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Windsor Winchester 1 of 1

Windsor Winchester

$4,083 – $5,179/mo

585 Winchester Blvd, San Jose, CA, 95128

What floor plans are available at Windsor Winchester?

Windsor 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.

D

Starting at $4,083

1 Bedroom • 1 Bath • 704 – 709 Sq Ft

2 available unitsPriceSq ftAvailableOpen unit
337$4,083704Oct 17
614$4,162709Nov 11

J

Starting at $4,349

1 Bedroom • 1 Bath • 772 – 795 Sq Ft

3 available unitsPriceSq ftAvailableOpen unit
506$4,349795Oct 19
753$4,494772Oct 24
606$4,360795Nov 5

O

Starting at $5,179

2 Bedrooms • 2 Baths • 1,138 Sq Ft

1 available unitPriceSq ftAvailableOpen unit
373$5,1791,138Oct 28

What are the fees and lease terms at Windsor Winchester?

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/mo
  • Lease term

    15 months
  • Earliest move-in

    Oct 17

What amenities does Windsor Winchester have?

Windsor 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


What do the amenities at Windsor Winchester look like?

  • Pool

Where is Windsor Winchester?

Windsor Winchester is at 585 Winchester Blvd, San Jose, CA, 95128.

585 Winchester Blvd, San Jose, CA, 95128


What is the neighborhood around Windsor Winchester like?

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.

4.70 · 200+ reviews
Overall rating
Positive
Mixed
Neutral
Negative
Management3.4
Maintenance4.0
Building Quality3.0
Amenities and Shared Spaces3.6
Location3.3

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.


Is Windsor Winchester walkable?

Windsor Winchester is very walkable (grade B+), transit is minimal (grade F), and biking is bikeable (grade C).

WALK

Very Walkable

TRANSIT

Minimal Transit

BIKE

Bikeable


What is Windsor Winchester like?

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.


How big is Windsor Winchester?

Windsor Winchester is an apartment.

  • Building

    Apartment

What schools are near Windsor Winchester?

Action Day Moorpark is 0.1 miles from Windsor Winchester. 10 schools are listed nearby.

SchoolTypeLevelDistance

Action Day Moorpark

Private · Preschool
PrivatePreschool0.1 mi

KidsPark - San Jose West

Private · Preschool
PrivatePreschool0.5 mi

Ballard Montessori School

Private · Preschool
PrivatePreschool0.7 mi

Monroe Middle School

Charter · Middle
CharterMiddle0.7 mi

St. Martin Of Tours School

Private · Middle
PrivateMiddle0.8 mi

Bethel Pre-School

Private · Elementary
PrivateElementary0.9 mi

Bethel Preschool & Kindergarten

Private · Elementary
PrivateElementary0.9 mi

Rosa Elena Childcare Center

Private · Elementary
PrivateElementary0.9 mi

San Jose City Collge Child Development

Private · Preschool
PrivatePreschool1.0 mi

Heritage Academy

Private · High
PrivateHigh1.0 mi

How do I contact Windsor Winchester?

Windsor Winchester is managed by Windsor Communities. Call (669) 280-5646 to tour or ask about availability.