We analyze thousands of real estate agents in Windsor 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 November 2026.*
*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 Windsor real estate market. *
Jul 1, 2026 - Sep 30, 2026
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Jul 2026 - Sep 2026).
Inventory in Windsor has expanded notably in this rolling three-month view, with active listings up sharply year over year and holding at 39. Contract activity has also picked up compared with a year ago, as homes sold have increased significantly while new listings have risen even faster, suggesting more options but also more movement through the pipeline.
Pricing is adjusting to this added supply, with the typical home value down double digits from a year earlier even as the median list price has climbed substantially. Longer marketing times, now at a median of 51 days and higher than a year ago, indicate buyers have more breathing room to evaluate properties before committing.
Conditions have shifted from very tight to more balanced, with months of supply jumping severalfold year over year to 5.7, yet the area still registers as a seller’s market. Even in this cooler environment, roughly 31 percent of recent sales closed above list price and the average sale-to-list ratio remains close to 100 percent, showing that well-priced homes can still attract strong offers. Buyers and sellers who want to navigate these changing dynamics can rely on Agent Pronto to connect them with a local Windsor agent who understands both sides of the deal.
Windsor offers residents a close-knit community with small-town charm, convenient access to outdoor recreation and local amenities, and a welcoming, neighborly atmosphere.
Windsor offers small town living with practical access to larger job and shopping centers in Suffolk, Chesapeake, and Norfolk. Located along U.S. Route 460, it provides a straightforward commute while keeping a quieter, residential feel that appeals to both long‑time residents and newcomers.
Daily life is centered around local amenities and community services. Families appreciate Windsor Elementary School and Georgie D. Tyler Middle School, both part of Isle of Wight County Schools. Outdoor time often revolves around Windsor Town Center and Garris Park, with playgrounds, walking areas, and town events that make it easy to connect with neighbors.
Local dining spots and everyday conveniences line the main corridor, while bigger-box shopping and healthcare options are a short drive away in Isle of Wight County. The Windsor Library and community programs offer activities for all ages, and town services like public works and planning are coordinated through the Town of Windsor offices.
Whether you are moving across town or relocating from a nearby city, a real estate agent who knows Windsor’s streets, school zones, and back‑road commute routes can simplify every step. Agent Pronto connects buyers and sellers with local experts who help reduce stress and keep the process on track.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“Jasmine was AMAZING!! Attentive, well informed, and VERY PROFESSIONAL! Best Customer Service Support I’ve experienced in ages! The rest of team as well went above and beyond to help get me my new home. Every question was answered quickly and accurately. They made sure there were no unexpected surprises. All deadlines were explained and met. EXCELLENT AND JOB WELL DONE!!!”
“Kristina Price was so helpful, kind, was willing to explain anything I had questions about and supportive for my first home buying experience. She was also willing to back me up and give me honest and constructive information on the homes i was looking to buy. I would highly suggest her for anyone buying a home!”
“Joel was absolutely exceptional in the process of selling our property. He was friendly, communicative, and very knowledgeable of the market and the area we were listing. We had a horrific experience with our previous realtor, ultimately resulting in the house being on the market for 4 months with no offers. Joel suggested small improvements/things to boost curb appeal, connecting us with professional stagers and photographers. And, after listing were under contract in only 2 weeks. Even during the pending sale time we still had regular communication with Joel on updates, and he was able to connect us seamlessly to professionals we needed for updates/picra items. We cannot recommend him enough!!!”
“I just closed on my house today. Tracy has been patient with the whole process with me through some bumps in the road. In the whole process she has kept in touch till I was ready and when I was she jumped into action always had my best interest first. I will always appreciate that and always will use her again if I ever want to sell or buy!!! She is the best there is!!!!”
“Wonderful experience from start to finish! He was always responsive, helpful, and made the entire home-buying process so much easier. I truly felt like he had my best interest in mind. I would absolutely recommend him to anyone buying or selling a home!”
“Oh my goodness! This process was as smooth as a home purchase could be but it’s all due to the wonderfulness of Lyz Wilson!! She definitely made this more pleasurable and exciting than stressful. She is extremely knowledgeable and responsive which I love because I had billions of questions and her patience is Barre none!! We definitely felt like we had an advocate on our side as opposed to someone who didn’t care. I have made not only a new realtor but a friend! She and her team are amazing and I would use them time and time again!!! Thank you Lyz Wilson for ALL of your dedication to my family in this process, you rock!!!”
“Jen was amazing to work with. We live out of state and she was very thorough with our virtual walk throughs and showings and very honest. We found a great home. We really enjoyed working with Jen.”
“Jeremy was an amazing realtor for us as first-time home buyers! He is clearly knowledgeable and experienced & made the whole process as smooth as possible. I will be recommending him to everyone!”
“There are not enough words to express how thankful we were to have found Megan as our agent. As first-time home buyers, the whole journey seemed so unfamiliar and intimidating. Megan and her network treated us as if we had known them personally for our entire lives. She was compassionate enough to put our needs in front of her own and never made us feel like we were pressured into doing anything. We looked at over 20 houses with 4 offers, and she turned every stressful, disappointing, and exhausting moment into an optimistic opportunity until we found our home. From our baby crying through our phone conversations to dealing with all our hesitation and uncertainty, Megan was not only professional but joyous through it all. If there was one thing we did correctly in our home buying experience, it was choosing Megan Costa. We cannot thank her enough.”
“I had an excellent experience working with Maureen . From start to finish, she was professional, knowledgeable, and truly dedicated to helping our family find the right home. She took the time to understand my needs, answered all my questions promptly, and guided me through every step of the process with patience and clarity. What stood out most was her attention to detail and strong communication. I always felt informed and confident in my decisions because she made sure I understood all my options. She also went above and beyond in negotiating and ensuring everything stayed on track. I highly recommend Maureen to anyone looking to buy or sell a home. Her expertise and commitment made the entire experience smooth and stress-free.”
“I can’t say enough good things about Erika my realtor. From day one, she treated my family and I more than just a client. She truly cared about helping us find the right home. Erika was patient, understanding, and always made sure we felt comfortable with every decision. Buying a home can be stressful, but she made the process feel easy and even enjoyable even when things where rough , Erika stayed on top of everything, kept us informed, and always had our best interest in mind. Because of her, we found a home that we genuinely excited about, and I’m grateful for all the effort she put in. I would recommend her to anyone without hesitation 100/100.”
“We had an outstanding experience working with our realtor, Michelle Bollinger of Berkshire Hathaway, during the purchase of our home in Williamsburg. From start to finish, Michelle was exceptionally knowledgeable, responsive, and genuinely invested in our success. She took the time to understand our needs and priorities and consistently went above and beyond to ensure every detail was handled with care. Michelle was a true advocate for us throughout the entire process, providing clear guidance, honest advice, and steady reassurance at every step. Her ability to coordinate seamlessly with NFCU—no small feat—was invaluable, and her professionalism and persistence made what could have been a stressful experience feel smooth, organized, and completely manageable. We always felt informed, supported, and confident in our decisions because Michelle communicated clearly, anticipated potential issues, and addressed them proactively. Her expertise, attention to detail, and warm, personable approach made all the difference. We couldn’t be happier with our new home and are incredibly grateful for her dedication and hard work. We wholeheartedly recommend Michelle to anyone looking to buy or sell a home—you will be in excellent hands.”
“Cas did a great job helping us buy our condo. The process was so smooth. Any hiccups she handled promptly. Would definitely recommend to work with :)”
“I cannot say enough.Amazing things about Melissa!! From the very beginning, she was professional kind.And incredibly patient, walking me through every step of the home buying process with genuine care and clarity. What stood out the most is how she truly listened.And never rushed or pressured me, always making sure I felt comfortable.And was informed. It is rare to find someone who combines such deep expertise with such a warm and personal touch. If you're looking for a real estate agent who will treat you more than just a transaction, someone who truly cares Melissa Boyce is the agent you want on your side.”
“Our realtor Jessica Estrada is top-notch - she goes above and beyond in everything she does. She showed up numerous times to help our property be ready to sell and did whatever it took. Our house sold within two months due to her ads and persistence. Because of her, our house closed on time. She is knowledgeable, experienced, professional, and teaches others in her group. We are so thankful for Jessica.”
“Bottom Line: Without Adam’s help—which went far beyond the role of a typical buyer’s agent—I wouldn't be a homeowner today. My home-buying journey was unusually challenging due to unresponsive sellers, misleading listings, and issues with a poor lender. Despite all that, Adam was there every step of the way. He leveraged his network and experience to ensure everything stayed on track and deadlines were met. His online tools and resources are excellent—well-organized, informative, and uniquely tailored. For example, he created a custom search that excluded properties in hurricane zones—something I haven't seen offered by other agents. Adam is exceptionally honest and supportive. Not once during the process did I question whether I could trust him. That kind of confidence is invaluable when making such a significant decision as buying a home. Based on my experience, I wholeheartedly recommend Adam to anyone in need of a reliable, knowledgeable, and genuinely caring real estate agent.”
“It was a short sale with a lot going on, and she was able to weather the storm She helped me buy my house and I wasn’t even in the state! Amazing work done by Lee.”
“I reached out to a friend and asked her if she would send me her realtor’s contact info, and when I received it, it read “ Brad Rosenberg Worlds Best Realtor “. It made me laugh, but little did I know that this was all too true! Brad guided my husband and I through the whole home buying process from the first call to our closing date. We talked with him daily and he always made sure that we understood what was happening. No question was too small to ask and Brad always reassured us in our decisions. Brad is knowledgeable and willing to do everything he can to get you into the home you desire. There is not enough accolades that I can give to him, other than a huge THANK YOU! We appreciate you and look forward to continuing our relationship with Brad.”
“Matthew was extremely professional and helpful in locating property and during the negotiation process. His insight was so helpful making the process seamless!! We have bought and sold 6 properties and this was by far the easiest!!”
“Deb Kelly did a fantastic job!”
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 Windsor. 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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