“Amy did a great job for the second time helping sell and by my home , Amy is a fan favorite and does is great a doing her job”
Century 21 Elite
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Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for November 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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Winslow real estate Market Report.
Information and statistics on the latest trends in the Winslow real estate market. *
Latest Rolling 3-Month Snapshot
Jul 1, 2026 - Sep 30, 2026
Median sale price
$96K
-28%
from Q2 '26
Median list price
$163K
+5.3%
from Q2 '26
Active listings
6
-25%
from Q2 '26
Homes sold
2
-67%
from Q2 '26
New pendings
3
-25%
from Q2 '26
New listings
3
-40%
from Q2 '26
Quarterly Pricing Trends for Winslow
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Winslow
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Winslow
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Inventory and Sales Activity for Winslow
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 Winslow
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 Winslow
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
20
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).
Winslow currently leans toward sellers, with the market gauge signaling a seller’s market. Months of supply has risen to 3.2, showing more inventory than earlier in the year but still not tipping to buyers. Homes are taking longer to sell, with the median days on market up to 37 in this rolling three-month view.
Looking more closely at prices and listings, the typical home value sits around the mid-$90,000s, down slightly year over year, while the median list price has climbed more than 50 percent over the same period. This gap suggests sellers are testing higher asking prices even as closed sale values stay relatively steady. Active listings are up modestly from a year ago, but homes sold and pending sales are both down sharply, indicating slower buyer activity.
Another sign of mixed conditions is that about half of recent sales closed above list price, yet the average sale-to-list ratio has slipped to just under 90 percent, pointing to meaningful discounts on others. Compared with a year ago, properties are generally staying on the market longer, and there are fewer new listings entering the pipeline. With this blend of seller leverage and cooler demand, local dynamics can be tricky to read, and Agent Pronto can connect both buyers and sellers with an agent who understands how to navigate Winslow’s current numbers.
Learn more about what Winslow has to offer.
Winslow offers residents a close-knit community, convenient local amenities, inviting neighborhoods, and plenty of outdoor spaces that support a balanced, connected lifestyle.
Winslow stands apart from nearby spots like Petersburg and Oakland City with its quieter, close-knit feel and strong ties to the surrounding countryside. Daily life here still revolves around community routines, school events, and familiar faces at the gas station or local diner, giving Winslow a grounded identity that appeals to both lifelong residents and newcomers.
Outdoor time is a big part of living in Winslow. Patoka River National Wildlife Refuge is just a short drive away, offering hiking, birding, and fishing through its official refuge site. Families appreciate access to Pike Central through Pike County School Corporation, which serves the broader area with academics and extracurriculars. For a change of pace, shopping, dining, and services in Princeton and Jasper are within reasonable reach, while regional resources from Pike County support residents and local businesses.
Winslow’s housing options range from long-held family homes on quiet streets to properties with more land on the outskirts, attractive to buyers who want space without giving up access to nearby towns. With evolving buyer interest in small communities and ongoing shifts in inventory, timing and preparation matter. A knowledgeable local agent can help sellers position their property effectively and guide buyers through pricing, inspections, and negotiations. Agent Pronto connects both buyers and sellers with the right Winslow real estate professional to be ready for the market when the moment is right.
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“Dawn Brown is absolutely amazing. We are almost sad we found a house because we don't get to see Dawn anymore. She is always responsive, helpful, kind, and knowledgeable about all aspects of the process. We were buying our first house and needed a lot of help understanding what to look for (and look out for) in houses we were viewing - Dawn was always honest and proactive in assisting us. She truly went above and beyond throughout our house-buying journey. She was also very patient with us in what turned out to be a prolonged search in a challenging market. We could not recommend Dawn more!”
Century 21 Affiliated
“Kim went above and beyond. She always does and she is an amazing asset for your company. My wife and I absolutely love her and will always go to her for any realty treated things. Thank you so much for all you do Kim.”
Century 21 Bradley Realty Inc
“Patty was always accessible and willing to go anywhere! Great personality and always gave us an honest appraisal of each property. We were lucky to have her!”
Century 21 Circle
“We have purchased two houses and sold one with Rachel. Her knowledge of the local market and of buyer expectations in general proved invaluable in all our transactions. Rachel is responsive, thorough, and trustworthy. She truly cared about finding the best fit for us. She even steered us away from a purchased she did not think was a good fit. Considering the property we ended up with, we are very glad she did!”
Howard Hanna Real Estate Services F.C. Tucker Company
“From the very beginning of making him self very available to look at listings with us before we even decided to go with him and giving him a 15 minute heads up through the ups and downs of houses he had our backs and accomadated us how ever we needed!”
Century 21 Bradley
“Raymond was a dream to work with. He was very patient and helpful in navigating the whole process. From understanding and finding what home would fit our family all the way through to closing he was our champion with a refreshing honesty about options.”
F. C. Tucker Company
“We cannot recommend our realtor enough! As first-time homebuyers with three little ones and another baby on the way, buying a home was such a big step of faith for our family. We had a lot of questions, a lot to learn, and plenty of nerves throughout the process, but Shelley made us feel supported and cared for every step of the way. From putting in our offer to navigating inspections, negotiations, and all the little details that come with buying a home, she helped make an overwhelming process feel manageable. This wasn’t just about buying a house for us. It was about finding a place where our children could grow, where we could build memories, and where our family could put down roots for years to come. We are so thankful for the time, effort, patience, and care that went into helping us get to closing day. This home means so much to our family, and we are incredibly grateful to have had someone we could trust walking alongside us through this season.”
JB
Century 21 Classic Realty
“Ed and his team were true professionals. He made home buying very easy. His knowledge of the area and house construction took some fear out of the homebuying process. We will use and recommend Ed and his team to anyone looking to buy or sell a house. Thank you for making our homebuying less stressful Ed and Jenn.”
1 Percent Lists Real Estate Solutions
“As a first-time home buyer, I honestly couldn't have asked for a better experience. She explained the entire process to me and walked me through every step, making sure I understood everything along the way. Buying a house can be stressful, especially when it's your first time, but she made the whole process smooth and easy. I'm extremely happy with how everything went and really appreciate all the help. I'd definitely recommend her to anyone looking to buy a home!”
Key Associates Signature Realty
“Dashawn did an excellent job with his negotiation skills second to none. His responsiveness is swift and exceeds in going the extra mile making sure all my questions concerns were answered and taken care of. I met Dashawn in 2016. He assisted me in the finding a beautiful home in Pike Township. He aided me in giving me on going resources after closing. So on I called on him again to help me build my forever home. Although it took several months to complete. Dashawn was there every step of the way with the Builders Sales representative, Building Superintendent and Independent Inspector. Dashawn is resourceful and eager to make sure all my needs were met. Thank you Dashawn. My friend!”
AMR Real Estate
“Zach went above and beyond showing us houses as we were in another state making showings with family members and was really over the top to make things work. Super great person to have showing houses would recommend him to anyone looking for a house.”
eXp Realty
“Tracy was amazing and understanding. She helped me every step of the way she is phenomenal.”
EXP Realty
“Rebekah went above and beyond in every way. She worked hard to find us the perfect house in the best location. We would definitely recommend her to all of our friends and family.”
Century 21 Scheetz
“We used Danyelle Hubbs as our realtor and had an amazing experience! We are first time home buyers for background so we had a lot of questions and she answered them in such an understanding way. She made herself plenty available for calls, texts, tours, etc. Her group worked very efficiently to organize next steps after we accepted an offer to make it the most smooth process! We couldn’t recommend Danyelle and her group more. Thank you for getting us our dream home!”
The Racolta Group Encore Sotheby's International Realty
“Dennis helped sell a tough one due to itss age and needed repairs, he didnt shy away tho and took it on, great work”
Cressy & Everett Real Estate
“Wendy Hammonds was an absolute pleasure to work with! She was appreciative of our expectations and used her experience to guide us in the right direction. She was professional and caring at the same time, which made for an overall wonderful experience in the sale of our home! I would highly recommend her! Thank you!”
Key Realty
“An absolute pleasure working with”
Century 21 Bradley
“Lauren Blake was absolutely wonderful to work with! My buying process was especially complicated due to other circumstances, but Lauren and her team guided me through every step with patience, professionalism, and genuine care. She went above and beyond to help navigate the challenges and make sure everything came together. Thanks to her dedication and support, I ended up with the condo of my dreams! I’m so grateful to have had Lauren by my side throughout the process and would highly recommend her to anyone looking to buy a home.”
Berkshire Hathaway Home Services of Indiana
“Jim was recommended by my broker and was awesome! He was out of town when we first connected but that didn’t stop him from getting me set up for viewings and he was still very attentive. When he got back in town, he didn’t play around! He got right to business and helped with more viewings until I found the house I wanted. And he was there through the whole process and answered all my questions no matter the time or how crazy my questions were, he would get the answer. Really appreciate everything he has done and continues to do to help me with my first home.”
Parkside Realty
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 Winslow. 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 Winslow Realtor® or real estate agent today.
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