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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 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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Winston real estate Market Report.

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

Latest Rolling 3-Month Snapshot

May 1, 2026 - Jul 31, 2026

Median sale price
$347K
-1.9% from Q2 '26
Median list price
$365K
+1% from Q2 '26
Active listings
39
+15% from Q2 '26
Homes sold
14
-6.7% from Q2 '26
New pendings
18
+50% from Q2 '26
New listings
25
+14% from Q2 '26

Quarterly Pricing Trends for Winston

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

Quarterly Pricing Trends for Winston Q3 '21 Q3 '22 Q3 '23 Q3 '24 Q3 '25 Q2 '26 Median sale price in Jul 2021 - Sep 2021: $279K 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 list price in Jul 2021 - Sep 2021: $319K 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: $260K 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: $366K Median list price in Jan 2026 - Mar 2026: $362K Median list price in Apr 2026 - Jun 2026: $362K Jul 2021 - Sep 2021 Median sale price $279K Median list price $319K 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 $260K 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 $366K Jan 2026 - Mar 2026 Median sale price $308K Median list price $362K Apr 2026 - Jun 2026 Median sale price $353K Median list price $362K
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
22
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 (May 2026 - Jul 2026).

Winston is seeing more homes come to market in this rolling three-month view, with new listings up sharply from a year ago. Active inventory is also slightly higher year over year, while homes sold have increased at a faster pace. Pending sales show a modest year-over-year gain, signaling steady contract activity despite the larger pool of listings.

Prices are adjusting gradually in response to these shifts. The typical home value is down slightly compared with a year ago, while the median list price has edged up only a bit, indicating sellers are not pushing prices aggressively. The average sale-to-list ratio sits just under 100 percent, and the share of homes selling above list has dipped from last year, both signs that bidding pressure has eased.

Conditions have clearly cooled from the faster-paced periods of recent years. Months of supply has nearly doubled year over year, and the median days on market has stretched significantly, giving buyers more time and options. Even with those changes, Winston still registers as a seller’s market on the local gauge, so well-priced homes can perform strongly. With this mix of rising inventory, moderate pricing, and longer marketing times, both buyers and sellers can benefit from having an Agent Pronto–recommended real estate agent to help them navigate the Winston market with confidence.



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 →


Trusted by over 500,000 buyers and sellers.

See why so many people rely on Agent Pronto to make their real estate journey a success.

“Working with Josh was an incredible experience from start to finish. As first-time homebuyers Josh made the entire process feel simple, stress-free, and exciting. He took the time to understand exactly what we were looking for and helped us find a home that fits our needs today and our future needs. Thanks to Josh, we were able to secure our home on our very first offer. He navigated the negotiation wonderfully and made us feel secured and informed at every step. His communication was great, his knowledge of the area was top notch, and his commitment to helping us find the right home truly fullfilled our expectations. We were so happy with our experience and would recommend Josh to anyone looking to buy or sell a home. He genuinely cares about his clients and goes above and beyond to make the experience a positive one. Thank you, Josh, for helping us find our perfect home!”

Chanra San · Beaverton, OR

Photo of Josh Kaplan
Soldera Properties, Inc.
“Arica went up and beyond to sell our property. She was very professional and helped us with every step of the process. I would highly recommend hiring Arica to help with you home needs.”

Kevin Newberry · Santa Cruz, OR

Photo of Arica Mitchell
Song Real Estate
“We had the pleasure of meeting Emily and she was a great realtor. She is very accommodating to your schedule. Anytime we had a question, she would respond very quickly. She was a delight to work with and very knowledgeable. I woukd highly recommend Emily anytime you are looking for a home.”

Debbie Kirby · Brookings, OR

Photo of Emily Groves
Pacific 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
“Brent worked hard for us, making phone calls checking on issues, following up with everyone involved. Brent is an asset to have on your team. Thank you for everything finding us our forever home. Terry and Georgie kelley.”

Georgie Kelley · Roseburg, OR

Photo of Brent Sutton
Coldwell Banker Professional Group
“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.”

Audra Kenyon · Phoenix, OR

Photo of Kassidy Lowe
Oregon Adventure Realty
“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.”

Marna H. · Cottage Grove, OR

Photo of Jennie Dillon
Hybrid Real Estate
“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!!”

Eva R. · Coos Bay, OR

Photo of Shai Cancino
Pacific Properties
“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.”

Saundralee R. · Myrtle Creek, OR

Photo of Kat Puchta
Stellar Real Estate Concepts
“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. ”

David T. · Cave Junction, OR

Photo of Chuck Wetherald
Worthland Real Estate
“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!”

Alex and Joanne · Cottage Grove, OR

Photo of Ian Gray
Windermere Real Estate/Lane County
“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!”

Hannah S. · Springfield, OR

Photo of Amy Nelson
ICON Real Estate Group
“Pat was great! Followed through with all her promises and facilitated a good buying experience.”

Melissa H. · Independence, OR

Photo of Pat Pendley
RE/MAX Integrity

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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