We analyze thousands of real estate agents in Wilmington’s Winter Park neighborhood and nationwide to find you proven local professionals, for free.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for April 2026. *
245 recent sales
$12K-$3.5M price range
$385K median price
* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.
Sell faster. Buy smarter. Get matched with proven agents who know your market—all for free.
Information and statistics on the latest trends in the Winter Park real estate market, updated for April 2026. *
Year-over-year, Winter Park’s housing values have climbed strongly, with the typical home value up 11.51% even as nearby Wilmington has seen a 2.8% decline. At the same time, buyer activity has cooled compared to last year, as pending sales are down 18.18% and new listings have dropped 52.94%, tightening choices for shoppers.
In February 2026, the typical home value in Winter Park reached about $407,000, while the median list price sat lower at roughly $301,850. Homes spent around 34.5 days on the market, more than double from a year earlier but slightly faster than the prior month, and about 28.57% of recent sales closed above the asking price with an average sale-to-list ratio near 0.99.
Looking ahead to March 2026, typical home values are projected to edge up to about $422,375 even as the projected median list price dips to roughly $285,325. Inventory is expected to tighten further from 5 to 4 homes, underscoring Winter Park’s current seller’s market conditions and its contrast with Wilmington’s much larger supply of 566 listings. In this kind of environment, both buyers and sellers can benefit from Agent Pronto’s help connecting with an agent who understands the local dynamics.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Winter Park offers residents a close-knit, walkable community with tree-lined streets, convenient parks and local amenities, and a welcoming calendar of events that supports an active, balanced lifestyle.
Winter Park in Wilmington offers practical suburban living with strong connectivity to the rest of the city. Located between Independence Boulevard and College Road, the neighborhood provides quick access to downtown Wilmington, University of North Carolina Wilmington, midtown employment centers, and the beaches.
Residents appreciate everyday convenience. Winter Park is minutes from grocery stores, medical offices, and big box retailers along South College Road. Families are drawn to nearby schools such as Winter Park Elementary School and Roland-Grise Middle School, along with a variety of youth programs offered through Wilmington Parks & Recreation.
Green space and recreation are close at hand. Bradley Creek and Bradley Creek Elementary area are just to the south, while New Hanover County’s Hugh MacRae Park offers trails, playgrounds, athletic fields, and picnic shelters a short drive away. Dining options range from local favorites along Oleander Drive to cafes near Independence Mall, giving residents plenty of choices without long commutes.
Housing in Winter Park spans older brick ranches, renovated homes, and some infill construction, which can make pricing and value analysis more complex. A local real estate professional who understands street by street differences, school zones, and evolving traffic patterns can help reduce stress, whether you are planning to buy or preparing to sell. Agent Pronto connects both buyers and sellers with the right Winter Park expert so your move feels more informed and manageable.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“Working with Liz was an amazing experience during the purchase of our first home! Liz was pivotal in us figuring out our ideal home style and what was around that fit our needs. Once we found THE home for us Liz worked even harder to get us the best price and all of the best inspectors and lawyers to complete the process. We couldn't imagine going this process again with anyone but Liz and will be referencing her to all of our friends!”
“He came prepared agreed with me about the price. Knew my dream, made it happen. He is congenial, I was very happy to work with him.”
“From start to finish, Pam was friendly, professional, great communicator, patient, and knowledgeable of the complete process. Pam listened to our needs and wants and strived to help us find a new home that was a perfect new start.”
“Chris Roper was absolutely outstanding and exceeded all of my expectations. As a first-time homeowner, I was unfamiliar with many aspects of the home-buying process, but Chris went above and beyond to guide me every step of the way. He took the time to explain everything clearly, showed incredible patience, and made the entire experience feel manageable and stress-free. I would highly recommend Chris to anyone looking to purchase a home. He is kind, knowledgeable, and truly exceptional at what he does.”
“Neil is great! He is very knowledgeable and a pleasure to work with. I will definitely refer him to anyone that asks if I know a local agent.”
“Kelly Bossman was wonderful to work with. She made herself available for any and all questions and very supportive even when I was 'clueless' about the whole process. Very thankful to have had her at my side!”
“I had an amazing experience working with Sherry. From start to finish, she made the home-buying process smooth, stress-free, and even enjoyable. Sherry was knowledgeable, patient, and always quick to answer my questions. Their guidance helped me find the perfect home, and I couldn’t be happier with my purchase. I highly recommend Sherry Pitman to anyone looking to buy or sell a home!”
“Bea Desmond was exceptional! Extremely knowledgeable about the market, always responsive to the many questions we had & always the utmost professional! We could not have asked for a better agent.”
“Oscar was great to deal. I will use him to buy my next home.”
“Terri i Parrish is no longer my Realtor....she is my friend! She "held my hand" through a difficult process for me as I am older and not as strong as I have been. She brought me coffee on the days the gas had been stopped and not restarted. She helped me move my belongings to storage! She returned every one of my frantic calls and soothed my concerns. She made sure every i was dotted and t crossed on every document. I must say that if one needs compassion in a Realtor and skills to sell, call Terri. I have one more to sell and she will be the listing agent!”
“Dave Robertson was very patient and got the job done! He was very positive and professional throughout this experience!”
There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise covering the housing market in and around Winter Park. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.
Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents. Find your Winter Park Realtor® or real estate agent today.
We’ll match you with top-rated real estate agents in just about any city—wherever your next move takes you.
