801 S Winchester Blvd, Unit 2100
801 S Winchester Blvd
San JoseCA95128
Cheap Homes for Rent in Winchester Neighborhood of San Jose, CA from $2,800 (13 Rentals)
Search the lowest-cost Homes available for rent right now in the Winchester area of San Jose.
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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
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333 Santana Row
San JoseCA95128
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.
656 Stokes St
CampbellCA95008
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589 N Monroe St
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 | $4,500 | $4,500 | $4,500 |
| Winchester 3 Bedroom Homes for Rent | $4,900 | $4,500 | $5,200 |
Browse Homes for Rent 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
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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 $1,627. Regency & Lexington has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,923. 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 | $1,627 |
| Regency & Lexington | Regency - a50 | 1BR,1BA | $1,923 |
| Colonial House Apartments | 1 Bedroom | 1BR,1BA | $1,980 |
| David Avenue | a60 | 1BR,1BA | $1,995 |
| 2928 Magliocco Dr, | 1 Bed 1 Bath | 1BR,1BA | $2,150 |
Best Value Apartments for Rent in Winchester, CA
As of July 30, 2025 the best value apartment in the Winchester area is the $3.76 price per square foot 2 Bed 2 Bath Model at Misora in the in the South San Jose neighborhood starting from $5,291. The second greatest value Winchester apartment is the 2991 Neet Ave Model at 2991 Neet Ave, Unit 3 starting at $2,950 with a $2.74 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. |
|---|---|---|---|
| Misora | 2 Bed 2 Bath | 2BR,2BA | $3.76 |
| 2991 Neet Ave, Unit 3 | 2991 Neet Ave | 2BR,1.5BA | $2.74 |
| Livorno Square | Bernini | 2BR,1BA | $2.88 |
| Regency & Lexington | Lexington - b60 | 2BR,1BA | $3.64 |
| West Park Apartments | The Southern | 1BR,1BA | $3.09 |
| Village of Taxco | Jr. 1 Bedroom, 1 Bathroom | 1BR,1BA | $3.69 |
| 2928 Magliocco Dr, | 1 Bed 1 Bath | 1BR,1BA | $3.07 |
| The Monterey Apartments | One Bedroom | 1BR,1BA | $3.14 |
| Colonial House Apartments | 1 Bedroom | 1BR,1BA | $3.00 |
| The Dudley Apartments | 1 Bed 1 Bath | 1BR,1BA | $2.87 |
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Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 401 Apartments for Rent in Winchester, CA with pricing that ranges from $1,923 to $17,707. There are also 14 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $2,800 to $5,200.
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 $2,800 to $5,200 with an average monthly rent of $4,066.
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.
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Written by: Christine Leonard, Esq.
Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.
The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.