Timeless Living in Jacksonville

The Windsor at Ortega

Starting at $4,580 /month

5939 Roosevelt Boulevard, Jacksonville, Florida, USA

Close to the charm of Avondale and the waterside lifestyle of Ortega, life at The Windsor at Ortega blends heritage with modern convenience. This welcoming community provides comfort, connection, and support for every day with assisted living and memory care services.

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Joy is here

A Trusted Approach to Senior Living

At The Windsor at Ortega, 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.

Explore the Legend Lifestyle

Care and Living Options

Personalized Support, Shaped Around You

Life at The Windsor at Ortega 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 Ortega 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 Ortega

Aug 18, 2026 | 3:00-4:00PM

Dementia Caregiver Support Group

Caring for a loved one with dementia can be overwhelming at times, and it’s okay to need support. You are not alone. Our no-cost, registered dementia caregiver support group offers a welcoming space to connect with others who are walking a similar path. Through shared stories, understanding, and learning together, you’ll find comfort, perspective, and renewed strength—so you can continue caregiving with compassion for your loved one and yourself.

The Windsor at Ortega
5939 Roosevelt Blvd, Jacksonville, FL 32244

RSVP: 3:00-4:00PM | Aug 18

Sep 15, 2026 | 2:00-4:00PM

Music Bingo

Join us for an afternoon of fun, music and friendly competition! Instead of numbers your BINGO will feature popular songs and favorite hits from across the decades. Let’s connect, laugh, and bring back some great memories!

The Windsor at Ortega
5939 Roosevelt Blvd, Jacksonville, FL 32244

RSVP: 2:00-4:00PM | Sep 15

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

Fitness Center

Furnished Balcony

Game Room

Hair Salon

Hurricane Design

Library

Massage Therapy

Movie Theater

Patio

Post Office

Private Dining

Spa

Sun Room

Wellness Center

The Neighborhood

There is Always Something to Do in Jacksonville

Located in one of the oldest, most established neighborhoods in Jacksonville has its perks. Residents enjoy easy access to the Florida Yacht Club and the Timaquana Country Club as well as many places of worship.

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.

“

Deandre, an associate, is the one that got me out of the wheelchair. He said, “Barb, if you’ll get out of that wheelchair, I promise I’ll dance with you.” And he did dance with me… She stood up and I just lost if because it reminded me of the 11 months of healing that she went through.

Resident & Daughter | The Windsor at Ortega

Connected communities, quality care

Alongside The Windsor at Ortega, 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.

Windsor Pointe of Jacksonville

4060 San Pablo Pkwy, Jacksonville, FL 32224

Living Options

Independent Living

904-490-6300

View Community

The Gables of Jacksonville

3455 San Pablo Rd S, Jacksonville, FL 32224

Living Options

904-821-8030

View Community

ALF #9726

The Windsor at San Pablo

4000 San Pablo Pkwy, Jacksonville, FL 32224

Living Options

904-928-3700

View Community

ALF#12539

Looking for another location?

Plan your visit to The Windsor at Ortega

See how comfort, care, and community come together in Jacksonville, FL. Schedule your tour today and discover what makes The Windsor feel like home.

In-Person Visitation Policy

Schedule a Tour

The Windsor at Ortega

A Trusted Approach to Senior Living

Personalized Support, Shaped Around You

Assisted Living

Memory Care

An Invitation to Feel at Home

Upcoming Events at The Windsor at Ortega

Dementia Caregiver Support Group

Music Bingo

Programs That Bring Comfort and Connection

A Variety of Options for Everyday Living

Life happens here

There is Always Something to Do in Jacksonville

Every day offers meaning & purpose

Connected communities, quality care

Windsor Pointe of Jacksonville

The Gables of Jacksonville

The Windsor at San Pablo

Looking for another location?

Plan your visit to The Windsor at Ortega

The Windsor at Ortega

Contact Us

The Windsor at Ortega

Living Options

Legend Lifestyle

Resources

About Us