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Windsor Winchester 1 of 1

Windsor Winchester

$4,083 – $5,179/mo

  • 1–2 bedrooms
  • 1–2 baths
  • 704–1,138 sq ft
  • 6 units available
  • Pet friendly
585 Winchester Blvd, San Jose, CA, 95128

As of October 14, 2026, Windsor Winchester in San Jose, CA has 6 apartments for rent from $4,083 to $5,179/mo. One-bedrooms start at $4,083 and two-bedrooms at $5,179. The average asking rent has risen 10.4% since April 16, 2026, from $4,018 to $4,438.


Floor plans

Windsor Winchester has 6 units available across 3 floor plans: 2 one-bedroom layouts (704–795 sq ft) and a two-bedroom layout (1,138 sq ft). Prices checked October 14, 2026.

D

1 Bedroom • 1 Bath • 704 – 709 Sq Ft

Starting at $4,083/mo

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

J

1 Bedroom • 1 Bath • 772 – 795 Sq Ft

Starting at $4,349/mo

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

O

2 Bedrooms • 2 Baths • 1,138 Sq Ft

Starting at $5,179/mo

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

See all 99 units listed at Windsor Winchester, including ones no longer available.


Cost to rent here

At Windsor Winchester, a one-bedroom starts at about $4,406 a month all-in: $4,083 rent and an estimated $323 for electric, gas, water, internet, and renters insurance. A two-bedroom starts at about $5,598.

All-in from$4,406/mo

Estimates are local averages, not quotes from the property.

Can you afford it?

Most landlords ask for a monthly income of about 3× the rent, so qualifying at Windsor Winchester takes about $146,988 a year for a one-bedroom and $186,444 for a two-bedroom. Keeping the $4,406 all-in month for a one-bedroom within 35% of take-home pay takes an income of about $228,200 a year.

Total monthly housing cost

$4,406/mo

Income to afford it comfortably

$228,200/yr

Income to qualify

$146,988/yr

Your estimated budget

Suggested rent budget, 1 bedroom

$ —/mo

See what you can afford here

Add your income and debts for a rent budget at this building.

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Rent history

Over the past year, the average asking rent at Windsor Winchester has ranged from $3,793 to $5,038. The current average is $4,438, up $420 (10.4%) from $4,018 at the start.

Prices reflect the average advertised rent across units listed as available each day (155 days observed).

Fees & lease terms

At Windsor Winchester, leases run 15 months.

  • Rent

    $4,083 – $5,179/mo
  • Lease term

    15 months
  • Earliest move-in

    Oct 17

Amenities

Windsor Winchester is pet friendly and has in-unit washers and dryers. It lists 40 amenities, including ev charging stations.

  • 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


Amenity photos

  • Pool

Location

585 Winchester Blvd, San Jose, CA, 95128


Resident reviews

Windsor Winchester has a 4.7 out of 5 rating from more than 200 resident reviews. Residents rate maintenance (4.0) and amenities and shared spaces (3.6) highest and building quality (3.0) lowest.

4.7 · 200+ reviews
Overall rating
Positive
Mixed
Neutral
Negative
Management3.4
Maintenance4.0
Building Quality3.0
Amenities and Shared Spaces3.6
Location3.3
Overall100 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. 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.

Summaries are written by AI from reviews residents posted on public review sites such as Google and ApartmentRatings. Each topic shows how many of those reviews discuss it.

Getting around

Windsor Winchester is very walkable and bikeable, and transit is minimal.

Walking
Very walkable
Grade B+
Transit
Minimal
Grade F
Biking
Bikeable
Grade C

Climate and air quality

Air quality near Windsor Winchester was good on 150 of the past 365 days, and at its worst in October (average AQI 63, moderate). Daily highs averaged 84°F in July, the warmest month, and lows averaged 46°F in January, the coldest.

Air quality

150 good-air days

of the past 365

: Moderate, AQI 53

Temperature

84° / 46°

average July high / January low

: 79° high, 55° low

Pollen

None

Oct 14–18 forecast

Tree: none, grass: none, weed: none

MonthAverage highAverage lowAverage AQIGood-air days
January59°F46°F53 (moderate)10 of 31
February63°F47°F50 (good)14 of 28
March76°F53°F53 (moderate)8 of 31
April69°F50°F48 (good)15 of 30
May76°F54°F48 (good)16 of 31
June83°F57°F47 (good)17 of 30
July84°F59°F45 (good)22 of 31
August84°F60°F49 (good)14 of 31
September81°F58°F53 (moderate)12 of 30
October77°F55°F63 (moderate)4 of 31
November64°F50°F56 (moderate)8 of 30
December58°F47°F58 (moderate)10 of 31
Daily readings from Oct 15, 2025 to Oct 14, 2026. The pollen chart shows typical US seasons.

About this property

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.


Nearby schools

The closest school to Windsor Winchester is Action Day Moorpark, a private preschool 0.2 miles away.

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

Contact & management

Windsor Winchester is managed by Windsor Communities. The leasing office's phone number is (669) 280-5646.


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