Woodside Glens Real Estate

Welcome to Woodside Glens, a hidden gem nestled in the heart of San Mateo County, California. This enchanting neighborhood is a serene retreat, offering residents a perfect blend of natural beauty and a close-knit community atmosphere. With its picturesque tree-lined streets and lush greenery, Woodside Glens is an idyllic place for families, outdoor enthusiasts, and anyone seeking a tranquil lifestyle.

One of the standout features of Woodside Glens is its proximity to nature. The area is surrounded by stunning parks and trails, including the expansive Huddart Park and the scenic Windy Hill Open Space Preserve, where residents can enjoy hiking, biking, and picnicking amidst breathtaking vistas. The neighborhood also boasts easy access to the San Francisco Peninsula, making it a convenient location for commuters who want to escape the hustle and bustle of city life.

Education is a priority in Woodside Glens, with highly-rated schools serving the community, ensuring that families have access to quality education right at their doorstep. The neighborhood fosters a strong sense of community, with local events and gatherings that bring neighbors together, creating lasting friendships and connections.

In addition to its natural beauty and community spirit, Woodside Glens offers a variety of charming homes that reflect the character of the area. From cozy cottages to modern residences, there’s something for everyone looking to make this delightful neighborhood their home.

Discover the allure of Woodside Glens, where nature meets community, and find your perfect sanctuary in this enchanting corner of California!

Newest Listings in Woodside Glens

$4,795,000

4 Beds ⋅ 4 Baths ⋅ ML82051662 MLS

Inspired by traditional Norwegian farmstead architecture, this home was extensively rebuilt and expanded in 2002 with views of the western hills and Kite Hill Wildflower Preserve across the street. The home showcases exceptional craftsmanship with solid cedar siding, windows, doors, and screens, a slate roof, old-growth redwood trim, wide-plank Tennessee longleaf pine floors, soapstone countertops, Venetian plaster around the fireplace, and salvaged Douglas fir beams. The flexible 3-level floor plan includes lower-level quarters with kitchenette and private bath, two main-level bedrooms and a bath, plus upstairs primary suite and second suite. Beautifully landscaped grounds feature winding paths, specimen plantings, numerous fruit trees, a rare bamboo grove, pond, flagstone terrace with fireplace, spa, and large chicken coop. Additional features include dual-zone air conditioning, EcoFlow battery backup system and generator, distributed sound, EV charging for 2, and a detached garage. Minutes to Town Center, miles of trails, and acclaimed Woodside Elementary School (K-8).

144 Alta Mesa RD, Woodside

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

$3,695,000

3 Beds ⋅ 3 Baths ⋅ ML82047690 MLS

Classic architecture & beautifully updated interiors define this exceptional home in the Central Woodside, tucked away at the end of a peaceful cul-de-sac just one mile from the Woodside town center. The property offers a distinctive presence with an added sense of privacy & refinement. Freshly painted interiors & hardwood floors introduce warm, inviting spaces filled with natural light. Traditional character is complemented by contemporary finishes, custom cabinetry, granite surfaces, expansive windows, & sliding glass doors opening to the outdoor living areas. Cathedral ceilings enhance the open-concept design, creating wonderful scale for everyday living & entertaining. The flexible floor plan includes 3 bedrooms, a dedicated office, & 2.5 baths, including a spacious primary suite with fireplace, customized walk-in closet, & newly finished bath. There is also expansion & ADU potential (subject to Town approval & applicable development standards). Fully fenced front & rear yards offer expansive areas for entertaining & relaxation with level lawn, expansive deck, paver stone terrace, & large spa, all in a tranquil park-like setting. Access to the excellent Woodside Elementary School (TK-8) further enhances the appeal of this special offering.

63 Ridgecourt, Woodside

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

$5,495,000

4 Beds ⋅ 4 Baths ⋅ ML82046648 MLS

Classic architecture & beautifully curated grounds define this inviting Woodside home set on more than one-third acre moments from the town center. Stone-clad exteriors, newly planted lawns, & a picture-perfect approach introduce interiors that are warm, welcoming, & thoughtfully designed for everyday living. Natural light fills the home through expansive windows, hardwood floors, detailed millwork, & a floor plan that offers both openness & comfortable separation of spaces. Main living areas transition easily from formal rooms to casual gathering spaces, welcoming family room & well-appointed kitchen designed for both function & connection. Lower-level recreation/media room adds flexibility for entertainment or office use. Privately located primary suite with jetted tub & steam shower, bedroom with its own outside entrance & adjacent bath ideal for guest quarters. Outdoor living is a central focus, with a large arbor-covered deck extending from the home & terraced grounds below featuring a play area & garden spaces, all enhanced by refreshed landscaping. Located on a cul-de-sac street in the Woodside Glens neighborhood, with acclaimed Woodside School & offers a combination of traditional appeal, updated comfort, & an exceptionally convenient setting with a true sense of retreat.

103 Toyon CT, Woodside

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

$2,150,000

3 Beds ⋅ 2 Baths ⋅ ML82032924 MLS

BEST VALUE IN WOODSIDE!! Nestled under Woodside's heritage oaks, this 1929 Woodside Glens retreat offers a rare blend of vintage character, privacy, and views. The nearly 0.5 acre lot features abundant, verdant scenery and a wrap-around deck to take it all in. The main level boasts a large, open-beam living room anchored by a cozy wood-burning stove, and is surrounded by windows which bring the natural beauty of the Glens inside. The floor plan includes a vintage kitchen, a dining area overlooking the oaks, and two bedrooms -- one featuring its own fireplace. Central air-conditioning provides year-round comfort. Upstairs is a versatile loft with a storage area. The lower level features a large bedroom with a bathroom and shower, an oversize 2-car garage, plus driveway space for 2 additional vehicles. With the large lot, an ADU is possible (buyer to confirm with the town). Located in the district for top-rated Woodside Elementary (K-8) and Woodside High, this home is moments from Woodside Village and offers a convenient commute to the entire Bay Area via Hwy 280. Experience the quintessential Woodside lifestyle in this timeless woodland sanctuary.

235 Hillside DR, Woodside

Listed by Steve Rumberg, 408-981-2383 from Keller Williams Realty-Silicon Valley
(If provided) CoList: from

$1,575,000

ML81968553 MLS

Architectural design takes advantage of expansive views of the western hills from most rooms. The front garden area of the property was carefully designed to create an expansive flat area for entertaining and gardening. Abundant parking onsite which includes a 2 car garage, a 3 car uncovered off street parking area, plus 2 parking spaces along the street. In addition to the main house is a self-contained ADU which can serve for extended family or as a rental unit. A rare opportunity on a large scenic lot presents a great opportunity to create a brand-new beautiful home in central Woodside with a private setting. Close to the heart of Silicon Valley and just minutes to Stanford shopping and medical center. Award winning Woodside Schools are a short walk from the site as well as restaurants and shopping in the Village of Woodside. 3615 total sq. ft. consisting of 3,175 livable & 440 garage. All public utilities available.

221 Highland TER, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(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 Fine Group Real Estate 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.