We analyze top real estate agents in Winston and across the country to find you the most proven local agents, for free.
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for August 2025. *
* 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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“We worked with Josh to help us buy our first home. He went above and beyond what I expected from a real estate agent, helping us to understand all the nitty gritty details of the homebuying process while also coaching and supporting us through the emotional ups and downs. Josh is a great negotiator and will go the extra mile to help you get all the information you need to make a decision.”
“Set”
“Very knowledgeable and hard working realtor. From start to finish, Kevin was on top of everything. Such quick responses and he handled things for me, so I never worried about a thing. Kevin's dedication to his clients is amazing. He assisted with making my dream of becoming a homeowner, a reality! Highly recommend Kevin for all your real estate needs.”
“Kassidy is an amazing professional with the endless array of knowledge that helped support me with all my real estate needs from beginning to end and beyond. She goes above and beyond to help support, like family, rather then clients. Kassidy stays calm while remaining a pillar of strength. In any situation, I thought was a crisis, she continued to remind me it would be ok and it always was. I tell everyone about Kassidy's professionalism and that she's the best agent and person I know. I recommend her to anyone who is even considering a real estate venture as she is a rare treasure.”
“Jennie Dillon was an excellent agent who really went beyond what I expected. She was very professional and took action on whatever needed to be done with the seller. I ended up with a great buy, all accomplished in a short time frame.”
“Melanee was knowledgeable about the entire process! She was very helpful in answering every question that I had. I was confident she knew her job and she did!”
“My agent was very professional and followed up with me for about a year to get the listing. He did a great marketing job to get it sold. I had upgraded the property and never once did I have to visit the property to take care of an issue. My agent made sure it sold as is.”
“Shai was a real pleasure to work with! He and his realtor partner Ryan were both very professional at all times and kept us informed of what was going on. Any questions we had were answered quickly. We will definitely recommend them! If you are wanting great realtors, and hoping to get your home sold fast, then these are your go-to guys!! Great job Shai and Ryan!!”
“I had a professional experience working with Kat. She helped me overcome many issues and made the whole sale comfortable. I thank her for always answering my questions and helping me sell this property...Very happy with the whole process, especially since I was in California and the property was in Oregon. Thank you, Kat.”
“Chuck was fantastic!!!! He helped me and my wife through all of the "sometimes stressful" process of buying a home. While I never met Chuck in person, he made me feel like he was right there the whole time always getting the info we needed in a very timely way. I would highly recommend him to anyone who wishes to purchase a home. I have bought and sold a few homes in my life, and I feel that I could trust Chuck at all times. ”
“By the time we started working with Ian, my wife and I had been actively making offers on homes for five months with another agent. We are currently living in the home that we made our first offer on with Ian as our realtor. He was proactive in guiding us through the transaction, securing our offer at over $20,000 under asking—a huge feat in this current housing market. Our home appraised with instant equity. It it wasn’t for Ian we wouldn’t have gotten our home at such an amazing price, including all of the appliances! Thank you so much, Ian!”
“Working with Agent Pronto was easy and efficient. They recommended Amy Nelson to us and she was a pleasure to work with. We were buying out of state and having the right agent was key in the success of our move. Couldn't have asked for a better fit than Amy!”
“Pat was great! Followed through with all her promises and facilitated a good buying experience.”
Information and statistics on the latest trends in the Winston real estate market, updated for August 2025. *
The typical home value in Winston is projected to be $343,500 for the month of July. June’s finalized data reported the typical value of a home in the city to be $362,000—up 6.63% over the previous 12 months. For comparison, county-level data pegged home values at $365,000 in Douglas County for the most recent reporting period. That number is expected to float around $372,530 in July.
Winston had 6 new listings and 5 listings that went under contract in June, decreasing the area’s total available inventory to 19—down 0.0% from the previous month. Inventory is projected to have further decreased in July.
Of those 19 active listings, 15.79% reduced their price in the month of June. The median listing price for homes in Winston fell 1.4% from May to June, bringing the current median listing price to $384,450. Based on projected data for July, listing prices may continue to fall.
The number of days that homes have been on the market prior to going under contract rose year-over-year. In June 2025, the median time for a listed property to go pending was 7 days, compared to -23 days in June 2024. In recent months the median number of days from listed to pending appears to be increasing. That trend is predicted to have carried through to this July.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Winston offers residents a vibrant community atmosphere with charming local events, scenic outdoor spaces, and a welcoming spirit that makes it a wonderful place to call home.
Winston is an inviting, family-oriented community that balances small-town warmth with easy access to adventure. One of the area’s crown jewels is Wildlife Safari, a renowned animal park where you can drive through habitats that are home to giraffes, cheetahs, and elephants—offering a unique opportunity to get up close with exotic wildlife without leaving town. If you’re looking for outdoor recreation, the South Umpqua River winds through the area, creating a scenic backdrop for fishing, boating, and riverside strolls.
Education is a community focal point, and Winston-Dillard School District provides a full spectrum of learning opportunities, including McGovern Elementary and Winston Middle School, both celebrated for their dedicated teachers and strong extracurricular programs. Just a short drive north, Roseburg expands your options for shopping, dining, and entertainment. Winston’s convenient location in Douglas County means you’re never far from the scenic beauty of wine country, the hiking trails of Lookingglass, or the excellent healthcare at CHI Mercy Health.
Winston’s sense of community is exemplified through annual events, local farmers markets, and family-friendly spaces like Riverbend Park, perfect for barbecues, sports, or a relaxing afternoon picnic. Whether you’re seeking the peace of rural living or the comfort of close-knit neighborhoods, Winston offers both along with exceptional connectivity to Southern Oregon’s treasures.
Considering a move or thinking of selling your home in Winston? Agent Pronto is ready to match you with a trusted real estate expert who knows the local landscape inside and out, ensuring a smooth and successful experience in this unique, welcoming community.
Within a few minutes, I was paired up with an awesome agent who really knew the local area and helped me find a great condo in a super tight market. It was daunting to think about how to find the right agent. Agent Pronto got me the right agent, pronto!
With over 2 million real estate agents across the U.S., it’s not easy deciding who to trust when buying or selling a home.
We’ve analyzed performance metrics, close rates, specialties, and client reviews of the top real estate agents in Winston to qualify the best agents for your specific needs.
We know that choosing the right real estate agent can be a stressful task. With Agent Pronto, it doesn’t have to be.
Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in Winston. But we don’t stop there.
Our Agent Specialists will take into account any special requests you have when searching for your real estate agent recommendation.
Need a great agent who speaks fluent Spanish and is a luxury condo expert in your neighborhood? No problem!
Tips and market insights to make your Winston real estate journey a success.
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. 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.
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