Winchester

San Jose, CA

Background Image

Winchester - San Jose, CA Area Guide

Located a quick five miles from downtown San Jose, the Winchester neighborhood is a mix of upscale businesses and residences. Hop on I-280, and travel to the downtown area in under 10 minutes. Winchester's proximity to I-880 also makes this neighborhood an excellent option for commuters to the surrounding cities of Los Gatos and Santa Clara. Rental options mostly consist of luxury apartment complexes. Shopping enthusiasts delight in Santana Row, a deluxe combination of stores, restaurants, and living space. Enjoy a sweet snack at Kara's Cupcakes or find the perfect outfit at H&M. Throughout the year, Santana Row also hosts free events such as music and film series. Those who prefer indoor malls head to Westfield Valley Fair and its mix of national chains, including Macy's and the Cheesecake Factory.

Rent Trends

As of May 2026, the average apartment rent in Winchester is $2,902 for one bedroom, and $2,927 for two bedrooms. Apartment rent in Winchester has decreased by -3.4% in the past year.

  • 1 BR

  • 643 sq ft

    Average Sq Ft

  • $2,902/month

    Average Rent

  • 2 BR

  • 902 sq ft

    Average Sq Ft

  • $2,927/month

    Average Rent

Getting Around

Moderately Walkable

Walkability

60 / 100

Limited Public Transit

Transit

30 / 100

Exceptionally Drivable

Drivability

90 / 100

Fairly Bikeable

Bikeability

50 / 100

Daily Essentials

Supermarket Within a 10 Minute Walk

Groceries

80 / 100

Good Restaurant Variety Nearby

Restaurants

70 / 100

Fair Café Variety Nearby

Cafes

50 / 100

Good Variety of Shops Nearby

Shopping

70 / 100

Recreation

Large Amount of Park Space Nearby

Parks

60 / 100

Fair Wellness Amenity Variety Nearby

Wellness

40 / 100

Local Vibe

Mostly Calm Atmosphere

Vibrancy

30 / 100

Limited Nightlife Variety Nearby

Nightlife

30 / 100

Not Noisy

Quiet Score

100 / 100

Points of Interest

Top Apartments in Winchester

Property Management Companies

Search Nearby Rentals

Methodology

† Our analysis of utilities, groceries, transportation, healthcare, home prices, and other goods and services is sourced from the Cost of Living Index, a respected benchmark published by the Council for Community and Economic Research (C2ER) that provides a thorough overview of living expenses across different regions.

Rent data is provided by CoStar Group’s Market Trend reports. As the industry leader in commercial real estate information, analytics, and news, CoStar conducts extensive research to produce and maintain a comprehensive database of commercial real estate information. We combine this data with public record to provide the most up-to-date rental information available.

Consumer goods, services, and home prices are sourced from the Cost of Living Index published by the Council for Community and Economic Research (C2ER). The data on this page is updated quarterly. It was last published in February 2026.

Demographic information comes from Neustar and combines detailed address data with U.S. Census and American Community Survey statistics to produce reliable local estimates.