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monte sereno neighborhood guide · property nerds® at compass
Daves Avenue & Vineland, Monte Sereno Homes for sale, recent sales and a Property Nerd’s guide
East Monte Sereno between Palos Verdes Drive and Winchester Boulevard: Daves Avenue Elementary, the Vineland Avenue blocks and Karl Avenue, with lots that step down from an acre to 8,000 sq ft near Winchester.
Daves Avenue by the numbers
daves avenue by the numbers · live from the mls
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Calculated in your browser from MLS data for Daves Avenue (approximate outline traced from the boundary streets). Sales are single-family homes, townhomes and condos.
homes in daves avenue · live from the mls
Homes for sale, for rent and recently sold in Daves Avenue
Every active listing, rental and closed sale in Daves Avenue 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 (Daves Avenue (approximate outline traced from the boundary streets)); it may not match every local definition.
the story
How Daves Avenue came to be
Daves Avenue was ranch road before it was a school street. A 1954 aerial in the city's history file labels a 'Daves Estate' and a '10 Acre Ranch' along it, next to the new school and the Billy Jones Wildcat Railroad. Billy Jones, a former working railroad engineer, opened his one-third-scale steam railroad on his Daves Avenue orchard in 1943. After Jones died in 1968 the railroad was moved, and it reopened in Oak Meadow Park in Los Gatos on July 26, 1970.
Daves Avenue Elementary opened in September 1953 as an eight-room building for about 265 Los Gatos Union pupils, and when Monte Sereno incorporated in 1957 its first council met in the Daves Avenue schoolhouse, per clippings in the city's history file. The same file shows rockets being made on Daves Avenue in the 1930s by a local fireworks business, and electric interurban cars crossing Daves Avenue on a trestle beside the then-gravel Los Gatos-Saratoga road, on a line that ran from about 1902 into the 1930s.
The Vineland side was contested ground. One of the early annexation fights, over an area called Robinson Heights, took in Pleasant View Avenue, Rancho and Vineland Avenue, and Pleasant View Avenue was named for its open view of the mountains. While the city's first mayor was in office (1957-1967), the high school district pushed for a third high school on the east side of Karl Avenue, south of Zena Avenue; the council, sitting as its own planning commission, slow-walked the use permit, and the land is zoned residential today. By 1992 the debate was house size, and a newspaper profile pointed to new two-story homes at Winchester Boulevard and Vineland Avenue as one flashpoint.
streets and homes
The streets and the houses
Daves Avenue and Vineland Avenue both run east to Winchester Boulevard, and Daves Creek passes under each. Between them sit Blanchard Drive, Vineland Court, Elaine Court, Palos Verdes Drive and the north end of Kavin Lane. Carril Court, Dorado Lane and Michael Lane are short spurs off Daves Avenue; to the south, Poppy Lane, Bruce Avenue, Bruce Court, Vista Avenue, San Benito Way and Via Sereno fill the blocks against the Los Gatos line. North of Vineland, Robin Ann Lane and Karl Avenue head toward the city's north tip, and Eaton Lane, Via del Sur, Zena Avenue, Clara Street and Natalye Road fill the corner by Winchester, along with a string of short courts. El Rancho Avenue and Pleasant View Avenue are the small piece of Monte Sereno east of Winchester.
Zoning changes block by block. On the city's March 2025 zoning map, the Karl Avenue and Robin Ann Lane side north of Vineland is R-1-44 (one acre), much of the middle is R-1-20 (half an acre), and the blocks along Winchester, the Zena Avenue corner, El Rancho and Pleasant View, and the streets south of the school are R-1-8. In R-1-8 a new lot needs 8,000 sq ft and 70 feet of frontage, and the house tops out at 3,300 sq ft on one story or 3,000 on two, garage included, with 40 percent structural coverage. R-1-20 allows 4,950 or 4,500 sq ft on 21,780 sq ft; R-1-44 allows 6,600 or 6,000 on an acre. The school is zoned Public, and green Open Space strips run between Vineland Avenue and Eaton Lane.
Expect a mix of older single-story ranch houses and newer two-story homes; we found no source that dates the individual tracts. One thing to watch on Winchester: the city's 2023-2031 Housing Element (Program Q) picked 15785 and 15791 Winchester Boulevard, just past the school, for rezoning to allow multi-story rental apartments at a minimum of 20 units per acre.
streets in daves avenue
- Daves Avenue
- Vineland Avenue
- Blanchard Drive
- Vineland Court
- Elaine Court
- Palos Verdes Drive
- Kavin Lane
- Poppy Lane
- Carril Court
- Dorado Lane
- Michael Lane
- Bruce Avenue
- Bruce Court
- Vista Avenue
- San Benito Way
- Via Sereno
- Robin Ann Lane
- Karl Avenue
- Fairway Circle
- Eaton Lane
- Via del Sur
- Zena Avenue
- Clara Street
- Natalye Road
- Creekside Court
- Pine Cone Court
- El Rancho Avenue
- Pleasant View Avenue
- Winchester Boulevard
parks and places
Parks, shops and landmarks near Daves Avenue
- landmark
Daves Avenue Elementary School
The city's only public school, a Los Gatos Union kindergarten-through-fifth-grade campus at 17770 Daves Avenue, open since 1953. Drop-off and pick-up set the traffic rhythm on Daves Avenue between Poppy Lane and Winchester Boulevard.
- park
Vasona Lake County Park and Oak Meadow Park
East of Winchester Boulevard, roughly 0.6 mile from the middle of this guide (straight-line, park centers). Monte Sereno residents can use Oak Meadow Park free of charge, and the Billy Jones Wildcat Railroad that started on Daves Avenue runs there now; the Los Gatos Creek Trail passes through the parkland.
- landmark
La Rinconada golf course
The La Rinconada Country Club course sits just past the city's northeast edge. The Safety Element names the open space between Vineland Avenue and the club as a possible emergency walk-out route.
- shopping
North Santa Cruz Avenue and Blossom Hill Road
No stores in Monte Sereno. The shops along North Santa Cruz Avenue are about a mile south, the Blossom Hill Road and Los Gatos Boulevard corner about a mile southeast, and downtown Los Gatos about 1.6 miles (all straight-line, approximate).
schools and commute
School districts and getting around
School districts
Census school-district boundaries (January 2026) put every street in this guide in Los Gatos Union School District for elementary and middle school and Los Gatos-Saratoga Joint Union High School District for high school. Daves Avenue Elementary, the Los Gatos Union campus at 17770 Daves Avenue, is inside the guide, and the city's General Plan report notes it serves kindergarten through fifth grade. Being close to a school doesn't settle attendance: boundaries change, so confirm the exact address with the districts.
Los Gatos Union guide · Los Gatos-Saratoga high schools · Silicon Valley school districts
Getting around
- Winchester Boulevard runs along the east edge, one lane each way per the city's Safety Element, with a bike route; it heads north toward Highway 85 and Campbell.
- Daves Avenue runs west to Highway 9; the Safety Element names Daves Avenue and Winchester Boulevard as the alternate connections to Highways 85 and 17.
- The Highway 17 interchange at Highway 9 is about 0.6 mile from the city line, per the Safety Element.
- VTA light rail's Winchester Station in Campbell is about 2.9 miles northeast (straight-line).
- The Los Gatos Creek Trail runs through the Vasona and Oak Meadow parkland east of Winchester; downtown Los Gatos is about 1.6 miles south (straight-line).
nerd notes
Buying or selling in Daves Avenue: what we check
Buying here
- Confirm the city for every edge address. East Vineland Avenue, Millrich Drive, Milani Court, Vasona Terrace and Bersano Lane are Los Gatos, as are the Oak Knoll Drive pocket and parts of Kavin Lane, Poppy Lane, Bruce Avenue and Clara Street.
- Find the zone before you plan: R-1-8 caps the house at 3,300 sq ft single-story or 3,000 two-story, R-1-20 at 4,950 or 4,500, R-1-44 at 6,600 or 6,000, garage included. Coverage limits shrink on larger or steeper lots (see each zone's handout).
- Expect school-hour traffic on Daves Avenue. The city's General Plan accepts slower service (level of service D) at the Daves Avenue intersections with Poppy Lane and Winchester Boulevard during drop-off and pick-up.
- Watch the Winchester frontage: Program Q targets 15785 and 15791 Winchester Boulevard for multi-family rezoning. Check the city's planning records for anything filed near your lot.
- If a lot backs onto Daves Creek or an Open Space strip, ask about drainage, setbacks and easements. The Safety Element notes local drainage problems in parts of the city and no citywide drainage plan.
Selling here
- Lead with the zone math: lot area, the R-1-8, R-1-20 or R-1-44 house allowance, and the ADU limit (850 sq ft one-bedroom or 1,000 sq ft two-plus in R-1-8 and R-1-20).
- For an older ranch house, put the permit history next to the rebuild numbers so buyers can see both options.
- If you are near Daves Avenue Elementary, describe the distance, and point buyers to Los Gatos Union to confirm attendance.
- Gather creek, drainage and easement paperwork if the lot touches Daves Creek or an Open Space strip, plus any shared-driveway agreements on the courts.
nerd noteCommissions are always negotiable, and we offer bundled services, so ask us what's included.
faq
Daves Avenue questions, answered
Is Daves Avenue in Monte Sereno or Los Gatos?
Monte Sereno. Daves Avenue runs through the city from Highway 9 to Winchester Boulevard with Los Gatos 95030 addresses, though the city line follows the street along part of its west end. Nearby, East Vineland Avenue and the Oak Knoll Drive pocket are Los Gatos.
Which school district serves Daves Avenue and Vineland?
Census boundaries put this whole guide in Los Gatos Union and Los Gatos-Saratoga Joint Union High. Daves Avenue Elementary is on Daves Avenue; confirm the address with the district.
Where was the Billy Jones railroad?
On Billy Jones's orchard on Daves Avenue, from 1943 until he died in 1968. It reopened in Oak Meadow Park in Los Gatos in 1970.
How big a house can I build here?
It depends on the zone: up to 3,300 sq ft single-story in R-1-8, 4,950 in R-1-20 and 6,600 in R-1-44, garage included, with lower two-story caps and smaller limits on sloped lots. Confirm the parcel's zone with the city.
Are apartments planned on Winchester?
The Housing Element's Program Q identified 15785 and 15791 Winchester Boulevard for rezoning to multi-story rental housing. Check the city's planning department for current status.
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