- Agent Pronto
- Oregon
- Winston
Find the perfect real estate agent in Winston, OR
We analyze top real estate agents in Winston and across the country to find you the most proven local agents, for free.
Compare the top real estate agents in Winston
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for June 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.
The easiest way to find the best real estate agent.
Sell your home fast and for top dollar or find your dream home at the best possible price. Use our free service to find top agents you can trust.
- Tell us what you need.
- Answer a few quick questions about your real estate needs so we can begin our search.
- Match with the perfect agent.
- Our personalized matching system will connect you with a top-rated real estate agent with the local expertise and experience you need.
- Meet your agent.
- Review the details of your top agent recommendations and speak with them to learn exactly how they can make your real estate journey a success.
- Buy and sell with confidence.
- While real estate decisions are among the most important financial and personal decisions we make, you can rest easy knowing that you have a proven real estate professional on your side.
Home buyers and sellers love Agent Pronto.
Here’s what some of the 400,000+ home buyers and sellers have had to say about our service.
“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!”
“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!!”
“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.”
“Worked out wonderfully. Terri O'Neil was the best find ever!”
“Ms. Lu was very patient and met all of our needs. As we are in Florida and sold our home in Oregon, her actions as our Relator were above-and-beyond!”
“Mr. Mitchell Stolfus, my real estate agent, was very very much helpful throughout the whole process. His communication, initiative, and willingness was impeccable. Great to get along with and who allows you to feel comfortable to ask those questions most feel uncomfortable or awkward to ask...I 'HIGHLY' recommend this great man as a recent client to anyone else searching for a home as their real estate agent.”
“Excellent. Shannon couldn't have been more helpful. She was efficient and professional, was able to receive an acceptable offer within 24hours after listing the home. We sold our home the next day. Best experience my wife and I have ever had throughout the six times we sold homes over the previous 45 years.”
“Fast. Easy. Efficient. Effective. I was very pleased with the realtor that I was referred to. The whole process was quick and effortless.”
“Very happy with listing the sale of my property with Chris Forrette. I appreciated the great customer service my brother and I had with Chris. He was very professional, knew the business, yet was easy to work with!”
“Chris was knowledgeable about the area. He priced the house correctly and it sold for over asking in one day. He was readily available by text at anytime. He promoted the home with lovely pictures and drone coverage. Pleasant to work with.”
Winston real estate Market Report.
Information and statistics on the latest trends in the Winston real estate market, updated for June 2025. *
The typical home value in Winston is projected to be $429,000 for the month of June. May’s finalized data reported the typical value of a home in the city to be $399,000—up 5.28% over the previous 12 months. For comparison, county-level data pegged home values at $349,950 in Douglas County for the most recent reporting period. That number is expected to float around $357,180 in June.
Winston had 7 new listings and 7 listings that went under contract in May, decreasing the area’s total available inventory to 20—down 9.09% from the previous month. Inventory is projected to have further decreased in June.
Of those 20 active listings, 30.0% reduced their price in the month of May. The median listing price for homes in Winston grew 16.39% from April to May, bringing the current median listing price to $389,900. Based on projected data for June, listing prices may continue to grow.
The number of days that homes have been on the market prior to going under contract fell year-over-year. In May 2025, the median time for a listed property to go pending was 143 days, compared to 279 days in May 2024. In recent months the median number of days from listed to pending appears to be decreasing. That trend is predicted to have carried through to this June.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Learn more about what Winston has to offer.
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!
Take the guesswork out of finding an agent.
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.
Data analysis with a human touch.
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!
Resources for buyers and sellers.
Tips and market insights to make your Winston real estate journey a success.
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. 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.
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