cupertino neighborhood guide · property nerds® at compass
Jollyman, Cupertino Homes for sale, recent sales and a Property Nerd’s guide
South-central Cupertino between Stelling Road, Highway 85 and De Anza Boulevard: mostly single-story 1959-64 ranch tracts on 6,000 to 9,800 sq ft lots around the 11-acre Jollyman Park.
Jollyman by the numbers
jollyman by the numbers · live from the mls
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Calculated in your browser from MLS data for Jollyman: Stevens Creek Blvd to Hwy 85, Stelling Rd to De Anza Blvd (city planning-area outline). Sales are single-family homes, townhomes and condos.
homes in jollyman · live from the mls
Homes for sale, for rent and recently sold in Jollyman
Every active listing, rental and closed sale in Jollyman 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 (Jollyman: Stevens Creek Blvd to Hwy 85, Stelling Rd to De Anza Blvd (city planning-area outline)); it may not match every local definition.
the story
How Jollyman came to be
Jollyman is the City of Cupertino's planning name for the block of south-central Cupertino between Stelling Road, Highway 85 and De Anza Boulevard. It shares the name with Jollyman Park, the 11-acre city park near its middle, and with a short Jollyman Lane just north of the park.
The annexation map tells the story of how it came together. The blocks north of McClellan Road, and a few just south of it near De Anza Boulevard, were inside Cupertino's original city limits when the city incorporated in 1955. Most of the area south of McClellan joined through the San Jose-Cupertino boundary reorganization of July 1979, and a string of small annexations along Stelling Road filled in the gaps between about 1970 and 1988 (city annexation records).
House-building came earlier and fast. County records date a handful of homes on Sunrise and Scofield drives, John Way and Lonna Lane to about 1950-52, but most of the neighborhood's single-family homes went up from 1959 to 1964 in a patchwork of small subdivisions. The Roundtree townhouse courts followed around 1969-71. Jollyman Park came last, built in the early 1990s, and in 2025 the city opened its first all-inclusive playground there.
streets and homes
The streets and the houses
The street map is a quilt of small tracts. Kirwin Lane, Erin Way and Kim Street sit just south of McClellan Road; the flower streets (Rose Blossom Drive, Lily Avenue, Lilac Way, Sage Court) run off Stelling Road, where the street names read like a seed catalog. De Foe and Dumas drives sit along Bollinger Road, and Kentwood Avenue, Steeplechase Lane, Stanford Place and Rollingdell Drive fill the south end. North of McClellan, Bonny Drive, Westacres Drive, Shelly and Cheryl drives, Tonita Way and Pepper Tree Lane fill the blocks below Stevens Creek Boulevard.
Most houses are single-story ranch homes from 1959-64 on lots zoned R1-6, R1-7.5 or R1-10; the median single-family lot is about 7,500 square feet. County records list about 822 one-story and 286 two-story single-family homes, so two-story rebuilds are scattered rather than the rule. The older R1-10 blocks on Sunrise and Scofield drives, Felton Way and Rodrigues Avenue have bigger lots.
Two pockets carry Cupertino's single-story overlay, the 'i' at the end of the zoning code: Heatherwood Drive, Fallenleaf Lane, Tiptoe Lane, Colony Hills Lane and part of Westlynn Way near Bollinger Road (R1-6i), and John Way (R1-10i). There, homes are limited to one story and 18 feet, and a two-story house needs a conditional use permit. Near McClellan Road and Stelling Road, Red Fir and White Fir courts are 1969-71 townhouses on cluster zoning with a homeowners association, and Hooshang Court is a small 1971 planned development by Highway 85.
streets in jollyman
- South Stelling Road
- McClellan Road
- Bollinger Road
- Rodrigues Avenue
- Kirwin Lane
- Erin Way
- Rose Blossom Drive
- Lily Avenue
- Lilac Way
- De Foe Drive
- Dumas Drive
- Kentwood Avenue
- Steeplechase Lane
- Stanford Place
- Rollingdell Drive
- Heatherwood Drive
- Fallenleaf Lane
- Tiptoe Lane
- Colony Hills Lane
- Westlynn Way
- Bonny Drive
- Westacres Drive
- Shelly Drive
- Cheryl Drive
- Pepper Tree Lane
- Scofield Drive
- Sunrise Drive
- John Way
- Jollyman Lane
- Red Fir Court
- White Fir Court
parks and places
Parks, shops and landmarks near Jollyman
- park
Jollyman Park
1000 S. Stelling Road: an 11.2-acre city park built in the early 1990s, with soccer space, a baseball field with batting cage, playground areas, picnic areas with barbecues, restrooms and a walking loop. Its all-inclusive playground, about 0.85 acre of core play area by the Stelling Road parking lot, was designed for people of all abilities and opened in 2025.
- park
Three Oaks Park
A 3.1-acre neighborhood park on Shadowhill Lane, just south of the neighborhood (about 0.6 mile from Jollyman Park, straight line), built in 1980, with playgrounds, picnic areas, lawn and the large oaks it is named for.
- shopping
De Anza Plaza and McClellan Square
The shopping centers at McClellan Road and De Anza Boulevard sit right on the neighborhood's east edge; Cupertino Crossroads is at Stevens Creek and De Anza boulevards at the northeast corner.
- landmark
De Anza College and the Civic Center
De Anza College, one of the city's listed landmarks, is across Stelling Road from the neighborhood's northwest corner. The Cupertino Library and City Hall on Torre Avenue are about 0.6 mile east of the middle of Jollyman (straight line), across De Anza Boulevard.
schools and commute
School districts and getting around
School districts
Jollyman is in the Cupertino Union School District (K-8) and the Fremont Union High School District. Faria Elementary is inside the neighborhood on Barbara Lane, north of McClellan Road. Attendance boundaries change, so check the exact address with the districts before relying on a school assignment.
Cupertino Union guide · Fremont Union guide · Silicon Valley school districts
Getting around
- VTA Routes 25 and 55 run on Stelling Road (Route 25 also uses McClellan Road), Route 51 runs on De Anza Boulevard, and Route 23 and Rapid 523 run on Stevens Creek Boulevard. Check VTA for current schedules.
- Highway 85 has interchanges at De Anza Boulevard near the south tip (about 0.7 mile from the middle of the neighborhood, straight line) and at Stevens Creek Boulevard (about 0.7 to 1 mile).
- I-280 is reached by driving north on De Anza Boulevard or by taking Highway 85 north.
- Sunnyvale Caltrain station is about 4.6 miles north (straight line).
- De Anza College's campus is across Stelling Road, and the Civic Center and library are about 0.6 mile east.
nerd notes
Buying or selling in Jollyman: what we check
Buying here
- Check the zoning suffix. R1-6i and R1-10i parcels (Heatherwood Drive, Fallenleaf Lane, Tiptoe Lane, Colony Hills Lane, part of Westlynn Way, John Way) are single-story only, 18 feet maximum, and a second story needs a conditional use permit.
- On other lots, a second story is allowed under the R1 rules, with floor area and lot coverage each capped at 45 percent of net lot area; a second floor larger than 66 percent of the first, or within 15 feet of a side property line, triggers design review.
- Most houses are 1959-64 originals or partial remodels. Inspect the electrical panel, sewer lateral, attic and wall insulation, windows and foundation, and ask for permits on past additions.
- Flood map: the city's GIS puts about half the parcels in FEMA's 0.2-percent-annual-chance (500-year) flood area, and a handful on Bollinger Road touch Zone A. Confirm the specific parcel's zone.
- Buying a townhouse on Red Fir or White Fir Court? Read the Cupertino Roundtree HOA's CC&Rs, budget, reserve study and recent minutes before you remove contingencies.
Selling here
- Know your overlay. If you are on an R1-6i or R1-10i street, say so up front; if you are not, a buyer will want to know a second story is possible.
- Have lot dimensions and the floor area on hand. On 6,000 to 9,800 sq ft lots, buyers run the 45 percent math before they tour.
- Pull permits and final sign-offs for additions, garage conversions and any second-story work.
- Distances sell themselves here: Jollyman Park, Faria Elementary, De Anza College and the McClellan and De Anza shops are all close. Put the walking distances in the listing rather than adjectives.
nerd noteCommissions are always negotiable, and we offer bundled services, so ask us what's included.
faq
Jollyman questions, answered
Where exactly is Jollyman?
It is the city's planning area south of Stevens Creek Boulevard between Stelling Road (and Highway 85 south of McClellan Road) and De Anza Boulevard, running south to where Highway 85 meets De Anza. De Anza College and the commercial lots on the two boulevards are not part of it.
Can I build a second story in Jollyman?
On most lots, yes, within Cupertino's R1 rules and design review triggers. On the single-story overlay streets (R1-6i and R1-10i: Heatherwood, Fallenleaf, Tiptoe, Colony Hills, part of Westlynn, John Way), homes are limited to one story and 18 feet unless the city grants a conditional use permit.
What are the homes like?
Mostly single-story ranch houses built from 1959 to 1964 on lots of about 6,000 to 9,800 square feet, with scattered two-story rebuilds, a few early-1950s blocks with larger lots, and the 1969-71 Roundtree townhouses on Red Fir and White Fir courts.
What is at Jollyman Park?
About 11 acres with soccer space, a baseball field with batting cage, playgrounds, picnic areas, restrooms and a walking loop, plus the city's first all-inclusive playground, which opened in 2025 by the Stelling Road parking lot.
Which school districts serve Jollyman?
Cupertino Union School District for K-8 and Fremont Union High School District for high school. Faria Elementary is inside the neighborhood. Confirm the assigned schools for a specific address with the districts.
talk to a property nerd
Thinking about Jollyman? Let's run your numbers.
Eric, Janelle and the Boyenga Team have sold more than 2,520 Silicon Valley homes, $2.6+ billion in all, since 1996. Get a value, a plan, or a straight answer about a street.
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