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Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for January 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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“W gave William a 10 star., he exceeded his hard work in making everything happen. (Through the process of me & my family finding this beautiful home) !!! Always on top of everything ( which made a smooth success!! Sooooo thankful for him!!! I promise you will not not go wrong ( So give him a call today!! We thank you William!!! God Bless!!”
“Working with this agent was a great experience. They were always available to answer questions, offer guidance, and provide support every step of the way. Their expertise and dedication made the entire process easy and enjoyable. I couldn’t recommend them more highly.”
“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.”
“Debbie was a pleasure to work with with. She and her staff are always quick to answer any questions. They ensure the process for was was as easy as it could be. They were ready to help with every step. I would not hesitate to use them again in the future.”
“My overall experience has been great! My wife and I decided on the same Realtor - which is rare we agree after 38 years. We chose Raquel Ott and she has done a superb job for us!!”
“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.”
Information and statistics on the latest trends in the Windsor real estate market, updated for January 2026. *
Windsor had 4 new listings and 4 listings that went under contract in December, increasing the area’s total available inventory to 13—up 8.33% from the previous month. Inventory is projected to have further increased in January.
Of those 13 active listings, 7.69% reduced their price in the month of December. The median listing price for homes in Windsor fell 20.38% from November to December, bringing the current median listing price to $429,950. Based on projected data for January, listing prices may continue to fall.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Windsor offers its residents a charming community with rich history, welcoming atmosphere, and convenient access to local parks and amenities.
Windsor blends an easygoing pace with practical access to opportunity. Set along US 460, residents enjoy quick commutes to Suffolk and Norfolk, while daily life revolves around friendly neighborhoods, locally owned cafés, and town traditions highlighted by the Town of Windsor. Located in Isle of Wight County, the community takes pride in responsive services and year-round gatherings, from holiday parades to youth sports that fill local fields. History lovers can delve into the area’s colonial roots at Historic St. Luke’s Church & Museum, a short drive away and a compelling look at America’s earliest chapters.
Families are drawn to the strong public school options within Isle of Wight County Schools. Students progress from Windsor Elementary and Georgie D. Tyler Middle to Windsor High School, home of the Dukes, where career and technical education, arts programs, and Friday-night games bring the town together. The Windsor branch of Blackwater Regional Library adds story times and maker activities to the calendar, while nearby parks and walkable streets make evening strolls and bike rides a simple pleasure. Thanks to regional employers in logistics, shipbuilding, and healthcare, many residents find a balanced routine—manageable commutes paired with space to breathe.
Thinking about a move? Whether you’re buying your first home or listing a longtime residence, Agent Pronto can connect you with a top local real estate pro who knows Windsor’s market inside and out, helping you navigate every step with confidence.
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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