“She was great to work with. Professional, personable, responsive, and reliable. I highly recommend working with her.”
Realty of America
- Agent Pronto
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- Winchester
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Compare top Winchester real estate agents.
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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Winchester real estate Market Report.
Information and statistics on the latest trends in the Winchester real estate market. *
Latest Rolling 3-Month Snapshot
Jul 1, 2026 - Sep 30, 2026
Median sale price
$366K
-6.2%
from Q2 '26
Median list price
$248K
-45%
from Q2 '26
Active listings
5
No change
from Q2 '26
Homes sold
3
+50%
from Q2 '26
New pendings
4
+100%
from Q2 '26
New listings
3
-25%
from Q2 '26
Quarterly Pricing Trends for Winchester
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Winchester
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Winchester
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Inventory and Sales Activity for Winchester
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Winchester
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Winchester
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
13
Seller’s Market
Seller’s Market
Buyer’s Market
0
20
40
60
80
100
0
25
50
75
100
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Jul 2026 - Sep 2026).
Winchester’s rolling three-month housing data shows notable shifts compared with a year ago. Typical home values are up about 11 percent year over year, even as the median list price has dropped by roughly one-third. At the same time, the share of homes selling above list has about doubled compared with last year, underscoring strong buyer interest.
Looking at the latest rolling period through September 2026, inventory remains limited with just 5 active listings and about 2.1 months of supply, indicating conditions still favor sellers. Even with that tight supply, homes are changing hands quickly, with a median of 43 days on the market and nearly three-quarters going off the market within two weeks.
Pending sales have surged more than 100 percent from a year ago, suggesting more buyers are getting under contract even as new listings have barely increased. Sellers are often seeing strong pricing power, with about two-thirds of recent sales closing above list price and an average sale-to-list ratio near 104 percent. In a small market with fast-moving properties and shifting price patterns, Agent Pronto can connect both buyers and sellers with an experienced Winchester agent who understands these trends and can guide them through each step of the process.
Learn more about what Winchester has to offer.
Winchester offers residents a tight-knit community with convenient local amenities, ample outdoor recreation, and friendly neighborhoods that make everyday life comfortable and enjoyable.
Winchester offers a quieter, more rural identity than nearby Oshkosh, yet remains close enough for commuting, shopping, and entertainment. Life here centers on open space, productive farmland, and long standing family properties, which gives the community a strong sense of continuity that can be hard to find in larger cities.
Residents value local gathering spots like the Winchester Town Hall and nearby Winchester Park, where youth sports, picnics, and seasonal events bring neighbors together. Families often look to schools in the surrounding Winnebago County area, including options in the Neenah and Winneconne districts, while outdoor enthusiasts take advantage of access to Lake Butte des Morts and regional snowmobile and biking routes.
Housing in Winchester ranges from historic farmhouses to newer country subdivisions, with space for workshops, gardens, and recreational vehicles. Inventory can be limited, and properties with acreage or outbuildings often attract strong interest from both local buyers and those relocating from places like Appleton.
Whether you are planning to buy into the community or sell a long held homestead, timing and preparation matter in this tightly watched market. A knowledgeable local real estate agent who understands Winchester’s pace, pricing, and buyer expectations can help you position your move wisely. Agent Pronto connects both buyers and sellers with the right professional to navigate Winchester’s opportunities with confidence.
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“We were looking to move, and had a referral for Krag. We couldn't be more pleased. Krag made the entire process of buying and selling our homes stress free. He is very personable, quick to respond, and answered any and all questions/concerns we had. It was an excellent experience. We definitely recommend Krag, and wouldn't hesitate to have him as our agent again.”
RE/MAX Affiliates
“Renee is an incredibly knowledgeable agent that has a lot of experience, cares about her clients, and is trustworthy !! She knows the ins and outs of current real estate markets and how to strategically price a property so that it will sell in a timely manner but with the highest yield!! She has sold two of our properties over the last eight years (one in Illinois and one in Wisconsin) and we received more than we expected on each of the sales!! We cannot recommend her highly enough! Thank you so much, Renee!!”
Keller Williams North Shore West
“Jim was brought into our search by my daughter who knows him. He was very helpful even though we weren't sure what we were looking to do. He was always available for chats when we needed him and had a sense of humor when we thought we were being a pain! Appreciate everything he did for us in the process of buying our home.”
Century 21 Ace Realty
“Levi fully understood our needs. He was always honest and direct. He told us what our house should list at and sold it very close to our asking price. We would highly recommend Levi to family and friends looking to buy or sell a home!”
RE/MAX Port Cities
“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.”
Forward Realty Partners
“Libby was so patient with me through the whole process. I changed locations and type of house I was looking amongst other things. It never seemed to bother her. She was very honest with me through every house we looked through. I could really tell she cared about me finding a house that felt right for me. She helped me get to the bottom of a question I had about the house I finally did purchase over a year later. I would highly recommend Libby to anyone looking to buy a home! She made me feel very taken care of and supported through the whole process.”
Berkshire Hathaway Bay Area Realty
“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!”
Century 21 Selling Paradise
“Braylee was amazing with all the time and effort she put in to help us every step of the way!”
Resource One Realty
“Brian did a great job on helping us to find the right condo. We started our search without not really knowing what we were looking for. Brian helped us figure it out. I looked at a lot of properties, until we narrowed it down to 4 And we found what we were looking for. Thanks Brian!”
Coldwell Banker Realty
“Erika was great to work with and had a lot of good contacts to make the home buying process easy and efficient. I woukd definitely recommend her to people buying a house!”
Erika Braatz Exp Realty
“I felt immediately comfortable having Bob as my realtor. He explained everything clearly, discussed the plan for selling my property&never made me feel the sale of my property wasn't as important to him as it was to me. I highly recommend Bob for anyone looking for a dedicated realtor. He's dedicated, knowledgeable, calm&never once did I feel he wasn't motivated to sell my property. I was completely comfortable with Bob. If you're looking for someone who has your best interests in mind,hire Bob.”
Homestead Realty Inc.
“We strongly recommend Larry Nielson for selling/buying your next home. He was very knowledgeable, confident and easy to work with.”
Nielson Real Estate Services
“Jen Burns is extremely good realtor I was an out of state buyer and her help was greatly appreciated negotiating with the builders and making sure the house was done to my specifications. I greatly appreciated her help for the last 9 months to keep it on track. Thank you again Jen Burns I really appreciate. Jen also found me a realtor for my home in St. Louis Missouri Jen is very professional and experienced in her profession. Thank you again. Mark Ruess”
Century 21 Affiliated
“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.”
Synergy Real Estate Group
“They were very prompt. Within minutes of completing the AgentPronto form, I received a call. On a Saturday! Everyone was so nice, and they kept checking in to make sure the realtor was good and if I had questions. An overall good experience.”
Trimberger Realty
“The team was efficient, thoughtful, disciplined and committed. The access to immediate contractor support was also helpful.”
RE/MAX Advantage Plus
“Alyssa was very professional and accommodating. Definitely recommend her.”
eXp Realty
“Amy was very helpful and knowledgeable. Everything went well.”
Keller Williams Premier Realty
“Adam Adler is an excellent agent. We couldn't be more pleased.”
Coldwell Banker The Real Estate Group
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 Winchester. 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 Winchester Realtor® or real estate agent today.
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