Reimagining Elegance:

Transforming the Roosevelt Collection into a Chicago Landmark

Creating an English garden in the heart of Chicago’s bustling South Loop may sound like an ambitious—and perhaps unlikely—endeavor. Yet for the team at Woodlawns Landscape Company Inc., this challenge was an opportunity to showcase their creativity and commitment to excellence. Through meticulous planning, innovative problem-solving and a passion for collaboration, the Roosevelt Collection project has evolved from an uncertain vision into a vibrant, community-focused outdoor destination.

We sat down with Melissa Dorsey of Woodlawns Landscape to learn how the team overcame early obstacles, navigated constant changes and turned a once-struggling space into a shining example of urban landscape design.

The Challenge of Getting Started

When the project first came to Woodlawns Landscape, the property manager expressed frustration with a previous landscaping provider’s inability to meet expectations. The initial vision—a classic English garden complete with boxwoods and a carefully or- ganized layout—seemed incompatible with the space’s urban setting.

Starting with a limited budget and an unclear scope, the Woodlawns team had to reverse-engineer the project. By working backward from the available budget, they were able to craft a design that captured the client’s objectives while respecting the space’s unique demands.

“It was about clarity and partnership,” Melissa explains. “We focused on understanding what the property manager truly wanted and building trust through our process.”

Over the years, as property management and goals shifted, the team’s ability to adapt proved invaluable. Woodlawns consistently worked within evolving budgets and expectations to deliver the best possible outcomes for the site.

Adapting to Changing Visions

One of Woodlawns’ core strengths lies in their commitment to partnership. When new property managers—this time from CBRE—took over the Roosevelt Collection, the team had to reimagine the scope of the project once again.

For example, the budget for annuals, a key feature in the original plan, was reduced from the original scope. Instead of simply cutting costs, the team collaborated with CBRE to identify impactful alternatives that maintained the area’s aesthetic appeal.

“It’s not just about reducing expenses,” Dorsey says. “We take horticultural best practices into account while understanding the practicalities of how the space is used by the community.”

The Roosevelt Collection is more than a backyard garden—it’s a destination in the heart of a vibrant neighborhood. With heavy foot traffic, dog walkers and frequent events, the space demands a design that’s as durable as it is beautiful.

Overcoming Setbacks

Every major project comes with its hurdles, and this one was no exception. Early on, the team faced a devastating setback: the sudden loss of 800 boxwoods due to winter salt damage and poor vendor decisions. With no budget to replace them, Woodlawns had to innovate.

Instead of sticking to the original English garden plan, the team embraced the urban environment, incorporating design elements that were better suited to the location and its unique challenges.

“We turned a loss into an opportunity,” Melissa notes. “By rethinking the concept, we created a space that felt more connected to the community and the city around it.”

Another creative solution came in response to heavy usage in certain areas. One frequently trodden patch of turf required constant replacement, which became both costly and inefficient. Woodlawns recommended astroturf, a practical solution that enhanced functionality and longevity without compromising the area’s aesthetic.

The Power of Seasonal Color

One standout feature of the Roosevelt Collection is its focus on seasonal color. Rather than relying on generic, low-impact annuals, Woodlawns curated a palette of vibrant blooms that enhance the site’s visual appeal year-round.

“We focus on ‘better,’ not ‘more,’” says Melissa. “It’s about making every choice intentional.”

A perfect example of this philosophy is the 8,000 tulips planted each year. These high-quality blooms create an unforgettable spring display that delights visitors and elevates the site’s reputation. Though these tulips come at a higher cost, their stunning impact makes them a worthwhile investment.

This attention to detail ensures that every transition—from spring to summer to fall— feels seamless, offering a dynamic and engaging experience for patrons and residents alike.

Maintaining Excellence

Behind the Roosevelt Collection’s beauty is a dedicated team of professionals who keep it running smoothly. Regular maintenance is handled by three Woodlawns crew members who focus on fine gardening and detail work rather than routine mowing.

During peak seasons, the team expands significantly, with four crews of three workers and two supervisors tackling the site’s seasonal transformations. The team’s efficiency and expertise ensure that the space always looks its best, even during high-traffic times.

For specialized tasks like irrigation or large tree pruning, Woodlawns brings in subcontractors, ensuring that every aspect of the project benefits from expert care.

A Shared Vision for Success

What sets the Roosevelt Collection apart is the strong partnership between Woodlawns

Landscape and the property management team. By approaching the project as a collaboration, the team can propose innovative ideas, make strategic adjustments and consistently exceed expectations.

From the loss of 800 boxwoods to the transformation of high-traffic areas, the Roosevelt Collection’s journey is one of resilience and reinvention. Today, it stands as a vibrant centerpiece for the South Loop community—a space that balances beauty, functionality and sustainability.

“It’s all about the details,” Melissa says. “When you care about the client’s happiness and take pride in the work, the results speak for themselves.”

Get In Touch With

Melissa Dorsey

Woodlands Landscape www.woodlawnslandscape.com