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 10 years of sales experience as a Top Producer.

Everyday I follow the Oahu real estate market and have an in-depth understanding of our dynamic neighborhood-specific market that our island offers. I help clients to make informed fact-based decisions, and dedicate myself to making the steps of buying and selling property as fluid as possible. I work very hard for my clients, and If you like a person who is communicative, quick, dependable and a strong negotiator, I am the Realtor for you.

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 love to connect with people. My main focus when working with clients is not only to meet their real estate needs, but to bring them peace of mind.

When I am not matchmaking people with property, I am an avid sailor and race every Friday night and in multiple regattas a year out of the Hawaii Yacht Club. Along side of real estate, I can assist you with delivering your yacht to Hawaii, finding a yacht to purchase or help you find a slip when you relocate to the islands. I am an ocean lover and really enjoy surfing both North Shore & South Shore, cooking Italian fare, practicing yoga, traveling internationally, sailing to new destinations, entertaining guests, and spending time with my sister and friends. Life is great here on Oahu. Please reach out to me if you are thinking of buying or selling real estate. I would love to meet you!

What Ashley's clients say about her:

"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

"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 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

"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

"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

My Blog Posts
The Ultimate Beach Town: Kailua, Oahu 96734
Lanikai beach and view of the Mokulua Islands Oahu offers so many different lifestyles depending on what part of the island you live on. There is the pe...
Condo Living in the Most Walkable Location: Kaka'ako's 400 Keawe on the Market
Kaka’ako has become one of the most walkable, dog-friendly, street art, food and wine forward neighborhoods on Oahu. It's also known right now for its c...
Laukaha Mauka Estate: Auction to Own a Rare Piece of Paradise
Starting on Tuesday, September 25th, 2018, one of the rarest and most exceptional properties I have seen in Honolulu is going to be auctioned online by ...