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$2,075 - $2,6101 to 2 Bedroom Apartments Available Now
Colonial House Apartments
3052 Colonial WaySan Jose, CA 95128
Cheap Apartments for Rent in the Winchester Neighborhood of San Jose, CA from $1,425 (37 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winchester area of San Jose.
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$2,3451 Bedroom Apartments Available Soon
Colonial Way Apartments
3051 Colonial WaySan Jose, CA 95128
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$2,379 - $3,2992 to 3 Bedroom Apartments Available Now
Regency & Lexington
1315 Eden AveSan Jose, CA 95117
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$2,422 - $4,919Studio to 2 Bedroom Apartments Available Sep 19
Village of Taxco
1324 S WinchesterSan Jose, CA 95128
1331 Castlemont Ave
San JoseCA95128
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$2,675 - $3,1951 to 2 Bedroom Apartments Available Now
West Park Apartments
3200 Payne AveSan Jose, CA 95117
3361 Madonna Dr
San JoseCA95117
1474-1476 Merry Ln
San JoseCA95128
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$3,420
Total Monthly Price
Base Rent$3,420
Total Monthly Price$3,420
3003 Olin Ave, Unit SI FL4-ID845
3003 Olin AveSan Jose, CA 95128
Living and Working in San Jose: A Local Expert’s Guide to the Best Neighborhoods to Rent Near San Jose’s Top Employers
Find the ideal San Jose neighborhood to rent based on your job and preferred commute. Discover the best local spots and housing options near tech giants.
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$3,710
Total Monthly Price
Base Rent$3,710
Total Monthly Price$3,710
388 Santana Row, Unit SI FL2-ID2017
388 Santana RowSan Jose, CA 95128
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$3,797 - $14,779
Total Monthly Price
Base Rent$3,797 - $14,779
Total Monthly PriceVaries
Misora
388 Santana RowSan Jose, CA 95128
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$3,900
Total Monthly Price
Base Rent$3,900
Total Monthly Price$3,900
367 Santana Hts, Unit SI FL4-ID1756
367 Santana HtsSan Jose, CA 95128
2990 Neet Ave
San JoseCA95128
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$4,090
Total Monthly Price
Base Rent$4,090
Total Monthly Price$4,090
388 Santana Row, Unit SI FL3-ID315
388 Santana RowSan Jose, CA 95128
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$4,150
Total Monthly Price
Base Rent$4,150
Total Monthly Price$4,150
367 Santana Row, Unit SI FL5-ID814
367 Santana RowSan Jose, CA 95128
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$4,263 - $13,295
Total Monthly Price
Base Rent$4,263 - $13,295
Total Monthly PriceVaries
Levare
3003 Olin AveSan 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
Rent According to Income: A Look at Income-Restricted Rentals
Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.
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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
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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
928 Ravenscourt
928 Ravenscourt AveSan Jose, CA 95128
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2 Bedroom Apartments
Ravenscourt Heights
948-954 Ravenscourt AveSan Jose, CA 95128
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
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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 2 Bedroom Apartments
Moorpark Garden Apartments
2966 Moorpark AveSan Jose, CA 95128
682 S Genevieve Ln
San JoseCA95128
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Studio to 3 Bedroom Apartments
Windsor Winchester
585 S Winchester BlvdSan Jose, CA 95128
1144 Yarwood Ct
San JoseCA95128
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$2,058 - $2,200Studio to 2 Bedroom Apartments Available Now
Agrihood Senior Community (Ages 55+)
76 N Winchester BlvdSanta Clara, CA 95050
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$3,121 - $4,166
Total Monthly Price
Base Rent$3,121 - $4,166
Total Monthly PriceVaries
The Franciscan
601 Almarida DrCampbell, CA 95008
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1 to 3 Bedroom Apartments
Hacienda Hamilton
160 W Hamilton AveCampbell, CA 95008
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.
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1 to 2 Bedroom Apartments
Santana Terrace
190 N Winchester BlvdSanta Clara, CA 95050
Showing Results 1-37, 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 | $3,180 | $2,058 | $3,953 |
| Winchester 1 Bedroom Apartments | $3,621 | $2,075 | $5,292 |
| Winchester 2 Bedroom Apartments | $4,336 | $2,200 | $7,419 |
| Winchester 3 Bedroom Apartments | $6,302 | $3,299 | $9,371 |
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 37 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
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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 Studio unit found at Agrihood Senior Community (Ages 55+) priced from $2,058. Colonial House Apartments 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 |
|---|---|---|---|
| Agrihood Senior Community (Ages 55+) | Studio | Studio,1BA | $2,058 |
| Colonial House Apartments | Remodeled 1 Bedroom | 1BR,1BA | $2,075 |
| Regency & Lexington | Regency - b60 | 2BR,1BA | $2,379 |
| West Park Apartments | The Southern | 1BR,1BA | $2,675 |
| The Franciscan | 1 Bed, 1 Bath | 1BR,1BA | $3,121 |
| Santana Terrace | A2 | 1BR,1BA | $3,903 |
| Misora | Studio A | Studio,1BA | $3,927 |
| Levare | 2 Bed 2 Bath Flat + Den A | 2BR,2BA | $5,457 |
Best Value Apartments for Rent in Winchester, CA
As of September 11, 2026 the best value apartment in the Winchester area is the $4.28 price per square foot 2 Bed 2 Bath Flat + Den A Model at Levare in the in the South San Jose neighborhood starting from $5,457. The second greatest value Winchester apartment is the Lexington - b60 Model at Regency & Lexington starting at $2,801 with a $3.67 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 | 2 Bed 2 Bath Flat + Den A | 2BR,2BA | $4.28 |
| Regency & Lexington | Lexington - b60 | 2BR,1BA | $3.67 |
| West Park Apartments | The Southern | 1BR,1BA | $3.61 |
| Santana Terrace | A2 | 1BR,1BA | $5.26 |
| Colonial House Apartments | Remodeled 1 Bedroom | 1BR,1BA | $2.92 |
| The Franciscan | 1 Bed, 1 Bath | 1BR,1BA | $4.46 |
| Misora | Studio A | Studio ,1BA | $6.21 |
| Agrihood Senior Community (Ages 55+) | Studio | Studio ,1BA | $4.90 |
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 ArticleNavigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
Read ArticleReal Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
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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 #121
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 $3,974.
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.
How do the prices of cheap apartments compare to the average apartment in Winchester?
Cheap apartments in Winchester have an average cost of $549 which is $3,425 cheaper than the average rent for all rentals in Winchester.
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.
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Living and Working in San Jose: A Local Expert's Guide to the Best Neighborhoods to Rent Near San Joses Top Employers
Written by: Shannon Hilson
San Jose is absolutely one of those places where your zip code and your job eventually wind up in a very serious relationship.
Beyond Campus: Finding Your Perfect San Jose Student Apartment and Neighborhood
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Sunny San Jose is so much more than just an incredible place to go to school, get an education, and prepare for the next chapter of your life.
A Local Expert's Guide to the Top 10 Best Affordable Neighborhoods for Renters in San Jose
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Rent According to Income: A Look at Income-Restricted Rentals
Written by: Robin Stewart
The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.
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