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 September 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. *
May 1, 2026 - Jul 31, 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 (May 2026 - Jul 2026).
Inventory in Windsor has expanded sharply in this rolling three-month view, with active listings up more than 150 percent year over year and months of supply rising to 6.4 from roughly 1.8 a year and a half ago. Contract activity is still moving, as pending sales have increased more than 28 percent annually even though the number of homes sold is only slightly higher than a year ago.
Pricing is adjusting to this looser environment, with the typical home value down about 7 percent year over year while the median list price has climbed more than 30 percent. Sellers are no longer seeing the same bidding pressure, shown by the share of homes selling above list dropping more than 11 percent annually, even as the average sale-to-list ratio holds near 100 percent.
Days on market tell a clear story of slower pace, rising to about six weeks on a typical sale and increasing dramatically compared with a year ago. More inventory and longer marketing times give buyers additional options and negotiation room, while sellers must price carefully to stand out, and Agent Pronto can help both buyers and sellers find an agent who understands these Windsor trends.
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.
“It was a pleasure working with William Mallory. He is patient, diligent, and has the buyers best interest at heart. I recommend working with him as he makes the home buying experience exciting and makes you feel supported throughout the process.”
“Harvey Raffensperger at Iron Valley Real Estate was fantastic. We sold our home in Hampton in under three months, and honestly the whole process was way less painful than I expected. Harvey knows the local market well, kept us in the loop throughout, and was always easy to reach. The real test came when we ran into a really difficult buying agent — Harvey handled it calmly and professionally and kept everything from falling apart. We barely even felt the turbulence. If you're selling in the Hampton area, I'd go with Harvey without hesitation. Just a solid, trustworthy agent who gets the job done.”
“As a first-time homebuyer, working with Catherine was an amazing experience from start to finish. She was incredibly patient, knowledgeable, and always took the time to explain each step of the process in a way that made everything feel manageable and stress-free. Catherine was always responsive, professional, and truly had our best interests at heart. She made what could have been an overwhelming experience feel exciting and smooth. We couldn't have asked for a better person to guide us through our first home purchase and would highly recommend her to anyone-especially first-time buyers.”
“Our previous agent insisted that we find a different agent who was more familiar with the Hampton roads area after spending almost 3 months on the market. Rhodonna was highly recommended to us by a family friend, we heard so many great stories about her working hard on the buying and selling side. Once we were dropped by our previous agent, we then decided to reach out to Rhodonna and she agreed to represent us with no hesitation. She came in immediately casting vision for the staging of the home, targeting of potential buyers, and ensuring that we would walk away from the table satisfied. She fully agreed with us on our desirable outcome and worked very hard until it was done. In about 1 month, despite a tough market, Rhodonna had us under contract. Her follow up and follow through with the potential buyers that ended up purchasing our home was very professional and ideal for desired representation in an agent. We highly recommended Rhodonna! Hard worker, master negotiator, & closer!!”
“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.”
“Debbie Martin is such a wonderful person. Very knowledgeable in her field. She has such a strong community of friends that she can reach out to for advice for repairs. I would strongly recommend her to anyone who is looking to purchase a home.”
“Deb Kelly did a fantastic job!”
“Kimberly and Holly were very personable and professional. They were very informative. They guided us through this cumbersome and tedious process. They both were great to work with and kept us abreast with what we needed to do to sell our home. We are most grateful to work with them. They know what it takes to sell a house!”
“Mark was a great person to work with. I found him to have a high level of integrity and I would not hesitate to recommend Mark or use him again if conditions warranted. Mark was a pleasure to work with and I feel that he placed my requirements above his, a wonderful representation of a professional realtor and individual. Highly recommended!!”
“Because I was trying to do a long distance short sale, I needed someone who really knew what they were doing. I was given the name and number of Colin. He took on the challenge and a little over two years later, we finally closed. If you have done a short sale before, it is a very trying ordeal! Colin took good care of the house, had repairs done, and always had clients waiting in line with a new contract. I believe it was the 5th contract and a lot of patience that got us to closing.”
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.
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 Windsor Realtor® or real estate agent today.
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