Skip the search. We analyze thousands of real estate agents in Four Corners’ Windwood Bay neighborhood and nationwide to find you proven local pros, for free.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for March 2026. *
172 recent sales
$100K-$1.8M price range
$395K 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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Information and statistics on the latest trends in the Windwood Bay real estate market, updated for March 2026. *
The typical home value in Windwood Bay is projected to be $207,500 for the month of March. February’s finalized data reported the typical value of a home in the neighborhood to be $275,000—down 38.33% over the previous 12 months. For comparison, city-level data pegged home values at $417,500 in Four Corners for the most recent reporting period. That number is expected to float around $423,750 in March.
Windwood Bay had 4 new listings and 6 listings that went under contract in February, decreasing the area’s total available inventory to 5—down 0.0% from the previous month. Inventory is projected to have further decreased in March.
The median listing price for homes in Windwood Bay grew 20.0% from January to February, bringing the current median listing price to $420,000. Based on projected data for March, listing prices may continue to grow.
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 141 days, compared to 188 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.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Windwood Bay offers residents a welcoming, family-friendly community with well-maintained parks and green spaces, convenient access to shops and schools, and a range of outdoor and social amenities that foster an active, connected lifestyle.
Windwood Bay in Four Corners stands out from nearby resort communities by feeling more like a true neighborhood than a short‑term vacation enclave. Many homes allow flexible use, but you will also find full‑time residents, longer term rentals, and streets where neighbors actually know one another.
Set just off Ronald Reagan Parkway, Windwood Bay offers easy access to Four Corners, Davenport, and Kissimmee, yet it stays pleasantly residential. Tree‑lined sidewalks, ponds, and conservation areas give the community a calm atmosphere, while proximity to Northeast Regional Park adds boat ramp access, sports fields, and dog‑friendly green space. Families appreciate options like Loughman Oaks Elementary and Ridge Community High School, along with nearby programs at the Four Corners Community Center.
Daily convenience is strong, with shopping and dining along US 27 and quick trips to Clermont or Orlando for work and entertainment. Short drives to major theme parks appeal to second‑home owners and investors, which helps support values while still keeping a lived‑in community feel.
Because Windwood Bay serves primary residents, vacation owners, and investors, timing and preparation matter. Whether you are buying into the neighborhood or planning a sale, partnering with the right local agent through Agent Pronto can help you navigate pricing, competition, and the best moment to move.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“This is the 2nd time I've utilized Debra's services. She is very good at her job. She is knowledgeable, efficient, always available and cares about the customer. I highly recommend her to anyone looking to buy or sell. Thanks, Debra!!”
“Cory did an excellent job from start to finish. He was professional, responsive, and made the entire process smooth and stress-free. I really appreciated his attention to detail and clear communication. Highly recommend working with him.”
“David is truly a professional and dedicated to his trade. Extremely strong communication and answered all concerns in a timely fashion. It is clear David has a great deal of experience in real estate and it shows! Would highly recommend David and 100% will utilize him again in the future if it is needed.”
“I would recommend Kimberly to anyone trying to sell a high-priced home. She is knowledgeable about the market and was able to sell our house in 2 weeks, even though it had previously sat on the market for 9 months pre-COVID. Her customer service is excellent, and she is helpful with questions and contacts throughout the selling process.”
“Great expreience start to finish. I threw some challenging cureballs and she dealt with them professionally and quickly. I would definatlely use her again for any selling or buyiong I had to do in the area. 5 star experience.”
“My name is Kenneth Martin my family and I had a really bad experience with a different real estate agent while trying to find a house and we stumbled upon Cassandra through days of research and reading every review on every realtor on the Internet and it was a blessing we closed on a house in two weeks and Cassandra was one of the best thing that happened to my family.”
“A Heartfelt Recommendation for Tony Fuentes, Realtor in Kissimmee, Florida! I recently had the pleasure of working with Tony Fuentes, and I can't express enough how remarkable my experience was! From the moment I reached out, Tony was quick to respond, returning my call in less than 30 minutes. His knowledge of the real estate market is awe-inspiring, and his enthusiasm for helping me get everything in order made the process feel effortless. What stood out most was that Tony never pressured me to sign anything. Instead, he provided valuable referrals to help get my villa ready for sale. In less than thirty days, my house was beautifully painted, thoroughly cleaned, and all those little fixes were taken care of. I was amazed at how smoothly everything went, especially considering I didn’t even live in the state! Thanks to Tony’s expertise, I was able to sign my paperwork remotely with a notary, making the entire experience incredibly convenient. He truly goes above and beyond!”
“Zach has been nothing but 100% professional. He answers all correspondence quickly and effectively. I must also say that his ability to get a deal finished is unparalleled. He truly has a gift with working in real estate.”
“I highly recommend Rich Noto for new home construction. He was a fantastic advocate throughout my build, especially since I was relocating from Pennsylvania to Florida. Living states away, he sent detailed videos of construction progress and found defects during various inspections. His communication and availability far exceeded my expectations. Rich has a keen eye for potential issues and a deep understanding of building codes that many other agents, and even some inspectors, might miss. He truly knows the critical phases of construction, from the foundation on, and when to schedule inspections. He understands the tricks builders use to hide problems and is a fierce advocate for his clients. I have no doubt he saved me from future headaches. He is an invaluable resource who ensured I ended up with a high-quality home.”
“Excellent experience”
“I had the pleasure of working with Claudia Garzón as my realtor, and I couldn't be more satisfied with her work. From the very beginning, she showed a high level of professionalism, responsibility, and an inspiring motivation that made the entire process much smoother and more manageable. Claudia has an exceptional ability to solve any issues that may arise, always finding quick and effective solutions. Her experience and dedication made a real difference at every stage of the transaction. I highly recommend her with complete confidence. Thank you, Claudia, for your outstanding work!”
“Charles listened to all of our wants, showed us an amazing house that we instantly loved and was more helpful then we could have imagined”
“Sam sheen realty was FANTASTIC !! I COULDN'T HAVE ASKED FOR BETTER AGENTS”
“Enjoyed working with Stanley Watts, he was very professional, friendly, knowledgeable and was always there to answer my questions and made my experience in buying my home a quick and pleasant experience. I highly recommend him. Thank you Stanley!”
“Daniel is an amazing person to work with. The level of communication and knowledge that he brings to the table everyday is top notch. I would recommend him to anyone looking to purchase a new home or sell their existing home. People say they care about their clients, Daniel shows this in his actions and commitment. It was a pleasure having the opportunity to work with him!”
“Zac Hernandez was brilliant in the entier process and I cannot thank him enough. You are lucky to have him on the Keller Williams team. He guided me through every step of the way and was not only professional, but very kind and patient with me. Thank you, Zac!”
“We would like to commend Alan on the great job he did handling all the details and processes of our homebuying experience. He is a valuable representative to the Coldwell Banker name. Alan was attentive to our needs and took the stress out of purchasing a home. He was able to spell out in advance all of the details we would have to cover. He was always upbeat and had a tremendous attitude. I would highly reccomend him to anyone we know that is interested in buying a home in the state of Florida.”
“Great Experience!”
“Fabio was very professional, open, transparent, and reliable throughout the entire process. He really cared about us, understood our entire needs... Best realtor I've ever met.”
“A friend of mine suggested that I speak with Lance about selling my Condo. Once I spoke with him in person, I knew that he would be my agent. He is very professional, knowledgeable and ready to get the job done. He showed me his Marketing Plan for my Condo and I liked it. With my prior home sales, my previous agents had never explained or even spoke of their marketing plan with me. I was very impressed with Lance's suggestions and plans. My Condo went under contract within approximately 2 weeks of being on the market. Thank you for a job well done, Lance!!”
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 Windwood Bay. 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 Windwood Bay Realtor® or real estate agent today.
