Best Realtors in Woodside, CA (2026 Guide)
By Matthew Martinez
Woodside is a rural incorporated town of about 5,200 people in the hills west of Redwood City and Atherton, reaching from the Woodside Road village center up toward Skyline Boulevard. Homes sit on large lots, many with barns, arenas or trail access for horses, and the town’s design review shapes what can be built. The agents who name Woodside on their profiles work mostly from Woodside and Portola Valley offices.
This guide is published by Diamond Real Estate Group, one of the brokerages listed. Our broker is listed first; other agents are in alphabetical order. The order is not a ranking, and inclusion is not an endorsement.
How we chose the agents in this guide
Each agent below met three checks in October 2026:
- A current California license. We opened each agent’s record on the California Department of Real Estate (DRE) public lookup and confirmed the name, license type (salesperson or broker) and a "Licensed" status, with a responsible broker that matches the brokerage on the agent’s profile.
- A named brokerage. Each agent’s DRE record shows the brokerage they work under.
- A public page that names Woodside. We opened each agent’s brokerage or MLS profile and confirmed it names Woodside, in a service-area list, the agent’s bio or office location.
We did not rank agents, and we did not consider sales volume, reviews or awards. Licenses and affiliations change, so check the license yourself before you sign anything, and interview more than one agent.
Woodside housing in numbers
| Census measure | Woodside town |
|---|---|
| Population (July 1, 2025 estimate) | 5,181 |
| Owner-occupied housing unit rate (2020–2024) | 87.4% |
| Median value of owner-occupied homes (2020–2024) | $2,000,000+ |
| Median gross rent (2020–2024) | $3,500+ |
| Median household income (2020–2024, 2024 dollars) | $250,000+ |
| Persons per household (2020–2024) | 2.87 |
| Mean travel time to work (2020–2024) | 28.8 minutes |
Source: U.S. Census Bureau QuickFacts, Woodside town, California. Values marked "+" are at the top of the Census reporting range, so the true medians are higher.
Nearly nine in ten Woodside homes are owner-occupied, and the Census caps its value figure, so it gives no useful price guide. Ask agents for recent sales with similar acreage, improvements and road access.
Estates, horse property and the hills
Woodside’s village center sits along Woodside Road near Cañada Road. Around it, estate areas along roads such as Mountain Home Road and Old La Honda Road hold homes on one-acre and larger lots, while the western hills rise toward Skyline and the open space preserves. Many properties include stables or connect to the town’s trail network. For more, see our Woodside real estate guide, residential and equestrian property, private road and site access and estate infrastructure inspections pages.
Costs and rules specific to a Woodside purchase
- Transfer tax. The San Mateo County Clerk-Recorder levies the documentary transfer tax at 55 cents per $500, or $1.10 per $1,000 of value: $5,500 on a $5 million sale. The only city conveyance tax the Recorder mentions is the City of San Mateo’s; confirm on your escrow estimate that no other tax applies. Our California transfer tax guide explains who usually pays.
- Design review. The Town’s Architectural and Site Review Board (ASRB) reviews residential applications for community character, site planning, building design and landscaping, and checks them against the Town’s Residential Design Guidelines. The board is advisory; the Planning Director or Planning Commission decides. Budget time for review if you plan a rebuild or large addition.
- Fire hazard and AB 38. Much of the town is wooded hillside. Look up the address on the State Fire Marshal’s Fire Hazard Severity Zone maps; in High or Very High zones, sellers must provide defensible space documentation or an agreement for the buyer to obtain it. See our AB 38 guide and get an insurance quote before you remove contingencies.
- Earthquake faults and slopes. The San Andreas Fault runs through the western part of town. The natural hazard disclosure report shows state-mapped fault and landslide zones; order a geotechnical review for hillside lots.
- Septic, wells and private roads. Many estates use septic systems, and some rely on wells or share private roads. Ask for septic and well records and any road maintenance agreement.
Woodside agents with verified licenses
Matthew Martinez, Diamond Real Estate Group (publisher of this guide)
Matthew Martinez is the Founder, CEO and Managing Broker of Diamond Real Estate Group. He is based in Sonoma County; contact him to discuss a purchase or sale in Woodside. Contact Matthew · Broker #01869679 · Diamond Group Estates Inc DBA Diamond Real Estate Group, DRE #02163490
| Agent | Brokerage | License | Areas named on profile |
|---|---|---|---|
| Derek Cappiello (licensed as Derek Robert Cappiello) | Sotheby’s International Realty | Salesperson #01983178 | Woodside, Atherton, Menlo Park, Redwood City, Los Altos, Half Moon Bay, La Honda |
| Linda Crose-Andersen | Coldwell Banker Realty, Half Moon Bay | Salesperson #01957715 | Woodside, Half Moon Bay, Pescadero, La Honda, El Granada, Montara, Pacifica |
| Erika Demma | Compass, Woodside | Salesperson #01230766 | Woodside, Portola Valley, Atherton, Menlo Park, Palo Alto |
| Scott Hayes (licensed as Scott Packard Hayes) | Compass, Woodside | Salesperson #01401243 | Woodside, Portola Valley, La Honda, the Coastside |
| Ginny Kavanaugh (licensed as Virginia McTigue Kavanaugh) | Coldwell Banker Realty, Portola Valley | Salesperson #00884747 | Woodside, Portola Valley, Atherton, Menlo Park, Palo Alto, Los Altos, Los Altos Hills |
| Stephanie Nash | Compass, Woodside | Salesperson #01104524 | Woodside, Portola Valley, Redwood City, San Carlos |
| Patrick Ryan (licensed as Patrick Joseph Ryan) | Compass, Woodside | Salesperson #01044049 | Woodside office; Pescadero, Half Moon Bay, La Honda, Menlo Park, Redwood City (listings and sales) |
On the DRE record, Coldwell Banker Realty agents are licensed under NRT West, Inc. (DRE #01908304), Compass agents under Compass California II, Inc. (DRE #01527235), and Derek Cappiello under Sotheby’s International Realty Inc (DRE #00899496). License status and brokerage affiliations change; check the DRE record before you hire anyone.
How to vet a Woodside agent
- Ask about estate and horse property. Ask for recent sales with similar acreage, barns or arenas, and how they priced improvements.
- Ask how they handle design review. If you plan to rebuild or add on, ask what they know about ASRB timing and the Residential Design Guidelines.
- Ask about fire and insurance. Ask when they recommend getting quotes and how they handle AB 38 documentation.
- Check septic, wells and roads. Request septic and well records and private road agreements early.
- Confirm permit history. Ask how they verify that guest houses, barns and pools were permitted by the Town.
- Check the license yourself. Confirm a "Licensed" status with a current broker on the DRE lookup.
Woodside questions we hear
Does Woodside have its own transfer tax?
The San Mateo County Clerk-Recorder mentions only the City of San Mateo’s conveyance tax in addition to the county tax of $1.10 per $1,000. Confirm the total on your escrow estimate.
Do I need design review to remodel a Woodside home?
Many residential projects go to the Town’s Architectural and Site Review Board, which makes recommendations to the Planning Director or Planning Commission. Ask the Town’s Planning department what your project requires.
What is the median home value in Woodside?
The Census reports $2,000,000+ for 2020–2024, the top of its range, so the real median is higher. Ask an agent for comparable recent sales.
Why are several of these agents also in the Portola Valley guide?
Woodside and Portola Valley share a market, and many agents list both towns. Our Portola Valley guide lists more agents from the Coldwell Banker office on Portola Road.
Sources & notes
- California DRE public license lookup (individual records linked in the table)
- U.S. Census Bureau QuickFacts, Woodside town, California
- Town of Woodside, Architectural and Site Review Board
- San Mateo County Clerk-Recorder, documentary transfer tax
- CAL FIRE Office of the State Fire Marshal, Fire Hazard Severity Zones
- Agent profiles on coldwellbankerhomes.com, compass.com and mlslistings.com, linked in the table
- License records checked October 2026 on the California DRE public lookup. Last reviewed October 2026 by Matthew Martinez.
Nearby agent guides: Portola Valley · Emerald Hills · Atherton
Related: Woodside real estate guide · Woodside home valuation · San Mateo County agents guide · 20 tips for choosing a real estate agent
License-status update: the linked California DRE public records were checked November 2, 2026 and showed "Licensed." Public profile research retains the dates stated above. Names on DRE records may differ from public profile names; verify status and brokerage before selecting an agent.
