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$1,945Studio Apartments Available Now
Moorpark Garden Apartments
2966 Moorpark AveSan Jose, CA 95128
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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$1,9451 Bedroom Apartments Contact Us For Availability
Colonial Way Apartments
3051 Colonial WaySan Jose, CA 95128
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$1,986 - $3,3041 to 3 Bedroom Apartments Available Now
Regency & Lexington
1315 Eden AveSan Jose, CA 95117
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$2,085 - $2,6101 to 2 Bedroom Apartments Available Now
Colonial House Apartments
3052 Colonial WaySan Jose, CA 95128
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Studio to 2 Bedroom Apartments
The Dudley Apartments
355 Santana RowSan Jose, CA 95128
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Studio to 2 Bedroom Apartments
Turnleaf Apartments
3201 Loma Verde DrSan Jose, CA 95117
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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1 to 2 Bedroom Apartments
3137 Cadillac Dr
3137 Cadillac DrSan Jose, CA 95117
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1 Bedroom Apartments
3200 Cadillac Dr
3200 Cadillac DrSan Jose, CA 95117
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Studio to 2 Bedroom Apartments
Welcome to Cadillac Apartments
3189 Cadillac DrSan Jose, CA 95117
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Studio to 2 Bedroom Apartments
The Monterey Apartments
3510 Moorpark AveSan Jose, CA 95117
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Studio to 3 Bedroom Apartments
Bundy Ave
401 Bundy AveSan Jose, CA 95117
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1 to 2 Bedroom Apartments
Driftwood Apartments
1390 Castlemont AveSan Jose, CA 95128
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.
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Studio to 2 Bedroom Apartments
Agrihood Senior Community (Ages 55+)
76 N Winchester BlvdSanta Clara, CA 95050
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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 | $2,641 | $1,945 | $3,282 |
| Winchester 1 Bedroom Apartments | $3,482 | $1,945 | $4,678 |
| Winchester 2 Bedroom Apartments | $4,620 | $2,141 | $10,000+ |
| Winchester 3 Bedroom Apartments | $5,154 | $3,175 | $6,497 |
| Winchester 4 Bedroom Apartments | $6,574 | $6,024 | $7,124 |
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 The Dudley Apartments priced from $1,687. Moorpark Garden Apartments has the second lowest priced unit, which is a Studio apartment currently listed from $1,945. 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 | $1,687 |
| Moorpark Garden Apartments | Studio | Studio,1BA | $1,945 |
| Regency & Lexington | Regency - a50 | 1BR,1BA | $1,986 |
| Colonial House Apartments | Remodeled 1 Bedroom | 1BR,1BA | $2,085 |
| David Avenue | 1 BR, 1 BA - 60% | 1BR,1BA | $2,318 |
Best Value Apartments for Rent in Winchester, CA
As of January 20, 2026 the best value apartment in the Winchester area is the $4.19 price per square foot 1 Bed 1 Bath Flat + Den D Model at Levare in the in the South San Jose neighborhood starting from $4,184. The second greatest value Winchester apartment is the Remodeled 2 Bedroom Model at Colonial House Apartments starting at $2,610 with a $2.90 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. |
|---|---|---|---|
| Levare | 1 Bed 1 Bath Flat + Den D | 1BR,1BA | $4.19 |
| Colonial House Apartments | Remodeled 2 Bedroom | 2BR,1BA | $2.90 |
| Livorno Square | De Rossi | 1BR,1BA | $3.43 |
| Village of Taxco | Large 1 Bedroom, 1 Bathroom | 1BR,1BA | $3.06 |
| Misora | Studio | Studio ,1BA | $3.89 |
| Regency & Lexington | Lexington - c60 | 3BR,2BA | $4.16 |
| West Park Apartments | The Southern | 1BR,1BA | $3.23 |
| Lynhaven | A1.1 | 1BR,1BA | $4.64 |
| Hacienda Hamilton | One Bedroom One Bath | 1BR,1BA | $4.42 |
| The Dudley Apartments | 1 Bed 1 Bath | 1BR,1BA | $2.98 |
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.
Read ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
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Pet Friendly LifestyleWinchester, San Jose, CA
Ranked #123
Among cities in California for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
4.0Pet Friendly
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 $1,687 at The Dudley Apartments.
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 $2,610 at Colonial House Apartments.
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.
Articles, How-To's, and Tips
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.
A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
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.