Simon Sahi Real Estate — Real Results

Portola Valley, California

Alpine
Valley

Oak-studded estates along Alpine Road, minutes from the Alpine Inn and the foothill trails of western Portola Valley.

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The neighborhood

Alpine Portola Valley homes for sale in a singular setting.

Alpine is the eastern gateway to Portola Valley’s hill country, where Alpine Road winds past heritage oaks, gated acreage and some of the town’s most significant estates. Homes here range from classic ranch properties to newly built architectural showpieces set behind private gates.

Buyers choose Alpine for its blend of seclusion and access: the Alpine Inn’s historic beer garden is moments away, Portola Valley Ranch and Los Trancos Woods share the ridgeline, and Highway 280 puts Stanford, Sand Hill Road and the wider Silicon Valley within an easy commute. For sellers, Alpine’s larger parcels and estate settings reward presentation that honors the land.

Estate settingGated acreage and heritage oaks along Alpine Road
ConnectedMinutes to Highway 280 and Sand Hill Road
OutdoorsFoothill trails and open-space preserves nearby

A sense of place

Secluded, storied and close to everything.

Alpine feels like countryside with a commute. Winding stretches of Alpine Road pass vineyard estates, shingle-style compounds and modern glass pavilions, all framed by California oaks. The rhythm is quiet and private, yet the town’s social anchors — the Alpine Inn, the Town Center, the Thursday farmers’ market — are a short drive away.

ArchitectureGated estates, ranch compounds and contemporary architectural homes on acreage.
LandscapeHeritage oaks, meadows, vineyard rows and long private drives.
Daily lifeAlpine Inn gatherings, trail rides and quick hops to 280 and Sand Hill Road.

01 / Education

Schools near Alpine Portola Valley homes.

Public school placement is determined by the local districts and can change. Confirm the exact property address directly with the district before relying on an assignment.

California school campus building framed by mature trees
District resources

District and campus resources for Alpine buyers.

Alpine is served by the Portola Valley School District for kindergarten through eighth grade, with high school through the Sequoia Union High School District. Confirm the exact property address directly with each district before relying on an assignment.

Portola Valley School District

Official district and enrollment resources

Official site

Ormondale School

Grades K–3 · 200 Shawnee Pass, Portola Valley

Official site

Corte Madera School

Grades 4–8 · 4575 Alpine Road, Portola Valley

Official site

Woodside High School

Sequoia Union High School District · nearby Woodside

02 / Parks

Open space at the doorstep.

Windy Hill Open Space Preserve rises just south of Alpine Road, and the Los Trancos corridor opens onto miles of Midpeninsula trails.

Hiking trail through golden grassland hills near Portola Valley
01

Windy Hill Open Space Preserve

1,335-acre preserve · 555 Portola Road · summit views to the bay

Official site
02

Portola Valley Town Center

Library, historic schoolhouse and Thursday farmers’ market · 765 Portola Road

03

Alpine Road cycling routes

A beloved Peninsula road-cycling corridor toward Skyline

Facilities and access conditions can change. Review the official preserve and town listings before visiting.

Nearby outdoors

Hiking & Trails

From Alpine, riders and hikers head west into the Santa Cruz Mountain preserves or climb toward Skyline Boulevard.

01

Windy Hill trails

Spring Ridge Trail climbs to the 1,900-foot summit with bay views.

Official site
02

Monte Bello Open Space Preserve

Los Trancos Trail and canyon routes in the hills west of Alpine.

03

Coal Creek Open Space Preserve

Redwood-lined trails off Alpine Road toward Skyline.

Trail conditions, seasonal closures and access rules can change. Check the linked official resources before heading out.

03 / Local life

Amenities near Alpine Portola Valley homes.

The Alpine Inn anchors local social life, while the Town Center, Stanford Shopping Center and downtown Palo Alto cover dining, shopping and services.

Estate home exterior at dusk in Portola Valley
Estate architecture among heritage oaks
Outdoor patio living space at a Portola Valley home
Grounds designed for outdoor living
Dining

The Alpine Inn

Alpine Inn — founded in 1852 as Casa de Tableta and the second-oldest continually operating tavern in California — pours in its beer garden on the banks of Los Trancos Creek at 3915 Alpine Road. Nearby Portola Valley kitchens and Woodside tables round out everyday dining.

Shopping

Town Center & beyond

The Portola Valley Town Center hosts the Thursday farmers’ market in front of the historic schoolhouse at 765 Portola Road. Stanford Shopping Center and downtown Palo Alto are a short drive east.

Everyday

Markets & services

Bianchini’s Market in nearby Ladera and Roberts Market in Woodside cover daily groceries, with coffeehouses, dry cleaners and professional services along the Alpine Road corridor.

Map & getting around

Getting around Alpine.

Alpine sits near the eastern edge of Portola Valley, close to Highway 280 and the Alpine Road corridor. These are the everyday destinations Alpine residents drive to most.

8 min

Portola Valley Town Center

8 min drive · Portola Valley area

Directions
4 min

Alpine Inn

4 min drive · Portola Valley area

Directions
10 min

Windy Hill Open Space Preserve

10 min drive · Portola Valley area

Directions
12 min

Stanford University

12 min drive · Portola Valley area

Directions
14 min

Downtown Palo Alto

14 min drive · Portola Valley area

Directions
25 min

Norman Y. Mineta San Jose International Airport

25 min drive · Portola Valley area

Directions
30 min

San Francisco International Airport

30 min drive · Portola Valley area

Directions
Drive times are approximate and vary with traffic. Tap Directions for live routing.

Market snapshot

Home values in Alpine.

Portola Valley commands some of the Peninsula’s strongest home values. Here’s a quick snapshot of the market around Alpine.

$250K+

Median household income

Citywide approx. · U.S. Census ACS 5-year

$4.0M

Median home price

Citywide approx. · Zillow & Redfin market data

$20M+

High-end price point

Citywide approx. · recent top sale $56M, Nov 2025

Figures are approximate as of Sept 2026. Sources: U.S. Census Bureau (ACS), Zillow/Redfin market data.

Buyer guidance

Buying a home in Alpine?

Alpine’s estate market rewards a property-by-property approach. Compare acreage, usable land, privacy, improvements and access, then consider how each address connects to Alpine Road, the Alpine Inn corridor and Highway 280.

School assignments and property details should be verified for the exact address. Local guidance can help you evaluate comparable estate sales and understand how an original ranch, a remodeled compound or a newer architectural home fits the Alpine landscape.

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Seller guidance

Selling your Alpine home?

An Alpine marketing plan should bring the property’s setting into focus. Acreage, heritage oaks, views, guest houses, pools and proximity to Portola Valley’s trail network and town anchors all shape how an estate is presented.

Thoughtful preparation starts with the specific property, its land and relevant comparable sales. From pricing and presentation to launch strategy, the goal is to connect the estate with buyers who understand what makes Alpine distinctive.

Call (650) 274-1134Email Simon

Buyer & seller questions

Alpine real estate FAQ.

What types of homes are found in Alpine?

Alpine includes gated estates on multi-acre parcels, ranch compounds, shingle-style residences and contemporary architectural homes, many framed by heritage oaks and long private drives.

Which public school districts serve Alpine?

Alpine is served by the Portola Valley School District for grades K–8 and the Sequoia Union High School District for high school. Assignments can change, so buyers should confirm the exact property address directly with each district.

What outdoor recreation is near Alpine homes?

Windy Hill Open Space Preserve, Monte Bello and Coal Creek preserves, and the Alpine Road cycling corridor are all close by, with miles of hiking, riding and road-cycling routes.

What should buyers consider when comparing Alpine homes?

Compare usable acreage, privacy, improvements, guest facilities and exact location along the Alpine Road corridor, then independently verify school placement and property-specific details before making a decision.

How should an Alpine seller prepare for the market?

A strong plan should present the estate’s land, architecture, improvements and setting clearly, supported by property-specific pricing and marketing guidance from a local specialist.

Continue exploring

Explore more Portola Valley neighborhoods.

Local guidance

Explore Alpine with Simon Sahi.

For a property-specific view of Alpine homes, school placement, neighborhood edges and nearby amenities, begin with the exact address and a thoughtful local conversation.

Simon Sahi
Visit SimonSahi.com(650) 274-1134SIMON@SPSILICONVALLEY.COMCA DRE #01953287