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from $1,9231 to 3 Bedroom Apartments Available Now
Regency & Lexington
1315 Eden AveSan Jose, CA 95117
Cheap Apartments for Rent in the Winchester Neighborhood of San Jose, CA from $800 (13 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winchester area of San Jose.
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from $1,9801 Bedroom Apartments Available Now
Colonial House Apartments
3052 Colonial WaySan Jose, CA 95128
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Studio to 2 Bedroom Apartments
Agrihood Senior Community (Ages 55+)
76 N Winchester BlvdSanta Clara, CA 95050
Showing Results 1-13, Page 1 of 1
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 | $2,982 | $2,782 | $3,391 |
| Winchester 1 Bedroom Apartments | $3,369 | $1,923 | $6,890 |
| Winchester 2 Bedroom Apartments | $5,049 | $2,400 | $10,000+ |
| Winchester 3 Bedroom Apartments | $6,279 | $3,200 | $10,000+ |
| Winchester 4 Bedroom Apartments | $7,207 | $6,657 | $7,757 |
Browse Apartments in this Neighborhood
There are currently 13 rentals with your search options within a 2 mile radius of the Winchester Neighborhood of San Jose, CA.
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Winchester, San Jose, CA Local Guide
- Nearby San Jose neighborhoods
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Cheapest Available Winchester Apartments for Rent
The cheapest available apartment rental in the Winchester area of San Jose, CA is a 1 Bed unit found at Regency & Lexington priced from $1,923. Colonial House Apartments has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,980. Here are the most affordable Winchester apartments for rent in San Jose, CA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Regency & Lexington | a50 | 1BR,1BA | $1,923 |
| Colonial House Apartments | 1 Bedroom | 1BR,1BA | $1,980 |
| David Avenue | a60 | 1BR,1BA | $1,995 |
| The Monterey Apartments | One Bedroom | 1BR,1BA | $2,120 |
| 2928 Magliocco Dr, | 1 Bed 1 Bath | 1BR,1BA | $2,150 |
Best Value Apartments for Rent in Winchester, CA
As of July 15, 2025 the best value apartment in the Winchester area is the $2.69 price per square foot 334 Santana Row Model at 334 Santana Row, Unit #300M in the in the South San Jose neighborhood starting from $5,500. The second greatest value Winchester apartment is the 2 Bed 2 Bath Flat + Den Model at Levare starting at $5,200 with a $4.14 price per square foot in the South San Jose neighborhood. Here is today’s list of the best values for Winchester apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 334 Santana Row, Unit #300M | 334 Santana Row | 2BR,2BA | $2.69 |
| Levare | 2 Bed 2 Bath Flat + Den | 2BR,2BA | $4.14 |
| 2991 Neet Ave, Unit 3 | 2991 Neet Ave | 2BR,1.5BA | $2.74 |
| Livorno Square | Bernini | 2BR,1BA | $2.88 |
| Regency & Lexington | b60 | 2BR,1BA | $3.43 |
| West Park Apartments | The Southern | 1BR,1BA | $3.23 |
| Village of Taxco | Jr. 1 Bedroom, 1 Bathroom | 1BR,1BA | $3.81 |
| 2928 Magliocco Dr, | 1 Bed 1 Bath | 1BR,1BA | $3.07 |
| The Monterey Apartments | One Bedroom | 1BR,1BA | $3.14 |
| Colonial House Apartments | 1 Bedroom | 1BR,1BA | $3.00 |
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Pet Friendly LifestyleWinchester, San Jose, CA
Ranked #94
Among neighborhoods in San Jose, CA for Apartment listings with Pet Friendly Amenities
Pet Friendliness Lifestyle Score
4.0Pet Friendly
Getting Around the Winchester Neighborhood in San Jose, CA
Walk Score®
68 / 100
Somewhat Walkable
Some errands can be accomplished on foot
Bike Score®
78 / 100
Very Bikeable
Biking is convenient for most trips
Transit Score®
48 / 100
Some Transit
A few nearby public transportation options
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about Cheap Winchester Apartments
How much is rent for a Cheap One Bedroom Winchester Apartment?
The lowest price for a Cheap One Bedroom Winchester Apartment is $1,923 at Regency & Lexington.
What is the lowest price for a Cheap Two Bedroom Winchester Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Winchester is starting from $2,299 at Regency & Lexington.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.
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.
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.
The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.
Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.