“Working with Kathryn Wetherell was an outstanding experience from beginning to end. She took the time to truly understand what I needed and guided me with patience, honesty, and expertise throughout the entire process. Kathryn was always available to answer questions, explain next steps, and provide reassurance when I needed it most. Her professionalism, attention to detail, and genuine care made all the difference. She consistently went above and beyond to make everything smooth, stress-free, and successful. I couldn’t have asked for a better agent, and I would recommend Kathryn to anyone who wants a knowledgeable, reliable, and dedicated real estate professional in their corner.”
- Agent Pronto
- Florida
- Naples
- Windstar
The best way to find top real estate agents in Windstar, Naples, FL
Skip the search. We analyze thousands of real estate agents in Naples’ Windstar neighborhood and nationwide to find you proven local pros, for free.
Compare top Windstar real estate agents.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for December 2025. *
764 recent sales
$13K - $12.1M price range
$575K 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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“Ryan was great. I had a couple properties but needed to at least sell one of them in this calendar year, with only about 3 months to go. I made it clear to Ryan and he worked hard to deliver in very short order. We adjusted to pricing down after a few fell through, and closed near end of October. He communicated often and effectively and followed up to ensure I was in contact with the Title compant etc. Having been nearly defrauded myself before finding Ryan, he assured and convinced me that this was legitimate and all legal. I maintain my other properties with Ryan and will until they sell likely sometime in 2026. Thanks Ryan, and best wishes.”
“I would recommend Barrett because he is trustworthy , professional and patient. We were very comfortable working with him. He exhibited a genuine concern for our needs and was very responsive to our concerns and questions.”
“Michelle was great to work with. She helped us through each process of purchasing our new home. She made herself available for all questions and concerns.”
“James Boyer was always on top of it. I was informed throughout the entire process, from photos/videos to marketing the property. He wasn't only able to sell this one but was able to bring several buyers for our other model homes. I have worked with other agents and James sets the standard very high, I have always had to chase our agents for updates but not with James. I am very happy we chose James out of the many agents we interviewed to list our new construction homes. This one was under contract in days from listing and like many others we are pending before completion. I would recommend James to anyone looking to sell their house in South West Florida.”
“As I mentioned I used Kevin as my agent when I bought my house in N. Naples He was AWESOME.. So it stands to reason that IF & or when I sold it I would have to reach out to Kevin again!!! He Also was my agent BEFORE my house sold on my new house that I had built! I already recommended Kevin to a childhood friend who will be calling him in a few weeks he told me!! Kevin went WAY beyond his duties as my agent to make sure everything was great and it was!!! Having Kevin as your agent is a no brainer!!! Worked togather 3 times now!!! Nough said !!! Thank you Kevin”
“My husband and I highly recommend Realtor, John Rice due to his professionalism, knowledge of the market, his attention and dedication towards us as clients in showing us homes that met our criteria, and his personality, which is always caring and supportive. From the start of the process to the closing, John Rice has been "by our side" every step of the way and made this an even more enjoyable experience!”
“Agent Pronto introduced me to a very professional agent, Christina Diaz. Thank you, Christina - you made this transaction very quick & easy.”
“Larry is by far the most AMAZING Realtor. He was always very responsive to my calls, texts, request, etc. We built up such a great relationship through this crazy process, that even after we closed on our new home, he reached out to check on us. He is always looking to get the best deal for his clients. He is like family now to us and will always have his own seat next to the firepit in our backyard. I would DEFINETLY recommend Larry to anyone and everyone looking to buy or sell. AMAZING.. Can't say enough Great things about Larry.”
“Krysta Sylvester helped us look for that perfect house for over 7 months. I could not be happier with the dedication and knowledge Krysta shared with us, as we were from another state. She does not disappoint, I will not go with any other agent in the future. Thank you Krysta.”
Windstar real estate Market Report.
Information and statistics on the latest trends in the Windstar real estate market, updated for December 2025. *
The typical home value in Windstar is projected to be $686,240 for the month of November. October’s finalized data reported the typical value of a home in the neighborhood to be $745,000—down 31.96% over the previous 12 months. For comparison, city-level data pegged home values at $847,000 in Naples for the most recent reporting period. That number is expected to float around $695,500 in November.
Windstar had 20 new listings and 12 listings that went under contract in October, increasing the area’s total available inventory to 22—up 37.5% from the previous month. Inventory is projected to have further increased in November.
The median listing price for homes in Windstar fell 15.86% from September to October, bringing the current median listing price to $1,195,000. Based on projected data for November, listing prices may continue to fall.
The number of days that homes have been on the market prior to going under contract rose year-over-year. In October 2025, the median time for a listed property to go pending was 91 days, compared to -150 days in October 2024. However, in recent months the median number of days from listed to pending appears to be falling. That trend is predicted to have carried through to this November.
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 Windstar has to offer.
Windstar neighborhood offers residents a refined, amenity-rich lifestyle anchored by golf and waterfront views, with a welcoming clubhouse, active social calendar, and convenient access to beaches, dining, and shopping.
Windstar is a rare blend of bayfront serenity and country club energy, where sunrise over Naples Bay meets the emerald sweep of a Tom Fazio–designed course at Windstar on Naples Bay. Within this gated community, residents enjoy a deep-water marina with direct Gulf access via Gordon Pass and a private boat shuttle to Keewaydin Island—weekend traditions that feel like everyday luxuries. Downtown Naples and the galleries, cafés, and beaches of Old Naples are just minutes away, while neighboring Royal Harbor extends the waterfront vibe beyond the gates.
Recreation unfolds in every direction. Cyclists and walkers trace quiet streets to Bayview Park’s public ramps and scenic overlooks, perfect for paddlers and anglers; its details and programs are maintained by Bayview Park. Families and garden-lovers gravitate to the award-winning Naples Botanical Garden, and the nearby Bayshore Arts District buzzes with food trucks, live music, and waterside sunsets. On-site, members savor tennis, pickleball, fitness, and bay-view dining, with social calendars that make it easy to plug in.
Windstar is served by Collier County Public Schools, with choice programs, athletics, and arts offerings located a short drive from home. Whether you’re prioritizing boating, golf, or an easy connection to downtown, this community delivers a uniquely coastal lifestyle built around the water. If you’re considering a move, Agent Pronto can connect buyers and sellers with top local real estate agents ready to help.
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 Windstar. 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 Windstar Realtor® or real estate agent today.
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