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$1,923 - $3,2001 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 (42 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 Available May 15
Colonial Way Apartments
3051 Colonial WaySan Jose, CA 95128
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$2,075 - $2,6101 to 2 Bedroom Apartments Available Now
Colonial House Apartments
3052 Colonial WaySan Jose, CA 95128
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$2,075 - $2,3181 to 2 Bedroom Apartments Available Now
David Avenue
3080 David AveSan Jose, CA 95128
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$2,3451 Bedroom Apartments Available May 15
2991 Neet Ave, Unit 2
2991 Neet AveSan Jose, CA 95128
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$2,3451 Bedroom Apartments Available Jun 1
2991 Neet Ave, Unit 2
2991 Neet AveSan Jose, CA 95128
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$2,4601 Bedroom Apartments Available Now
367 Santana Hts, Unit SI FL4-ID1756
367 Santana HtsSan Jose, CA 95128
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$2,4951 Bedroom Apartments Available Now
West Park Apartments
3200 Payne AveSan Jose, CA 95117
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.
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Rent Specials
$2,735 - $5,587Studio to 2 Bedroom Apartments Available Now
Village of Taxco
1324 S WinchesterSan Jose, CA 95128
1483-1485 Merry Ln
San JoseCA95128
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$3,213 - $5,384
Total Monthly Price
1 to 3 Bedroom Apartments Available NowTotal Monthly Price
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$3,213 - $5,384
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Lynhaven
919 S Winchester BlvdSan Jose, CA 95128
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$3,292 - $14,063
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1 to 4 Bedroom Apartments Available Jun 7Total Monthly Price
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$3,292 - $14,063
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Santana Row
377 Santana RowSan Jose, CA 95128
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$3,2952 Bedroom Apartments Available Now
Moorpark Garden Apartments
2966 Moorpark AveSan Jose, CA 95128
1329 Essex Way
San JoseCA95117
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$3,445 - $15,278
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Studio to 3 Bedroom Apartments Available NowTotal Monthly Price
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$3,445 - $15,278
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Misora
388 Santana RowSan Jose, CA 95128
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$3,552 - $9,255
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1 to 3 Bedroom Apartments Available NowTotal Monthly Price
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$3,552 - $9,255
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Levare
3003 Olin AveSan Jose, CA 95128
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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$3,8401 Bedroom Apartments Available Jun 1
367 Santana Hts, Unit SI FL3-ID1755
367 Santana HtsSan Jose, CA 95128
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$3,9701 Bedroom Apartments Available Now
388 Santana Row, Unit SI FL2-ID2040
388 Santana RowSan Jose, CA 95128
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$4,000
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2 Bedroom Apartment Available NowTotal Monthly Price
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$4,000
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$4,000
333 Santana Row, Unit #208, Unit #208
333 Santana RowSan Jose, CA 95128
471 Maplewood Ave
San JoseCA95117
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$4,0701 Bedroom Apartments Available May 1
388 Santana Row, Unit SI FL3-ID315
388 Santana RowSan Jose, CA 95128
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$4,1801 Bedroom Apartments Available Jun 5
3003 Olin Ave, Unit SI FL4-ID845
3003 Olin AveSan Jose, CA 95128
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$4,2201 Bedroom Apartments Available May 2, 2030
3003 Olin Ave, Unit SI FL4-ID831
3003 Olin AveSan Jose, CA 95128
3063 Westfield Avenue
San JoseCA95128
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
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
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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
401 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
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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1 to 2 Bedroom Apartments
Raintree Apartments
1058 S Winchester BlvdSan Jose, CA 95128
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2 Bedroom Apartments
Ravenscourt Heights
948-954 Ravenscourt AveSan Jose, CA 95128
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2 Bedroom Apartments
928 Ravenscourt
928 Ravenscourt AveSan Jose, CA 95128
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1 to 2 Bedroom Apartments
Santana Place, San Jose
2955 Neet AveSan Jose, CA 95128
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1 to 3 Bedroom Apartments
Livorno Square
3101 Magliocco DrSan Jose, CA 95128
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Studio to 3 Bedroom Apartments
Windsor Winchester
585 S Winchester BlvdSan Jose, CA 95128
3063 Westfield Ave
San JoseCA95128
1445 Lexington Dr
San JoseCA95117
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.
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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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1 to 3 Bedroom Apartments
Hacienda Hamilton
160 W Hamilton AveCampbell, CA 95008
Showing Results 1-42, 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 | $3,588 | $3,445 | $3,697 |
| Winchester 1 Bedroom Apartments | $3,509 | $1,923 | $4,767 |
| Winchester 2 Bedroom Apartments | $5,195 | $2,299 | $10,000+ |
| Winchester 3 Bedroom Apartments | $4,077 | $2,299 | $9,255 |
| Winchester 4 Bedroom Apartments | $4,627 | $4,077 | $5,177 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Apartments in this Neighborhood
There are currently 42 rentals with your search options within a 2 mile radius of the Winchester Neighborhood of San Jose, CA.
See all Apartments in San JoseExplore San Jose
Winchester, San Jose, CA Local Guide
- Nearby San Jose neighborhoods
- Nearby Cities
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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 Colonial House Apartments priced from $2,075. David Avenue has the second lowest priced unit, which is a 1 Bed apartment currently listed from $2,075. Here are the most affordable Winchester apartments for rent in San Jose, CA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Colonial House Apartments | Remodeled 1 Bedroom | 1BR,1BA | $2,075 |
| David Avenue | One Bedroom - 60% AMI | 1BR,1BA | $2,075 |
| Regency & Lexington | Regency - b50 | 2BR,1BA | $2,299 |
| Village of Taxco | Jr. 1 Bedroom, 1 Bathroom | 1BR,1BA | $2,735 |
| Lynhaven | A1 | 1BR,1BA | $3,213 |
| Moorpark Garden Apartments | 2 Bedroom Townhouse W/D Patio and Balcony | 2BR,1BA | $3,295 |
| Levare | 1 Bed 1 Bath Flat + Den A | 1BR,1BA | $3,552 |
| Misora | Studio | Studio,1BA | $3,606 |
Best Value Apartments for Rent in Winchester, CA
As of April 28, 2026 the best value apartment in the Winchester area is the $3.20 price per square foot 333 Santana Row Model at 333 Santana Row, Unit #208 in the in the South San Jose neighborhood starting from $4,000. The second greatest value Winchester apartment is the 2 Bedroom Townhouse W/D Patio and Balcony Model at Moorpark Garden Apartments starting at $3,295 with a $3.30 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. |
|---|---|---|---|
| 333 Santana Row, Unit #208 | 333 Santana Row | 2BR,1.5BA | $3.20 |
| Moorpark Garden Apartments | 2 Bedroom Townhouse W/D Patio and Balcony | 2BR,1.5BA | $3.30 |
| Levare | 1x1 A | 1BR,1BA | $5.20 |
| Regency & Lexington | Lexington - b60 | 2BR,1BA | $3.64 |
| West Park Apartments | The Southern | 1BR,1BA | $3.36 |
| Colonial House Apartments | Remodeled 1 Bedroom | 1BR,1BA | $2.92 |
| Village of Taxco | Jr. 1 Bedroom, 1 Bathroom | 1BR,1BA | $3.88 |
| Lynhaven | A1 | 1BR,1BA | $4.68 |
| Misora | Studio | Studio ,1BA | $6.35 |
| David Avenue | One Bedroom - 60% AMI | 1BR,1BA | $4.77 |
10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
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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
Read ArticleDon'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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How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
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Pet Friendly LifestyleWinchester, San Jose, CA
Ranked #128
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
What is the price of a cheap apartment in Winchester?
The cheapest apartment in Winchester is Colonial House Apartments which is listed at $2,075, while the average apartment in Winchester costs $5,068.
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 5 regular apartments in Winchester that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.
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.
Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.
Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.