Homes Near Homestead High School | Cupertino Real Estate

Homes near Homestead High School attract buyers looking for established Cupertino and nearby Sunnyvale neighborhoods, convenient Silicon Valley commute routes, and access to the Fremont Union High School District. The school is located at 21370 Homestead Road in Cupertino, close to the Sunnyvale border, Interstate 280, Highway 85, De Anza Boulevard, Foothill Expressway, and major Silicon Valley employment centers.

The surrounding housing market includes single-family homes, remodeled ranch homes, newer custom residences, townhomes, and condominiums across several distinct neighborhoods. School attendance is determined by the property's exact address rather than simply its distance from the campus, so buyers should verify current assignments directly with Fremont Union High School District.

Homestead High Cupertino

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10200 N Stelling, Cupertino

$5,500,000

10200 N Stelling, Cupertino

6 Beds 5 Baths 3,791 SqFt Residential MLS® # ML82058541

Tracy Hsu U16818 Financial ServicesBridge MLS Logo

10481 N Stelling Road, Cupertino

$5,398,000

10481 N Stelling Road, Cupertino

6 Beds 6 Baths 3,753 SqFt Residential MLS® # ML82053390

Tracy Hsu U16818 Financial ServicesBridge MLS Logo

20696 Hanford Drive, Cupertino

$4,150,000

20696 Hanford Drive, Cupertino

4 Beds 3 Baths 1,987 SqFt Residential MLS® # ML82056280

Tracy Hsu U16818 Financial ServicesBridge MLS Logo

21075 Greenleaf Drive, Cupertino

$3,880,000

21075 Greenleaf Drive, Cupertino

8 Beds 5 Baths 4,132 SqFt Residential MLS® # ML82053598

Ripple Xiao Gaea RealtyBridge MLS Logo

1768 Laurentian Way, Sunnyvale

$3,738,888

↓ $50,000

1768 Laurentian Way, Sunnyvale

4 Beds 3 Baths 1,902 SqFt Residential MLS® # ML82052856

CompassBridge MLS Logo

1678 Lewiston Drive, Sunnyvale

$3,088,000

1678 Lewiston Drive, Sunnyvale

3 Beds 2 Baths 1,512 SqFt Residential MLS® # ML82055534

Renna Shee Keller Williams ThriveBridge MLS Logo

1031 Payette Avenue, Sunnyvale

$2,899,000

1031 Payette Avenue, Sunnyvale

3 Beds 2 Baths 1,350 SqFt Residential MLS® # ML82058023

Jennifer Chen Keller Williams ThriveBridge MLS Logo

1592 S Mary Avenue, Sunnyvale

$2,798,000

1592 S Mary Avenue, Sunnyvale

3 Beds 2 Baths 1,603 SqFt Residential MLS® # ML82043395

Mike Masoumi RE/MAX Santa Clara ValleyBridge MLS Logo

1610 Ottawa Court, Sunnyvale

$2,398,000

↓ $100,000

1610 Ottawa Court, Sunnyvale

10 Beds 0 Baths 3,860 SqFt Residential Income MLS® # ML82039256

Jinny Ahn Coldwell Banker RealtyBridge MLS Logo

New Open House
10417 Ann Arbor Avenue, Cupertino

$1,998,000

10417 Ann Arbor Avenue, Cupertino

2 Beds 1 Bath 1,191 SqFt Residential
Sat, Sep 5th, 2026 @ 2pm - 5pm
MLS® # ML82059507

Magic Li Coldwell Banker RealtyBridge MLS Logo

10425 Mary Avenue, Cupertino

$1,200,000

10425 Mary Avenue, Cupertino

2 Beds 2 Baths 1,216 SqFt Residential MLS® # ML82054194

David Ku Happy Real Estate IncBridge MLS Logo

New Open House
10459 Mary Avenue, Cupertino

$1,170,000

10459 Mary Avenue, Cupertino

3 Beds 2 Baths 1,560 SqFt Residential
Sat, Sep 5th, 2026 @ 1pm - 4pm
MLS® # ML82059128

Jeline Gonzaga RedfinBridge MLS Logo

10323 Mary Avenue, Cupertino

$1,130,000

10323 Mary Avenue, Cupertino

2 Beds 3 Baths 1,216 SqFt Residential MLS® # ML82053480

Namita Kurdekar Coldwell Banker RealtyBridge MLS Logo

10439 Mary Ave, Cupertino

$1,100,000

10439 Mary Ave, Cupertino

2 Beds 3 Baths 1,216 SqFt Residential MLS® # 41136722

Jayanta Samanta Intero Real Estate ServicesBridge MLS Logo

10745 N De Anza Boulevard 215, Cupertino

$1,080,000

10745 N De Anza Boulevard 215, Cupertino

2 Beds 2 Baths 1,169 SqFt Residential MLS® # ML82033923

Nora Ing Real Estate eBroker IncBridge MLS Logo

10477 Mary Avenue, Cupertino

$999,000

↓ $99,000

10477 Mary Avenue, Cupertino

2 Beds 2 Baths 1,216 SqFt Residential MLS® # ML82035186

Mary Tan CompassBridge MLS Logo

Open House
20714 Celeste Circle, Cupertino

$975,000

20714 Celeste Circle, Cupertino

2 Beds 2 Baths 1,206 SqFt Residential
Sun, Sep 6th, 2026 @ 1:30pm - 4pm
MLS® # ML82054977

Shuyi Kuo Intero Real Estate ServicesBridge MLS Logo

20740 Celeste Circle, Cupertino

$949,888

↓ $48,112

20740 Celeste Circle, Cupertino

2 Beds 2 Baths 1,206 SqFt Residential MLS® # ML82051835

Vasanthi Jayaraman Anthem RealtyBridge MLS Logo

20720 Celeste Circle, Cupertino

$768,000

20720 Celeste Circle, Cupertino

1 Bed 1 Bath 871 SqFt Residential MLS® # ML82055526

Karen Pai Intero Real Estate ServicesBridge MLS Logo

1564 Hollenbeck Avenue 1, Sunnyvale

$2,700

1564 Hollenbeck Avenue 1, Sunnyvale

2 Beds 1 Bath 3,200 SqFt Residential Lease MLS® # ML82056093

Tj Keating Coldwell Banker RealtyBridge MLS Logo

Where Is Homestead High School?

Homestead High School is located at 21370 Homestead Road in Cupertino, near the intersection of Homestead Road and Mary Avenue and close to the Cupertino-Sunnyvale border. Its location provides relatively direct access to Interstate 280, Highway 85, Foothill Expressway, De Anza Boulevard, Apple Park, De Anza College, and employment centers throughout the western Santa Clara Valley.

Buyers looking throughout Cupertino can also use the Cupertino School District Guide to understand how Cupertino Union School District and Fremont Union High School District overlap and why city limits do not always match school attendance boundaries.

Neighborhoods Near Homestead High School

Homestead Villa

Homestead Villa is one of the most relevant Cupertino neighborhoods for buyers researching Homestead High School. Located near Homestead Road and De Anza Boulevard, the neighborhood contains established residential streets with a mix of original homes, expanded residences, extensively remodeled properties, and newer construction.

Buyers comparing Homestead Villa homes often evaluate lot size, renovation quality, street location, commute convenience, elementary and middle school assignments, and the relationship between the asking price and recent nearby sales.

Northwestern Cupertino

Northwestern Cupertino includes residential streets extending toward Foothill Expressway, Mary Avenue, Stevens Creek Boulevard, and the western edge of the city. This part of Cupertino tends to appeal to buyers who want a residential setting while remaining close to Apple Park, Mountain View, Sunnyvale, Los Altos, and major commute routes.

For a broader comparison of neighborhoods throughout the city, see the Cupertino Real Estate Guide.

Cupertino Village and North-Central Cupertino

Buyers researching the northern side of Cupertino may also compare homes near Cupertino Village. This area offers access to Asian grocery stores, restaurants, shopping, Interstate 280, Apple Park, and surrounding employment centers.

Cupertino Village and the Homestead High School area overlap geographically in buyer searches, but they should not be treated as identical school-boundary searches. The individual property's address remains the determining factor.

Nearby Sunnyvale

The broader Homestead High School search also reaches into areas near the Cupertino-Sunnyvale boundary. Buyers may therefore encounter homes with Sunnyvale addresses while researching neighborhoods close to the campus.

This is one reason it can be useful to search beyond the word “Cupertino.” A home a short distance across a municipal boundary may offer a different combination of price, lot size, housing type, schools, city services, and commute convenience.

Homestead High School and Fremont Union High School District

Homestead High School is one of five comprehensive high schools operated by the Fremont Union High School District, along with Cupertino High School, Fremont High School, Lynbrook High School, and Monta Vista High School.

FUHSD serves multiple communities and uses address-based attendance areas. Buyers making a purchase partly because of a particular school should verify the exact property through current district boundary resources before relying on an MLS entry, neighborhood name, marketing description, or proximity to the campus.

Buyers comparing school areas can also explore:

What Types of Homes Are Near Homestead High School?

The housing stock surrounding Homestead High School reflects several generations of Silicon Valley development. Buyers may find:

  • Mid-century single-story ranch homes
  • Expanded ranch homes with larger floor plans
  • Substantially remodeled single-family homes
  • Newer custom-built residences
  • Two-story family homes
  • Townhomes and condominiums
  • Properties purchased partly for land or redevelopment potential

Two homes with similar square footage can sell at substantially different prices because of lot size, condition, remodeling quality, floor plan, street location, traffic exposure, school assignment, and future expansion potential. Buyers should evaluate the underlying real estate as carefully as they evaluate the school area.

Buying a Home Near Homestead High School

School-focused buyers often benefit from narrowing the search differently than someone simply looking anywhere in Cupertino. Instead of beginning only with city boundaries, buyers can identify acceptable school areas and then evaluate suitable homes individually.

Important factors include:

  • Current high school assignment for the exact address
  • Elementary and middle school assignments
  • Home condition and remodeling quality
  • Lot size and expansion potential
  • Street traffic and noise
  • Walking and biking routes
  • Commute time during normal work hours
  • Access to Interstate 280, Highway 85, and Foothill Expressway
  • Distance to Apple Park and other Silicon Valley employers
  • Resale demand for the individual location

The 95014 Real Estate & Development Guide provides a broader look at Cupertino housing, schools, neighborhoods, development, and market conditions.

Commuting From the Homestead High School Area

This portion of Cupertino has access to several major Silicon Valley transportation corridors. Interstate 280 connects toward Santa Clara, San Jose, Mountain View, Palo Alto, and the Peninsula, while Highway 85 and Foothill Expressway provide additional north-south routes.

De Anza Boulevard and Homestead Road also connect residential areas with Apple Park, Cupertino shopping districts, Sunnyvale, and nearby technology employers. Buyers with regular commutes should test their likely route during the hours they normally expect to travel rather than relying only on off-peak travel estimates.

Shopping, Restaurants and Daily Convenience

Homes in the broader Homestead High School area are close to shopping and dining along De Anza Boulevard, Homestead Road, Stevens Creek Boulevard, Cupertino Village, Downtown Sunnyvale, and Main Street Cupertino.

The mix allows buyers to choose between quieter residential streets and locations closer to restaurants, grocery stores, services, coffee shops, fitness options, and larger commercial centers.

How Does the Homestead High Area Compare With Cupertino High?

Buyers often compare Homestead High and Cupertino High because both school areas contain established Silicon Valley neighborhoods with convenient access to major employment centers. The housing choices, however, can differ by street, neighborhood, lot size, home condition, commute route, and price.

The Homes Near Cupertino High School Guide provides a closer look at another major FUHSD-focused home search.

How Does the Homestead High Area Compare With Lynbrook High?

Lynbrook High School is another common comparison for buyers looking in Cupertino and West San Jose. That search frequently crosses municipal boundaries as well, making exact address verification and property-by-property comparison especially important.

See the Homes Near Lynbrook High School Guide for housing, neighborhood, and market information in that area.

The Rise and Future Cupertino Housing

Buyers researching established neighborhoods near Homestead High School may also want to follow The Rise at Town Square West, the large redevelopment of the former Vallco Mall site. The project is expected to create a different type of future housing choice, with new residential development integrated with retail, public spaces, and other mixed-use components.

Buyers interested in existing housing around the development can review Homes for Sale Near The Rise.

Get The Rise Buyer Updates

If future homes at The Rise or Town Square West could fit your Cupertino plans, join The Rise Cupertino & Town Square West waiting list for buyer-oriented updates about future for-sale homes, project milestones, pricing information when available, and nearby Cupertino opportunities.

The waiting list is maintained by Bruce Wagg for prospective real estate buyers. It is not the developer's sales list, the City of Cupertino, a leasing office, or an affordable-housing application list.

Selling a Home Near Homestead High School

For sellers, a verified Homestead High School assignment can be an important component of property marketing, but it should be presented accurately and alongside the home's other advantages.

A strong marketing strategy may highlight lot size, improvements, floor plan, street location, outdoor space, commute access, parks, nearby shopping, and current verified school assignments. Pricing should still be based on relevant comparable sales, condition, housing type, location, and buyer demand rather than assuming the school name alone determines value.

Frequently Asked Questions About Homes Near Homestead High School

Where is Homestead High School located?

Homestead High School is on Homestead Road near Mary Avenue in northwestern Cupertino, close to the Sunnyvale city boundary. The campus location provides convenient access to De Anza Boulevard, Interstate 280, Highway 85, Foothill Expressway, and residential neighborhoods on both sides of the Cupertino-Sunnyvale border.

Does living near Homestead High School guarantee attendance?

No. Being physically close to the campus does not by itself establish school eligibility. Fremont Union High School District uses address-based attendance boundaries, so buyers should check the exact property through current district resources before making a purchase decision based on school assignment.

What neighborhoods are near Homestead High School?

Homestead Villa is one of the most recognizable nearby Cupertino neighborhoods. Buyers also search residential areas in northwestern and north-central Cupertino as well as nearby sections of Sunnyvale, depending on budget, commute, housing preference, and school requirements.

Are there Sunnyvale homes near Homestead High School?

Yes. Homestead High School sits close to the Cupertino-Sunnyvale border, so some geographically nearby homes have Sunnyvale addresses. Buyers should compare city services, property characteristics, pricing, commute routes, and verified school assignments rather than using the city name alone to define the search.

What kinds of homes are available near Homestead High School?

The surrounding area includes original ranch homes, expanded and remodeled houses, custom residences, townhomes, and condominiums. Values vary significantly according to lot size, condition, floor plan, location, school assignment, and remodeling quality.

How does the Homestead High area compare with Cupertino High or Lynbrook High?

Each school area contains different neighborhoods, housing types, lot sizes, commute patterns, and price points. Buyers should compare actual properties and neighborhoods rather than assuming one school-area search provides the same housing choices as another.

Work With a Cupertino Real Estate Agent

Buying a home near Homestead High School requires more than entering a school name into a listing portal. Pricing, condition, school boundaries, city boundaries, neighborhoods, commute routes, lot characteristics, and resale demand all need to be evaluated together.

Bruce Wagg works with buyers and sellers throughout Cupertino, 95014, and the surrounding Silicon Valley market. For help comparing homes near Homestead High School, Homestead Villa, Cupertino High School, Lynbrook High School, or other Cupertino neighborhoods, call or text (669) 202-7777 or visit BruceWagg.com/contact.php.

For broader research, explore the Cupertino Real Estate Guide, Cupertino School District Guide, and 95014 Real Estate & Development Guide.