“We were looking for a house in a certain area and told Pam of our needs. A house came on the market and she emailed me the listing right after it went live. We were the first people to call and tour the house and put in an offer, and I believe that the fast work that Pam put in was a decisive factor in how we got the home. There were days when I might call Pam half a dozen times and she always answered the phone and I could tell she had a smile on her face. This is the second time I've worked with her and I will definitely do it again in the future.”
- Agent Pronto
- Virginia
- Windsor
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Compare top Windsor real estate agents.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for August 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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Windsor real estate Market Report.
Information and statistics on the latest trends in the Windsor real estate market. *
Latest Rolling 3-Month Snapshot
Apr 1, 2026 - Jun 30, 2026
Quarterly Pricing Trends for Windsor
Rolling three-month data ending on quarter boundaries when available.
Quarterly Pricing Trends for Windsor
Rolling three-month data ending on quarter boundaries when available.
Quarterly Pricing Trends for Windsor
Rolling three-month data ending on quarter boundaries when available.
Quarterly Inventory and Sales Activity for Windsor
Rolling three-month supply and activity totals for the selected period.
Quarterly Inventory and Sales Activity for Windsor
Rolling three-month supply and activity totals for the selected period.
Quarterly Inventory and Sales Activity for Windsor
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 (Apr 2026 - Jun 2026).
Inventory in Windsor has expanded notably in this rolling three-month view, with active listings up sharply from a year ago and new listings rising even faster. Contract activity is also stronger than last year, as homes sold and pending sales have both increased, while months of supply has climbed to 5.4, signaling more options even as the market still leans toward sellers.
Price trends show a mixed but generally elevated picture. Typical home values are slightly below where they were a year ago, yet the median list price is up strongly year over year, suggesting sellers are testing higher price points in response to increased demand.
Days on market have lengthened significantly compared with last year, indicating buyers have a bit more time to decide even though nearly a third of recent sales still close above list price and sale-to-list ratios remain near 100 percent. With inventory, pricing, and speed all shifting at once, buyers and sellers in Windsor can benefit from Agent Pronto’s help in finding an agent who understands these evolving conditions.
Learn more about what Windsor has to offer.
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.
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“Jamie and his team are top tier. I have full confidence that we would not have had the same level of success had we not partnered with them. For those looking for a team that differentiates themselves, James Strum and the Strum Group is the obvious choice!”
“It was a pleasure working with Debra. Her approach to getting my house sold quickly and for the best price was just what I needed. She easily navigated the many obstacles that came up during the process and her knowledge and experience really made the difference. I felt very much at ease knowing Debra was on the job.”
“I can't say enough great things about how Bree handled my whole sales experience. She was on top of every aspect in getting my house exposed to as many potential buyers as possible. She kept me completely informed and handled every aspect with ease. She is truly a Professional! It was a pleasure having her represent me!! Thank you, Bree!”
“Mike was an excellent agent to work with! He took time to listen to our hopes and expectations with our property. And then worked diligently to meet our needs. Mike was very accessible and handled any questions or concerns quickly and completely. I highly recommend Mike in the management of the sale of any property!”
“Brooke was amazing!! She truly went above and beyond to help me find a house to call home. I truly could not be more thankful I got to work with her!!!”
“a excelent realtor. very profecional”
“A professional who is always ready to meet your needs and match your intensity in the home search if required. Her knowledge, contacts, and communication with my lender were the only reasons we were able to close on time. She was instrumental in helping me find the home that I wanted, as well as being the reason that I was able to move into my home by the date of closing.”
“It was my pleasure working with you Daniel. You listened to my concerns and responded positively. Thank you”
“We were so happy we picked Karen as our realtor. The only realtor that told us Virginia is a buyer beware state. The process is long and Karen has the patience and flexibility to work with you. We received excellent customer service and highly recommend her for all your realtor needs. Thank You, Karen for helping us find our new home.”
“We have known Judy for several years and always knew we would select her as our realtor when it came time to sell our house. She did an amazing job and we couldn't be happier! As people who believe in planning, we especially appreciated Judy's support as we got ready to put the house on the market. Our conversations regarding the sale of our home took place over many months ensuring that when listing day came we were more than ready. Judy is exceptionally knowledgeable on the northern Virginia market and all of her recommendations were on point. Our house sold in one weekend with multiple competitive offers and we give Judy the credit. She priced the house appropriately and marketed it exceptionally well. While selling a house is never easy, Judy made the process as painless as possible and was there to support us throughout the process. We would highly recommend Judy.”
“Working with William Mallory was a real pleasure. From our very first meeting, his professionalism and dedication were front and center. He took the time to truly understand our needs, navigated every step of the process . William is communicative, and a true expert in his field. I would strongly recommend working with William”
“I cannot recommend Lindsay enough. She was always available to answer my questions, kept me updated throughout the entire process, and made what could have been a stressful experience feel smooth and manageable. She genuinely cared about helping me find the right home and was there every step of the way. I am extremely grateful for all of her hard work and would not hesitate to work with her again or recommend her to my family and friends.”
“Debbie not only helped us find exactly what we were looking for, and where, but she helped us set up the sale of our previous house, and helped us negotiate consecutive closing dates as well as a possession maintenance period of our previous house in order to make our move easier. Having now worked with her on a sale and a purchase, plus her having done wonders for other family members, we would recommend her to anyone looking to purchase a home.”
“Carla is a seasoned agent with a wealth of knowledge in the Northern Virginia area. We worked with her in the past, both buying and selling homes. We were extremely happy throughout the process then, and on the recent sale of our home. She is the only agent I would use going forward should the need arise. Thank you Carla!!”
“Nick was great to work with! He was very personable and easy going. He made time for every home we wanted to see at the exact times we wanted to see it. He stuck with us even after a 6 month lull in looking at homes. I would consider Nick not only a professional, but he has become a friend.”
“Working with Boris in DC was an outstanding experience from start to finish. He was knowledgeable, responsive, and truly understood the DC market. Throughout the entire process, he made us feel informed and supported, always going above and beyond to answer questions and advocate for our interests. His professionalism, honesty, and attention to detail made what could have been a stressful experience feel smooth and manageable. I would highly recommend Boris to anyone looking to buy or sell a home in the DC area.”
“I cannot recommend Wes Sparks at eXp Realty highly enough! My father and I recently worked with Wes to sell my father's home, and the entire experience was seamless, professional, and incredibly successful. From our very first meeting, it was clear that Wes is an expert in his field. He brought a wealth of market knowledge and a strategic approach that gave us immediate confidence. Selling a family home can often be an emotional and complex process, but Wes handled everything with the utmost respect and patience.”
“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.”
“Barbie consistently arrives on time, communicates clearly and efficiently, and maintains a high level of professionalism.””
Frequently Asked Questions
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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.
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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.
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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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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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