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 June 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. *
Mar 1, 2026 - May 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 (Mar 2026 - May 2026).
Year-over-year, Windsor’s rolling three-month data shows notable price strength, with the typical home value up about 14 percent. At the same time, the share of homes selling above list has risen roughly 10 percent from a year ago, underscoring firm buyer demand even as conditions evolve.
Looking at the most recent rolling period ending in May 2026, typical home value sits around $640,000 while the median list price is lower, near $575,000. That gap, along with an average sale-to-list ratio just above 100 percent, suggests many sellers are still achieving or slightly exceeding their asking prices.
Inventory and pace tell a more nuanced story for both sides of the table. Months of supply has nearly doubled year over year to about 4.4 months and active listings are down compared with last year, while nearly half of homes go off the market within two weeks even though the median time on market stretches to 79 days, so Agent Pronto can help both buyers and sellers find an agent who understands these cross-currents and can guide their next move wisely.
Windsor offers residents a close-knit community, abundant parks and outdoor spaces, solid schools, and easy access to the amenities and opportunities of nearby Madison, all contributing to a high quality of life.
Windsor is a growing community just north of Madison, known for easy commuting, strong schools, and a relaxed suburban atmosphere. With quick access to I‑39/90/94 and Highway 51, residents can reach downtown Madison, Sun Prairie, or DeForest in minutes, making Windsor appealing for both daily commuters and remote workers who want nearby city amenities.
Families appreciate the DeForest Area School District, including Windsor Elementary School, along with convenient services and neighborhood parks. Outdoor recreation is a major draw, with local paths connecting to regional routes and easy access to Token Creek County Park, which offers disc golf, trails, and winter activities. Residents also frequent Cherokee Marsh Conservation Park for wildlife viewing and paddling opportunities.
Daily living is straightforward, with nearby shopping and dining in Windsor and adjacent communities, along with larger retail options in Dane County. Community events, youth sports, and local businesses give Windsor a friendly, rooted feel without sacrificing privacy or quiet.
Whether you are weighing different neighborhoods or preparing to list your home, working with a real estate agent who knows Windsor’s traffic patterns, school boundaries, and future development plans can make decisions clearer and timelines smoother. Agent Pronto connects buyers and sellers with experienced local agents who help reduce stress and keep the process on track from first meeting to closing.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“I love working with Kyle. His communication is excellent, his marketing is top notch, and we consistently sell our properties quickly and often over ask. Working with a professional is a priority for us and Kyle consistently exceeds our expectations. Thank you, Kyle!”
“Matt and his wife were very helpful throughout the sales process. They went above and beyond to facilitate the sale and showings of our home. Communication was excellent throughout.”
“My experience with Mo Simmons was one of respect support and professionalism for my decision to sell my home of 41 years. From the first prompt contact until closing Mo has been available in all phases in the process with any suggestions or recommendations I was always aware of my options before making my decisions. It has been my pleasure to work with her.”
“Thank you, Agent Pronto, for recommending Karl. He was an amazing agent and just got the job done! I would recommend your service and Karl to any future home sellers or buyers!!!”
“Very good. Rena did an excellent job representing us for both the purchase of our new house and the sale of our previous house. I greatly appreciated being paired with her and saving the time and stress of searching for her myself.”
“Liz was always available. She gave me confidence when it was needed because this was a huge challenge for my husband and I. her communication skills were at the top of the list. She was also patient with us and not push us.”
“Amy was a fantastic broker to have on our side. She helped us understand the process, kept us informed during the entire process, and was always available for communications with prompt replies and follow up. She is very knowledgeable and was able to clearly convey details and processes to us. We didn't worry about anything as Amy was on top of everything at all points in the process. We trusted Amy to work on our behalf and in our best interested and she lived up to that trust without question. We highly recommend Amy!”
“Attentive and caring agent. Worked hard in a less than optimal market to get our house sold.”
“She is great!”
“Quick contact made by assigned real estate agent. Was able to make an appointment at my earliest convenience!”
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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