333 Santana Row, Unit 208
333 Santana Row
San JoseCA95128
Cheap Homes for Rent in Winchester Neighborhood of San Jose, CA from $2,400 (4 Rentals)
Search the lowest-cost Homes available for rent right now in the Winchester area of San Jose.
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.
736 Opal Dr
San JoseCA95117
Navigating 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.
1141 Yarwood Ct
San JoseCA95128
Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.
333 Santana Row
San JoseCA95128
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Winchester, San Jose, CA Local Guide
How much does it cost to rent a home in Winchester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $4,003 | $2,490 | $5,500 |
| Winchester 4 Bedroom Homes for Rent | $11,000 | $10,000 | $10,000+ |
Browse Homes for Rent in this Neighborhood
There are currently 4 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
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Best Value Apartments for Rent in Winchester, CA
As of May 16, 2025 the best value apartment in the Winchester area is the $2.92 price per square foot Palladio B Model at Livorno Square in the in the South San Jose neighborhood starting from $3,890. The second greatest value Winchester apartment is the 2 Bed 2 Bath Model at 2928 Magliocco Dr, starting at $2,650 with a $2.28 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. |
|---|---|---|---|
| Livorno Square | Palladio B | 3BR,2BA | $2.92 |
| 2928 Magliocco Dr, | 2 Bed 2 Bath | 2BR,2BA | $2.28 |
| 333 Santana Row, Unit #340 | 333 Santana Row | 2BR,1.5BA | $3.64 |
| 925 Ravenscourt Ave, Unit 2 | 925 Ravenscourt Ave | 2BR,1BA | $2.94 |
| Village of Taxco | Large 1 Bedroom, 1 Bathroom | 1BR,1BA | $3.12 |
| West Park Apartments | The Southern | 1BR,1BA | $3.09 |
| The Monterey Apartments | One Bedroom | 1BR,1BA | $3.14 |
| Colonial House Apartments | 1 Bedroom | 1BR,1BA | $3.00 |
| Cedar Glen | Pine Cone | 1BR,1BA | $3.91 |
| The Dudley Apartments | 1 Bed 1 Bath | 1BR,1BA | $2.87 |
Quick Rent Budget Calculator
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Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 413 Apartments for Rent in Winchester, CA with pricing that ranges from $1,867 to $17,532. There are also 6 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $150 to $11,000.
What is the current price range for Rental Homes in Winchester?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winchester ranges from $150 to $11,000 with an average monthly rent of $5,051.
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.
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.
Rise of Digital Nomads: Remote Work Tips for Apartment Renters
Written by: Brandie Parton
As a digital nomad, you no longer call a set address or office building your home for eight hours of the day or more.