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Regency
1315 Eden AveSan Jose, CA 95117
Cheap Apartments for Rent in the Winchester Neighborhood of San Jose, CA from $800 (14 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winchester area of San Jose.
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from $1,905Studio to 2 Bedroom Apartments Available Now
eaves West Valley
700 S Saratoga AveSan Jose, CA 95129
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from $1,9801 Bedroom Apartments Available Now
Colonial House Apartments
3052 Colonial WaySan Jose, CA 95128
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from $1,9951 Bedroom Apartments Available Now
David Avenue
3080 David AveSan Jose, CA 95128
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
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from $2,050Studio to 3 Bedroom Apartments Available Now
The Grove
1919 Fruitdale AveSan Jose, CA 95128
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Studio to 2 Bedroom Apartments
Agrihood Senior Community (Ages 55+)
76 N Winchester BlvdSanta Clara, CA 95050
Check Out San Jose’s Best Affordable Neighborhoods
Learn about San Jose and the best places to live with original content written by our Local Expert Shannon Hilson
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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 | $2,443 | $1,905 | $4,232 |
| Winchester 1 Bedroom Apartments | $3,199 | $1,980 | $6,470 |
| Winchester 2 Bedroom Apartments | $4,698 | $2,166 | $10,000+ |
| Winchester 3 Bedroom Apartments | $5,999 | $3,555 | $9,022 |
| Winchester 4 Bedroom Apartments | $7,032 | $6,482 | $7,582 |
Browse Apartments in this Neighborhood
There are currently 14 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
- Nearby Cities
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- Local Counties
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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 The Dudley Apartments priced from $1,627. eaves West Valley has the second lowest priced unit, which is a Studio apartment currently listed from $1,905. Here are the most affordable Winchester apartments for rent in San Jose, CA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| The Dudley Apartments | 1 Bed 1 Bath | 1BR,1BA | $1,627 |
| eaves West Valley | 405 | Studio,1BA | $1,905 |
| Colonial House Apartments | 1 Bedroom | 1BR,1BA | $1,980 |
| David Avenue | a60 | 1BR,1BA | $1,995 |
| The Grove | Ruby- 475 sq ft | Studio,1BA | $2,050 |
Best Value Apartments for Rent in Winchester, CA
As of May 22, 2025 the best value apartment in the Winchester area is the $3.90 price per square foot Unit C Model at Santana Row in the in the South San Jose neighborhood starting from $4,657. The second greatest value Winchester apartment is the 333 Santana Row Model at 333 Santana Row, Unit #340 starting at $4,000 with a $3.64 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. |
|---|---|---|---|
| Santana Row | Unit C | 2BR,2BA | $3.90 |
| 333 Santana Row, Unit #340 | 333 Santana Row | 2BR,1.5BA | $3.64 |
| Livorno Square | Bernini | 2BR,1BA | $2.88 |
| 925 Ravenscourt Ave, Unit 2 | 925 Ravenscourt Ave | 2BR,1BA | $2.94 |
| 2928 Magliocco Dr, | 2 Bed 1 Bath | 2BR,1BA | $3.16 |
| West Park Apartments | The Southern | 1BR,1BA | $3.09 |
| Village of Taxco | Jr. 1 Bedroom, 1 Bathroom | 1BR,1BA | $3.77 |
| The Monterey Apartments | One Bedroom | 1BR,1BA | $3.14 |
| Colonial House Apartments | 1 Bedroom | 1BR,1BA | $3.00 |
| The Dudley Apartments | 1 Bed 1 Bath | 1BR,1BA | $2.87 |
Quick Rent Budget Calculator
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Pet Friendly LifestyleWinchester, San Jose, CA
Ranked #55
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
What is a cheap apartment in Winchester?
A cheap apartment is any apartment up to the 30% percentile of cost for the area, which in Winchester is under $2,555.
What is the price of a cheap apartment in Winchester?
The cheapest apartment in Winchester is The Dudley Apartments which is listed at $1,627, while the average apartment in Winchester costs $7,032.
What types of apartments are the cheapest in Winchester?
Student, low-income, and by-the-bed apartments are typically the cheapest rentals in most cities, though they require qualifying criteria to rent. There are 15 regular apartments in Winchester that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.
How do the prices of cheap apartments compare to the average apartment in Winchester?
Cheap apartments in Winchester have an average cost of $277 which is $6,755 cheaper than the average rent for all rentals in Winchester.
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.
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.
The Freedom of Short-Term Leases: Exploring the Advantages for Renters
Written by: Bobbi Jackson
If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.
Navigating the Rental Market: Tips for First-Time Renters
Written by: Sandy Baker
Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.