We analyze thousands of real estate agents in Winslow 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 September 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 Winslow real estate market. *
Jun 1, 2026 - Aug 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 (Jun 2026 - Aug 2026).
Winslow currently sits in a seller’s market, with conditions tilted toward homeowners who choose to list. Months of supply is low at about 1.6, and there are only a handful of active listings in the area. Homes are also selling quickly, with a median of just seven days on the market in this rolling three-month view.
Prices have moved up sharply compared with a year ago, helping explain why the market leans toward sellers. The typical home value over the latest three months is up more than 80 percent year over year, while the median list price has climbed at a strong pace as well. At the same time, new listings and homes sold have both dropped significantly from last year, so fewer properties are changing hands even as values rise.
Tight inventory and strong pricing power show up in how close final sale prices are to asking prices. The average sale-to-list ratio is just under 100 percent, and about half of recent sales closed above the list price, a much higher share than a year ago. For buyers, that means being prepared to move quickly and make competitive offers, and for sellers it highlights the importance of smart pricing and timing. Agent Pronto can connect both buyers and sellers with an agent who understands these conditions and can guide each step of the process.
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.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“Jeff was extremely helpful when purchasing our home. He communicated with us and was able to get us in for showings of the homes within a very timely manner. Jeff was always very upbeat and understood what we were looking for when purchasing a home. Jeff was accessible when we had questions, all we had to do was call or text him and he would always get back with us. Working with Jeff has made purchasing a home less stressful and much easier!”
“Great working with Dennis!!”
“This is the second property that we've sold with Rebekah in the previous year. As with our first experience, we truly have no notes for what Rebekah could have done better. In both instances she provided an action plan for items that were and weren't worth addressing prior to listing and in both cases her initial estimate is exactly what the property sold for, with little to no friction throughout the process. You won't find a better realtor and we will continue to work with her for all future endeavors.”
“I had a great experience working with my real estate agent to sell my home. He made the entire process so much easier and was always there whenever I had questions or needed help. He kept me informed throughout the whole process, was professional, knowledgeable, and truly worked hard to get my house sold. Selling a home can be stressful, but having someone you trust guiding you through it makes such a difference. I really appreciated everything he did for me and would definitely recommend him to anyone looking to buy or sell a home!”
“Erica Dickey was amazing to work with. she is extremely patient, knowledgable, and professional. she truly cared about what was important to me when it came to selling and buying my home. she made this entire process feel much less stressful and was there every time i needed anything. i would highly recommend Erica to anyone who is looking to buy or sell a home.”
“I've known Rachel since high school, and follow her on social media. I watched her consistently show how much she cares about the people she works with to find them a home that meets their needs. And she did the same for us! She was very educational through the whole process, which was so important to us because it was our first home purchase. I would highly recommend her to anyone looking to buy or sell. Know you'll be in good hands.”
“Shelley is excellent and will represent you well! Highly recommend!”
“"Alyssa Swiger is phenomenal! She brings unmatched professionalism, excellent communication, and strong expertise to the table. She made the whole experience smooth and successful from day one. I would absolutely work with her again and highly recommend her services!"”
“We couldn't have been happier! Excellent work!”
“Although our deal was super unconventional, I truly believe Nick did all that he could do for us during the entire process. I really appreciated his calmness when I wasn't so calm. It was nice to see someone understanding of our situation and pushing things forward when needed.”
“I drove Deborah crazy doing this sale and she hung in there like a trooper she sold my house within 5 days she done an excellent job, thank you for everything!!!”
“We just closed on a house with Century 21's Dan Mervar as our agent. Dan was knowledgeable and patient throughout the process. We would 100% recommend Dan! Thank you!”
“Patty, was professional, easy to work with and extremely knowledged in my area. We had several fall-throughs that were no fault of Patty's or mine but she got it done. I highly recommend Patty!”
“Amy was super helpful in every part of selling our old home and then buying a new one. I would recommend everyone to go to Amy for any help selling or buying!”
“Tyler was such a delight to work with. He absolutely listened to all of my concerns and needs when looking for a home. Tyler was easy to communicate with and always available for answering my questions. His professionalism outshines any other agent I have ever known. Tyler always kept me up-to-date with any and all progression during my home buying experience. I couldn't have asked for anyone better because I don't think someone out there exists. Thank you Tyler!”
“Zach was very informative and knowledgeable! I've never sold a property of any kind so being new to the process he definately made sure I understood what I needed to do! We listed and closed in less than 30 days!! Thanks Zach great job !!”
“Caring realtor, very patient”
“Excellent Service.”
“Dawn was courteous professional honest and trusting. She was highly recommended and rightfully so. Dawn was very timely in her responses. Took time to follow up on items I was responsible for. All these attributes culminated in a quick sale. Thank you Dawn!”
“Kim was fantastic to work with and always very honest with us! She helped set us up for success as first time homeowners!”
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.
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 Winslow Realtor® or real estate agent today.
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