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$1,923 - $3,3041 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 (12 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winchester area of San Jose.
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Rent Specials
$1,980 - $2,6101 to 2 Bedroom Apartments Available Now
Colonial House Apartments
3052 Colonial WaySan Jose, CA 95128
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Rent Specials
$1,995 - $2,7801 to 2 Bedroom Apartments Available Dec 31
David Avenue
3080 David AveSan Jose, CA 95128
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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
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Studio to 2 Bedroom Apartments
Agrihood Senior Community (Ages 55+)
76 N Winchester BlvdSanta Clara, CA 95050
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
Showing Results 1-12, 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 | $3,283 | $3,283 | $3,283 |
| Winchester 1 Bedroom Apartments | $3,485 | $1,980 | $5,229 |
| Winchester 2 Bedroom Apartments | $4,599 | $2,250 | $10,000+ |
| Winchester 3 Bedroom Apartments | $5,449 | $3,304 | $8,681 |
| Winchester 4 Bedroom Apartments | $6,574 | $6,024 | $7,124 |
Browse Apartments in this Neighborhood
There are currently 12 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
- School Districts
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 $2,085. Here are the most affordable Winchester apartments for rent in San Jose, CA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Regency & Lexington | Regency - a50 | 1BR,1BA | $1,923 |
| Colonial House Apartments | Remodeled 1 Bedroom | 1BR,1BA | $2,085 |
| Hacienda Hamilton | One Bedroom One Bath | 1BR,1BA | $2,650 |
| Village of Taxco | Jr. 1 Bedroom, 1 Bathroom | 1BR,1BA | $2,703 |
| Livorno Square | De Rossi | 1BR,1BA | $2,772 |
Best Value Apartments for Rent in Winchester, CA
As of December 03, 2025 the best value apartment in the Winchester area is the $3.05 price per square foot The Western Model at West Park Apartments in the in the South San Jose neighborhood starting from $3,495. The second greatest value Winchester apartment is the B2 Model at Santana Terrace starting at $4,128 with a $3.92 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. |
|---|---|---|---|
| West Park Apartments | The Western | 3BR,2BA | $3.05 |
| Santana Terrace | B2 | 2BR,2BA | $3.92 |
| Misora | 1 Bed 1 Bath | 1BR,1BA | $3.94 |
| Levare | 1 Bed 1 Bath Flat + Den A | 1BR,1BA | $4.25 |
| Colonial House Apartments | Remodeled 2 Bedroom | 2BR,1BA | $2.90 |
| Livorno Square | Battista | 1BR,1BA | $3.28 |
| Santana Row | Unit B1 | 1BR,1BA | $4.48 |
| Regency & Lexington | Lexington - c60 | 3BR,2BA | $4.19 |
| Village of Taxco | Jr. 1 Bedroom, 1 Bathroom | 1BR,1BA | $3.84 |
| Hacienda Hamilton | One Bedroom One Bath | 1BR,1BA | $4.42 |
Beyond Campus: Finding Your Perfect San Jose Apartment in the Perfect Student Friendly Neighborhood
Going to college in San Jose? Our local expert gives you the inside scoop on the best neighborhoods to live near Near SJSU, SCU, SJCC, and EVC
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Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
Read ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
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Pet Friendly LifestyleWinchester, San Jose, CA
Ranked #122
Among cities in California for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.5Pet 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 the price of a cheap apartment in Winchester?
The cheapest apartment in Winchester is Regency & Lexington which is listed at $1,923, while the average apartment in Winchester costs $6,574.
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 8 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 $460 which is $6,114 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.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.