April 2026 — Invest: spoke with Randy Knight, city manager of the city of Winter Park, about managing redevelopment in a fully built-out community while advancing infrastructure and cultural investment. “Winter Park remains a vibrant part of the Greater Orlando area, and the residential market continues to be strong,” Knight said.
How would you characterize the economic momentum in Winter Park, and what major milestones are you most proud of?
Winter Park remains a vibrant part of the Greater Orlando area, and the residential market continues to be strong. Because we are a built-out community, we do not have new subdivisions or large undeveloped commercial areas coming online, so most activity is redevelopment.
Over the past year, we have seen some commercial redevelopment slow, although we do have a new Class A office building coming online, and there is continued demand for high-quality office space. Residential redevelopment, however, is extremely strong, with older homes being replaced by new construction as buyers continue to see Winter Park as a desirable place to live.
A major milestone for us has been celebrating 20 years of owning and operating our electric utility. We took it over in 2005 from what was then Progress Energy, now Duke Energy. One of our long-term goals has been placing power lines underground, and we are now a little over 83% underground. That work has reduced outages during hurricane season and improved reliability for residents and businesses.
As Central Florida continues to grow, how is that growth impacting a fully built-out community like Winter Park?
Growth creates real pressure on a city like Winter Park, particularly because we sit just north of Orlando. A large share of our traffic is regional through traffic from people commuting to downtown Orlando from Seminole County or East Orange County, and those patterns affect daily mobility and quality of life.
The good news is that we have seen stronger coordination among regional partners in recent years. MetroPlan Orlando helps keep jurisdictions aligned on transportation priorities, and FDOT District 5 has been responsive when communities need to work together on roadway improvements, signal timing, and broader mobility initiatives.
What do you consider to be the most pressing infrastructure and service needs facing the city today?
For a mature, built-out community, one of our biggest challenges is adapting our transportation network to today’s expectations. There is far more demand for safe bicycle and pedestrian routes than there was 25 years ago, and retrofitting those options into an established street grid is complex.
We have developed a transportation master plan that looks at vehicles, pedestrians, bicycles, and other mobility devices. Winter Park has many tree-lined streets and limited right-of-way, so adding bike lanes can be difficult without affecting what makes neighborhoods special. Our goal is to improve safety and connectivity in a way that fits the character and constraints of the community.
What conversations are happening about the CRA and its future role?
We worked with Orange County and secured a 10-year extension of our CRA. The county also approved a geographic expansion to include the West Fairbanks area, south of Fairbanks Avenue near I-4, which we see as ripe for reinvestment in the commercial sector.
That extension gives us resources to partner with developers and help rehabilitate the area. We believe the county supported the extension because the original CRA performed exceptionally well. Over its life, property values increased by more than 500%, making it a strong CRA success story in Florida and a foundation for the next phase of targeted reinvestment.
How have the Winter Park Library and Events Center reshaped the city’s cultural and tourism footprint?
Both facilities have exceeded expectations. The library continues to rank among the top libraries in Florida, is the #1 children’s library in the state, and the newer facility has increased memberships and circulation. The Events Center has also become a major civic asset, regularly booked for weddings, community gatherings, and nonprofit fundraisers.
Beyond the calendar, the facilities contribute to Winter Park’s identity as a destination. People visit from across the region to experience the space, and it has strengthened our cultural footprint in a very tangible way.
How are you protecting Winter Park’s neighborhood character while addressing housing pressures across the region?
We recently completed the seven-year renewal of our comprehensive plan, and one of the major focus areas was balancing reinvestment with neighborhood protection. We want to allow new homes and continued renewal, but we also have to manage issues like scale, setbacks, drainage, and overall compatibility so reinvestment does not diminish quality of life.
Our approach has been to protect the character of established neighborhoods while still allowing thoughtful redevelopment that reflects market demand and the realities of a built-out city.
As Orlando becomes more known as an innovation and technology hub, how is Winter Park staying ahead of the curve while preserving its historical importance?
We have made steady progress on foundational tools, such as public Wi-Fi, that support residents and visitors. We are also beginning to explore how emerging technologies, including AI, could improve city operations and customer service.
Our departments are paying attention to what peers are doing and learning through professional conferences and industry networks, whether the topic is utilities, public works, or communications. The key for us is separating the useful, practical applications from the hype, and implementing changes that genuinely improve the resident experience.
Tourism and arts remain core pillars in Central Florida. How are you ensuring those sectors remain economically vibrant amid regional competition and evolution?
We have an economic development advisory board that helps us stay focused on the sectors that have long supported Winter Park’s identity and economy. Winter Park has a strong wealth-management and private banking presence, and we work to maintain an environment where those businesses can thrive.
Arts and culture are also central to who we are. We have an Arts & Culture Alliance of cultural organizations and advisory groups that meet regularly, collaborate on priorities, and keep Winter Park’s arts and culture scene visible and active. That ecosystem supports tourism, small business vitality, and the overall quality of place that continues to draw residents and guests to our city of arts & culture.
Looking toward the next three to five years, what top priorities will you be focused on as the city moves into its next stage?
One of the biggest issues we are watching is the state-level conversation about tax reform, including proposals that could affect property taxes on homesteaded properties. Depending on how those proposals are structured, they could significantly impact municipal revenues and our ability to fund core services.
At the same time, we are dealing with new mobility realities. E-bikes and e-scooters have become more common, but regulations have not fully caught up at either the state or local level. They can provide affordable mobility, but they also create safety concerns when riders do not follow traffic rules or use appropriate safety equipment. Finding the right balance will be an important priority for communities across Florida.
Is there anything else you would like to include?
A major focus for us over the next three years is the Park Avenue Refresh project. Park Avenue is our crown jewel, the shopping and dining district that helps define Winter Park. We have begun a multi-year phased project expected to total between $8 million and $10 million.
The work will include infrastructure, safety and aesthetic enhancements such as new street lights equipped with integrated smart hubs and technology such as Wi-Fi capabilities and ability to control remotely, upgrades to irrigation and underground electrical infrastructure, and improvements to landscape and hardscape elements, sidewalks and planter beds. It has been almost three decades since the corridor saw a major renovation, and residents and businesses are excited about the city reinvesting in the long-term strength and experience of downtown.
Want more? Read the Invest: Greater Orlando report.






