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 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 Winslow real estate market. *
Feb 1, 2026 - Apr 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 (Feb 2026 - Apr 2026).
Winslow currently leans toward sellers, with the market gauge indicating a seller’s market. Months of supply sit at just 1.8, pointing to relatively limited inventory for buyers to choose from. Active listings have climbed compared with last year, but demand is still strong enough that conditions favor sellers.
Viewed over the latest rolling three-month period ending in April 2026, prices and activity have shifted notably from a year ago. The typical home value is up sharply year over year, while the share of homes selling above list has risen to 40 percent, suggesting many properties are still attracting solid offers even if not bidding frenzies. Homes are also moving more quickly than they did a year earlier, with median days on market at 28 days in the current window.
Supply and demand trends highlight how tight conditions have become. Active listings are up more than 80 percent from a year ago, yet months of supply are still down compared with last year, and homes sold are up more than 70 percent over that same period. At the same time, new listings have more than tripled year over year on a rolling three-month basis, signaling more owners are willing to test the market. Whether you are a buyer trying to compete in this seller-leaning environment or a seller aiming to price and time your listing well, Agent Pronto can connect you with a local Winslow agent who understands these dynamics.
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.
“Shelly is very helpful and knowledgeable in all aspects of the buying process. She was always very polite and has a pretty smile. Very comfortable working with her.”
“We truly appreciate the hard work, attention to detail, and genuine care you showed throughout this journey. Thanks to your efforts, we were able to successfully sell our home and move forward into the next chapter with confidence. We couldn’t have asked for a better realtor and would gladly recommend you to anyone looking to buy or sell a home.”
“I have enjoyed working with Michele since day one. She has been kind, knowledgeable, professional, and has always had our best interests in mind and at the forefront. She is also great under pressure and working with difficult contracts. Highly recommend for anyone looking to both sell and buy a new house.”
“There is not enough space to give Amy the credit she deserves. When we bought our first home, we had minimal communication with our prior realtor and so many questions and unknowns when starting the buying process again. Amy answered every call, text and random question with full transparency. When going to different houses, Amy never pressured to buy and would point out possible things to consider. Having her support and guidance throughout this buying/selling process was amazing and we are so grateful!”
“Nicole was a great help in purchasing our new home. She worked with us closely, was always available for showings, was a part of our house inspection and final walkthrough to ensure everything was covered. She gave us great advice and we got a great place to live. I will definitely call on Nicole for our next sale or purchase!”
“Awesome job , you dug in and got the job done if I ever need a realtor again you will be the one. Thanks again”
“My husband and I have worked with Stockton a few times now, both for buying and selling. After having worked with Stockton, I would trust no one else in the area with my business. At every step he was knowlegable, communicative, and accessible. He has truly gone above and beyond every single time to make things as easy as possible for us, and we have had great results because of him! Thanks so much, Stockton!”
“Thank you Tracy for helping. Tracy actually made sure to teach how the market works and kept at every single step of this process. She was detailed and organized throughout the whole time and answered all the questions that came along. If you want a stress-free experience, go with her!!!!”
“Rachel is extremely knowledgeable about all aspects of the real estate process from beginning to end. She goes above and beyond, making the home-buying/selling process less daunting. I can't recommend her enough.”
“Dan, along with his wife, picked me up for every property viewing, every open house, every place we went to see a property. My schedule is very difficult and finding a house without this transportaion assistance would have been close to impossible. I have already recommeded him to my colleagues as I know he will go above and beyond to assist them.”
“Robert has extensive knowledge and experience in real estate. He is very trustworthy, responsive, and professional in his preparation, listing, and communication. I highly recommend Robert for anyone interested in buying or selling a home!”
“Laura is knowledgeable, helpful, and makes the buying process not just easy, but fun!”
“Brandi was recommended to us by family. She is super friendly, knowledgeable, understanding, hard-working, thoughtful, and overall amazing to work with. I am grateful that we had her throughout our home buying journey and won't hesitate to contact her again if we want to sell/buy another home in the future.”
“We love Patty. She worked hard for us to finally get this property sold.”
“Rebekah came highly recommended from a trusted friend and she was as good as advertised. Our experience couldn't have gone any better. I'd highly recommend Rebekah to anyone looking for an agent in the Bloomington and surrounding areas.”
“Amy had sold a previous home for me so when we began the early stages of just thinking about selling our current home Amy was our go-to. Amy guided us through the steps of getting our home ready to show, when to list and at what price point. Amy put in motion all the behind the scene things that make for a successful sale. Amy walked us through all the offers and negotiations making sure we understood and were comfortable in our decisions. Amy was right there with us from the beginning, when the for sale sign when into the yard. To the end, when the "Sold" sign when on top. I cannot say enough great things about Amy, from her quick responses to her knowledge in the real estate field, she is the best agent!”
“James was totally amazing. He was great to work with. He was respectful of the owners homes that we visited. He understood our needs and desires. We looked at many homes and he was always patient and thuroughly explained things. He worked with our daughter and son in law after we returned to Texas to continue the search. He stayed with them and us throughout the search. When we found the right house he provided insight in to how to craft the offer and used his market knowledge to help us determine the price to offer. That offer was accepted. He worked with us to arrange the various inspections. Those inspections were thurough and gave us confidence that the home was of good quality and in good shape. That was major as we were back home and had not seen the house. Jim maintained contact with us thru all the steps to get to closing. In conclusion, Jim is great at his job. He is personable, respectful, knowledgeable, easy to work with, communicates well, and get the job done.”
“Debra Is absolutely. wonderful. I could compliment and praise her for days. She is professional knowledgeable Kind and courteous. I have worked with her for a couple of years Looking for my home.She has shown me homes near and far I highly recommend her to anyone who needs a real estate agent.”
“We met Jeff at an Open House. He started helping us since then. He referred us to a mortgage broker and it really paid off. Jeff was really patient showing us numerous houses and options. He was also very knowledgeable of the area. My family appreciated working with him. I would recommend him to family and friends. He was great to work with.”
“She was extremely helpful and understanding on everything that came up at any point in time. She was easy to work with. I would recommend her to help out anyone that I do know is looking for a house.”
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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