close
View Me
Cheap Homes for Rent in Winchester Neighborhood of San Jose, CA from $3,900 (11 Rentals)
Search the lowest-cost Homes available for rent right now in the Winchester area of San Jose.
close
View Me
1369 Cherrywood Square
San JoseCA95117
close
View Me
close
View Me
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.
close
View Me
close
View Me
close
View Me
close
View Me
432 Bundy Ave
San JoseCA95117
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.
339 Cypress Ave
San JoseCA95117
Showing Results 1-11, Page 1 of 1
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 | $3,950 | $3,950 | $3,950 |
| Winchester 3 Bedroom Homes for Rent | $4,750 | $4,500 | $5,000 |
| Winchester 4 Bedroom Homes for Rent | $4,700 | $4,700 | $4,700 |
Browse Homes for Rent in this Neighborhood
There are currently 11 rentals with your search options within a 2 mile radius of the Winchester Neighborhood of San Jose, CA.
Explore San Jose
Winchester, San Jose, CA Local Guide
- Nearby San Jose neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
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 $1,582. 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 | $1,582 |
| Regency & Lexington | Regency - a50 | 1BR,1BA | $1,923 |
| Colonial House Apartments | Remodeled 1 Bedroom | 1BR,1BA | $2,085 |
| Colonial Way Apartments | 1 Bedroom Large | 1BR,1BA | $2,345 |
| Village of Taxco | Jr. 1 Bedroom, 1 Bathroom | 1BR,1BA | $2,644 |
Best Value Apartments for Rent in Winchester, CA
As of November 03, 2025 the best value apartment in the Winchester area is the $3.90 price per square foot 3 Bed 2 Bath Model at Misora in the in the South San Jose neighborhood starting from $5,861. The second greatest value Winchester apartment is the D1 Loft Model at Lynhaven starting at $5,516 with a $4.15 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 | 3 Bed 2 Bath | 3BR,2BA | $3.90 |
| Lynhaven | D1 Loft | 3BR,2BA | $4.15 |
| The Monterey Apartments | Large Two Bedroom | 2BR,2BA | $2.68 |
| 684 Teatree Ct, Unit 2 Bedroom 2 Bath for Rent | 684 Teatree Ct | 2BR,2BA | $3.47 |
| Levare | 1 Bed 1 Bath Flat + Den A | 1BR,1BA | $4.18 |
| Colonial House Apartments | Remodeled 2 Bedroom | 2BR,1BA | $2.90 |
| Livorno Square | Battista | 1BR,1BA | $3.28 |
| Colonial Way Apartments | 1 Bedroom Large | 1BR,1BA | $2.76 |
| Village of Taxco | Jr. 1 Bedroom, 1 Bathroom | 1BR,1BA | $3.76 |
| The Dudley Apartments | 1 Bed 1 Bath | 1BR,1BA | $4.01 |
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 Article
Apartment Common Area Rules: What Renters Need to Know
From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.
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 ArticleQuick Rent Budget Calculator
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.
Let everyone know!
Do you know the Winchester area?
If you’re an expert on all things Winchester, tell us what you love (and don't) by rating it and writing a review.
Write a Review
Pet Friendly LifestyleWinchester, San Jose, CA
Ranked #130
Among cities in California for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
4.0Pet Friendly
Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 404 Apartments for Rent in Winchester, CA with pricing that ranges from $1,980 to $17,074. There are also 12 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $3,950 to $5,000.
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 $3,950 to $5,000 with an average monthly rent of $4,466.
How much are larger Three and Four Bedroom Rentals in Winchester?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Winchester range from $3,304 to $8,681, while Three Bedroom Homes, Condos, and Townhomes for rent range from $4,500 to $5,000. Four Bedroom Single-Family rentals are also available starting from $4,700 and Four Bedroom Apartments start at $6,024.
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.
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.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.