21 Valley Oak Street, Portola Valley, California 94028, Portola Valley, 94028 - 4 bed, 4 bath
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Portola Valley, California 94028
This Private Luxury Retreat is listed at $3,499,000, offering exceptional price stability at its $3,499,000 Fair Market Value. Boasting a Well-Maintained Condition Rating, the 3,470 SF residence features soaring ceilings, a gourmet kitchen, and a spa-inspired primary suite. The expansive 25,966 SF lot is enveloped by iconic oaks, providing a secluded oasis with a serene wooded view and private deck. Residents benefit from proximity to Silicon Valley hubs and access to Top-Rated Schools, including Henry M. Gunn High School. This turnkey sanctuary is ideal for Growing Families or Owner-Occupants seeking a prestigious lifestyle.
Comparables within 1 miles sold in recently
| Address | Sold Price | Beds | Baths | Sq Ft | $/Sqft | Distance |
|---|---|---|---|---|---|---|
★ 21 Valley Oak Street Subject | $3,499,000* List Price | 4 | 4 | 3,470 | $1,008 | - |
A 11 Hawk View Sold | $4,025,000 | 4 | 4 | 4,106 | $980 | 0.2 mi |
* Subject property listed price vs sold prices of comps.
Property is move-in ready.
While built in 1988, the property has undergone significant renovations likely within the 5-15 year range. The bathrooms feature modern dark wood vanities, stone countertops, and updated tile work, while the kitchen includes stainless steel appliances. With new paint and lighting throughout, the home is well-maintained and move-in ready.
The property has a large lot size, which is more than 4 times of its living area. lot size in square feet = 25966, living area = 3470.
High School: Henry M. Gunn High School (9/10).
Situated on a generous 25,966 SF lot surrounded by iconic oaks, this property offers a rare level of seclusion and a serene outdoor oasis while remaining close to Silicon Valley tech hubs.
While cosmetically updated, the 1988 construction may soon require significant investment in major systems or structural maintenance typical for a home of this vintage.
The $540 monthly association fee represents a notable recurring carrying cost that may be a drawback for buyers seeking a traditional single-family residence without oversight or additional fees.
Escape to serenity in this very private 4-bedroom, 3.5-bathroom retreat priced at $3,499,000. Spanning 3,470 square feet on a 25,966 SF lot, this 1988-built residence blends timeless elegance with modern sophistication. The light-filled interior boasts soaring ceilings, large windows, new paint, and lighting throughout, creating an inviting open-concept layout ideal for both grand entertaining and tranquil living. A gourmet kitchen, featuring stainless steel appliances flows seamlessly into spacious living and dining areas. The private primary suite offers a luxurious, spa-inspired ensuite, creating a serene haven. Outside, the beautifully landscaped lot, enveloped by Portola Valley's iconic oaks, provides a secluded oasis for relaxation or outdoor gatherings. Enjoy an excellent community of neighbors and access to top-rated schools, including Ormondale Elementary, Corte Madera Middle, and Woodside High School (buyer to verify eligibility).Perfectly positioned to get away from the lights of the city while remaining close to Silicon Valley's tech hubs, scenic trails, and Roberts Market, this home offers unmatched privacy and convenience. Seize this rare opportunity to own a slice of Portola Valleys idyllic lifestyle!
No exterior & parking available.
Grades K-3 • 1.3 mi
Grades K-5 • 4.1 mi
Grades 4-8 • 0.6 mi
No sensitive facilities data found.
| Feature | Subject | Average Home | Neighborhood Ranking (50 Listings) |
|---|---|---|---|
| Beds | 4.0 | 4.0 | 50% |
| Baths | 4.0 | 4.0 | 50% |
| Square foot | 3,470 | 3,070 | 59% |
| Lot Size | 25,966 | 21,045.5 | 55% |
| Price | $3.50M | $3.96M | 36% |
| Price per sq ft | $1.0K | $1.3K | 23% |
| Built year | 1988 | 1968 | 77% |
| HOA | $540.0 | $0 | 86% |
| Days on market | 92 | 188 | 14% |
Jan 20, 2026
$3,499,000
Initial Listing
Nov 8, 2012
$2,300,000
Public Record
Nov 5, 2004
$1,850,000
Public Record
Sep 12, 1995
$819,000
Public Record