Ashley Bailey


Committing myself to finding that perfect property for you that fits your lifestyle, needs and dreams is what truly drives me. The real estate market moves very quickly here and having a professional on your side is invaluable. I have over 15 years of sales experience as a top producer.

The Hawai'i real estate market is dynamic, neighborhood-specific and location is so important. I strive to be an expert here on Oahu, and assist my clients to make informed fact-based decisions, whether buying or selling. Dedicating myself to making the steps as seamless as possible is very important to me. I work diligently for my clients, and If you like a person who is responsive, driven, dependable and a strong negotiator, I am the broker for you. I am honored to have been featured on two episodes of HGTV's "Hawaii Life" and to have received the following awards: "Aloha 'Aina" realtor nominee, Top 500 Realtor's in Hawaii, Honolulu Magazine's "Best in Real Estate 2021", and "Best of Zillow" Agent.

With a strong background in business marketing from the University of Massachusetts, Dartmouth, I truly understand creative and effective ways to market and sell property. I follow a detailed process in order get your property show ready, on the market for the right price, and in front of as many eyes as possible. I offer light staging including art and professional photography to all of my clients as part of my listing services. My main focus when working with my clients is not only to meet their real estate expectations, but to exceed them, and bring them peace of mind throughout the entire transaction. I go above and beyond in representing my clients.

When I am not matchmaking people with property, I am an avid sailor and race almost every Friday night and in multiple regattas a year out of the Hawaii Yacht Club. I am the membership and marketing chair for the yacht club. Along side of real estate, I am very connected in the sailing world. I can assist you with delivering your yacht to Hawaii or help finding a yacht to purchase.

Assisting my clients in buying or selling property worldwide is a passion. I am also a citizen of Italy and travel there often. With our partnership with Leading Real Estate Companies Of The World & Luxury Portfolio, I can help with your real estate needs anywhere in the world. I sit on the board of the Friends of Italy Society of Hawaii. I have a lot of great Italian travel + real estate connections I'd love to share. For more info on any of the above please contact me. I'm happy to hear from you!

Life is great here on the Islands for all different types of lifestyles. Please reach out to me. I would love to meet you and talk about your real estate goals.

What Ashley's clients say about her:

"We wanted to write to thank you again for all your help with the sale of our condo at 400 Keawe. It seems like so long ago that we first became aware of you through the flyer you dropped off in our building. From that initial flyer, we were immediately impressed by your strong work ethic.
You made the whole process as stress-free as possible, and it is hard for us to imagine accomplishing so much with any other agent on our side. You went so above and beyond in the way you helped us sell our beloved home, from the initial staging, to the great photography, to writing up our property, to even assisting us with general relocation. You are truly an asset to Hawaii Life and the Oahu community, and we wish you much continued success! We will always think of you first and enthusiastically recommend you when we hear anyone considering a home sale or purchase.
Please feel free to share this recommendation and message of gratitude with any potential clients or Hawaii Life management. We look forward to keeping in touch! Mahalo nui loa!"
-Mark Bogie & Jackie Nguyen

"I have bought & sold many properties over my career, and I can say without a doubt that Ashley is the best realtor that I have ever worked with. She is extremely responsive, diligent and professional. She exceeded all of my expectations, and was able to sell and close our property 1 week ahead of schedule. I will certainly be using her again for my future purchases. Job well done!" - Joe Mancuso, Honolulu

"I was very grateful to have Ashley handling the sell of my condo. I am a long term owner at Tropic Seas on the Gold Coast of Oahu. When I decided to sell, I was hoping to find a realtor who I felt confident and comfortable to work beside. Ashley was that and more. She came up with wonderful ideas to improve the appearance and livability of my place within my budget. She helped me replace the flooring, chose the material and colors and handled the entire installation from start to finish. She did a beautiful job of staging that made the place look very inviting. Ashley has been diligent on every aspect of marketing solutions. If I had a question or concern, she would respond immediately.
She kept me informed and helped me throughout the whole process. I am very thankful to her for she has worked very hard to make this a pleasant and successful process." -Sue Tony-Dillon, Portland OR

"Ashley is all about her clients. I have never met anyone who goes so far in servicing her customers. It isn't about the money to her. She cares. Ashley goes out of her way to insure every detail is handled. She listens to her customer's needs and takes care of them in a selfless way. She is professional in her dealings with everyone in the deal and everyone respects her. Real estate transactions are made so much easier when the other agent, escrow, title, and mortgage professionals respect your agent, and that is EXACTLY what you get in Ashley. Do yourself a favor and let Ashley Bailey handle all of your real estate needs." -Daniel Verdin, Kaimuki

"Ashley is very professional, attentive to detail and very easy to work with. She was able to align with my schedule for meetings which other realtors just did not get. I would not work with anyone else in Oahu other than Ashley B, you’re a star. Ashley is a straight shooter and extremely honest with her clients. I can highly recommend her to anyone seeking a truly professional Realtor." - Alan Mullin, Waikiki

"Ashley assisted us in purchasing our dream beach cottage. She was great to work with, she was very professional, but also very pleasant and fun to be around, like being with a longtime friend. She is detail oriented, she followed up and ensured that everything went smoothly and timely, she generously even brought us very thoughtful gifts upon closing. I would highly recommend Ashley to anyone looking for a perfect realtor to find their perfect property." - Dennis and Susan Mathewson, North Shore Oahu

"Ashley made my VA home buying process very simple. Being that I was new to the whole idea and wasn't sure how it worked, she kept me well informed. Any advice or questions I had she was able to answer in a very timely and professional manner. She knows the island well and I would recommend her to anyone looking to buy or sell property here in Hawaii!" - David King, Honolulu

"Ashley helped us find and purchase our new home recently. We were pre-approved through Veterans United, had been looking on our own for about 3 months and knew generally what we wanted. When we contacted Ashley, she took the time to listen and get a better understanding of our wants and needs. She explained the processes involved in purchasing a home, immediately gave us listings for both open houses and personal showings that were within and outside of our budget. This gave us better insight to the housing market on Oahu. It also helped us to really hone in on what we wanted and didn’t want. Properties go fast here in the budget range we were working within. She got us lined up, put an offer in, and had the paperwork signed and locked in very quickly once we found the ideal place. Ashely worked with our lender and kept us informed in every aspect of the process. Thanks to her we were ahead of the rest and purchased the perfect home under the market value! This, in itself, is miraculous! From start to finish she answered all of our questions and had tools outside of the common apps/ websites that most use when looking for condos and homes. We highly recommend working with Ashley! She will look out for your best interests, be tenacious in finding the perfect place for you, and will be there for you every step of the way! Ashley has integrity and honesty that is very refreshing to find in today’s world! Mahalo Nui Loa Ashley! You are phenomenal!!" - Craig and Jen Wicke, Honolulu

"I just wanted to say Ashley was wonderful!! She made this stressful process such a breeze and was extremely knowledgeable and helpful." - Chris Brown, Waikiki

"Ashley was excellent to work with! She was very knowledgeable of the area of town that I was interested in and took the time to figure out the type of place that would suit me best. She was very, very patient, not at all pushy and quick to point out places I initially thought were great but that wouldn't have worked out in the long run. "It's all about location, location, location!" as she reminded me often. I absolutely love the place I finally bought :) " - Roger Brewer, Waikiki
"I have had the privilege of having Ashley assist me in an contract negotiations and she is very detail oriented! She made me aware of items that I wasn't noticing and it saved me a substantial amount of dollars! Ashley will always represent her clients and company in a positive light, keeping her clients best interest in mind." -Brian Kitaoka, Ewa Beach

"My real estate interaction with Ashley confirmed that her amazing personal and social talents spill into her professional arena. I was thinking of selling a property on Kauai, she is on Oahu, yet she went out of her way to connect me with an agent here to help me. She kept me informed about the sales of similar properties for comparison, and stayed in contact to make sure my needs were being met. Ashley is a good person to have in your court. She's not only driven and energetic, she is honest and compassionate, and an exceptional team player. I highly recommend contacting Ashley for any real estate transactions." -Pam Salibi, Kauai

"Ashley is very professional yet easy going. She is driven and exceeded my expectations! She works efficiently, quickly and thoroughly. We had a great time working together. I highly recommend her, and will use her as my agent for future ventures. Thank you Ashley!" -Katie Burgess, Hilo

"Thank you for your professional work and great service. Especially with your great personality, I am happy to refer you to my friends." - Kevin Kim, Kahala



$845k | Mililani | Learn More About this Property

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