We analyze top real estate agents in Windsor 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 August 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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“Judy new exactly what we wanted and where we wanted to buy. She narrowed it down so didn't waste time seeing places that didn't interest us. She responded immediately whenever we reached out to her. She was straightforward with us and told us the pros and cons of every place we visited. We got exactly what we wanted.”
“James is the best realtor I've worked by far. I've moved a lot meaning I've bought and sold many properties and James' dedication and professionalism stands out as unique and uncommon. James made this sell very easy, taking care of all the details and anticipating what would be needed next. He landed on a selling price higher than we had imagined and he called it right. We found a buyer at that exact price. I couldn't be happier. I highly recommend James and his staff for you next purchase or sell.”
“This is our second time working with Debra as our realtor, and there’s no question why we chose her again—she’s simply outstanding at what she does. After our first experience with her seven years ago, my wife and I knew we’d work with her again when the time came. What truly sets Debra apart is the way she continues to stay connected. For the past seven years, she’s dropped by before every holiday with thoughtful, delicious treats—something we’ve come to really look forward to and appreciate. When it comes to buying a home, having Debra by your side is a huge advantage. She genuinely looks out for your best interests and has an amazing ability to understand what you’re looking for—even before you say it. Debra goes above and beyond in every way, and we’re so grateful for the care and dedication she brings to her work.”
“You're just not going to find a more professional, knowledgeable, and thoughtful realtor than Gurdeep. She genuinely cares about finding the best outcome for you, and that shows itself in so many different ways. Genuinely at the top of her field.”
“Jurgen is great! He's transparent, always available, and consistently fight for what's best for you. Can't think of a better combination of qualities when it comes to buying/selling a home!”
“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.”
“Carla was referred to us from a neighborhood friend and we could not have been more IMPRESSED with her! We had other choices in selecting an agent but none had the same level of professionalism, market knowledge & attention to detail as Carla. She was strategic in her marketing and price position which resulting in mutiple offers & no contingencies in a summer market that had definitely slowed. We sold above the asking price in 4 days! She is Our forever realtor and we will definitely be referring her to others! Thank you Carla for a job well done! You are the BEST!”
“Sara is the best agent we've worked with across 3 states. She has worked with us and our friends over numerous properties. Very knowledgeable, exceptional networking to make deals happen. Exhibits professionalism every step of the way. If we move back to VB, she'll be the first one we call.”
“She is very personable and professional. She guided me through a very tough decision. I appreciated her commitment to help me reach my goal.”
“Bree navigated tricky circumstances. She was 2 hours away and not local but, she took the necessary steps to make it not negatively impact the buying process. She was personable while still being professional. When things went wrong she took quick action and made me glad a chose her despite being a far distance away. She is a natural and knowledgeable in real estate. Anyone would be lucky to have her represent them. She made me feel important and like I was the only client she was dealing with at the time. Thank yu so much Bree. I'm a big fan :-)”
“Amy offered solid advice to help ready our home for sale. She suggested what items needed to be updated to sell quickly, provided staging advice, offered to help clean when we were feeling overwhelmed, was readily available when we had questions, and was present for the entire day of our pre-inspection. This was the first time we had ever sold a home and we were extremely nervous. She was very reassuring and rightfully so. Her suggested sale price was spot on. We had 3 showings and 2 offers within 24 hours. We would highly recommend Amy to anyone!”
“It was a pleasure to have Candace helping me sell my home. She help me every step from beginning to end, and I am grateful for that. She is very professional and knows her job well. I would definitely recommend her and am very satisfied.”
“Laura was professional, she was personable. She answered all my questions. She was always available whenever I needed. She walked me through every process. I would highly recommend her. If I ever move back to Virginia, she will be the first person I call. This was the easiest home sale I have ever done thanks to her. I can't say enough good things about her.”
“Kelly was a pleasure to work with. She was very professional and helpful throughout this entire process. Kelly has always made herself available to any questions or concerns that I had. I would definitely recommend her to any future home buyers.”
“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!!”
“Lindsay Clark was excellent. She really listened to the needs of my family and responded with the right choices for us to look at. As we are not from the DC area, she also helped walk us through the closing process and was available to help when we were out of town. We will continue to use her for advice and recommendations.”
“Deb Kelly did a fantastic job!”
“Aaron Gilbert was a pleasure to work with. He sold our house in 3 days. He did things above and beyond the call of duty. I would recommend him to anyone selling a house.”
“Josh was very reachable and accommodating. He always had a smile and very knowledgeable, however when he didn't know something he would research it and provide us the correct answer. Josh never tried to pressure us to do anything. He would always keep us upto date on what was going on.”
“Excellent. Very professional and supportive. It was a pleasure working with Dwight.”
Information and statistics on the latest trends in the Windsor real estate market, updated for August 2025. *
Windsor had 1 new listings and 2 listings that went under contract in June, decreasing the area’s total available inventory to 3—down 57.14% from the previous month. Inventory is projected to have further decreased in July.
The median listing price for homes in Windsor fell 11.33% from May to June, bringing the current median listing price to $399,000. Based on projected data for July, 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.
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 Realtors® and 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 Windsor 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 Windsor. 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 Windsor 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. 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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