1. Agent Pronto
  2. Oregon
  3. Winchester

Find the perfect real estate agent in Winchester, OR

We analyze top real estate agents in Winchester and across the country to find you the most proven local agents, for free.

Winchester, OR real estate

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.
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Home buyers and sellers love Agent Pronto.

We’ve helped over 500,000 home buyers and sellers find their ideal real estate agent.

“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.”

Ian Alger · Portland, OR

Photo of Josh Kaplan
Soldera Properties, Inc.
“Set”

Shanna · Myrtle Point, OR

Photo of Emily Groves
Pacific Properties
“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.”

Lorinda Wilcox · Lebanon, OR

Photo of Kevin Pena Aceves
eXp Realty
“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
“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!”

Julia Floyd · North Bend, OR

Photo of Melanee Woodman
Ocean Dunes Realty
“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.”

Gary A C. · Bay City, OR

Photo of Shane Schuster
exp Realty llc
“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
Mast Realty Group
“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
LPT Realty LLC
“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

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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

Learn more about what Winchester has to offer.

Winchester offers its residents a charming small-town atmosphere with a close-knit community and access to scenic outdoor recreation.

Winchester, OR real estate

Winchester offers an exceptional blend of outdoor adventure, community spirit, and scenic beauty in the heart of the Douglas County landscape. Known for its prime location along the tranquil North Umpqua River, this city is a magnet for those who love fishing, hiking, or simply unwinding at riverfront parks such as Winchester Recreation Area, which provides ample space for family picnics or a spontaneous stroll by the water. Water enthusiasts are drawn to the boating and kayaking options while nearby destinations like Roseburg offer expanded shopping, dining, and cultural attractions just moments away.

Education is a cornerstone of life in Winchester. The community is served by Umpqua Community College, whose scenic campus is perched above the river and renowned for both academic programs and community events. Local families benefit from access to well-regarded schools within the Roseburg School District, nurturing both educational and extracurricular growth.

Winchester is uniquely positioned for those who appreciate a small-town feel but crave access to amenities. The city’s close proximity to spectacular natural sites like Watson Falls and recreational hubs such as Stewart Park makes it an ideal spot for anyone seeking a blend of tranquility and activity. Additionally, frequent community gatherings at venues like River Forks Park foster a friendly, welcoming atmosphere.

Whether you are considering making Winchester your new home or planning to sell, Agent Pronto is ready to connect you with top local real estate agents who understand the unique appeal and opportunities within this vibrant community.

Woman smiling

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!

Sarah W.

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 Winchester 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 Winchester. 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!


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. 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.