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Rent Specials
$1,923 - $3,3041 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 (11 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winchester area of San Jose.
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$1,980 - $2,6101 to 2 Bedroom Apartments Available Now
Colonial House Apartments
3052 Colonial WaySan Jose, CA 95128
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$1,995 - $2,7801 to 2 Bedroom Apartments Available Dec 5
David Avenue
3080 David AveSan Jose, CA 95128
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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.
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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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Studio to 2 Bedroom Apartments
Agrihood Senior Community (Ages 55+)
76 N Winchester BlvdSanta Clara, CA 95050
Showing Results 1-11, 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 | $2,913 | $2,829 | $3,179 |
| Winchester 1 Bedroom Apartments | $3,439 | $1,980 | $6,686 |
| Winchester 2 Bedroom Apartments | $4,586 | $2,395 | $10,000+ |
| Winchester 3 Bedroom Apartments | $5,711 | $3,304 | $8,727 |
| Winchester 4 Bedroom Apartments | $6,574 | $6,024 | $7,124 |
Browse Apartments 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.
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Winchester, San Jose, CA Local Guide
- Nearby San Jose neighborhoods
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- Local Counties
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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 Regency & Lexington priced from $1,923. Colonial House Apartments has the second lowest priced unit, which is a 1 Bed apartment currently listed from $2,085. Here are the most affordable Winchester apartments for rent in San Jose, CA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Regency & Lexington | Regency - a50 | 1BR,1BA | $1,923 |
| Colonial House Apartments | Remodeled 1 Bedroom | 1BR,1BA | $2,085 |
| The Monterey Apartments | Large One Bedroom | 1BR,1BA | $2,215 |
| West Park Apartments | The Southern | 1BR,1BA | $2,295 |
| Colonial Way Apartments | 1 Bedroom Large | 1BR,1BA | $2,345 |
Best Value Apartments for Rent in Winchester, CA
As of October 08, 2025 the best value apartment in the Winchester area is the $3.72 price per square foot 3 Bed 2 Bath Model at Misora in the in the South San Jose neighborhood starting from $5,591. The second greatest value Winchester apartment is the Leoni Model at Livorno Square starting at $3,160 with a $2.76 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 | $3.72 |
| Livorno Square | Leoni | 2BR,2BA | $2.76 |
| 684 Teatree Ct, Unit 2 Bedroom 2 Bath for Rent | 684 Teatree Ct | 2BR,2BA | $3.47 |
| Colonial House Apartments | Remodeled 2 Bedroom | 2BR,1BA | $2.90 |
| Santana Row | Unit G2 | 1BR,1BA | $4.26 |
| Colonial Way Apartments | 1 Bedroom Large | 1BR,1BA | $2.76 |
| Regency & Lexington | Lexington - c60 | 3BR,2BA | $4.19 |
| West Park Apartments | The Southern | 1BR,1BA | $3.09 |
| The Monterey Apartments | Large One Bedroom | 1BR,1BA | $3.08 |
| The Franciscan | 1 Bed, 1 Bath | 1BR,1BA | $3.94 |
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Pet Friendly LifestyleWinchester, San Jose, CA
Ranked #105
Among cities in California for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.5Pet Friendly
Getting Around the Winchester Neighborhood in San Jose, CA
Walk Score®
68 / 100
Somewhat Walkable
Some errands can be accomplished on foot
Bike Score®
78 / 100
Very Bikeable
Biking is convenient for most trips
Transit Score®
48 / 100
Some Transit
A few nearby public transportation options
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about Cheap Winchester Apartments
What is the Cheapest Studio apartment in Winchester?
Currently the most affordable Cheap Studio Apartment in Winchester is at Misora listed at $3,101.
How much is rent for a Cheap One Bedroom Winchester Apartment?
The lowest price for a Cheap One Bedroom Winchester Apartment is $1,923 at Regency & Lexington.
What is the lowest price for a Cheap Two Bedroom Winchester Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Winchester is starting from $2,610 at Colonial House Apartments.
What is the most affordable Winchester Three Bedroom Apartment?
The best deal on a cheap Winchester Three Bedroom Apartment rental is at Regency & Lexington and starts from $3,200.
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.
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.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.