Matthew Gilman

Windermere Central Oregon Real Estate Redmond

9 Years of Experience

(52)

$18M

Total Sales Last Year

Years of Experience

Recent TransactionsTransactions from the last 3 years

$533.9K

Average Price Point

Service Areas

Bend, OR Powell Butte, OR Prineville, OR Redmond, OR Sisters, OR Terrebonne, OR

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About Matthew Gilman

There is no better joy than helping someone find the house of their dreams. What else can you use every day that that actually increases in value and keeps you warm at night? Real estate here in Central Oregon is on the rise and for good reason. I am here to help you find not only that house that has caught your eye, but also the hidden gems you might have overlooked. Whether you are looking for small acreage properties or a place right in downtown Redmond or Bend, you won't find an agent that is more dedicated to finding you the place that works for you. I moved to Central Oregon with my wife and kid for the absolutely stunning beauty and pioneering attitude of the place. Feel free not only to ask me questions about the housing market, but also the schools, outdoor activities, and local hotspots. Before transitioning to working as a Realtor, I worked marketing jobs in the tech world. After too many cubicle hours, I have spent the last few years decided to do something I love. You will notice this in my enthusiasm and positive spirit that I bring into my relationship with my clients. See my reviews and give me a call. I look forward to helping you take that next great step forward in your life!

Specialties

Sellers
Buyers
Residential Property

Awards

2025
TOP AGENT
Redmond, OR
2025
TOP AGENT
Prineville, OR
2025
TOP AGENT
Sisters, OR

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Matthew Gilman's Reviews & Ratings

52 Reviews

(5/5)

Note: Reviews may include other agents on their team

What clients say about this agent....

Responsive
Professional
Communicative
Knowledgeable
Outstanding
Trustworthy
Hard working
Available Remotely
Attentive

Kenable

Review for Member: Kenable

July 25, 2025

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Stop looking for another agent, there are literally none better! We started with another agent and it just wasnt happening. But as soon as we got connected with Matt, things started happening in a positive way. I'm writing this on day 1, sitting in front of the house Matt got us. Seriously, look no further.

John Henry

Review for Member: John Henry

February 25, 2025

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Matt was great to work with, especially as a first time buyer. He helped listen to what we wanted but also inputted some local knowledge to help us understand what the best offers were in our area. If I buy again someday I will definitely be reaching back out to him

Kelrosepark77

Review for Member: Kelrosepark77

December 12, 2024

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Matt is the hardest-working Real Estate Agent we have ever worked with! He found us the perfect home. He kept us up to date on the entire process and was always available to answer any questions. Our first loan fell through, and he was able to very quickly find us another lender with a better interest rate! We will always use him for future real estate transactions in Central Oregon.

Kyle Simonton

Review for Member: Kyle Simonton

November 20, 2024

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Matt did a great job helping us navigate the home buying process. He was familiar with the area and worked with us long distance to show us some homes we couldn't see in person. Matt was always proactive and followed up quickly. I would strongly recommend working with Matt.

Saraheberenz

Review for Member: Saraheberenz

January 23, 2024

Local Knowledge

Process Expertise

Responsiveness

Negotiation skills

ZillowVERIFIED

Matt was super relatable and realistic when it came to the details of inspections, financing, etc. We trusted him right away and felt that he really understood our wants and needs. We found a home we love and he helped us navigate through the process in the midst of our busy lives.