Apartments for Rent in the Winchester Neighborhood of San Jose, CA (416 Rentals) Page 6 of 9

How Many Bedrooms?Done
Select your price rangeDone
to
Lifestyle Matching SearchDone
Learn more about Lifestyle Search
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done
close
View Me
1408 Essex Way
2 to 3 Bedroom Apartments

1408 Essex Way

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

3077 David Ave

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

3061 David Ave

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

1414 Essex Way

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

3027 David Ave

3027 David AveSan Jose, CA 95128
close
View Me
3069 David Ave
Studio Apartments

3069 David Ave

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

3087 David Ave

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

1409 Lexington Dr

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

3219 Williamsburg

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

2939 David Ave

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

2923 David Ave

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

1420 Essex Way

1420 Essex WaySan Jose, CA 95117
close
View Me
3170 Williamsburg Dr
2 Bedroom Apartments

3170 Williamsburg Dr

3170 Williamsburg DrSan Jose, CA 95117
  • Smoke Free
close
View Me
1428 Essex Way
Studio Apartments

1428 Essex Way

1428 Essex WaySan Jose, CA 95117
close
View Me
1445 Eden Ave
2 to 3 Bedroom Apartments

1445 Eden Ave

1445 Eden AveSan Jose, CA 95117
close
View Me
1434 Essex Way
Studio Apartments

1434 Essex Way

1434 Essex WaySan 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, July 27, 2026, there are currently 416 available Winchester apartments priced from $2,075 to $9,171, with an average monthly rent of $4,284.

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 $5,461 with an average monthly rent of $3,702.

What does renting a Two Bedroom Apartment in Winchester cost?

The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $2,545 to $8,176. Today's average rental price for Two Bedrooms here is $5,126.

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

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

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.

decorative image for Beyond Campus: Finding Your Perfect San Jose Student Apartment and Neighborhood article

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.

decorative image for A Local Expert's Guide to the Top 10 Best Affordable Neighborhoods for Renters in San Jose article

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

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

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.

decorative image for Apartment Occupancy Rates: Renter Attraction vs Renter Retention article

Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

decorative image for How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide article

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

decorative image for Pet-Friendly Renting: Everything You Need to Know Before You Move article

Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.