Inside Winter Park’s Luxury Real Estate Market
by Jonathan Friese | Photo by Kimberly Jefcoat
We sat down with Audra Wilks to discuss the latest real estate trends in Winter Park. With more than 24 years of experience in the Winter Park and Central Florida luxury real estate market, Audra is a trusted global advisor known for her deep local expertise and relationship-driven approach. She specializes in connecting discerning buyers and sellers through both on-market and off-market opportunities, and is recognized for her strategic insight, elevated marketing, and commitment to delivering exceptional results through her work with Premier Sotheby’s International Realty.
Jonathan: What trends are you currently seeing in the luxury real estate market in Winter Park and how has buyer demand evolved over the past year?
Audra: The most meaningful shift is not just in pricing or pace, but in how the market functions. A significant portion of Winter Park’s luxury transactions are relationship-driven, with many of the most desirable properties trading before they ever reach the public market.
Over the past year, buyer demand has not softened. It has become more strategic. Buyers are no longer simply reacting to available inventory. They are aligning themselves with advisors who can provide access to opportunities before they are widely known. This has created a layered market where what is publicly visible online represents only a portion of total market activity.
After more than 24 years working in this market, what stands out most is how consistently Winter Park rewards preparation and foresight. We are seeing a growing separation between homes that are fully realized and those that require vision. This is especially evident around the Chain of Lakes, where buyers often prioritize properties that support immediate lifestyle use, influencing pricing outcomes.
Winter Park is distinguished by its limited supply and established identity. From the brick streets near Interlachen Avenue to the walkable corridors surrounding Park Avenue, it offers a level of character that is difficult to replicate.
Jonathan: For buyers considering a move into the area, what features or lifestyle amenities are today’s luxury homebuyers prioritizing most—whether it’s lakefront access, walkability to Park Avenue, smart home technology, or resort-style outdoor living?
Audra: Luxury buyers are prioritizing ease, design, and lifestyle integration. Walkability to Park Avenue and access to the Chain of Lakes remain highly desirable, but the real driver is how seamlessly a home fits into daily life.
There is a strong emphasis on homes that feel complete, where architecture, interior design, and functionality are aligned. In neighborhoods like the Vias or Windsong, buyers gravitate toward properties that balance modern living with architectural character.
Outdoor living has become an extension of the home itself, with resort-style pools, covered lanais, and well-designed entertaining spaces playing a major role. Buyers also value dedicated spaces such as offices, wellness rooms, and guest accommodations.
Equally important is proximity to schools, dining, and cultural amenities, while still maintaining privacy at home.
Jonathan: How can sellers in the Winter Park luxury market best position their homes right now to command top value? Are there specific upgrades, staging strategies, or marketing approaches that make a significant difference?
Audra: In Winter Park, positioning often begins before a home reaches the market. Many of the strongest results come from strategic premarket exposure within a curated network of agents and qualified buyers.
This is particularly effective in areas like the Vias or along the Chain of Lakes, where demand often exists before a property is formally listed.
Presentation must meet expectations. Buyers respond to homes that feel intentional, where design and finishes are cohesive. Strategic updates to kitchens, baths, lighting, and outdoor spaces can significantly influence value.
Pricing remains critical. Homes that are positioned correctly from the outset generate stronger interest and better outcomes.
Jonathan: With many high-end buyers relocating from other states, how is the influx of out-of-state buyers influencing pricing, competition, and the types of homes that are most in demand in Winter Park?
Audra: Out of state buyers continue to shape the luxury segment. In recent transactions, there has been an increase in buyers purchasing in Winter Park as both primary residences and second homes, often influenced by Florida’s favorable tax structure.
While tax advantages may initiate the move, buyers ultimately choose Winter Park for its lifestyle. Walkability, architectural character, and a sense of permanence are key drivers.
We are also seeing a pattern where second-home buyers transition into full-time residents, reinforcing the area’s long-term appeal.
Jonathan: Looking ahead to the rest of 2026, what opportunities or shifts do you foresee in the luxury real estate market, and what advice would you give to someone who is considering buying or selling in the near future?
Audra: The market will continue to reward preparation, access, and strategic execution.
For buyers, the advantage lies in working with an advisor who can provide visibility into what is coming, not just what is available. For sellers, success comes from thoughtful positioning and targeted exposure.
Winter Park remains one of the most stable and desirable submarkets in Central Florida, driven by intentional demand and enduring appeal.
Follow Audra on Instagram: @realestatebyaudra
