20255 Skyline Boulevard, Woodside, California 94062, Woodside, 94062 - 3 bed, 3 bath
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Woodside, California 94062
Analysis of 20255 Skyline Boulevard, Woodside, California 94062 is currently available with a list price of $2,195,000. The property maintains a Good Condition Rating (78/100), reflecting solid structural condition with well-maintained systems. The property presents an attractive opportunity for buyers seeking a move-in ready home. Located in a high-demand neighborhood within the Woodside Unified School District, this asset is categorized as a low-risk, high-reward acquisition suitable for both Buy-and-Hold Investors and Owner-Occupants willing to undertake light renovation work.
Property is move-in ready.
Although originally built in 1963, the interior has undergone significant modern renovations. Images show updated bathrooms with contemporary subway tile and fixtures, high-quality laminate or engineered wood flooring, and fresh paint throughout. The home is in move-in ready condition with an open-plan layout that feels current. It falls into the 'Good' category rather than 'Excellent' due to the overall age of the structure and the rustic condition of the secondary barn/outbuildings.
The property has a large lot size, which is more than 4 times of its living area. lot size in square feet = 130223, living area = 2400.
The property features nearly 3 acres of usable, gently rolling meadows, making it an ideal and rare find for horse enthusiasts in the prestigious Woodside area.
Walls of windows and expansive balconies throughout the home capture stunning, unobstructed views of the Bay, city lights, and surrounding pastures.
Situated on Skyline Boulevard, the property is a 20-minute drive from Highway 280, which may pose a challenge for residents seeking quick access to shopping and services.
Originally built in 1963, the home may necessitate significant capital investment for modernizing systems and interior finishes to align with contemporary luxury standards.
Spanning approximately 2.92 usable acres of gently rolling meadows with picture-postcard views, this classic horse property offers miles-away tranquility just 20 minutes from Highway 280. A palatial driveway leads to a two-story, 3-bedroom, 3-bath, open-plan residence with walls of windows capturing the rolling hill and city-light views. Almost every room has glass doors to the long, view balcony. Lawn and mini orchard. A separate charming barn captures the Old West Woodside feel with a wood-beamed ceiling, full-sized bar, and French doors to a veranda with flowering vines. Just a mile to the Thomas Fogarty Winery and 8 minutes to Alice's Restaurant.
No exterior & parking available.
No sensitive facilities data found.
| Feature | Subject | Average Home |
|---|---|---|
| Beds | 3.0 | 4.0 |
| Baths | 3.0 | 4.0 |
| Square foot | 2,400 | 4,671 |
| Lot Size | 130,223 | 47,042 |
| Price | $2.19M | $4.65M |
| Price per sq ft | $915 | $1.4K |
| Built year | 1963 | 1981 |
| HOA | $0 | $260 |
| Days on market | 105 | 42 |
Jul 9, 2026
$2,195,000
$2,399,000
-9% Price Drop
Initial Listing
Apr 8, 2026
$2,399,000
Initial Listing
Nov 13, 2019
$1,875,000
Public Record
May 30, 2018
$1,875,000
Public Record
Mar 30, 2012
$1,170,000
Public Record
Sep 15, 1999
$799,000
Public Record
Jun 5, 1997
$650,000
Public Record