity to acquire over 19 acres of pristine forest land in one of the Bay Area's most desirable rural communities.

LOT27 Old La Honda Rd, Woodside

Listed by Mike Continillo, (925) 519-0794 from Villa Propertes
(If provided) CoList: from

$750,000

BE41106235 MLS

Tucked away in the serene hills of Woodside, this extraordinary 13.72-acre parcel offers a rare opportunity to immerse yourself in the natural beauty of a mature forest. Surrounded by towering trees, meandering trails, and peaceful wildlife, it's a private haven for those seeking quiet reflection, outdoor adventure, or a personal retreat. Enjoy the feeling of complete seclusion while still being minutes from the 280 freeway, offering easy access to Silicon Valley and beyond. Whether you're hiking, biking, or simply unwinding under the canopy of trees, this land provides an unmatched connection to nature. A truly special slice of Woodside-offering space, solitude, and endless potential for those who value privacy and the forest lifestyle. Adjacent 5.68 Acre lot (APN 075-220-290) also currently for sale. Offering a rare opportunity to acquire over 19 acres of pristine forest land in one of the Bay Area's most desirable rural communities.

Lot26 Old La Honda Rd, Woodside

Listed by Mike Continillo, (925) 519-0794 from Villa Propertes
(If provided) CoList: from

$25,000

CC41071813 MLS

Vacant Land full of tall trees within the confines of Redwood Park, CA. Lot located on Lilac Avenue at Mill Road, in the Redwood Park Community (west of Skyline Boulevard), HWY 35. Sparsely occupied area. Very quiet. No municipal services near. Great for off-the-grid types. Hikers paradise.

0 Lilac Avenue, Woodside

Listed by Brian Atizado, (510) 375-4221 from RE/MAX Regency
(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 Intero Real Estate Services 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.