We analyze top real estate agents in Naples’ Windstar neighborhood and across the country to find you the most proven local agents, for free.
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for October 2025. *
* 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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“Kimberly has been wonderful throughout this entire process of selling my home. I can't say enough about how awesome she was in answering questions or anything I needed during this time. I highly recommend Kimberly”
“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”
“Barrett was a pleasure to work with during the house search process. He was professional and knowledgeable in the real estate field. Barrett was very patient and empathetic to our needs. He was responsive and friendly throughout.”
“Matt was amazing ! Extremely knowledgeable with the market and went over and above the call of duty when helping us locate our new home !”
“Katy, Is professional and has a friendly demeanor. She is patient and knowledgeable with the local market. She went above and beyond to successfully sell my property. I highly recommend working with her.”
“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!”
“Everything was perfect, they did a great job.”
“Agent Pronto introduced me to a very professional agent, Christina Diaz. Thank you, Christina - you made this transaction very quick & easy.”
“Please see the previous comments. Tiffany is the best and truly world class! Tiffany was so wonderful to work with. She knew everything we needed and led us through a very unusual market with results beyond our expectations! We would not have trusted anyone else and she was gracious and kind even when we may not have been. We have referred our friends to work with her, she is the best. Grateful to her and the team.”
“Larry was more than a Real Estate Agent. He was more like a Family Friend. I am truly blessed and grateful to have worked with him. My home is everything I imagined it would be.”
“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.”
“Jonathan Pita was amazing, so patient and understanding of our needs and wants. He always answered all of our thousands of questions, and dealt with matters promptly. He went above and beyond to get us into our new home despite the competitive market. Will do business with him again when needed, and will recommend to anyone looking for a new home.”
Information and statistics on the latest trends in the Windstar real estate market, updated for October 2025. *
The typical home value in Windstar is projected to be $862,520 for the month of October. September’s finalized data reported the typical value of a home in the neighborhood to be $862,520—down 84.17% over the previous 12 months. For comparison, city-level data pegged home values at $1,150,000 in Naples for the most recent reporting period. That number is expected to float around $1,150,000 in October.
Windstar had 10 new listings and 8 listings that went under contract in September, increasing the area’s total available inventory to 14—up 7.69% from the previous month. Inventory is projected to have further increased in October.
The median listing price for homes in Windstar grew 86.48% from August to September, bringing the current median listing price to $1,445,250. Based on projected data for October, listing prices may continue to grow.
The number of days that homes have been on the market prior to going under contract rose year-over-year. In September 2025, the median time for a listed property to go pending was 84.5 days, compared to 53 days in September 2024. 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 October.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
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.
Within a few minutes, I was paired up with an awesome agent who really knew the local area and helped me find a great condo in a super tight market. It was daunting to think about how to find the right agent. Agent Pronto got me the right agent, pronto!
With over 2 million real estate agents across the U.S., it’s not easy deciding who to trust when buying or selling a home.
We’ve analyzed performance metrics, close rates, specialties, and client reviews of the top real estate agents in Windstar to qualify the best agents for your specific needs.
We know that choosing the right real estate agent can be a stressful task. With Agent Pronto, it doesn’t have to be.
Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in Naples. But we don’t stop there.
Our Agent Specialists will take into account any special requests you have when searching for your real estate agent recommendation.
Need a great agent who speaks fluent Spanish and is a luxury condo expert in your neighborhood? No problem!
Tips and market insights to make your Naples real estate journey a success.
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.
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.
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