Bailey Simon Real Estate


Your story.

Life happens fast. New job, new baby, a new adventure. Whatever that next step is, it's my job is to help you find a home that fits. A place to create new memories, tell old stories – start the next chapter.


My story.

Growing up in a small logging town, Bailey learned early on the beauty of her home state. Whether hiking in the Gorge or exploring the city, she appreciates the abundance Oregon has to offer.

Living in the Pacific Northwest for the past 30 years, including a two-year adventure in Alaska, Bailey has called much of Portland home and loves how each neighborhood has its own unique vibe. With an interior design studies background, family history in real estate, and experience in property management, helping people move and grow comes as a natural choice.

Whether buying a first house, selling a home full of memories, or assisting with investment properties for years to come, she operates on the mindset of making each and every client a client for life.

In her personal time, you can find Bailey enjoying her adorable daughter, Mila, attending many of the various live music performances in town, mastering DIY home projects, exploring the local nature scene, and hitting the trails in her favorite pair of Brooks.

Percentage of Homes Sold
Number of Succesful Years
Percentage of Happy Clients

I am an expert at providing the most expedient and certain path to a closing.


Bailey Simon with Windermere Stellar delivers positive results and enhanced value for clients through a combination of expert analysis, market knowledge, talent and collaboration. I am poised to provide services from purchase to sale, and/or the leasing of an asset. I assist with residential, multifamily and industrial assets for clients at any stage of their ownership cycle.

I am experienced in real estate and financial acumen to achieve optimum prices for my clients, whether it's a disposition or acquisition of an asset or assets. I am an expert at providing the most expedient and certain path to a closing.

The Real Estate Services team has deep talent and experience, boasting billions of dollars in career transactions. The extensive knowledge and expertise of these highly skilled professionals play a prominent role in achieving successful results.

I combine in-depth analysis of each asset with consideration from different investor perspectives, while including cash-flow models and anticipated returns to obtain information vital for making wise investment decisions.

Let's Get in Touch

“After a chance following on her website, I was contacted by Bailey Simon. At the time I thought to purchase a condo in Portland OR. Through her persistence I finally responded. Yes, this was a cold call. Actually more than one….or two! Bailey was very personable and seemed knowledgeable in the areas I thought I was interested in. At this time I had already travelled to Oregon and met with another realtor. Bailey felt like a better fit for me and I was not mistaken. At our first meeting she was very professional and personable. She continued to be throughout the process of buying my home!(not condo). Don’t hesitate to call Bailey Simon!”

John Tucker

"We had an all around excellent experience, Bailey made it as easy as it possibly could have been. Plus, we ended up on the house we ultimately wanted!”

Sarah & Michael Smith

"We would highly recommend Julee Bean for your realty needs in the Portland area. Based on a recent home buying experience."

Karen Jones

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