Homes near Kennedy Middle School place buyers in western Cupertino close to established residential neighborhoods, parks, foothill recreation and major Silicon Valley commute routes. Located at 821 Bubb Road, John F. Kennedy Middle School is part of the Cupertino Union School District and serves students in grades six through eight.

The area surrounding Kennedy Middle School includes a wide range of housing, from original ranch-style homes and remodeled properties to larger custom residences. Buyers often compare homes near Kennedy with properties in Monta Vista, Oak Valley, Seven Springs and other western Cupertino neighborhoods.

Important: Living near Kennedy Middle School does not guarantee enrollment. School boundaries, enrollment policies and assignments may change. Buyers should verify the assignment for a specific property directly with the Cupertino Union School District before making a purchase decision.

Homes for Sale Near Kennedy Middle School

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7246 Sharon Drive, San Jose

$13,500,000

7246 Sharon Drive, San Jose

5 Beds 4 Baths 2,400 SqFt Residential MLS® # ML82054389

Benjamin Wang Lexicon HomesBridge MLS Logo

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

21911 Dolores Avenue, Cupertino

$5,490,000

21911 Dolores Avenue, Cupertino

4 Beds 5 Baths 3,721 SqFt Residential MLS® # ML82051689

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

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

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

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

New Open House
1440 Kring, Los Altos

$4,499,888

1440 Kring, Los Altos

5 Beds 4 Baths 2,875 SqFt Residential
Sat, Jul 25th, 2026 @ 12pm - 6pm
MLS® # ML82055001

Lex Orosco Real Brokerage TechnologiesBridge 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

10185 Stonydale Drive, Cupertino

$4,000,000

10185 Stonydale Drive, Cupertino

4 Beds 3 Baths 2,648 SqFt Residential MLS® # ML82043195

Maria Segal CompassBridge MLS Logo

10621 Madera Drive, Cupertino

$3,999,000

10621 Madera Drive, Cupertino

3 Beds 2 Baths 1,632 SqFt Residential MLS® # ML82050734

Bobby Ohadi Abode Real EstateBridge MLS Logo

New
11113 Wilkinson Avenue, Cupertino

$3,888,000

11113 Wilkinson Avenue, Cupertino

4 Beds 3 Baths 2,119 SqFt Residential MLS® # ML82054650

Ensy Afdari Golden Gate Sotheby's International RealtyBridge 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

10675 Clubhouse Lane, Cupertino

$3,688,000

10675 Clubhouse Lane, Cupertino

4 Beds 3 Baths 3,253 SqFt Residential MLS® # ML82051852

CompassBridge MLS Logo

10140 Hillcrest Road, Cupertino

$3,688,000

10140 Hillcrest Road, Cupertino

4 Beds 2 Baths 2,170 SqFt Residential MLS® # ML82048728

Aspire HomesBridge MLS Logo

10200 Empire Avenue, Cupertino

$3,488,000

↓ $160,000

10200 Empire Avenue, Cupertino

4 Beds 4 Baths 2,408 SqFt Residential MLS® # ML82041938

Carol Jeans Christie's International Real Estate SerenoBridge MLS Logo

11055 La Paloma Dr, Cupertino

$3,380,000

11055 La Paloma Dr, Cupertino

3 Beds 2 Baths 1,656 SqFt Residential MLS® # 41140741

Longchen Ma CalCity Investments, IncBridge MLS Logo

1522 Jamestown Drive, Cupertino

$3,350,000

1522 Jamestown Drive, Cupertino

5 Beds 3 Baths 2,397 SqFt Residential MLS® # ML82053518

Debbie Shin Sterling AssociatesBridge MLS Logo

Open House
10178 Alpine Drive, Cupertino

$3,300,000

10178 Alpine Drive, Cupertino

7 Beds 0 Baths 3,136 SqFt Residential Income
Sun, Jul 26th, 2026 @ 2pm - 4pm
MLS® # ML82053409

David Katz Magnify Real EstateBridge MLS Logo

New
7864 Belknap Drive, Cupertino

$3,298,000

7864 Belknap Drive, Cupertino

4 Beds 3 Baths 2,031 SqFt Residential MLS® # ML82054396

Paul Prouty KW Bay Area EstatesBridge MLS Logo

Where Is Kennedy Middle School?

John F. Kennedy Middle School is located at 821 Bubb Road in Cupertino. The campus is in western Cupertino near McClellan Road, Stevens Creek Boulevard and residential areas extending toward the foothills.

Depending on the location of the home, nearby destinations and travel routes may include:

  • Blackberry Farm
  • McClellan Ranch Preserve
  • Stevens Creek Boulevard
  • Foothill Expressway
  • Highway 85
  • Interstate 280
  • De Anza College
  • Memorial Park and the Cupertino Civic Center
  • Apple Park and other Silicon Valley employment centers

Actual travel times and walking or bicycling routes vary by address. Buyers should personally evaluate traffic, street crossings, sidewalks and school arrival patterns instead of relying only on map distance.

For a citywide overview, visit the Cupertino real estate guide.

Neighborhoods Near Kennedy Middle School

Kennedy Middle School is associated geographically with western Cupertino, but neighborhood names and school attendance boundaries are not interchangeable. A property described as being in Monta Vista or near Bubb Road should still be checked individually through the school district.

Monta Vista

Monta Vista is one of western Cupertino’s best-known residential areas. Housing ranges from original mid-century homes to substantially remodeled properties and large custom residences. Buyers are often attracted to the neighborhood’s established streets, foothill setting and access to western Cupertino schools and recreation.

Lot size, elevation, street position and renovation quality can create significant price differences between properties that appear similar online. Some homes are close to major roads, while others occupy quieter interior locations or hillside settings.

Explore current housing and neighborhood information in the Monta Vista real estate guide.

Oak Valley

Oak Valley offers another western Cupertino option for buyers comparing homes near Kennedy Middle School. The neighborhood includes a mixture of compact homes, mid-sized residences and larger properties, with access toward Homestead Road, Foothill Expressway and the broader western Cupertino area.

School assignments vary by property, so buyers should not assume that every Oak Valley address is assigned to Kennedy Middle School.

Learn more about the neighborhood in the Oak Valley real estate guide.

Seven Springs

Seven Springs is an established residential community that buyers may compare with Monta Vista and other western Cupertino neighborhoods. Homes include larger executive-style floor plans, mature landscaping and properties with convenient access to Highway 85 and nearby employment centers.

Although Seven Springs is part of the broader western Cupertino housing market, its school assignments must be verified by parcel. Proximity to Kennedy Middle School should not be treated as proof of attendance eligibility.

See current neighborhood information in the Seven Springs real estate guide.

Homes Near Bubb Road and McClellan Road

Residential streets surrounding Bubb Road and McClellan Road include original ranch homes, expanded residences and newer custom construction. Buyers should compare interior-street locations with properties closer to busier roads, schools, parks or commercial routes.

Traffic patterns can change during school arrival and dismissal. Buyers concerned about congestion, noise or walking access should visit the area at different times of day before making an offer.

What Types of Homes Are Found Near Kennedy Middle School?

The area near Kennedy Middle School is not a single subdivision. Housing age, lot size, floor plan and condition can vary considerably within a relatively short distance.

Original Ranch-Style Homes

Many western Cupertino homes were constructed during the city’s major period of suburban development. Original properties may offer practical one-story layouts, attached garages and usable yards, but they may also require updates to roofing, electrical systems, plumbing, windows, drainage and interior finishes.

Buyers considering an older home should review inspections, disclosures and permit records carefully. A property that appears less expensive may require substantial work after closing.

Remodeled and Expanded Homes

Many owners have expanded or significantly remodeled their homes to create larger kitchens, additional bedrooms, home offices and more open living areas. The value of these improvements depends on design quality, permits, workmanship and how well the finished layout functions.

Buyers should confirm whether additions and conversions are reflected in public records. Reported living area, bedroom count and permitted square footage may not always match the way a property is marketed.

Custom and Rebuilt Residences

High land values have encouraged the replacement of some smaller homes with larger custom residences. These properties may include modern construction, energy-efficient systems, flexible living spaces and higher-end finishes.

A newer construction date does not eliminate the need for inspections and disclosure review. Buyers should still evaluate drainage, foundation work, waterproofing, mechanical systems and permit history.

Condos and Townhomes

Detached single-family homes make up much of western Cupertino, but buyers can also consider condominiums and townhomes elsewhere in the city. Attached housing may offer a lower-maintenance alternative, though buyers must evaluate homeowner association dues, reserves, insurance, rules and potential assessments.

Compare attached housing options in the Cupertino condos and townhomes guide.

Buying a Home Near a Cupertino School

A school-focused home search should begin with the exact property address rather than a neighborhood name, ZIP code or statement in a real estate listing. A home may be close enough to see the Kennedy campus while still having a different assigned middle school.

When evaluating a home near Kennedy Middle School, buyers should consider:

  • The current school assignment shown for the exact address
  • Confirmation from the appropriate school district
  • Walking, bicycling and driving routes
  • Traffic near the campus during arrival and dismissal
  • Lot size, orientation and expansion potential
  • Condition of the home and likely repair costs
  • Permit history for additions and remodeling
  • Access to parks, shopping and employment centers
  • Long-term suitability beyond the school name

A successful purchase should satisfy the buyer’s broader housing needs. School assignment can be important, but it should be considered together with the home, street, neighborhood, commute and long-term ownership plans.

How to Verify a Kennedy Middle School Assignment

The Cupertino Union School District provides an online school locator for preliminary address research. Final enrollment and placement decisions are controlled by the district, not by a real estate listing, agent remarks or third-party school website.

Before relying on a school assignment, buyers should:

  1. Enter the complete property address into the official CUSD school locator.
  2. Review the elementary and middle school results for that address.
  3. Contact the district if the assignment is unclear or important to the purchase.
  4. Verify the high school separately with the applicable high school district.
  5. Complete the research before removing any applicable purchase contingencies.

Check an address with the official CUSD School Locator.

School disclaimer: School attendance boundaries, enrollment policies, programs and assignments are controlled by the applicable school districts and may change. Information on this page is provided as a general real estate resource and does not guarantee enrollment or placement at Kennedy Middle School or any other school.

High School Assignments Must Be Verified Separately

Kennedy Middle School is part of the Cupertino Union School District. High school assignments in much of Cupertino are administered separately by the Fremont Union High School District.

Buyers should not assume that a Kennedy Middle School assignment automatically establishes a particular high school assignment. The high school should be checked independently using the exact property address and current district information.

Living in Western Cupertino

Western Cupertino combines established residential neighborhoods with access to foothill recreation, city services and major Silicon Valley employment centers. Buyers may find quieter interior streets, homes near parks and schools, larger lots and properties extending toward the western edge of the city.

The location can also provide access to Stevens Creek Boulevard, Foothill Expressway, Highway 85 and Interstate 280. Commute convenience depends on the property, destination and time of day, so buyers should personally test the routes they expect to use.

For buyers comparing neighborhood lifestyles throughout the ZIP code, the 95014 lifestyle guide provides an additional overview of Cupertino housing choices.

What Affects Home Prices Near Kennedy Middle School?

There is no single price range for homes near Kennedy Middle School. Values can vary substantially based on the home, lot and micro-location.

Important pricing factors include:

  • Verified school assignments
  • Lot size and usable outdoor space
  • Interior square footage and floor plan
  • Renovation quality and permit history
  • Age and condition of major systems
  • Interior-street versus major-road location
  • Foothill or hillside setting
  • Proximity to parks, schools and commute routes
  • Current inventory and buyer competition

Automated estimates may not account for differences in location, condition, topography or permitted improvements. A useful market analysis should compare the property with recent sales that are genuinely similar in neighborhood, size, lot, condition and school assignment.

Compare Other Cupertino School Areas

Buyers considering Kennedy Middle School may also want to compare central Cupertino and other school-focused locations. The homes near Lawson Middle School guide covers another Cupertino middle-school area with different neighborhood and commute characteristics.

The 95014 real estate and development guide provides a broader overview of Cupertino neighborhoods, housing and local development.

Work With a Cupertino Real Estate Agent

Buying near Kennedy Middle School requires more than searching listings by school name. A property may be geographically close while having a different assignment, significant repair needs, unpermitted improvements or a street position that affects value and daily convenience.

Bruce Wagg helps buyers compare Cupertino properties based on location, disclosures, inspection reports, recent comparable sales and individual housing priorities. School information can be researched during the process, but final assignments must always be verified directly with the appropriate district.

Call Bruce Wagg at 669-202-7777 to discuss buying or selling a home in Cupertino.

Request a Cupertino Home Search

Frequently Asked Questions About Homes Near Kennedy Middle School

Where is Kennedy Middle School located?

John F. Kennedy Middle School is located at 821 Bubb Road in Cupertino, California. The campus is in western Cupertino near McClellan Road, Stevens Creek Boulevard and established residential neighborhoods.

Does living near Kennedy Middle School guarantee enrollment?

No. Physical proximity does not guarantee enrollment or placement. Buyers should check the exact property address through the Cupertino Union School District and contact the district when the assignment is important to a purchase decision.

What neighborhoods are near Kennedy Middle School?

Kennedy Middle School is near the broader Monta Vista and western Cupertino area. Buyers may also compare homes in Oak Valley, Seven Springs and residential areas near Bubb Road and McClellan Road, although school assignments vary by address.

What types of homes are available near Kennedy Middle School?

The surrounding area includes original ranch-style homes, remodeled and expanded properties, custom residences and some larger homes closer to the foothills. Lot size, condition, floor plan and street location vary considerably.

Are there homes within walking distance of Kennedy Middle School?

Some homes are geographically close to the campus, but practical walking access depends on the exact address, street crossings, sidewalks and the route used. Buyers should personally evaluate the trip during normal school traffic conditions.

Does a Kennedy Middle School assignment determine the high school?

Not by itself. Middle schools and high schools are administered by separate districts in much of Cupertino. Buyers should verify the high school assignment independently for each property.

How do Monta Vista, Oak Valley and Seven Springs compare?

Monta Vista is one of western Cupertino’s best-known residential areas and includes a broad range of original, remodeled and custom homes. Oak Valley may offer different home sizes and price points, while Seven Springs is known for established residential streets and larger floor plans. Buyers should compare individual properties rather than relying only on neighborhood names.

How can I receive new listings near Kennedy Middle School?

Bruce Wagg can create a home search based on location, price, property type, lot size and other buyer priorities. Each potentially suitable property should then be checked individually for current school assignments, condition and market value.

Start Your Western Cupertino Home Search

Whether you are considering Monta Vista, Oak Valley, Seven Springs or another neighborhood near Kennedy Middle School, the right home should meet more than one requirement. Price, commute, property condition, lot size, street location and long-term plans should all be part of the decision.

Contact Bruce Wagg at 669-202-7777 for help evaluating homes near Kennedy Middle School and throughout western Cupertino.