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san jose neighborhood guide · property nerds® at compass
Cadillac-Winchester, San Jose Homes for sale, recent sales and a Property Nerd’s guide
San Jose's blocks between San Tomas Expressway and Winchester Boulevard south of Payne Avenue: 1960s ranch homes, apartment streets and 1972 townhome squares, with Campbell starting just short of Hamilton.
Cadillac-Winchester by the numbers
cadillac-winchester by the numbers · live from the mls
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Calculated in your browser from MLS data for Cadillac-Winchester (approximate outline traced from the boundary streets). Sales are single-family homes, townhomes and condos.
homes in cadillac-winchester · live from the mls
Homes for sale, for rent and recently sold in Cadillac-Winchester
Every active listing, rental and closed sale in Cadillac-Winchester from the MLS, updated automatically, with a map of the neighborhood outline.
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Listings come from MLSListings and other MLSs through IDX and show their listing brokerage; confirm details with the listing agent. The map outline is the neighborhood boundary used by our listing search (Cadillac-Winchester (approximate outline traced from the boundary streets)); it may not match every local definition.
the story
How Cadillac-Winchester came to be
The name comes from Cadillac Drive, which runs through the middle of these blocks. The City of San Jose's neighborhood map labels the area Cadillac Winchester, and the city's neighborhood-association map shows a Cadillac-Winchester Neighborhood Association covering the eastern half, out to Winchester Boulevard. Listing records mostly file homes here under the broad names West San Jose or Winchester, with a few small tract names such as Merrivale West Townhomes and Loma Verde.
County assessor years in public parcel data show the eastern blocks filling in over less than a decade. Apartment buildings went up on Cadillac Drive and Impala Drive in 1957-60 and fourplexes lined Williamsburg Drive in 1962. The single-family streets came at the same time: Antonio Lane and Maria Way around 1960, then Cadillac Drive, Merrimac Drive and Valley Forge Way in 1961-63. Duplexes and small apartment buildings followed on Essex Way and Lexington Drive in 1964-67. The city's tract map shows about 20 separately recorded tracts inside this outline.
The west end came later. In 1972 a single 249-lot tract filled the land beside San Tomas Expressway with townhome squares: Merrivale West Square, Charmwood Square, Cherrywood Square, Golden Meadow Square, Pinehurst Square and Woodgrove Square, plus Millich Lane and Millich Court. A 52-unit townhome complex on Loma Verde Drive followed in 1976-77, a small group on Phelps Avenue in 1980, and townhomes on Traviata Place and Payne Avenue in 2002. Since then the city's General Plan has drawn its Winchester Boulevard urban village over the Winchester frontage and the apartment blocks behind it; the city's growth-area layer marks that village plan as approved.
streets and homes
The streets and the houses
Payne Avenue and Winchester Boulevard frame the north and east sides, and the streets inside are short and mixed. The single-family blocks are Antonio Lane, Maria Way, Merrimac Drive, Valley Forge Way and parts of Cadillac Drive, Essex Way and Lexington Drive. The homes are single-story ranch houses on lots of about 6,000 square feet, and about four in five list three or four bedrooms in assessor records; only 34 of the 185 houses list a second story. Cadillac Drive itself is half houses and half apartment buildings, and Impala Drive, Williamsburg Drive, Eden Avenue and Loma Verde Drive are mostly apartments, duplexes and fourplexes.
The townhome squares at the west end are their own world: each square holds about 32 to 37 attached homes, all built in 1972 under one tract, with the shared areas run by homeowners associations. The Loma Verde Drive complex (52 units) and the 2002 townhomes on Traviata Place work the same way. Expect association documents, shared roofs and walls, and assigned parking rather than driveways.
On the city's zoning map, the apartment and townhome blocks are R-M (multiple residence), the single-family streets are R-1-8, parts of Cadillac Drive and Lexington Drive are R-2, and the Winchester Boulevard frontage is commercial. The General Plan calls the apartment blocks Urban Residential and the house and townhome streets Residential Neighborhood. In practice the single-family streets see remodels and rear additions rather than tear-downs, while the urban-village blocks along Winchester are where the city expects new, denser buildings over time.
streets in cadillac-winchester
- Payne Ave
- S. Winchester Blvd
- San Tomas Expwy
- Cadillac Dr
- Antonio Ln
- Maria Way
- Essex Way
- Lexington Dr
- Merrimac Dr
- Valley Forge Way
- Impala Dr
- Williamsburg Dr
- Eden Ave
- Loma Verde Dr
- Apple Blossom Ln
- Traviata Pl
- Phelps Ave
- Millich Ln
- Millich Ct
- Merrivale West Sq
- Charmwood Sq
- Cherrywood Sq
- Golden Meadow Sq
- Pinehurst Sq
- Woodgrove Sq
parks and places
Parks, shops and landmarks near Cadillac-Winchester
- park
Payne Ave Friendship Park
A 1.9-acre City of San Jose park at 3257 Payne Avenue, just across Payne Avenue on the north side (city parks layer).
- park
Marijane Hamann Park
About half a mile east across Winchester Boulevard, straight-line: 9.7 acres in the city parks layer, with three lighted tennis courts, soccer and softball fields, picnic areas and play areas.
- shopping
Winchester Boulevard frontage
The east edge is a commercial strip of shops, offices and service businesses on the city's zoning map, inside the Winchester Boulevard urban village.
- shopping
Santana Row and Valley Fair
The city's Valley Fair/Santana Row urban village is about 1.3 miles north across I-280, straight-line.
- landmark
San Tomas Aquino Creek
Public maps show the creek running beside San Tomas Expressway along the west edge.
schools and commute
School districts and getting around
School districts
Two elementary districts split this small area. U.S. Census school-district maps put the central and eastern streets (Cadillac Dr, Maria Way, Antonio Ln, Essex Way, Lexington Dr, Merrimac Dr, Valley Forge Way, Impala Dr, Williamsburg Dr, Eden Ave and Loma Verde Dr) in the Campbell Union School District, and the townhome squares along Millich Ln, Millich Ct and Phelps Ave in the Moreland School District. High school is the Campbell Union High School District throughout. No public school sits inside the outline. Moreland's Payne Elementary on Gleason Avenue is about 0.3 mile west across San Tomas Expressway, straight-line, and Campbell Union's Rosemary Elementary is on W. Hamilton Avenue in Campbell, just south of the city line. Attendance boundaries change, so check the exact address with each district.
Campbell Union guide · Moreland School District guide · Campbell Union High guide
Getting around
- Bus: VTA Route 60 runs on Winchester Boulevard between Winchester light rail station and Milpitas BART, with stops at Payne Avenue, Cadillac Drive (southbound) and Hamilton Avenue.
- Light rail: VTA's Hamilton station is about 0.8 mile east and Winchester station about 1.1 miles southeast of the nearest edge, straight-line; both are in Campbell.
- Driving: San Tomas Expressway runs along the west edge. Highway 17's Hamilton Avenue interchange is about 0.6 mile east of Winchester Boulevard and I-280's Winchester Boulevard interchange about 1 mile north, straight-line.
- Caltrain: the nearest stations, San Jose Diridon and Santa Clara, are about 3.3 to 3.6 miles away, straight-line.
- Walking: Payne Ave Friendship Park is across Payne Avenue, and Payne Elementary and the small Gleason Park are just across the expressway.
nerd notes
Buying or selling in Cadillac-Winchester: what we check
Buying here
- Confirm the city on the parcel record. The San Jose line stops short of Hamilton Avenue, and the south ends of Eden Ave, Merrimac Dr, Valley Forge Way, Millich Dr and Phelps Ave are in Campbell. County street data shows some of those Campbell segments with San Jose 95117 mailing addresses, so the address alone will not tell you which city issues permits.
- Check the elementary district by address: Census maps put the townhome squares at the west end in Moreland and the rest in Campbell Union. Boundaries change, so confirm with the district.
- For the 1972 townhome squares and the Loma Verde Drive complex, read the HOA budget, reserve study, CC&Rs, rules and recent minutes, and check current dues and any special assessments. Ask about roof, siding and plumbing work on 50-year-old buildings.
- Flood: FEMA's map puts nearly all of this area in Zone D, where flood hazards are possible but have not been studied. Look up the address on the FEMA map, ask your lender whether flood insurance is required, and get an insurance quote.
- Plans and zoning: much of the area is inside the Winchester Boulevard urban village, and the apartment blocks are zoned R-M, so neighboring parcels may redevelop over time. For houses on R-1-8 lots, check current San Jose ADU and SB 9 rules, the electrical panel, older plumbing and the sewer lateral before you plan a remodel.
Selling here
- List the city as San Jose and name the right elementary district for your street (Campbell Union or Moreland), plus Campbell Union High. Buyers often guess wrong this close to the Campbell line.
- Townhome and condo sellers: have the HOA documents, budget, reserve study and dues history ready before the listing goes live.
- Gather permits for additions, garage conversions and window or electrical upgrades; 1960s houses get close inspection of the roof, sewer lateral, panel and termite history.
- Mention ADU or SB 9 potential only after checking current San Jose rules for your lot, and disclose the FEMA Zone D mapping with any insurance quote you have.
nerd noteCommissions are always negotiable, and we offer bundled services, so ask us what's included.
faq
Cadillac-Winchester questions, answered
Is Cadillac-Winchester in San Jose or Campbell?
The blocks in this guide are City of San Jose land with San Jose 95117 addresses. Campbell begins just north of Hamilton Avenue, so Hamilton Avenue itself and the south ends of Eden Ave, Merrimac Dr, Valley Forge Way, Millich Dr and Phelps Ave are in Campbell. Check the parcel record for any address near the line.
Where does the name come from?
From Cadillac Drive and Winchester Boulevard. The city's neighborhood map labels the area Cadillac Winchester, and a Cadillac-Winchester Neighborhood Association appears on the city's association map for the eastern blocks.
Which school districts serve the area?
Two elementary districts: Campbell Union for the central and eastern streets and Moreland for the townhome squares at the west end, per Census maps. High school is Campbell Union High. Check the exact address with each district, since boundaries change.
What does FEMA Zone D mean here?
FEMA uses Zone D for areas with possible but undetermined flood hazards, where no flood study has been done. Nearly all of this area is mapped that way. Check the address on the FEMA map and ask your lender and insurer what it means for your loan and premium.
What is the Winchester Boulevard urban village?
It is a growth area in San Jose's General Plan, and the city's map shows its plan as approved. Here it covers the Winchester frontage and the apartment blocks around Eden Ave, Loma Verde Dr, Impala Dr, Lexington Dr, Essex Way and Williamsburg Dr. Check the plan and zoning for a specific parcel and its neighbors.
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