20255 Skyline Boulevard, Woodside, California 94062, Woodside, 94062 - 3 bed, 3 bath
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20255 Skyline Boulevard
Woodside, California 94062
ACTIVE
CONDITION: GOOD
3Beds
3Baths
2,400Sq Ft
130,223Lot Size
Property Price
LIST PRICE$2,195,000
SUMMARY
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.
Condition Analysis
See Full ReportOVERALL CONDITION SCORE
Good
TeardownExcellent
Property is move-in ready.
Although built in 1963, the property has undergone significant interior renovations likely within the last 5-15 years. Visuals show updated luxury vinyl plank flooring, recessed lighting, modern paint, and updated windows/sliders. The home appears well-maintained, functional, and move-in ready, despite some dated elements like popcorn ceilings.
PROSSTRENGTHS & OPPORTUNITIES
- High Available Lot Utilization
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.
- Expansive Acreage and Equestrian Potential
The property boasts nearly 3 acres of usable, gently rolling meadows, offering a rare opportunity for a classic horse property in the prestigious Woodside area.
- Exceptional Views and Indoor-Outdoor Flow
Walls of windows and glass doors in nearly every room lead to a long balcony, capturing breathtaking panoramic views of the Bay, city lights, and rolling hills.
CONSRISKS & DEFICIENCIES
- Extended Market Time and Price Adjustment
The property has been on the market for over 120 days and has already seen a significant price reduction, which may indicate initial overpricing or buyer hesitation regarding the location.
- Aging Infrastructure
Built in 1963, the residence may require modernization of its core systems and finishes to meet the expectations of contemporary luxury buyers in this price bracket.
About 20255 Skyline Boulevard
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.
Property Details
Public Facts
- Property Type
- Single Family Residence
- Year Built
- 1963
- Lot Size
- 130,223 Sq. Ft.
Interior
- Total Bedrooms
- 3
- Total Bathrooms
- 3 (3 Full, 0 Half)
Exterior & Parking
No exterior & parking available.
Utilities & Misc
- HOA Fee
- $0 / Month
Neighborhood Insights
Sensitive Facilities
No sensitive facilities data found.
Neighborhood Comparison
| Feature | Subject | Average Home |
|---|---|---|
| Beds | 3.0 | 3.8 |
| Baths | 3.0 | 3.7 |
| Square foot | 2,400 | 3,592.5 |
| Lot Size | 130,223 | 58,898.667 |
| Price | $2.19M | $4.34M |
| Price per sq ft | $915 | $1.3K |
| Built year | 1963 | 1975 |
| HOA | $0 | $260 |
| Days on market | 154 | 57 |
Pricing History
Listed for Sale
Jul 9, 2026
$2,195,000
$2,399,000
-9% Price Drop
Initial Listing
Price Change
Apr 8, 2026
$2,399,000
Initial Listing
Sold
Nov 13, 2019
$1,875,000
Public Record
Sold
May 30, 2018
$1,875,000
Public Record
Sold
Mar 30, 2012
$1,170,000
Public Record
Sold
Sep 15, 1999
$799,000
Public Record
Sold
Jun 5, 1997
$650,000
Public Record