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Winston, OR real estate

Compare top Winston real estate agents.

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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Winston real estate Market Report.

Information and statistics on the latest trends in the Winston real estate market. *

Latest Rolling 3-Month Snapshot

Jul 1, 2026 - Sep 30, 2026

Median sale price
$359K
+1.5% from Q2 '26
Median list price
$396K
+9.4% from Q2 '26
Active listings
45
+32% from Q2 '26
Homes sold
15
No change from Q2 '26
New pendings
16
+33% from Q2 '26
New listings
23
+4.5% from Q2 '26

Quarterly Pricing Trends for Winston

Rolling three-month data ending on quarter boundaries when available.

Quarterly Pricing Trends for Winston Q4 '21 Q4 '22 Q4 '23 Q4 '24 Q4 '25 Q3 '26 Median sale price in Oct 2021 - Dec 2021: $323K Median sale price in Jan 2022 - Mar 2022: $325K Median sale price in Apr 2022 - Jun 2022: $340K Median sale price in Jul 2022 - Sep 2022: $330K Median sale price in Oct 2022 - Dec 2022: $300K Median sale price in Jan 2023 - Mar 2023: $255K Median sale price in Apr 2023 - Jun 2023: $312K Median sale price in Jul 2023 - Sep 2023: $317K Median sale price in Oct 2023 - Dec 2023: $276K Median sale price in Jan 2024 - Mar 2024: $328K Median sale price in Apr 2024 - Jun 2024: $390K Median sale price in Jul 2024 - Sep 2024: $348K Median sale price in Oct 2024 - Dec 2024: $350K Median sale price in Jan 2025 - Mar 2025: $336K Median sale price in Apr 2025 - Jun 2025: $342K Median sale price in Jul 2025 - Sep 2025: $320K Median sale price in Oct 2025 - Dec 2025: $325K Median sale price in Jan 2026 - Mar 2026: $308K Median sale price in Apr 2026 - Jun 2026: $353K Median sale price in Jul 2026 - Sep 2026: $359K Median list price in Oct 2021 - Dec 2021: $335K Median list price in Jan 2022 - Mar 2022: $322K Median list price in Apr 2022 - Jun 2022: $366K Median list price in Jul 2022 - Sep 2022: $282K Median list price in Oct 2022 - Dec 2022: $264K Median list price in Jan 2023 - Mar 2023: $334K Median list price in Apr 2023 - Jun 2023: $335K Median list price in Jul 2023 - Sep 2023: $321K Median list price in Oct 2023 - Dec 2023: $307K Median list price in Jan 2024 - Mar 2024: $335K Median list price in Apr 2024 - Jun 2024: $364K Median list price in Jul 2024 - Sep 2024: $350K Median list price in Oct 2024 - Dec 2024: $360K Median list price in Jan 2025 - Mar 2025: $330K Median list price in Apr 2025 - Jun 2025: $343K Median list price in Jul 2025 - Sep 2025: $359K Median list price in Oct 2025 - Dec 2025: $363K Median list price in Jan 2026 - Mar 2026: $362K Median list price in Apr 2026 - Jun 2026: $362K Median list price in Jul 2026 - Sep 2026: $396K Oct 2021 - Dec 2021 Median sale price $323K Median list price $335K Jan 2022 - Mar 2022 Median sale price $325K Median list price $322K Apr 2022 - Jun 2022 Median sale price $340K Median list price $366K Jul 2022 - Sep 2022 Median sale price $330K Median list price $282K Oct 2022 - Dec 2022 Median sale price $300K Median list price $264K Jan 2023 - Mar 2023 Median sale price $255K Median list price $334K Apr 2023 - Jun 2023 Median sale price $312K Median list price $335K Jul 2023 - Sep 2023 Median sale price $317K Median list price $321K Oct 2023 - Dec 2023 Median sale price $276K Median list price $307K Jan 2024 - Mar 2024 Median sale price $328K Median list price $335K Apr 2024 - Jun 2024 Median sale price $390K Median list price $364K Jul 2024 - Sep 2024 Median sale price $348K Median list price $350K Oct 2024 - Dec 2024 Median sale price $350K Median list price $360K Jan 2025 - Mar 2025 Median sale price $336K Median list price $330K Apr 2025 - Jun 2025 Median sale price $342K Median list price $343K Jul 2025 - Sep 2025 Median sale price $320K Median list price $359K Oct 2025 - Dec 2025 Median sale price $325K Median list price $363K Jan 2026 - Mar 2026 Median sale price $308K Median list price $362K Apr 2026 - Jun 2026 Median sale price $353K Median list price $362K Jul 2026 - Sep 2026 Median sale price $359K Median list price $396K
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
28
Seller’s Market
Seller’s Market
Buyer’s Market
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).

Inventory in Winston has grown in this rolling three-month view, with active listings up more than 20 percent compared with a year ago. New listings have also risen by a similar margin year over year, giving buyers more options than last fall. At the same time, homes sold have dipped slightly from a year earlier, and pending sales are down more notably, signaling more cautious demand.

Pricing has been firm despite that softer contract flow, with the typical home value up over 12 percent year over year in the latest three-month window. Sellers are still pricing ambitiously, as the median list price has climbed more than 10 percent from a year ago, even as the average sale-to-list ratio hovers just under 100 percent.

Conditions have shifted toward a slower pace than last fall, with months of supply jumping from under two months a year ago to more than five months now. Even with that increase in available homes, properties are moving through the market faster, as median days on market have fallen from about 41 days a year ago to roughly 39 days, and the share selling above list price has edged up. With Winston showing mixed signals between rising inventory and resilient prices, both buyers and sellers can benefit from an Agent Pronto–recommended real estate agent who understands how to navigate these local trends.



Learn more about what Winston has to offer.

Winston offers residents a warm, close-knit community with affordable living, convenient local amenities, and easy access to outdoor recreation and small-town opportunities.

Winston stands out from nearby Roseburg and Green with its blend of small-town scale and regionally known attractions like Wildlife Safari, which brings visitors from across the Northwest. Daily life moves at a comfortable pace, yet the community is closely connected through schools, recreation and local events.

Residents enjoy easy access to outdoor spaces such as Riverbend Park along the South Umpqua River, while youth sports and activities center around Douglas High School and its facilities. Families appreciate the local library and programs at the Winston Branch Library as well as seasonal gatherings at city parks. Everyday needs are handled in town, with larger retail and medical services in nearby Roseburg.

Winston’s neighborhoods range from established streets near the historic core to newer pockets on the edges of town, offering options for first-time buyers, move-up households and downsizers. Commuters value the direct route along Highway 42 to surrounding employment hubs in Douglas County, while those working from home enjoy quieter residential streets and access to local coffee spots and family-owned restaurants.

In a market this compact, good preparation and timing matter. Homes can move quickly when they are priced and presented correctly, and buyers benefit from knowing about new opportunities early. Agent Pronto connects you with a Winston real estate agent who understands local inventory, pricing and community character, helping both buyers and sellers make confident decisions.

Find your Winston real estate agent today →


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“Exactly the kind of realtor you want in your corner! Selling our home was a big decision, and we couldn't have asked for a better agent to guide us through the process than Adrianne Bonsey. What stood out most about Adrianne was that she truly LISTENED. She took the time to understand our goals, our concerns, and what mattered most to us. She offered knowledgeable advice, honest feedback, and valuable insight throughout the selling process, but ultimately respected that the decisions were ours to make. We never felt pressured or pushed in a direction we weren't comfortable with. Selling a unique rural property comes with its own set of challenges, and Adrianne approached everything with professionalism, patience, and a level head. Her communication was excellent, she was always approachable, and we genuinely felt she had our best interests at heart. There's something incredibly reassuring about working with an agent who knows her business but also understands that it's YOUR home and YOUR journey. We are so grateful for Adrianne's guidance and dedication throughout this chapter of our lives. If you're looking for a seller's agent who will listen, advocate for you, and empower you to make informed decisions, we cannot recommend her highly enough! Team Kelly from here on out!”

Tanya Braukman ·

Photo of The Kelly Group Real Estate
The Kelly Group Real Estate
“As a buyer's agent, Cameron brought top shelf service and her positive attitude to help me navigate the troubled waters of a difficult transaction due to the condition and attributes of the property I was purchasing. Her behind-the-scenes coordination of several loose threads in the professional community were impressive, her integrity unimpeachable, and her willingness to dive into the deep end and defend me, the client, and my financial interests, was noteworthy. If the wheel of fortune of Zillow Realtor assignments lands you on Cameron, you are lucky indeed. I have no doubt she will do everything she can to guide you through the process of buying. I would not be surprised in the least if this same attitude carries over to listing and would not hesitate to use her when I sell.”

zinc spur ranch ·

Photo of Cameron Cohen
Harcourts Coast Realty
“We have known Arica Mitchell for several years, she has kept us up to date on the current housing market. When we finally decided to sell our home of, 42 years, we knew Arica would be the one to guide us through the process. We were very overwhelmed with the selling of our home but she was always available to answer questions and concerns, putting us at ease. She guided us through the home inspections, many home showings, contingent offers and when we received an offer she helped us review the contract, making a positive decision. We had total confidence in her ability to help us sell our home, Arica is our recommendation to anyone wanting to buy or sell there home.”

Rose Birchman · Pleasant Hill, OR

Photo of Arica Mitchell
Song Real Estate
“Sadena and Shannon are amazing. They worked with us diligently which was a little challenging since we currently live in Arizona but we found the perfect property to build our dream home on. I can't thank them enough for their dedication and hard work in this process.”

Robin Jutras ·

Photo of Sadena Abell
Pacific Coast Real Estate & Development LLC
“I highly recommend Russel and his team! They were very efficient and great with communication during the process of selling our home. Very quick to respond to my many many questions and I never felt ignored one time...Excellent service from the initial listing to the sale of our home!! Highly recommend!!!”

Sarah Fox-Hocking ·

Photo of Jordan Matin
Matin Real Estate
“It has been a pleasure to work with Josh. The service he provided was beyond our expections. We were not looking forward to going through the process but he helped us feel calmer by explaining everything as we proceeded. Thoughtful, knowledgable, dependable and always there with an answer to our questions. In a tough market for our neighborhood he sold our house in 5 days. Helped with the purchase of the new house also. We highly recommend Josh Kaplan to anyone considering selling their home.”

Phil and DaLee · Happy Valley, OR

Photo of Josh Kaplan
Soldera Properties, Inc.
“Emerald made the home-buying process very easy for us.”

Alicia Martin · Rogue River, OR

Photo of Emerald Burton
eXp Realty
“Jennifer is always a pleasure to work with, and does everything she can to be helpful and get the job done and get you what you want. This would be the second time I have worked with her, and because she did such a great job helping us sell and purchase the first time, when we wanted to sell this time we made sure to contact her first thing.”

Katie ·

Photo of Jennifer Parral
Oregon First Realty
“Matt, was very patient with us, while making recommendations in preparation for the selling of my property. Working with Matt reduced the stress normally associated with this process. Matt was very attentive and reliable. Our property sold quickly and efficiently. Thank you for your help and support Matt! David Jones, Oregon City”

zuser20160106113327456 ·

Photo of Fox Real Estate Group
Keller Williams Fox Real Estate Group
“There are not enough positive things I can say about Leanna. She went above and beyond for the entire process of selling my home. She was always available to answer any questions or concerns I had. I highly recommend using her for all your home needs.”

Bailey Hanson ·

Photo of Leanna Smotherman
River Valley Realty-KRRE
“Vanessa was extremely easy to work with and we appreciated her easy going approach. She showed us homes in Eugene and Salem, and we ultimately found our dream home in Salem. She’s easily the best realtor we’ve ever worked with!”

Elizabeth Senif ·

Photo of Vanessa Foltz
Knipe Realty ERA powered
“After buying and selling several homes over time with different realtors for each, I was so pleasantly surprised by Renee and Russ. My family bought our home together less than one month ago and we knew we were going to be a challenge. Deciding what exactly would work for our multigenerational situation - the dwelling, the amount and type of land needed to meet all of our needs, the location considering employment variances, etc. - seemed to change every other day. This incredible team never lost patience with us, pivoted seamlessly every time we changed direction, and with their help we quickly fine-tuned our search to find the perfect home. Their interpersonal skills with other realtors and with our lenders was impressive and made a huge difference for negotiating price and working through a complex process. Both Russ and Renee were so professional, attentive, consistently kind, and gave us spot-on advice that made all the difference throughout our journey, We have happily landed in the best possible home at the best possible price. These are two knowledgeable and experienced realtors, truly wonderful people, and an unbeatable team to have on your side!”

mamitchell2969 ·

Photo of Renee & Russell Kittrell
Camerelle Real Estate
“Cheyenne is a genuinely caring, dedicated, knowledgeable individual who gives her all to sell your home for the best possible terms. There is no way you can go wrong with her representing you! She is honest and innovative in this most difficult of markets. You won't regret signing her up TODAY!”

Kathie Granquist ·

Photo of Cheyenne Arbuckle
Pacific Properties
“I highly recommend Sally-Jo and Steve Wickham at Team Wickham in Eugene for anyone looking to buy or sell a home. From our very first meeting, they demonstrated incredible market knowledge and professionalism. We were living out of the country and had a broken pipe at the property, Steve helped us get a contractor and resolved the issue very quickly When it came time to close, their negotiation skills and attention to detail truly stood out. Thanks to Team Wickham the entire process was smooth and stress-free. If you want a dedicated, trustworthy, and results-driven real estate professionals, look no further!”

zuser20150823091052146 ·

Photo of TeamWickham
United Real Estate Properties
“Our entire experience with Dawn Kinert Castro was nothing short of exceptional! Her familiarity and knowledge of the local area is impressively thorough. Dawn really took the time and energy to understand what our likes and dislikes were, as well as our needs and wants in purchasing a home, which enabled her to provide a customized focused search for the perfect property. Dawn consistently went above and beyond for us and made us feel like family. We would not hesitate to use Dawn again for any real estate needs in the future or recommend her services to others... she is truly the best!”

Brian Wetzel · Prospect, OR

Photo of Dawn Kinert Castro
eXp Realty
“Emerald is amazing! She went above and beyond every step of the way! I was from out of state and so the process can be daunting…but Emerald was there for me at all times to answer all of my questions, provide contacts and recommendations. She is very tuned in to the market and really did a great job in finding me the perfect home for me! I highly recommend her should you be searching anywhere in Southern Oregon…or beyond!”

Tim DeGroote ·

Photo of Justin Burton
Justin Burton - eXp Realty
“Kristel's energy and enthusiasm reinvigorated what had come to feel like a slog after speaking and working with several other agents. She was marvelously responsive (often within minutes) and had answers for everything we had questions about, which helped make the buying process not feel like a convoluted bureaucracy keeping people out. We'll definitely work with her again should the time come and recommend her to others in the meantime.”

Jevan Sinnock ·

Photo of Kristel Greff
Knipe Realty ERA Poweres
“Kale helped us sell our property, there were a few hiccups with the buyers but he was always positive and professional. We also used him 2020 to purchase a property. I would definitely recommend him.”

tmarcolni ·

Photo of Kale Murray
Illinois Valley Real Estate
“Working with Blake was an outstanding experience from start to finish. He was professional, knowledgeable, and incredibly responsive throughout the entire process. Buying and selling a home can be stressful, but Blake made everything feel smooth and manageable. He took the time to answer every question, kept us informed at every step, and always had our best interests in mind. His expertise and attention to detail were clear in every part of the transaction, and we truly felt like we were in great hands. What stood out most was how dedicated and proactive he was—he consistently went above and beyond to make sure everything stayed on track. Because of Blake, the process was far less overwhelming than we expected. We’re incredibly grateful for his help and would absolutely recommend Blake to anyone looking for a trustworthy, hardworking, and knowledgeable realtor. We couldn’t be happier with the experience!”

justintroup1990 ·

Photo of Blake Mitchell
United Real Estate Properties
“Leanna was a wonderful find! She handled all our unusual concerns, like lead testing and getting a quote from a lead-safe painter, with both energy and aplomb. She did a video tour as we were out of town when we decided to look at the house. She found the most kind, helpful, and thorough professionals to handle inspections, testing, and bidding work. And through it all she maintained an upbeat yet not pushy attitude. Her communication with us and the sellers' agent was prompt and on point. I must add that without Leanna's creativity and tenacity we could not have bought this house. We are unusually detail-focused and had some paperwork questions she hadn't come across before, but she didn't let this slow her (or us) down as she promptly researched the answers and kept us moving forward. Would definitely go to her again for buying a house!”

hammerfell ·

Photo of Vicki Carpenter
BEYOND Real Estate Brokers

Frequently Asked Questions

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 Winston. 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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