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 October 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. *
Jul 1, 2026 - Sep 30, 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 (Jul 2026 - Sep 2026).
Year-over-year, Windsor’s rolling three-month numbers show prices holding fairly steady while activity cools. The typical home value is down less than 1% from last year, but homes sold have fallen about 17% and active listings are down roughly 7%, signaling fewer completed deals in a slightly tighter pool of options.
In the latest rolling period ending September 2026, buyers are seeing more time to decide, with median days on market at 67, about 12% faster than a year ago but still slower than the peaks seen earlier. Inventory has inched higher relative to demand, as months of supply is up nearly 8% year over year to 3.6, reflecting a shift away from the very tight conditions of prior years.
Price dynamics are mixed in this snapshot, with the average sale-to-list ratio just over 98% while the share of homes selling above list is up about 10% from last year, at a little more than a quarter of sales. With new listings down slightly year over year and pending sales dropping by about 11%, both buyers and sellers can benefit from an Agent Pronto–recommended local agent who understands Windsor’s current pace and pricing and can guide them through the next move.
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.
“Kyle did a wonderful job for my family. My first time selling a home and he answered every question I threw at him with no hesitation. I never give anyone a 10 because they can always be perfect. I would definitely reach out to Klye again when I sell my home in the future.”
“We worked with Matt and Candie on real estate transactions in Cape Coral, FL, Ft. Myers, FL and Madison, WI. With all 4 transactions, their knowledge of the market and neighborhoods was excellent. They have great negotiation skills when it came to purchasing and selling our homes. They were also very helpful in all the aspects of selling and buying a new home. Whether you needed help finding a service provider to get something repaired, coordinating with getting utilities switched over, or getting your modem out of the home before closing, Matt & Candie were always there. They are really great partners to have when selling or buying your home!”
“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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