“Jeff as always. Thank you and your team”
Century 21 Vanguard
- Agent Pronto
- North Carolina
- Wilmington
- Winter Park
The best way to find top real estate agents in Winter Park, Wilmington, NC
Skip the search. We analyze thousands of real estate agents in Wilmington’s Winter Park neighborhood and nationwide to find you proven local pros, for free.
Compare top Winter Park real estate agents.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for March 2026. *
Jeff Lesley
4.8
(346)
Century 21 Vanguard
241 recent sales
$12K-$3.5M price range
$380K 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.
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Winter Park real estate Market Report.
Information and statistics on the latest trends in the Winter Park real estate market, updated for March 2026. *
The typical home value in Winter Park is projected to be $422,380 for the month of March. February’s finalized data reported the typical value of a home in the neighborhood to be $407,000—up 11.51% over the previous 12 months. For comparison, city-level data pegged home values at $442,500 in Wilmington for the most recent reporting period. That number is expected to float around $435,000 in March.
Winter Park had 8 new listings and 9 listings that went under contract in February, decreasing the area’s total available inventory to 5—down 16.67% from the previous month. Inventory is projected to have further decreased in March.
The median listing price for homes in Winter Park fell 9.87% from January to February, bringing the current median listing price to $301,850. Based on projected data for March, listing prices may continue to fall.
The number of days that homes have been on the market prior to going under contract fell year-over-year. In February 2026, the median time for a listed property to go pending was 34.5 days, compared to 52 days in February 2025. In recent months the median number of days from listed to pending appears to be steady. That trend is predicted to have carried through to this March.
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Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Learn more about what Winter Park has to offer.
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.
Trusted by over 500,000 buyers and sellers.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“After Liz spent two years helping us find our ‘unicorn’ home, there was no one else we’d trust to sell our beach house in Surf City. Working with Liz feels like having a close friend in your corner rather than just an agent. She brought the same incredible patience and expert advice to this sale as she did to our purchase. Liz made the whole process feel effortless and kept us confident every step of the way. I’m so grateful for her support—she truly is the best and we would recommend her to anyone we know looking to by or sell.”
Sold Buy the Sea Realty
“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.”
Berkshire Hathaway HomeServices Carolina Premier Properties
“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.”
Berkshire Hathaway Carolina Premier Properties
“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!”
Bossman Real Estate LLC
“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!”
Century 21 Barefoot Realty
“I highly recommend Pam Wooddell for all your real estate needs. Her expertise, professionalism, and dedication has always exceeded my expectations. She guides one through the process with ease and achieved fantastic results. A top-notch realtor who goes above and beyond for her clients.”
Live Oak Real Estate
“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.”
BlueCoast Realty Corporation
“Oscar was great to deal. I will use him to buy my next home.”
Berkshire Hathaway Home Services, Carolina Premier Properties
“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!”
The Jason Mitchell Group Jason Mitchell Real Estate
“Dave Robertson was very patient and got the job done! He was very positive and professional throughout this experience!”
ERA Real Estate Coastal
Frequently Asked Questions
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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.
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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.
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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.
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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.
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