23 photos · MLS data verified October 9, 2026 · Updated every 15 min
$2,195,000
ActiveUnderContract
3 Beds·3 Baths·2,400 sqft·130,223 sqft lot·Built 1963
20255 Skyline Blvd, Woodside, CA 94062
Listed 184 days ago · | MLS# ML82042155
$914/sqft
20255 Skyline Blvd is a 3-bedroom, 3-bath single family home in Woodside 94062 with 2,400 square feet of living space, built in 1963. It is listed at $2,195,000, or $914 per square foot. The three most recent 3-bedroom sales in 94062 closed between $3,175,000 and $4,758,000 ($814 to $1,859 per square foot).
Est. $13,938/moP&I $11,389 · Tax $2,286 · Insurance $262 · HOA $0Assumes 20% down ($439,000) at 6.75% · Contact Timothy for a lender referralAegis Luxury Real Estate is a licensed California real estate brokerage (DRE# 01328224) and is not a mortgage lender, mortgage broker, or loan originator. The figures shown are estimates for general reference only and do not constitute a loan offer, pre-approval, pre-qualification, or commitment to lend. Estimates use a property tax rate of 1.25% of home price annually. Actual rates, payments, taxes, and insurance vary by lender and borrower qualifications. Contact Timothy for a referral to one of our preferred lending partners.
Single Family Price Position in Woodside
$2.2M$11.8M
27Active in Woodside
25Active Single Family Homes
5.4 moInventory
Why This Home Stands Out
🏠
3 Bed / 3 Bath, 2,400 sqft
Built in 1963.
Best fit forActive BuyersWoodside SearchersMove-Up / Move-In
About 20255 Skyline Blvd
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.
MLS ID #ML82042155, Jennifer Paulson. Listing provided by Christie's International Real Estate Sereno · MLSListings Inc.
Interested in 20255 Skyline Blvd?
Get a personalized analysis with comp data, offer strategy, and neighborhood context.
Property Details for 20255 Skyline Blvd
Overview
- Property Type
- Single Family Residence
- Year Built
- 1963
- Stories
- 2
- Bedrooms
- 3
- Bathrooms
- 3 Full
- Living Area
- 2,400 sqft
- Lot Size
- 130,223 sqft (2.99 acres)
- Price/sqft
- $914
- Status
- ActiveUnderContract
Interior
- Kitchen
- Countertop, tile
- Appliances
- Cooktop electric, Dishwasher, Oven built in, Refrigerator
- Heating
- Radiant
- Cooling
- None
- Laundry
- Inside, In utility room
- Family Room
- Separate family room
- Interior Features
- High ceiling
Exterior and Parking
- Roof
- Composition
- Foundation
- Concrete perimeterand slab
- View
- Bay, City lights, Pasture
- Lot Features
- Grade gently sloped
- Fencing
- Horse fencing
- Zoning
- Rm0000
Community and HOA
- Utilities
- Propane
- County
- San Mateo
- City
- Woodside
Schools
- School District
- La Honda Pescadero Unified
- Woodside Schools
- View Woodside schools
Listing
- MLS Number
- ML82042155
- Listed
- April 8, 2026
- Days on Market
- 184
- Listing Agent
- Jennifer Paulson
- Listing Brokerage
- Christie's International Real Estate Sereno
- Data Verified
- October 9, 2026
Source: MLSListings Inc. School attendance boundaries are set by the district and can change; verify directly with the district.
Free from Aegis · Updated for October 2026
Three Woodside Reports the Listing Does Not Give You
📄Woodside Market ReportFree 9-page PDF with bedroom breakdowns, comp data and pricing trends, updated monthly.Email Me the Report →📋Woodside Buyer BriefA personalized brief with comp data, offer strategy and neighborhood context.Email Me the Report →🎯Woodside Offer StrategyComp analysis and bid recommendations before you write an offer on this home.Email Me the Report →
Location
20255 Skyline Blvd, Woodside, CA 94062 · San Mateo County
Market Context
Price Positioning
🏠 Inventory: 7 3-bedroom homes and 25 single family homes currently active in Woodside.
Source: MLSListings Inc. Timothy Alston, Broker, DRE# 01328224.
Want to know what this home will actually sell for? Get a data-backed offer range based on recent comparable sales.
Get My Offer Range →Frequently Asked Questions
Listed at $2,195,000 ($914/sqft). The three most recent 3-bedroom sales in 94062 closed at $814 to $1,859 per sqft.
Listed April 8, 2026. That is 184 days on market as of October 9, 2026.
Est. $13,938/mo with 20% down ($439,000) at 6.75%. That is principal and interest $11,389, property tax $2,286 and insurance $262. The assumptions and lender disclosure are with the payment estimate at the top of this page.
There are 27 active listings in Woodside: 7 are 3-bedroom and 25 are single family homes.
The three most recent 3-bedroom sales in Woodside 94062 closed at $3,175,000, $3,705,000 and $4,758,000, or $814 to $1,859 per sqft.
Yes. As of October 9, 2026, 20255 Skyline Blvd is an active listing at $2,195,000. It is a 3-bedroom, 3-bath single family home.
See This Home · Scheduling Is Free
Timothy Alston
Broker · DRE# 01328224 · Over 23 Years Experience
Tour 20255 Skyline Blvd
Request a private showing and Timothy will confirm the time with you.
or call (408) 207-4593 nowBy proceeding, you consent to be contacted by Aegis Luxury Real Estate at the number and email provided. Privacy Policy
Not ready to tour yet?
🎯 Get the Offer Strategy report →Free Woodside Reports
October 2026. Built on the same live MLS data Timothy uses with clients.
Market ReportEmail it to me →Buyer BriefEmail it to me →Offer StrategyEmail it to me →
For Homeowners
Get My Home's Value
What would your Woodside home sell for today?
Woodside homes sold at N/A% of list price in a median of N/A days in the latest closed month.
N/A%Sale-to-List, recent
N/AMedian Days, recent
Free. No obligation. Takes 30 seconds.
More in Woodside
View All Listings →Explore Woodside real estate
Recently Sold in Woodside
Closed within 6 months · 3 bed / similar sqft · Woodside 94062
496 Raymundo Dr
Sold $3,175,000
3 bd · 2.5 ba · 3,900 sqft
$814/sqft
$814/sqft
Closed Sep 14, 2026 · 11 days on market
MLS ID #ML82054634, Don DeFranco. Listing provided by Compass · MLSListings Inc.855 Patrol Rd
Sold $3,705,000
3 bd · 2 ba · 2,105 sqft
$1,760/sqft
$1,760/sqft
Closed Sep 08, 2026 · 62 days on market
MLS ID #ML82050036, Helen Miller. Listing provided by Compass · MLSListings Inc.510 Woodside Dr
Sold $4,758,000
3 bd · 3.5 ba · 2,560 sqft
$1,858/sqft
$1,858/sqft
Closed Aug 26, 2026 · 2 days on market
MLS ID #ML82057851, Yu Chih Chiang. Listing provided by Casa Nova Realtors Inc. · MLSListings Inc.Source: MLSListings Inc. Closed sales data.
For Homeowners
Your neighbors are selling. Should you?
What happens when the right home lists and nobody knows you are looking for it?
In Woodside, 1 new listings hit the MLS this week. By the time most search sites update, the window has already narrowed.
Nearby Homes
View All 25 →
New
$14,900,000
600 Moore Rd, Woodside
7 bed8 bath7,155 sqft
MLS ID #ML82043745, Erika Demma. Listing provided by Compass · MLSListings Inc.
New
$19,950,000
235 Harcross Rd, Woodside
5 bed6.5 bath6,990 sqft
MLS ID #ML82064103, Helen Miller. Listing provided by Compass · MLSListings Inc.
New
$2,150,000
235 Hillside Dr, Woodside
3 bed2 bath1,500 sqft
MLS ID #ML82032924, Steve Rumberg. Listing provided by Keller Williams Realty-Silicon Valley · MLSListings Inc.
Similar Homes
View All 7 →3 bed · $1.6M-$2.7M · Active in Woodside
New This Week
$2,150,000
235 Hillside Dr, Woodside
3 bed2 bath1,500 sqft
MLS ID #ML82032924, Steve Rumberg. Listing provided by Keller Williams Realty-Silicon Valley · MLSListings Inc.
New This Week
$1,950,000
115 Forest View Rd, Woodside
3 bed3 bath2,724 sqft
MLS ID #ML82059245, Scott Dancer. Listing provided by Compass · MLSListings Inc.
New This Week
$2,100,000
20421 Skyline Blvd, Woodside
3 bed2.5 bath2,180 sqft
MLS ID #ML82056662, Scott Hayes. Listing provided by Compass · MLSListings Inc.
Nearby Open Houses
See All →
OPEN SAT, 1:30PM TO 4:30PM$10,988,000
160 Phillip Rd, Woodside
5 bd · 5.5 ba · 6,410 sqft
MLS ID #ML82037743, DeLeon Team. Listing provided by Deleon Realty · MLSListings Inc.
OPEN SAT, 2PM TO 4PM$1,599,000
164 Filbert Rd, Woodside
3 bd · 2 ba · 1,900 sqft
MLS ID #ML82063250, Kristjan Higdon. Listing provided by eXp Realty of California Inc · MLSListings Inc.
OPEN SAT, 1:30PM TO 4:30PM$4,588,000
61 Oak Haven Way, Woodside
4 bd · 3.5 ba · 4,150 sqft
MLS ID #ML82050181, DeLeon Team. Listing provided by Deleon Realty · MLSListings Inc.
OPEN SUN, 1PM TO 4PM$4,950,000
103 Toyon Ct, Woodside
4 bd · 3.5 ba · 3,090 sqft
MLS ID #ML82046648, Hugh Cornish. Listing provided by Coldwell Banker Realty · MLSListings Inc.
OPEN SUN, 2PM TO 4PM$3,389,000
411 Glenwood Ave, Woodside
3 bd · 2 ba · 1,690 sqft
MLS ID #ML82059026, Chris Iverson. Listing provided by Golden Gate Sotheby's International Realty · MLSListings Inc.
Buyers
See 20255 Skyline Blvd before the weekend
Listed 184 days ago.
Questions
Talk to Timothy directly
Timothy Alston, Broker, DRE# 01328224. Over 23 years in Silicon Valley real estate.
Explore Woodside Homes
Woodside by Listing Status
Explore Nearby San Mateo County Cities
San Mateo County Market Brief
- Weekly market data
- New listing alerts
- Price trend analysis
- Unsubscribe anytime
You'll receive a confirmation email. No spam. One-click unsubscribe.
