Apartments for Rent in the Winchester Neighborhood of San Jose, CA (418 Rentals) Page 6 of 9

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1408 Essex Way
2 to 3 Bedroom Apartments

1408 Essex Way

1408 Essex WaySan Jose, CA 95117
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3077 David Ave
Studio Apartments

3077 David Ave

3077 David AveSan Jose, CA 95128
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3061 David Ave
1 Bedroom Apartments

3061 David Ave

3061 David AveSan Jose, CA 95128
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1414 Essex Way
2 to 3 Bedroom Apartments

1414 Essex Way

1414 Essex WaySan Jose, CA 95117
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3027 David Ave
1 to 2 Bedroom Apartments

3027 David Ave

3027 David AveSan Jose, CA 95128
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3069 David Ave
Studio Apartments

3069 David Ave

3069 David AveSan Jose, CA 95128
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3087 David Ave
1 Bedroom Apartments

3087 David Ave

3087 David AveSan Jose, CA 95128
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1409 Lexington Dr
2 to 3 Bedroom Apartments

1409 Lexington Dr

1409 Lexington DrSan Jose, CA 95117
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3219 Williamsburg
2 to 3 Bedroom Apartments

3219 Williamsburg

3219 WilliamsburgSan Jose, CA 95117
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2939 David Ave
2 to 3 Bedroom Apartments

2939 David Ave

2939 David AveSan Jose, CA 95128
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2923 David Ave
2 to 3 Bedroom Apartments

2923 David Ave

2923 David AveSan Jose, CA 95128
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1420 Essex Way
2 to 3 Bedroom Apartments

1420 Essex Way

1420 Essex WaySan Jose, CA 95117
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1428 Essex Way
Studio Apartments

1428 Essex Way

1428 Essex WaySan Jose, CA 95117
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3170 Williamsburg Dr
2 Bedroom Apartments

3170 Williamsburg Dr

3170 Williamsburg DrSan Jose, CA 95117
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1445 Eden Ave
2 to 3 Bedroom Apartments

1445 Eden Ave

1445 Eden AveSan Jose, CA 95117
Showing Results 251-300, Page 6 of 9

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

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Living and Working in San Jose: A Local Expert's Guide to the Best Neighborhoods to Rent Near San Joses Top Employers

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San Jose is absolutely one of those places where your zip code and your job eventually wind up in a very serious relationship.

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Beyond Campus: Finding Your Perfect San Jose Student Apartment and Neighborhood

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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.

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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

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Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!

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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.

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

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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.

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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.

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

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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.