Hillstone

Where Hillstone Sits

Hillstone is a small enclave of 1990s estate homes in the Evergreen foothills of east San Jose, ZIP 95138, built along Hillstone Drive and the neighboring streets just south of Yerba Buena Road and east of Silver Creek Valley Road. Listing remarks usually call it Hillstone Estates, and it backs onto open hillside with valley views from many of the lots. An older version of this page described Hillstone as a 1960s ranch tract in Blossom Valley, and that was simply wrong, so if you saw it, set it aside.

This is a different kind of San Jose neighborhood than the flatland tracts most people picture. It sits between the older parts of Evergreen and the newer hillside communities of Silver Creek, with Silver Creek Valley Country Club a few minutes south. For the bigger picture on the east side, see my guide to living in San Jose.

Homes in Hillstone

The homes went up in the mid 1990s, with 1996 the build year on the recent sales I have reviewed. They are large single-level homes, typically five bedrooms and three baths in roughly 2,850 to 3,000 square feet, with three car garages and lots running from about three quarters of an acre to well over an acre. Pools, spas, mature fruit trees and big view yards are common, and several owners have added owned solar.

There is a homeowners association, but dues are modest, recently around $100 to $125 a month based on listing records. On any hillside lot this size I look closely at drainage, retaining walls, the age of the pool equipment, and fire insurance availability, since Redfin’s climate data puts wildfire risk here a notch above the flatlands.

Schools Serving Hillstone

Elementary and middle schools are in the Evergreen School District, and listing records show James Franklin Smith Elementary and Chaboya Middle as the assigned schools. High school is in the East Side Union High School District, with Silver Creek High assigned and Evergreen Valley High also close by. I confirm assignment with the district for a specific address before any offer.

Parks, Errands and Getting Around

This is a car neighborhood, with a Walk Score in the 20s. Groceries, pharmacies and restaurants are a few minutes away along Yerba Buena Road, San Felipe Road and Silver Creek Valley Road, and Evergreen Valley College and Montgomery Hill Park are close for a walk on the trails. The open hillside behind the homes is a big part of the appeal.

Highway 101 is roughly ten minutes away via Yerba Buena Road or Capitol Expressway, which puts downtown San Jose about twenty minutes out outside rush hour. Transit is limited this far up the hill, so plan on driving for nearly everything.

Healthcare and Senior Services Nearby

Regional Medical Center on North Jackson Avenue, now owned by Santa Clara County, and Kaiser Permanente’s San Jose Medical Center off Cottle Road are each about fifteen to twenty minutes away by car. Closer to home, the city’s Evergreen Community Center at 4860 San Felipe Road is one of the sites in San Jose’s programs for adults 50 and over, with Senior Nutrition Program lunches, classes and social activities.

Is Hillstone a Good Fit for Downsizers?

Hillstone is more often where people move up than where they downsize, but it has one big thing going for it: these are single-level homes, so the main living space has no stairs. The tradeoff is scale. A 3,000 square foot house on an acre with a pool is a lot to maintain, the streets are hilly, and nearly every errand means a drive. Many of the longtime owners I talk with here are weighing whether to stay and age in place or sell and move closer to services, and my article on whether to stay, downsize or move walks through that decision.

If you do sell, you may be able to take your current property tax base with you to a smaller home anywhere in California under Prop 19, and my Prop 19 calculator shows roughly what that is worth. For buyers coming the other way, the modest HOA and the single-level layouts are a real advantage over newer two-story hillside homes.

The Hillstone Housing Market

With only a few dozen homes, Hillstone does not have its own market statistics, so I look at individual sales alongside the ZIP code. Recent sales in the neighborhood include $3.1M in June 2025 and about $3.8M in 2026. For the wider 95138 ZIP, Redfin’s 95138 market data shows a median sale price of about $1.61M for the three months ending September 2026, down 2.1% from a year earlier, with homes selling in a median of 16 days. Hillstone sits well above that ZIP median because of the lot sizes and the views.

Frequently Asked Questions About Hillstone

If you have owned in Hillstone since the homes were new and the house is starting to feel like more than you want to manage, or you are looking for a single-level home with room and a view, I would be glad to talk it over. I work mostly with longtime homeowners and their families, so the conversation covers the whole move, not just the listing. Book a call with me or reach me at 408-413-3087.