Cadillac West

Where Cadillac West Sits

Cadillac West is a small pocket on the west side of San Jose, tucked between San Tomas Expressway and Eden Avenue just north of Hamilton Avenue. The core streets are Valley Forge Way, Cadillac Drive, Merrimac Drive, Maria Way and Millich Drive, and the name comes from Cadillac Drive itself, which continues east across Eden toward Winchester Boulevard. One thing I want to clear up, because an older version of this page had it wrong: this is not a south San Jose tract off Snell Avenue. It sits right on the San Jose and Campbell line, near the Winchester neighborhood and the rest of West San Jose.

That city line matters more than you might think. The detached homes on the 3300 and 3400 blocks generally carry San Jose 95117 addresses, while the townhomes and condos along Valley Forge Way and Millich Drive carry Campbell 95008 addresses, and the local MLS files the whole pocket under its Campbell area. In practice it lives like Campbell, with Campbell schools and downtown Campbell a few minutes away, so my Campbell area guide is worth a read alongside my guide to living in San Jose.

Homes in Cadillac West

There are really three kinds of housing here. The detached homes are single-story ranches from the early 1960s, the ones I have pulled records on were built around 1963, typically three or four bedrooms and two baths in the 1,300 to 1,750 square foot range on lots of roughly 6,000 square feet with two car garages. Then there are two-story townhomes of about 1,100 to 1,250 square feet with two or three bedrooms, and finally small two-bedroom, one-bath condos of about 840 square feet along Valley Forge Way.

That mix gives Cadillac West an unusually wide price range for such a small area, and it means the neighborhood median can swing a lot depending on which type happened to sell. Redfin’s climate data from First Street also flags a meaningful share of properties here for long-term flood risk, so on any purchase I pull the FEMA flood zone and get an insurance quote early rather than finding out in escrow.

Schools Serving Cadillac West

Even the San Jose addresses here are served by Campbell districts. Rosemary Elementary in the Campbell Union School District is only a couple of blocks away, and high school is Westmont High in the Campbell Union High School District. Middle school assignment has varied in listing records, so I confirm the current assignment for the specific address with the district before you write an offer.

Shopping, Parks and Getting Around

Redfin rates the area somewhat walkable, and the daily errands are along Hamilton Avenue and Winchester Boulevard, a short walk or bike ride from most of these streets. Downtown Campbell and the Pruneyard are a few minutes south, Westfield Valley Fair and Santana Row are about ten minutes north, and the Los Gatos Creek Trail through Campbell Park is close enough for a regular morning walk.

San Tomas Expressway runs right along the west edge, Highway 17 and Interstate 280 are both a few minutes away, and Highway 85 is a short drive south. VTA’s Green Line light rail stops at Hamilton station in Campbell, and VTA buses run along Hamilton and Winchester.

Healthcare and Senior Services Nearby

Good Samaritan Hospital is the closest full-service hospital, about ten minutes south, and the major medical groups along the Winchester and Saratoga Avenue corridors are close as well. For older adults there are two good senior centers within a few miles. The Campbell Adult Center at the Campbell Community Center serves adults 50 and over with classes, trips and a nutrition program lunch, and the city of San Jose’s Cypress Senior Center runs a weekday lunch program and a full activity calendar.

Is Cadillac West a Good Fit for Downsizers?

For a lot of my clients it is. The detached homes are all on one level with flat lots and attached garages, and if you want something smaller, the 840 square foot condos are single-level units, though you would want to check whether a given unit is upstairs. The townhomes are two-story, which is worth weighing if stairs are a concern. Shopping is walkable, two senior centers and a hospital are within a short drive, and my guide to single-level homes for downsizers covers what to look for.

The condos and townhomes come with HOA dues, so I review the budget, reserve study and any planned assessments before you commit. If you are 55 or older and selling a longtime home elsewhere in California, Prop 19 may let you bring your current property tax base with you, and my Prop 19 calculator gives you a quick estimate of what that is worth.

The Cadillac West Housing Market

With only a few dozen homes changing hands over several years, the numbers here are thin. According to Redfin’s Cadillac West market data, the median sale price for the three months ending September 2026 was $938K, down 29.5% from a year earlier, but that figure rests on just two sales and mostly reflects which type of home sold. A better read comes from recorded sales over the past three years: detached homes have sold from about $1.74M to $2.41M, townhomes from about $900K to $1.1M, and the small condos from about $555K to $625K.

Frequently Asked Questions About Cadillac West

If you have owned in this pocket for decades and are wondering what your home would bring, or you are looking for a one-level house close to downtown Campbell, I would be glad to help you sort through it. My work centers on longtime homeowners and their families, so we will talk about timing and where you are headed, not just price. Book a call with me or reach me at 408-413-3087.