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Windsor Winchester

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Rating Rating
Rated 4.7 out of 5 stars.
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*Price shown is the Base Rent, which does not include utilities or optional and required fees; deposit(s) may also apply. Please see the Costs Overview section of our floor plans page for more information on applicable fees.

Windsor Winchester

585 S Winchester Blvd
San Jose, CA 95128

Get Directions (669) 280-5646

Proud Moments, Shared Together

2025 Elite ORA 1 Percent awarded by J Turner

Top 1% of Communities for Online Reputation by J Turner Research.

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Windsor Communities Ranks #3 in the 2025 Division | ORA Power Rankings by J Turner Research

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#1 Ranked Property Management Company for Resident Satisfaction by Grace Hill Excellence Awards for the fifth consecutive year.

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We're Glad You're Here.

Beautiful spaces. Thoughtful amenities. Memorable details. Set in the heart of Silicon Valley, steps from Santana Row and Westfield Valley Fair, Windsor Winchester offers modern design, personalized service, and a convenient neighborhood all in one.

Go for a dip in the resort-style pool, lounge in a private cabana, or relax by the outdoor fireplace. Catch a movie in the screening lounge with cinema-style seating, work from home in cozy co-working spaces, or stay active in the fitness center with Echelon Reflect mirror and bikes. Hang outs in the resident kitchen and social lounge turn any ordinary night into lasting memories.

Clean, modern lines, high ceilings, and bright, airy floor plans are just the start. Chef-inspired kitchens featuring Italian cabinetry with soft-close drawers, quartz or granite countertops, and full-height backsplashes make every meal feel special. It’s hard not to admire our spacious bedrooms, spa-inspired bathrooms with frameless glass showers or soaking tubs, and high-end touches.

Every detail is tailored to the way you live, work, and unwind.

feel at home with windsor stamp Paper tear A decorative paper tear Modern apartment kitchen with light wood cabinets, stainless steel appliances, and a small island with a sink. Open layout leads to a bright living room with large windows and contemporary furnishings.

Find Your Perfect Fit

Choose between the timeless style and comfort of our studio, one-, two, or three-bedroom apartment homes. Every home features stainless-steel appliances, warm wood-style flooring, and premium finishes across three distinct design palettes.

Whether you’re after an open layout for entertaining or a comfy retreat for recharging, find a space to fit your needs.

Available Apartments

Everyday Exceptional

Living at Windsor Winchester comes with so much more than an amazing apartment in San Jose, CA. From our friendly team to our convenient amenities and services to our vibrant community of friends and neighbors. When you choose a Windsor Community, it’s not just where you live – it’s where you belong.

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Community WiFi

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City Views

Res Clubroom

Resident Clubroom

Coworking Space

Coworking Space

Pet Friendly

Pet Friendly

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Pool

Community Amenities

Lifestyle

Lifestyle

  • Resort-style pool with private cabanas
  • Expansive social courtyards with fire pits, grills, and open-air dining
  • Entertaining kitchen and resident social lounge with plenty of cozy seating for gathering and entertaining friends
  • Screening lounge with HD projector and cinema-style seating
  • 24-hour fitness center with Echelon Reflect mirror & bikes
Convenience

Convenience

  • Flexible co-working spaces and private meeting rooms
  • Resident bike lounge and storage, repair stations, and bike wash
  • LuxerOne package locker system with refrigerated storage
  • Onsite management
  • Onsite 24-hour emergency maintenance
  • Wifi access in common areas

Apartment Features

living-space

Living Space

  • Modern wide-plank wood-style flooring throughout*
  • Private terraces and balconies with city or mountain views*
  • In home washer/dryer
  • Programmable thermostats and energy-efficient lighting
bedroom

Bedroom

  • Spacious walk-in closets and linen closets*
kitchen

Kitchen

  • Stainless steel appliances

*Available in select apartments.

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Home Is Where Your Pets Are

The one thing we love just as much as our residents…is your pets. But Windsor Winchester doesn’t just welcome your furry (or finned) friends with open arms, we go above and beyond to make sure your pets feel just as at home with us as you do.

Learn More
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Tour Your Way

We can’t wait for you to explore our community and experience Windsor at your own pace. We offer flexible options so you can tailor your tour experience at Windsor Winchester.

Schedule a Tour
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Prime Location, Endless Possibilities

Nestled among the San Francisco Bay, the Santa Cruz Mountains, and the Pacific Ocean, this Silicon Valley city delivers everything from a rich culinary scene to exciting cultural experiences.

View Neighborhood

Connect & Explore Windsor Winchester

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Ready to schedule a tour?

Come visit your beautiful new home at Windsor Winchester.

Schedule a Tour