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Starting at $4,083
1 Bedroom • 1 Bath • 704 – 709 Sq Ft
| 2 available units | Price | Sq ft | Available | Open unit |
|---|---|---|---|---|
| 337 | $4,083 | 704 | Oct 17 | |
| 614 | $4,162 | 709 | Nov 11 |
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$4,083 – $5,179/mo
585 Winchester Blvd, San Jose, CA, 95128Windsor Winchester currently lists 3 floor plans across 6 available units, from one-bedroom to two-bedroom, starting at $4,083/mo. 5 one-bedrooms from $4,083 to $4,494/mo (704–795 sq ft), earliest move-in Oct 17. 1 two-bedroom at $5,179/mo (1,138 sq ft), earliest move-in Oct 28. Prices checked September 24, 2026.
Starting at $4,083
1 Bedroom • 1 Bath • 704 – 709 Sq Ft
| 2 available units | Price | Sq ft | Available | Open unit |
|---|---|---|---|---|
| 337 | $4,083 | 704 | Oct 17 | |
| 614 | $4,162 | 709 | Nov 11 |
Starting at $4,349
1 Bedroom • 1 Bath • 772 – 795 Sq Ft
| 3 available units | Price | Sq ft | Available | Open unit |
|---|---|---|---|---|
| 506 | $4,349 | 795 | Oct 19 | |
| 753 | $4,494 | 772 | Oct 24 | |
| 606 | $4,360 | 795 | Nov 5 |
Starting at $5,179
2 Bedrooms • 2 Baths • 1,138 Sq Ft
| 1 available unit | Price | Sq ft | Available | Open unit |
|---|---|---|---|---|
| 373 | $5,179 | 1,138 | Oct 28 |
Rent at Windsor Winchester is $4,083 – $5,179 per month. Leases are typically 15 months. The earliest listed move-in is Oct 17. Prices checked September 24, 2026.
Rent
$4,083 – $5,179/moLease term
15 monthsEarliest move-in
Oct 17Windsor Winchester lists 40 amenities, including a gym, a pool, and pet-friendly spaces.
24-Hour Fitness Center With Echelon Reflect Mirror & Bikes
9’ To 11’ Ceilings*
Adjacent To The Historic Winchester Mystery House, Adding Charm And Cultural Appeal To The Neighborhood
Built-In Desks And Bookshelves Ideal For Remote Work*
Chef-Inspired Kitchens With Custom Italian Cabinetry
Dual Vanities And Oversized Custom Closets*
Easy Access To Downtown San Jose And Major Freeways Including I-280 And I-880 For Seamless Commuting
Elevated Green Space With Outdoor Fireplace And Cozy Seating
Entertaining Kitchen And Resident Social Lounge With Plenty Of Cozy Seating For Gathering And Entertaining Friends
Ev Charging Stations
Expansive Social Courtyards With Fire Pits, Grills, And Open-Air Dining
Flexible Co-Working Spaces And Private Meeting Rooms
Floor-To-Ceiling Windows With Panoramic Views*
In Home Washer/Dryer
Located In The Heart Of Silicon Valley, Offering Unmatched Access To Tech Hubs, Shopping, And Entertainment
Luxerone Package Locker System With Refrigerated Storage
Modern Fixtures And Finishes
Modern Wide-Plank Wood-Style Flooring Throughout*
Online Payments And Maintenance Portal
Onsite 24-Hour Emergency Maintenance
Onsite Management
Open-Concept Layouts
Pet-Friendly Community With Dog Run, Grooming Stations, And Exclusive Dog Park
Private Terraces And Balconies With City Or Mountain Views*
Programmable Thermostats And Energy-Efficient Lighting
Quartz And Granite Countertops With Full-Height Backsplash
Resident Bike Lounge And Storage, Repair Stations, And Bike Wash
Resident Social Events
Resort-Style Pool With Private Cabanas
Screening Lounge With Hd Projector And Cinema-Style Seating
Smoke-Free Community
Spacious Bedrooms That Accommodate King-Size Beds*
Spacious Kitchen Islands And Pantries*
Spacious Walk-In Closets And Linen Closets*
Spa-Inspired Bathrooms With Frameless Glass Showers*
Stainless Steel Appliances
Steps From Santana Row And Westfield Valley Fair, Featuring Upscale Retail, Dining, And Nightlife
Versatile Studio, One-, Two-, And Three-Bedroom Layouts
Walkable To Parks, Cafes, And Everyday Conveniences, Making Errands And Leisure Effortless
Wifi Access In Common Areas
Windsor Winchester is at 585 Winchester Blvd, San Jose, CA, 95128.
585 Winchester Blvd, San Jose, CA, 95128
Windsor Winchester is in the Valley Fair neighborhood of San Jose.
Residents give Windsor Winchester an A grade (about 4.7 out of 5) from 200+ reviews. Windsor Winchester offers a modern, well-located community with strong maintenance support and generally positive leasing experiences, though recent management changes have created inconsistency in service quality and responsiveness. Residents and prospective tenants frequently praise the maintenance team and tour experience, but ongoing concerns include elevator outages, security issues (package theft, garage access), communication gaps with management, and rising rent increases.
Windsor Winchester offers a modern, well-located community with strong maintenance support and generally positive leasing experiences, though recent management changes have created inconsistency in service quality and responsiveness. Residents and prospective tenants frequently praise the maintenance team and tour experience, but ongoing concerns include elevator outages, security issues (package theft, garage access), communication gaps with management, and rising rent increases. The property's location near Santana Row and amenities are consistent strengths.
Management responsiveness and professionalism are inconsistent, with significant variation between leasing and maintenance teams. The maintenance staff consistently receives praise for quick, professional service, while leasing office communication has been a recurring concern—some residents report helpful, patient staff, while others describe unavailability, delayed responses, and dismissive interactions. Since new management took over in September 2025, several residents report declining service quality, unresolved infrastructure issues (elevators, gates), and rent increases without corresponding service improvements.
Maintenance response times are generally strong, with most work orders completed same-day or next-day, and staff consistently praised for professionalism and thoroughness. However, the property faces recurring infrastructure challenges including prolonged elevator outages (3-4 months reported), appliance failures in newer units, and delayed emergency repairs in some cases. Common area maintenance and cleanliness standards are inconsistent, with some residents noting dirty elevators and poor mailroom organization despite maintenance efforts.
The building presents well initially but residents report significant ongoing issues with elevator reliability, with multiple units out of service for extended periods (3-6 months), creating substantial inconvenience. Sound insulation is inadequate, with residents reporting noise transmission from adjacent units and common areas. Cleanliness and maintenance of common areas are inconsistent, though the maintenance team is frequently praised for responsiveness. Security concerns including package theft, vehicle break-ins, and lack of on-site personnel are recurring complaints.
The property offers well-designed amenities including a pool, gym, outdoor spaces, and courtyard areas that residents appreciate. However, recurring operational issues significantly impact quality of life: elevator outages lasting months, disorganized mailroom with frequent package theft, inadequate security presence, and inconsistent common-area maintenance. Maintenance staff receive consistent praise for responsiveness, but higher-level management responsiveness and follow-through on resident concerns remain problematic.
The property benefits from a strong location near shopping, dining, transit, and freeways, which residents consistently highlight as a major advantage. However, the location advantage is offset by significant operational challenges including package theft, elevator outages, mailroom disorganization, and limited guest parking. While maintenance staff receive praise for responsiveness, broader building infrastructure and security concerns impact the overall resident experience.
Windsor Winchester is very walkable (grade B+), transit is minimal (grade F), and biking is bikeable (grade C).
B+
Very Walkable
F
Minimal Transit
C
Bikeable
Live steps from Santana Row and Westfield Valley Fair at Windsor Winchester in San Jose. Enjoy tech-forward amenities, Echelon fitness, and walkable shopping and dining.
Windsor Winchester is an apartment.
Building
ApartmentAction Day Moorpark is 0.1 miles from Windsor Winchester. 10 schools are listed nearby.
| School | Type | Level | Distance |
|---|---|---|---|
Action Day Moorpark Private · Preschool | Private | Preschool | 0.1 mi |
KidsPark - San Jose West Private · Preschool | Private | Preschool | 0.5 mi |
Ballard Montessori School Private · Preschool | Private | Preschool | 0.7 mi |
Monroe Middle School Charter · Middle | Charter | Middle | 0.7 mi |
St. Martin Of Tours School Private · Middle | Private | Middle | 0.8 mi |
Bethel Pre-School Private · Elementary | Private | Elementary | 0.9 mi |
Bethel Preschool & Kindergarten Private · Elementary | Private | Elementary | 0.9 mi |
Rosa Elena Childcare Center Private · Elementary | Private | Elementary | 0.9 mi |
San Jose City Collge Child Development Private · Preschool | Private | Preschool | 1.0 mi |
Heritage Academy Private · High | Private | High | 1.0 mi |
Windsor Winchester is managed by Windsor Communities. Call (669) 280-5646 to tour or ask about availability.