Jollyman Homes for Sale | Cupertino CA

Jollyman is an established residential neighborhood in Cupertino where recent home sales showed a median sale price of approximately $3.16 million, median days on market of 7 days, and a median sold price of approximately $1,811 per square foot.

The neighborhood attracts buyers seeking mature residential streets, single-family homes, convenient access to Apple Park, nearby schools, shopping, parks, and major Silicon Valley employment centers.

If you have questions about buying or selling in Jollyman, call Bruce Wagg at 669-202-7777.

Jollyman Cupertino

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20858 Cherryland Drive, Cupertino

$5,990,000

20858 Cherryland Drive, Cupertino

7 Beds 6 Baths 4,170 SqFt Residential MLS® # ML82029351

Aspire HomesBridge MLS Logo

10468 S Stelling Road, Cupertino

$5,488,000

10468 S Stelling Road, Cupertino

6 Beds 6 Baths 4,073 SqFt Residential MLS® # ML82035457

Anson Ip CompassBridge MLS Logo

10468 S Stelling Road, Cupertino

$5,488,000

10468 S Stelling Road, Cupertino

6 Beds 6 Baths 4,073 SqFt Residential MLS® # ML82053479

Anson Ip CompassBridge MLS Logo

20870 Cherryland, Cupertino

$5,480,000

20870 Cherryland, Cupertino

7 Beds 5 Baths 3,570 SqFt Residential MLS® # ML82035993

Aspire HomesBridge MLS Logo

20876 Cherryland, Cupertino

$5,430,000

20876 Cherryland, Cupertino

7 Beds 6 Baths 3,570 SqFt Residential MLS® # ML82029350

Aspire HomesBridge MLS Logo

Open House
10476 S Stelling Road, Cupertino

$5,398,000

↑ $109,112

10476 S Stelling Road, Cupertino

7 Beds 6 Baths 4,128 SqFt Residential MLS® # ML82042922

Cindy Sun Giant Realty Inc.Bridge MLS Logo

20882 Cherryland Drive, Cupertino

$5,390,000

20882 Cherryland Drive, Cupertino

7 Beds 6 Baths 3,570 SqFt Residential MLS® # ML82007958

Aspire HomesBridge MLS Logo

20888 Cherryland Drive, Cupertino

$4,980,000

20888 Cherryland Drive, Cupertino

6 Beds 6 Baths 3,867 SqFt Residential MLS® # ML82046797

Aspire HomesBridge MLS Logo

20558 Kirwin Lane, Cupertino

$4,250,000

20558 Kirwin Lane, Cupertino

4 Beds 3 Baths 2,039 SqFt Residential MLS® # ML82042538

Anson Ip CompassBridge MLS Logo

7552 Tiptoe Lane, Cupertino

$3,300,000

↓ $200,777

7552 Tiptoe Lane, Cupertino

4 Beds 3 Baths 2,192 SqFt Residential MLS® # ML82032872

Donald Jessup Bayview Residential BrokerageBridge MLS Logo

Montebello Road, Cupertino

$2,750,000

Montebello Road, Cupertino

0 Beds 0 Baths 0 SqFt Land MLS® # ML82043457

Andy Pickering California Outdoor Properties, Inc.Bridge MLS Logo

New Open House
21543 Point Reyes Terrace, Cupertino

$1,598,000

21543 Point Reyes Terrace, Cupertino

3 Beds 3 Baths 1,435 SqFt Residential MLS® # ML82054330

KW AdvisorsBridge MLS Logo

Open House
820 Hooshang Ct, Cupertino

$1,299,000

820 Hooshang Ct, Cupertino

3 Beds 2 Baths 1,406 SqFt Residential MLS® # 41134537

Lingya Zhang Aveline RealtyBridge MLS Logo

Open House
7285 Ventana Drive, San Jose

$1,270,000

7285 Ventana Drive, San Jose

2 Beds 2 Baths 1,305 SqFt Residential MLS® # ML82050822

Paulina Chang Coldwell Banker RealtyBridge MLS Logo

20488 Stevens Creek Boulevard 1607, Cupertino

$1,098,888

↓ $51,000

20488 Stevens Creek Boulevard 1607, Cupertino

2 Beds 2 Baths 1,187 SqFt Residential MLS® # ML82034063

Siobhan O'sullivan CompassBridge MLS Logo

21072 Red Fir Court, Cupertino

$998,888

↓ $90,000

21072 Red Fir Court, Cupertino

2 Beds 2 Baths 1,003 SqFt Residential MLS® # ML82039802

Hans Masli MaxrealBridge MLS Logo

Open House
7299 Via Vico, San Jose

$996,000

7299 Via Vico, San Jose

2 Beds 3 Baths 1,192 SqFt Residential
Sun, Jul 19th, 2026 @ 2pm - 4pm
MLS® # ML82051452

Nadine Sun BRG RealtyBridge MLS Logo

Open House
20488 Stevens Creek Blvd 2302, Cupertino

$778,000

↓ $21,888

20488 Stevens Creek Blvd 2302, Cupertino

1 Bed 1 Bath 875 SqFt Residential
Sun, Jul 19th, 2026 @ 2pm - 4pm
MLS® # 41139279

Patty Ho Solution Real EstateBridge MLS Logo

20488 Stevens Creek Boulevard 1114, Cupertino

$749,888

↓ $28,112

20488 Stevens Creek Boulevard 1114, Cupertino

1 Bed 1 Bath 949 SqFt Residential MLS® # ML82041362

Alejandro J. Lopez Real Estate Experts ERA PoweredBridge MLS Logo

About Jollyman

Jollyman is one of Cupertino's established residential neighborhoods, offering a central location, mature landscaping, and convenient access to daily amenities. Buyers are often drawn to the area because it combines a traditional suburban neighborhood feel with strong access to Silicon Valley employment centers.

Like many Cupertino neighborhoods, Jollyman benefits from limited housing supply, school-driven demand, and long-term buyer interest from people seeking a foothold in the 95014 market. The neighborhood is frequently compared with nearby areas such as Homestead Villa, Rancho Rinconada, and Garden Gate.

Jollyman Market Snapshot

  • Median Sale Price: Approximately $3.16 Million
  • Median Home Size: Approximately 1,728 Square Feet
  • Median Days on Market: Approximately 7 Days
  • Median Sold Price Per Square Foot: Approximately $1,811

These figures show how competitive the Jollyman market remains. Homes selling in roughly one week at a median price above $3 million reflect strong buyer demand, limited inventory, and the continued premium placed on well-located Cupertino neighborhoods.

Homes and Architecture in Jollyman

Jollyman primarily features single-family homes on established residential streets. Many homes were built during Cupertino's mid-century growth period and have been updated, expanded, or remodeled over time. Buyers may find original ranch-style homes, renovated properties, larger expanded residences, and occasional newer custom homes.

Common features in the Jollyman area may include:

  • Single-family homes on mature residential streets
  • Ranch-style and mid-century floor plans
  • Remodeled kitchens and bathrooms
  • Expanded homes with larger living areas
  • Mature trees and established landscaping
  • Usable yards and outdoor living space

Because the recent median home size was approximately 1,728 square feet, buyers should expect pricing to vary significantly based on condition, lot size, upgrades, floor plan, and exact location.

Location and Commute Advantages

Jollyman's Cupertino location gives residents access to major South Bay commute corridors, Apple Park, De Anza Boulevard, Stevens Creek Boulevard, Interstate 280, and nearby employment centers throughout Sunnyvale, Santa Clara, Mountain View, and West San Jose.

For many buyers, the appeal is not only the home itself. It is the combination of location, schools, commute access, and neighborhood feel. A well-located home in Jollyman can reduce daily commute time while still providing access to shopping, parks, restaurants, and community amenities.

Buyers who are also considering lower-maintenance housing near major employers may want to review Cupertino condos and townhomes near Apple Park.

Schools Serving Jollyman

Jollyman is served by the Cupertino Union School District for elementary and middle school and the Fremont Union High School District for high school. School assignments may vary by address, so buyers should verify current school boundaries directly with the districts before relying on listing information.

School-related demand is one of the major forces supporting home values throughout Cupertino. Buyers comparing Jollyman may also consider Monta Vista, homes near Lynbrook High School, Homestead-area neighborhoods, and other school-focused parts of the 95014 market.

Jollyman vs. Homestead Villa

Jollyman and Homestead Villa are natural comparison neighborhoods for buyers focused on central Cupertino. Both areas offer established single-family homes, convenient access to major employers, and strong buyer demand.

Homestead Villa recently showed a median sale price of approximately $3.35 million, while Jollyman showed a median sale price of approximately $3.16 million. Buyers comparing the two areas should look closely at lot size, condition, school assignment, floor plan, commute pattern, and proximity to parks and services.

Jollyman vs. Rancho Rinconada

Another common comparison is Rancho Rinconada. Both neighborhoods appeal to buyers seeking established Cupertino streets, single-family homes, and access to Silicon Valley employment centers.

Rancho Rinconada is often associated with larger lots and a traditional neighborhood feel near Apple Park and Stevens Creek Boulevard. Jollyman offers its own central Cupertino advantages, including mature residential streets and convenient access to nearby schools, shopping, and commute corridors.

Jollyman and the 95014 Real Estate Market

Jollyman is part of the broader 95014 real estate market, one of the most competitive housing markets in Silicon Valley. Buyer demand in 95014 is influenced by schools, Apple Park proximity, limited single-family inventory, commute convenience, and long-term confidence in Cupertino real estate.

As Cupertino continues to evaluate future housing supply, redevelopment projects, and mixed-use development, established neighborhoods like Jollyman remain important because they offer something new construction often cannot replicate: mature residential streets, established lots, and long-standing neighborhood identity.

For additional context on citywide trends, visit the main Cupertino real estate guide and the Cupertino development videos page.

Close to Cupertino City Center

Jollyman also benefits from access to Cupertino's civic, retail, and commercial core. Shopping, dining, services, parks, and city amenities help support the neighborhood's convenience and long-term appeal.

Buyers interested in nearby housing and redevelopment activity may also want to review the Cupertino City Center Real Estate Guide.

Related Cupertino Real Estate Resources

FAQ

Where is Jollyman located?

Jollyman is an established residential neighborhood in Cupertino, California, located near central Cupertino, Homestead Road, De Anza Boulevard, and major Silicon Valley employment centers.

What is the typical home price in Jollyman?

Recent sales in Jollyman showed a median sale price of approximately $3.16 million, a median home size of 1,728 square feet, and a median sold price of approximately $1,811 per square foot.

How quickly do homes sell in Jollyman?

Homes in Jollyman sell in approximately 7 days at median, reflecting strong buyer competition and limited inventory in the Cupertino market.

Why do buyers choose Jollyman?

Buyers choose Jollyman for its established homes, mature residential streets, Cupertino location, school access, and convenient commute routes to Apple Park and other Silicon Valley employers.

How does Jollyman compare to Homestead Villa?

Jollyman and Homestead Villa are both central Cupertino neighborhoods with strong buyer demand. Homestead Villa recently showed a median sale price of approximately $3.35 million, while Jollyman showed a median sale price of approximately $3.16 million.

How does Jollyman compare to nearby Cupertino neighborhoods?

Jollyman competes with nearby Cupertino neighborhoods such as Homestead Villa, Rancho Rinconada, Garden Gate, and areas near Lynbrook High School, with each area offering different housing styles, location advantages, commute patterns, and school considerations.

Work With Bruce Wagg

Whether you are considering buying or selling in Jollyman, understanding local pricing, neighborhood differences, school considerations, and current market conditions can help you make better decisions.

Contact Bruce Wagg at 669-202-7777 or visit BruceWagg.com to discuss Jollyman homes for sale and the broader Cupertino real estate market.