108 Santa Maria Avenue, Portola Valley, California 94028, Portola Valley, 94028 - 3 bed, 2 bath
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Portola Valley, California 94028
This Updated 1929 Hillside Residence represents a rare opportunity in the Woodside Highlands, listed at $2,339,000—aligning closely with its $2,298,587 Fair Market Value. Maintaining a Condition Rating of 3, the home blends historic charm with modern updates, including a professional-grade kitchen and wide-plank flooring. The massive 23,242 sq. ft. lot offers a private retreat featuring East Bay Hill views, mature fruit gardens, and a flexible lower-level suite with a separate entrance. Located near scenic trails and served by top-rated Portola Valley schools, this is a perfect sanctuary for Owner-Occupants or lifestyle-driven buyers.
Comparables within 1 miles sold in recently
| Address | Sold Price | Beds | Baths | Sq Ft | $/Sqft | Distance |
|---|---|---|---|---|---|---|
★ 108 Santa Maria Avenue Subject | $2,339,000* List Price | 3 | 2 | 1,560 | $1,473 | - |
A 9 Russell Avenue Active | $1,849,000 List Price | 2 | 2 | 1,444 | $1,280 | 0.0 mi |
* Subject property listed price vs sold prices of comps.
Property is move-in ready.
Although built in 1929, the property is move-in ready and shows evidence of significant updates. The interior features newer wide-plank light wood flooring, updated light fixtures, and a refreshed kitchen equipped with a professional-grade stainless steel range and stone countertops. While some elements like the cabinetry and exterior siding reflect an older style, the home is well-maintained with no immediate signs of deferred maintenance.
The property has a large lot size, which is more than 4 times of its living area. lot size in square feet = 23242, living area = 1560.
Situated in the prestigious Woodside Highlands of Portola Valley, the property is served by top-rated schools and offers convenient access to local trails, Town Center, and Highway 280.
The property sits on over half an acre of lush, private land featuring mature trees, fruit gardens, and multi-level patios that provide a tranquil retreat with stunning East Bay Hill views.
Lot size discrepancy between mls listing and other public or private record. mls listing lot size in square feet =23242, other record lot size in square feet = 17343. Bedroom count discrepancy between mls listing and other public or private record. mls listing bedroom count = 3, other record bedroom count = 2.
Built in 1929, the home likely requires significant modernization and maintenance to update its century-old systems and finishes to contemporary standards.
With only 1,560 square feet of living space at a multi-million dollar price point, the value is heavily weighted in the land, which may be a deterrent for buyers seeking a larger move-in-ready residence.
Exceptional opportunity in Woodside Highlands on over half an acre of private, lush grounds. This light-filled 3-bedroom, 2-bath home is set on a quiet lot surrounded by mature trees, gardens, and fruit trees, offering a peaceful retreat in one of Portola Valleys most desirable neighborhoods. The main level features two bedrooms, one bath, hardwood floors, beautiful woodwork, and an oversized kitchen that opens to a sunny deckideal for indoor-outdoor living and entertaining. The lower level offers a flexible layout with a private bedroom or primary suite, full bath, and separate exterior entrance, perfect for guests, home office, or additional living space. Bonus room above the garage provides added versatility. Expansive multi-level grounds include wraparound patios, private garden areas, and tranquil natural surroundings. Elevated views overlook Portola Valley toward the East Bay Hills, offering stunning sunrises and full-moon views. Property offers excellent potential. Conveniently located near Town Center, Highway 280, scenic trails, and local favorites including the Alpine Inn. Served by top-rated Portola Valley schools, including Ormondale and Corte Madera.
No exterior & parking available.
No sensitive facilities data found.
| Feature | Subject | Average Home | Neighborhood Ranking (50 Listings) |
|---|---|---|---|
| Beds | 3.0 | 4.0 | 45% |
| Baths | 2.0 | 3.5 | 32% |
| Square foot | 1,560 | 2,930 | 14% |
| Lot Size | 23,242 | 21,045.5 | 55% |
| Price | $2.34M | $3.96M | 18% |
| Price per sq ft | $1.5K | $1.3K | 64% |
| Built year | 1929 | 1967 | 5% |
| HOA | $0 | $0 | 50% |
| Days on market | 72 | 188 | 14% |
Mar 18, 2026
$2,339,000
$2,499,000
-6% Price Drop
Initial Listing
Feb 9, 2026
$2,499,000
Initial Listing
Jun 2, 2014
$1,500,000
Public Record