Luxury Retirement Living in Downtown Sarasota

There comes a season of life when luxury begins to mean something different.

It is no longer only about square footage, home upkeep, or having more rooms to manage. True luxury becomes freedom — the freedom to spend more time enjoying Sarasota, more time staying active, more time connecting with others, and less time worrying about the responsibilities that often come with maintaining a home.

At CitySide Sarasota, that next chapter has been thoughtfully designed.

Located in the heart of downtown Sarasota, CitySide offers an elevated residential lifestyle designed for those who want the privacy and comfort of home with the amenities, services, and ease of a luxury resort. Here, residents can enjoy a beautifully maintained community with a resort-style pool courtyard, rooftop pickleball, fitness center, instructor-led fitness classes, dog park, social spaces, Saturday brunch experiences, and the confidence of 24/7 security and maintenance.

It is a lifestyle created for people who want to simplify without sacrificing the things they love.

Mornings may begin with coffee by the pool, an instructor-led fitness class, or a walk through downtown. Afternoons can be spent enjoying rooftop pickleball, meeting neighbors, relaxing in the courtyard, or taking advantage of CitySide’s exclusive access to University Park Country Club, where residents can enjoy golf, tennis, and country club amenities as part of an active Sarasota lifestyle. For golf enthusiasts, access to University Park Country Club’s golf course creates an exceptional opportunity to enjoy one of the area’s most beautiful club settings without giving up the convenience of downtown living. Residents can spend the day on the course, enjoy time outdoors, and experience the social rhythm of club life while still returning home to the ease of CitySide.

Tennis lovers can also take advantage of University Park Country Club’s tennis courts, creating another way to stay active, meet others, and enjoy Sarasota’s year-round sunshine. Whether residents prefer a casual match, regular play, or simply the lifestyle that comes with access to a well-appointed club environment, the tennis amenities add another layer of resort-style living.

The country club experience itself enhances the CitySide lifestyle by giving residents access to a refined setting beyond the community, ideal for recreation, social connection, and a more complete luxury living experience. It is one more way CitySide combines the ease of downtown apartment living with the privileges often associated with a resort or private club lifestyle.

CitySide also offers a convenient resident shuttle that takes residents within three miles of the community, adding another layer of ease to downtown living. Whether heading to dinner, shopping, appointments, arts venues, or nearby attractions, residents can enjoy the freedom of getting around without always needing to drive.

For beach lovers, CitySide’s Beach Club experience brings the resort lifestyle beyond the community itself. Residents are taken just next to The Ritz-Carlton, where CitySide’s team can help bring out chairs and coolers so the day feels effortless from the moment they arrive. Residents can relax by the water, enjoy the beauty of Sarasota’s shoreline, and walk over to experience the new beachfront tiki bar at The Ritz.

What makes CitySide especially unique is its balance of location and lifestyle. Residents enjoy the energy of downtown Sarasota while still having access to resort-inspired amenities that make everyday living feel effortless. Whether downsizing from a larger home, relocating seasonally, or simply seeking a more convenient way to enjoy Sarasota, CitySide offers a refined alternative to traditional retirement living.

This is not about slowing down. It is about living with more freedom, more access, and more intention.

CitySide was created for those who want a home that supports an active, social, and maintenance-free lifestyle. From private residences to shared amenities and curated resident experiences, every detail is designed to make daily life feel easier, more connected, and more enjoyable.

For those ready to embrace a new chapter in Sarasota, CitySide offers something rare: downtown convenience, resort-style living, country club access, beach club experiences, and a welcoming community - all in one address.

Schedule a private tour, reserve a Saturday brunch experience, or view available residences to discover how CitySide is redefining luxury retirement living in downtown Sarasota.