Portola Valley, California

Upland

Quiet hillside streets above Portola Road, where mid-century ranches and updated family homes sit among oaks near the town’s center.

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The neighborhood

Upland Portola Valley homes for sale in a singular setting.

Upland is a tucked-away residential pocket in north-central Portola Valley, reached from Portola Road and Alpine Road. Winding streets climb gently through oak woodland, lined with ranch homes, split-levels and thoughtfully remodeled residences on generous lots.

Buyers are drawn to Upland’s balance: a genuinely quiet, wooded setting that is still minutes from the Town Center, top-ranked Portola Valley schools and Highway 280. For sellers, the neighborhood’s privacy, mature landscaping and central location are the story to tell.

Wooded settingOak-lined streets on generous lots

CentralMinutes to the Town Center and 280

SchoolsClose to Ormondale and Corte Madera

A sense of place

Quiet, wooded and wonderfully central.

Upland feels like a retreat that happens to be central. Streets curve through native oaks and bays, homes sit back on landscaped lots, and the sounds are birdsong and breeze rather than traffic. Yet the Town Center’s library, farmers’ market and playing fields are only minutes away.

ArchitectureRanch and split-level homes, many remodeled, plus newer custom residences.

LandscapeNative oaks, terraced gardens and shaded private drives.

Daily lifeSchool commutes, Town Center errands and evening walks under the oaks.

01 / Education

Schools near Upland 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 elementary school campus building

District resources

District and campus resources for Upland buyers.

Upland 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

02 / Parks

Green space woven into everyday routes.

The Town Center’s redwood grove, playing fields and playground are the neighborhood’s front yard, with Windy Hill’s trails a short drive south.

Golden grassland hiking trail with hills near Portola Valley

Portola Valley Town Center

Redwood grove, playground, fields and library · 765 Portola Road

Windy Hill Open Space Preserve

1,335-acre preserve · 555 Portola Road · 12+ miles of trails

Official site

Neighborhood paths

Oak-shaded walking routes connecting Upland streets to Portola Road

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

Nearby outdoors

Hiking & Trails

Upland residents walk out the door into oak woodland, then drive minutes to the foothill trailheads.

Windy Hill trails

Spring Ridge and Anniversary trails with summit panoramas.

Official site

Coal Creek Open Space Preserve

Redwood canyon trails reached via Alpine Road.

Alpine Road cycling

A classic Peninsula climb from Portola Valley toward Skyline.

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

03 / Local life

Amenities near Upland Portola Valley homes.

The Town Center covers daily life — library, market, playing fields — while the Alpine Inn, Stanford Shopping Center and downtown Palo Alto handle dining and shopping.

Luxury home exterior at dusk among oak trees — Remodeled ranch home among native oaks

Modern patio and outdoor living space at a Portola Valley home — Terraced gardens and shaded outdoor rooms

Dining

Alpine Inn & local tables

Alpine Inn, the 1852 tavern and beer garden at 3915 Alpine Road, is the area’s beloved gathering spot. Portola Valley kitchens and nearby Woodside and Palo Alto restaurants cover the rest.

Shopping

Town Center & markets

The Thursday farmers’ market sets up in front of the historic schoolhouse at 765 Portola Road. Stanford Shopping Center and downtown Palo Alto are minutes east via Alpine Road.

Everyday

Groceries & services

Bianchini’s Market in Ladera and Roberts Market in Woodside serve daily needs, with banks, coffeehouses and professional offices along the Alpine Road corridor.

Map & getting around

Getting around Upland.

Upland sits in north-central Portola Valley, close to Portola Road and the Town Center. These are the everyday destinations Upland residents drive to most.

4 min

Portola Valley Town Center

4 min drive · Portola Valley area

Directions

6 min

Windy Hill Open Space Preserve

6 min drive · Portola Valley area

Directions

8 min

Alpine Inn

8 min drive · Portola Valley area

Directions

14 min

Stanford University

14 min drive · Portola Valley area

Directions

15 min

Downtown Palo Alto

15 min drive · Portola Valley area

Directions

20 min

Palo Alto Airport

20 min drive · Portola Valley area

Directions

28 min

Norman Y. Mineta San Jose International Airport

28 min drive · Portola Valley area

Directions

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

Market snapshot

Home values in Upland.

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

$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 Upland?

Upland’s wooded lots reward a property-by-property approach. Compare lot usability, tree cover, privacy, improvements and indoor-outdoor flow, then consider how each address connects to Portola Road, the Town Center and school routes.

School assignments and property details should be verified for the exact address. Local guidance can help you evaluate comparable sales and understand how an original ranch, an updated split-level or a newer custom home fits the neighborhood.

Call (650) 274-1134 Email Simon

Seller guidance

Selling your Upland home?

An Upland marketing plan should bring the setting into focus. Mature oaks, terraced gardens, remodeled interiors and the rare combination of seclusion and centrality all shape how the home is presented.

Thoughtful preparation starts with the specific home, its lot and relevant comparable sales. From pricing and presentation to launch strategy, the goal is to connect the property with buyers who value Upland’s quiet, wooded character.

Call (650) 274-1134 Email Simon

Buyer & seller questions

Upland real estate FAQ.

What types of homes are found in Upland?

Upland includes ranch and split-level homes — many thoughtfully remodeled — plus newer custom residences, set on generous oak-wooded lots above Portola Road.

Which public school districts serve Upland?

Upland is served by the Portola Valley School District for grades K–8 and the Sequoia Union High School District for high school. Buyers should confirm the exact property address directly with each district.

What parks are near Upland homes?

The Portola Valley Town Center’s redwood grove, playground and fields are minutes away, and Windy Hill Open Space Preserve offers 12+ miles of trails just south.

What should buyers consider when comparing Upland homes?

Compare lot usability, privacy, tree cover, improvements and exact location, then independently verify school placement and property-specific details before making a decision.

How should an Upland seller prepare for the market?

A strong plan should present the home’s setting, improvements, landscaping and central-yet-secluded location clearly, supported by property-specific pricing and marketing guidance.

Continue exploring

Explore more Portola Valley neighborhoods.

Local guidance

Explore Upland with Simon Sahi.

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

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