Timeless Living in Jacksonville

The Windsor at San Pablo

Starting at $6,395 /month

4000 San Pablo Parkway, Jacksonville, Florida, USA

With Mayo Clinic and Jacksonville Beach nearby, The Windsor at San Pablo offers an active, connected lifestyle in the heart of Jacksonville. Assisted living and memory care support residents in a community purpose-built for comfort, wellness, and connection.

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Joy is here

A Trusted Approach to Senior Living

At The Windsor at San Pablo, you’ll find more than care—you’ll find a rhythm of life that feels reassuring and meaningful. From evening strolls to a game of cards or bingo with friends, every detail reflects comfort, dignity, and connection. In the summer, the grounds come alive with events in the fresh air, adding to the vibrant, social atmosphere that defines our community. It’s classic living with everything you want, and all the opportunities to connect you need.

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Care and Living Options

Personalized Support, Shaped Around You

Life at The Windsor at San Pablo brings together everything you need in one place, including comfort, connection, and care that adapts as life does. With every level of service thoughtfully designed to support your well-being, you can relax knowing The Windsor at San Pablo will always feel like home.

Assisted Living

Everyday assistance provided with dignity, so you can focus on the things you enjoy most. Our associates are here 24/7 with steady, dependable support.

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Memory Care

Specialized care built around familiar routines and trusted therapies that create comfort, recognition, and belonging.

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Step inside The Windsor

An Invitation to Feel at Home

The best way to get to know The Windsor is to experience it. Step into our welcoming spaces, meet caring associates, and see how life here combines the reassurance of support with the warmth of community.

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Upcoming Events at The Windsor at San Pablo

Sep 14 – 18, 2026 | Various Times

Shining Through The Years: National Assisted Living Week

Join us for a fun week of events and activities during National Assisted Living Week. Come to one or all of our special events. We invite you to bring a friend or family member!

The Windsor at San Pablo
4000 San Pablo Pkwy, Jacksonville, FL 32224

RSVP: 3:30-5:00PM | Sep 14 | Kickoff Celebration RSVP: 6:00-7:00PM | Sep 15 | Family Fun Bingo RSVP: 1:30-3:00PM | Sep 16 | Sipping Around RSVP: 1:30-3:00PM | Sep 17 | Ice Cream Social RSVP: 12:00-2:00PM | Sep 18 | Western Friday

Each day offers something fresh

Programs That Bring Comfort and Connection

When you first arrive at The Windsor, you may not be sure what to expect. But for many, it doesn’t take long to feel the “spark.” A morning walk with a new friend, a spur of the moment art class that reignites your love of drawing (which might come in handy with grandkids) and the quiet sense of peace knowing your needs are personally cared for.

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Choose Your Perfect Fit

A Variety of Options for Everyday Living

Find the space that feels just right. Our variety of floor plans combines comfort and practicality for everyday living. Whether you love to gather with friends or unwind in a space all your own, each apartment offers the freedom to make it truly yours. Explore all the available layouts on our apartments page and see how natural home can feel.

Find your perfect fit

Life happens here

It’s a new day. And there is no lawn to mow, plumbing to fix or long “To Do” List. Take a look below, what combination of activities and amenities will it be today?

Activity Room

Bistro Café

Courtyard

Dining Room

Hair Salon

Hurricane Design

Library

Massage Therapy

Movie Theater

Patio

Post Office

Private Dining

Spa

Sun Room

The Neighborhood

There is Always Something to Do in Jacksonville

From trails at Castaway Island Preserve to exhibits at the Cummer Museum, local favorites surround every day with variety. Whether it’s a beach outing or an afternoon shopping at Town Center, residents stay connected to the best of the city.

Every day offers meaning & purpose

Life at The Windsor is centered on relationships and a lively courtyard that brings people together. Friends gather for coffee, associates stop by to chat, and families are always welcome. Music, games, and group events often fill the space, creating a social rhythm that makes each day feel vibrant. Every moment offers new chances to enjoy the steady comfort of a place that brings a new sense of life and all its possibilities.

“

The Windsor at San Pablo is a beautiful senior living residence. I helped an elderly friend relocate there, and everyone, residents and staff, went out of their way to make her feel welcome. The staff members are very friendly and always ready to help. The Windsor also offers a great variety of activities for the residents to enjoy on a daily basis, and their special events are exceptional.

Nanque

Connected communities, quality care

Alongside The Windsor at San Pablo, you’ll find other residences in the area that share the same commitment to dependable care and everyday comfort. Each has its own character while carrying forward Legend Senior Living’s values of dignity, support, and connection.