For sale Home

Listed Oct 23, 2026

$2,499,000 Est. $16,529/mo

215 Winding Way

  • 4

    Beds

  • 3

    Baths

  • 2,470

    Sq ft

The story

Nestled in the hills above downtown San Carlos, this striking contemporary residence designed by Fred Herring offers a masterclass in architectural character. The home immediately impresses with its signature curved vaulted ceilings and a dramatic wall of windows that frame sweeping canyon and neighborhood views. Thoughtfully designed for both entertaining and privacy, the layout features seamless living spaces on the entry level that flow naturally toward the scenery. Two bedrooms are tucked away on their own level, providing a serene retreat with peaceful views of the surrounding trees and landscape. A third bedroom and full hall bathroom are situated on a separate split level, offering a flexible and spacious floor plan. The primary suite occupies its own expansive wing, serving as a true sanctuary. Double doors open onto a private deck, while the luxurious en suite bathroom features a generous soaking tub and a separate shower. This residence offers a premier address with effortless access to tech hubs such as Meta and Google. Situated moments from the greenery of Highland Park, it blends urban convenience with the prestige of a highly sought-after school district. A standout choice in The City of Good Living.

Facts & features

Home type

Home

Year built

2003

Floors

2

Price per sq ft

$1,012

Parking

2-car garage

Included features

  • Fireplace

    Yes

  • Cooling

    Central Air

  • Heating

    Central

  • Appliances

    Dishwasher, Electric Oven, Freezer, Microwave, Refrigerator, Range Hood

  • Flooring

    Carpet, Wood

  • Roof

    Bitumen, Composition, Shingle

  • Lot Information

    Sloped Down

  • Water Source

    Public

  • Sewer

    Public Sewer

  • View

    Mountain

Mortgage calculator

Estimated monthly payment

$16,529 /mo

7% rate · 30-yr fixed · 20% down

  • Principal & interest $13,301
  • Property tax $2,499
  • Insurance $729

Includes principal, interest, taxes & insurance.

Your Property Journey

Interested in this, or something like it?

Submit an inquiry

Drop your details and we will help you find what you are looking for.

Not quite. Help me find the right one

Talk it through or type it out, whichever feels easiest.

Your contact details

An agent will reach out personally, no automated calls.

Smart Assistant

Hi, how can I help you find your dream home?

Tap the voice button to talk, or just start typing.

Tap anywhere to fix a word or add more

Tap stop when you’re done. You can edit the text before searching.

By submitting, you agree to our Privacy Policy and Terms.

Listing Broker

Compass

Broker Name

Compass

Agent

Soraya Orumchian

Location

Half Moon Bay CA 94019