
Apartments for Rent in the Winchester Neighborhood of San Jose, CA (418 Rentals) Page 4 of 9


3027 Van Sansul Ave

2989 Van Sansul Ave

2981 Van Sansul Ave

2999 Van Sansul Ave

2971 Van Sansul Ave

2961 Van Sansul Ave

2951 - 2955 Van Sansul Ave

3056 Van Sansul Ave

3036 Van Sansul Ave

3390-3392 Moorpark Ave

Van Sansul Apartments

Bahama Lanai Apartments

3026 Van Sansul Ave

2960 Van Sansul Ave

2980-3970 Van Sansul Ave

2994 Van Sansul Ave

2981 Neet Ave

2991 Neet Ave

Santana Place, San Jose

424 Monroe St

2964 Neet Ave

2990 Neet Ave

2972 Neet Ave

2980 Neet Ave

416 Monroe St

2958 Neet Ave

Sierra Crest

2952 Neet Ave

3015 Walgrove Ave

3001 Walgrove Way

2985 Walgrove Way

2975 Walgrove Way

3490-3492 Moorpark Ave

2953 Walgrove Way

2965 Walgrove Way

401 Bundy Ave

353 Bundy Ave

372-382 S Cypress Ave

364 S Cypress Ave

3512 Alden Way

3511 Alden Way

3055 Payne Ave

1301 Castlemont Ave

1307 Castlemont Ave

1315 Castlemont Ave

1319 Castlemont Ave

604-612 Genevieve Ln

1325 Castlemont Ave

1331 Castlemont Ave
Winchester, San Jose, CA Local Guide

How much does it cost to rent an apartment in Winchester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winchester Studio Apartments | $3,180 | $2,058 | $3,953 |
| Winchester 1 Bedroom Apartments | $3,621 | $2,075 | $5,292 |
| Winchester 2 Bedroom Apartments | $4,336 | $2,200 | $7,419 |
| Winchester 3 Bedroom Apartments | $6,302 | $3,299 | $9,371 |
How much does it cost to rent a home in Winchester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| 2 Bedroom Homes | $4,150 | $3,200 | $6,000 |
| 3 Bedroom Homes | $5,263 | $4,495 | $6,800 |
| 4 Bedroom Homes | $6,850 | $6,850 | $6,850 |
Browse Apartments in this Neighborhood
There are currently 418 rentals with your search options within a 2 mile radius of the Winchester Neighborhood of San Jose, CA.
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Frequently Asked Questions about Winchester
What is the current pricing and availability for apartments for rent in the Winchester area of San Jose, CA?
As of today, September 11, 2026, there are currently 418 available Winchester apartments priced from $2,058 to $9,371, with an average monthly rent of $4,460.
What is the current price range for One Bedroom Winchester Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Winchester ranges from $2,075 to $5,292 with an average monthly rent of $3,621.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $2,200 to $7,419. Today's average rental price for Two Bedrooms here is $4,336.
How expensive are Winchester Three Bedroom Apartments?
There are currently 85 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $3,299 to $9,371 - averaging $6,302 for the location.
Expert Rental Resources
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.
Helpful Local Expert Guides

Living and Working in San Jose: A Local Expert's Guide to the Best Neighborhoods to Rent Near San Joses Top Employers
Written by: Shannon Hilson
San Jose is absolutely one of those places where your zip code and your job eventually wind up in a very serious relationship.

Beyond Campus: Finding Your Perfect San Jose Student Apartment and Neighborhood
Written by: Shannon Hilson
Sunny San Jose is so much more than just an incredible place to go to school, get an education, and prepare for the next chapter of your life.

A Local Expert's Guide to the Top 10 Best Affordable Neighborhoods for Renters in San Jose
Written by: Shannon Hilson
If you’ve spent much time in San Jose, you’ve likely heard it referred to as “the capital of Silicon Valley” a time or two, and with good reason. San Jose has it all when it comes to the modern California lifestyle and then some.
Articles, How-To's, and Tips

Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.