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Timeless Senior Living in Jacksonville

The Windsor at Ortega Assisted Living & Memory Care

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 Jacksonville senior living community provides comfort, connection, and support for every day with Assisted Living and Memory Care services.

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Seniors laughing
Joy is here

A Trusted Approach to Senior Living

At The Windsor at Ortega, you’ll find more than Assisted Living and Memory 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 senior living community in Jacksonville, Florida. 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 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.

Smiling senior and stuff

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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Specialized care built around familiar routines and trusted therapies

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 in Jacksonville

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

Oct 21, 2026 | 10:00-11:00AM OR 2:00-3:00PM

Get the Most from Medicare with Confidence

Do the choices that come with Medicare leave you feeling overwhelmed and a little frustrated? You aren’t alone! Most of us are not fully confident when it comes to making the most of our Medicare benefits. Choose to join us and learn more about Medicare so that you can be the one who is certain about your choices this year and every year following.

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

RSVP: 10:00-11:00AM | Oct 21RSVP: 2:00-3:00PM | Oct 21
Nov 4, 2026 | 10:00-11:00AM

Unlocking VA Benefits: Clear Steps, Confident Choices

Veteran benefits can sometimes be complex, changing based on eligibility, type of service, and more. If you or your loved one is a Veteran, it is worth understanding more about the types of benefits that might be available to you. Join us as we welcome a local expert to walk us through the different types of VA benefits, including eligibility requirements, so that you can make your most confident decisions for the future.

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

RSVP: 10:00-11:00AM | Nov 4
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 Assisted Living and Memory Care 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.

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Senior smiling while holding grandchild

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
Activity Room
Bistro Café
Bistro Café
Courtyard
Courtyard
Dining Room
Dining Room
Fitness Center
Fitness Center
Furnished Balcony
Furnished Balcony
Game Room
Game Room
Hair Salon
Hair Salon
Hurricane Design
Hurricane Design
Library
Library
Massage Therapy
Massage Therapy
Movie Theater
Movie Theater
Patio
Patio
Post Office
Post Office
Private Dining
Private Dining
Spa
Spa
Sun Room
Sun Room
Wellness Center
Wellness Center
The Neighborhood

There is Always Something to Do in Jacksonville

The Windsor at Ortega is surrounded by the character of one of Jacksonville’s oldest neighborhoods, with the St. Johns and Ortega Rivers, historic homes, parks, and local gathering places nearby. Residents can enjoy convenient access to the Florida Yacht Club, Timuquana Country Club, Ortega River Marina, Avondale, and the shops, restaurants, and cultural attractions of nearby Riverside and Avondale.

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 it because it reminded me of the 11 months of healing that she went through.

Resident & Daughter | The Windsor at Ortega

Frequently Asked Questions

What types of programs, events, and activities are provided?

The Windsor at Ortega offers a variety of programs designed around residents’ interests, abilities, and preferences. Activities include painting classes, dancing, gardening, games such as blackjack, pool, and putt-putt golf, ice cream socials, live performances, fitness programs, and local outings.

Can residents transition between levels of care at The Windsor at Ortega?

Yes. Because The Windsor at Ortega offers both Assisted Living and Memory Care, residents can be evaluated for a transition to Memory Care if their needs change. Having both living options within the same community can provide familiarity and continuity, while associates who already know the resident can help support the transition.

What are the benefits of living in a senior living community in Jacksonville?

Jacksonville offers the benefits of a large coastal city, including access to quality healthcare, cultural attractions, outdoor recreation, and a wide variety of shopping and dining. The Windsor at Ortega is conveniently located near major healthcare providers, including Baptist Medical Center Jacksonville and other Baptist Health facilities, while attractions throughout Ortega, Avondale, and Riverside offer plenty to explore. Jacksonville International Airport is about 20 miles from the community, making visits from family members traveling by air convenient.

Connected communities across Jacksonville, Florida, quality care.

Alongside The Windsor at Ortega, you’ll find other senior living communities in the Jacksonville, Florida 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.

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.

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The Windsor at Ortega

5939 Roosevelt Boulevard, Jacksonville, Florida, USA
904-353-9500

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