Tim OLeary

Oct 4, 2026

Working with Tim all these years has been nothing but a pleasure! He has a way of making you feel like you and your clients are the only transaction he is working on. He takes the time to answer all your questions, is always responsive, and consistently follows up. Tim truly cares about his clients and the people he works with and you can feel it in every interaction. I highly recommend Tim to anyone looking for a knowledgeable, attentive, and trustworthy lender to help with their home financing needs!

Outstanding service & communication!

Friendly professional informative experienced Customer service

Tim O?Leary is very responsive and easy to work with

Apr 3, 2026

Tim is one of our most valued resource! When it comes to buyers, he is clear and professional and guides our clients to make the best decision for their family. Especially since buying a home is probably the biggest decision a person would make. He makes it easy to understand and gets them to closing. On the agent side, talk about a man whose wealth of knowledge extends deep, experience even more, and an exceptional leader. With weekly communication, he makes sure that he can provide us with the highest level of service and insight, especially with the changing economy. Just talking to him will make you understand why so many people place their trust in him. Mahalo Tim for all you do.

Apr 1, 2026

Tim is a great lender! He is very proactive and strategic in the way he helps buyers. He has helped many of our clients and they all love him. I highly recommend Tim!

Mar 6, 2026

If you are moving, PCS'ing, or retiring to the Big Island or surrounding islands of Hawaii, then I highly recommend Tim to support you through the home buying/Mortgage financing process! Whether you're a first time homebuyer or experienced investor looking for the best product to help make the numbers make sense for you, Tim is your guy! His knowledge, communication, and customer service is top tier and he will ensure you understand the numbers and what exactly you're getting into when purchasing your next property!

Very communicative and punctual on deadlines.

The entire process was digital which made it very easy to get things done. Tim O’Leary and Jennifer Lam kept me informed and were responsive. I felt reassured and confident working with them.

Oct 20, 2025

Purchasing a condo in Hawai'i is definitely an experience! I don't know what I would have done without Tim and his team. Tim reviewed the process with me in depth and provided timely updates along the way. He was always available when I had questions or just needed reassurance the process was on track. Tim's professionalism, knowledge, and ability to pivot and offer alternative solutions when roadblocks were encountered, allowed me to trust his judgement and recommendations. I'm so thankful to have Tim help guide me through this stressful process.

Sep 22, 2025

This is the second mortgage I have gotten from Tim and his team. Both transactions went smoothly and I couldn't be more thankful for the professionalism and help along the way. Highly recommend to anyone needing a morthage!

"Buying a home while facing financial uncertainty was daunting, but Tim Oleary and his team provided unwavering support every step of the way. From the start, they demonstrated empathy and offered practical, personalized solutions that made homeownership possible for us." "They took the time to understand our situation and helped us navigate our financing options that fit our budget. Their communication was clear, consistent, and always encouraging—even when things felt overwhelming." "Thanks to their dedication, we were able to secure a home we love despite the challenges. We’ll forever be grateful for their patience, professionalism, and sincere commitment to helping people like us achieve stability and hope."

Tim O'Leary is an expert of the mortgage industry. He worked seamlessly with all parties involved in the transaction. He stayed in constant communication throughout the entire process, taking the time to explain every step, and was readily available to answer questions along the way.

Jul 15, 2025

Tim is an expert of the mortgage industry. He worked seamlessly with all parties involved in the transaction. He stayed in constant communication throughout the entire process, taking the time to explain every step, and was readily available to answer questions along the way. I will be working with Tim again, and recommend him to anyone with mortgage/financing needs.

Jun 5, 2025

My wife and I recently purchased a home in Hawaii. We are forever grateful for Tim O’Leary and his team at Rate. Tim guided us through the mortgage lending process with patience, assertiveness, and professionalism. His attention to detail is impeccable and his communication is solid. As a retired fire captain, I gravitate towards people, who are task, team, and goal oriented. Tim blends all of those elements into the mortgage lending process for his clients. Through his guidance, Tim made our home buying dream a reality. I highly recommend Tim O’Leary and the team at Rate!

Knowledgeable professionals who gave viable options and correct information

Excellent customer service, completed way ahead of schedule and made it simple for me

Great loan results for the consumer! Tim O”Leary is a great broker that is responsive and attentive. This warrants a rating of 10.

Tim was sooo helpful.

Correspondence between us and those at Guaranteed Rate was always prompt and professional. They were able to assess our needs and facilitate our loan with professionalism and ease.

I feel they did a great in communicating with me as well as their exceptional work getting my loan prepared

very impressed with the knowledge shared with me

I would limit my recommendation to the local team I dealt with led by Tim O'Leary. I was able to close and purchase a house in less than 20 days. I needed that sort of attention in order to buy the house I wanted before it was listed and a bidding war ensued.

They closed in the time frame that was promised.

Very helpful and timely with providing information!

Tim was a big help

Tim and his Team went out of their way to make myself feel like the priority in our home buying process.

The team here was fast, friendly and efficient.

They were quick to respond and got my loan done way before closing!

Apr 9, 2024

I would highly recommend Tim O'Leary and Guarantee rate as a home buyer. Tim was professional, knowledgeable and easy to work with. There were obstacles along the way but he was able to overcome them to make our purchase possible. My husband and I could not be more happy and excited about our new home and of course Kudos to Tim for making that possible.. Thank you again for your hard work and determination. Much appreciated!!

Apr 8, 2024

As an experienced home buyer that has used a number of other loan officers in the past, I highly recommend Tim O'Leary. He is very experienced and helped me find a loan for a difficult to finance property. He is also is a problem solver. If any issues came up with the requests from the lender, he was great at helping to find solutions. I will definitely use Tim again.

Apr 4, 2024

Tim was a true professional. With the markets constantly changing, he stayed on top of it throughout the process to get me closed on time and meet all the challenges quickly. He went the extra mile. I would absolutely recommend Tim and would use him again without questions.

Mar 27, 2024

Tim was so accommodating and knowledgeable thru the entire loan process. I can’t recommend him enough as this was my first time purchasing a home I had so many questions along the way that Tim helped guide me thru it all. He was so fast at responding whether it was thru email, text or a phone call. Thank you Tim! So excited for my family to be able to start this next chapter in our new home.

Mar 5, 2024

I unequivocally recommend Tim O'Leary. As an experienced home buyer, I was very impressed with Tim's knowledge, professionalism, responsiveness and focus on getting me not only the best rate possible, but also being accessible anytime. He answered all of my questions (and I had a lot of them) and he made himself available on weekends. As a Veteran, going through the mortgage loan approval process can be quite daunting, but Tim made the process as smooth as possible and helped us to lock in a rate at the right time. Tim is a truly exceptional loan officer who is pleasant, and I very much enjoyed working with him. I highly recommend Tim O'Leary.

Mar 4, 2024

I highly recommend Tim O’Leary and Guaranteed Rate! Tim was absolutely wonderful to work with as a first time home buyer. He was so patient with me through this new experience and made sure I understood everything. He always took the time to explain things to me in a way that I would understand and relate to. I truly am grateful that I was able to work with Tim. He helped make my home buying process run smoothly.

Sep 25, 2023

If you are in search of the utmost professional and efficient services in search of a mortgage lender this is it. Tim and his team helped my wife and I secure our dream home in Oahu and we could not be anymore grateful for the dedicated service Tim and Guaranteed Rate provide. Tim is very prompt with his responses and will go out of his way to make you feel like the priority. His team dedicated endless man power hours in getting us the lowest rate possible and closed escrow in just about 30 days! I would actively reach out to Tim and his team again for future home buying needs!

Mar 4, 2021

Tim gave us great guidance and direction from the start. He helped us ensure we were able to due this process and the best part of him and his team is their communication and calm demeanor. They kept us informed, they were ahead of any obstacle and ready to hurdle it and when it did get tight or close to deadlines, Tim's demeanor reassured us that we were going to be okay.

Feb 5, 2021

I was a first time home buyer in Hawaii and without much planning ahead, I decided to try to buy a condo (if I could qualify). And Tim made it happen for me! I am so grateful to have worked with Tim and his whole team. He worked diligently to make things happen quickly and was very professional but personable too. I highly recommend him to anyone considering purchasing a home even if you are not sure if you can qualify. Thank you Tim for making this dream a reality for me and my son. Many thanks and Aloha.

Feb 4, 2021

In the middle of the pandemic I bought my first condo. It was a stressful time and was made more so when I worked with another lender who did not pay attention to detail and kept needing to send me corrected documents. It is overwhelming in the best scenarios, so it was particularly difficult to not feel like I could trust her. Then, I was referred to Tim O'Leary and I had a totally different experience. He explained everything in detail, using videos, phone calls, texts, emails, and Zoom calls. I asked a ton of questions and he always responded quickly and with clear information. Tim truly felt like a trusted colleague, helping me understand the details of the biggest purchase of my life. I recommend him to anyone who is buying a home, and especially for those who are going through the process for the first time. He was patient, encouraging, and got me a terrific rate as a self-employed, first-time homebuyer.

Jan 17, 2021

We worked with Tim 8 years ago so when it was a good time to refinance it was a “no brainer” that we would call Tim. He was quick to respond and very knowledgeable. Due to COVID the process was very different but Tim and his team made it easy to communicate and process the needed information. Thank you Tim!!

Jan 16, 2021

Tim and the team were very helpful and informative. Being a first time home buyer, going through the process from placing the house on escrow to closing went very smooth. Even with a few bumps I never felt lost, Tim and the team made sure i knew what was happening and provided constant updates so that i felt comfortable and safe. I definitely recommend him for first time home buyers, he is willing to help you and goes above and beyond to get you what you want!!

Jan 16, 2021

Tim is an absolute rock star! As a first-time buyer using a VA loan, I was a bit worried and overwhelmed. Tim made himself available 24/7 and carefully walked me through each step of the process. If I decide it's time to purchase another house in O’ahu, Tim will undoubtedly be my first call. Put your trust in Tim; he will not let you down.

Dec 24, 2019

Tim was excellent! He thoroughly explained everything and answered all our questions, even the dumb ones. He was patient, kind, and sincere. We look forward to a long-standing relationship with him and trust him immensely.

Dec 13, 2019

Tim O'Leary is the ultimate professional! I appreciate every opportunity I get to work with Tim and know when he is involved things get done. He is very prompt and efficient at keeping everyone informed and aware of each step in the loan process. Tim goes out of his way to make sure all involved feel comfortable with the process and understands the steps that are being taken. He works hard to make sure the client gets the best loan for their situation and that everything happens according to the timeline of the transaction. I always look forward to my next opportunity to work with Tim O'Leary!

Dec 3, 2019

We have used Tim's services for two refinances. Tim and his team went above and beyond to make both refinances happen for us. We couldn't be more pleased with our experiences with Tim!

Dec 3, 2019

Tim O'Leary and True with Prime Lending are outstanding, hardworking, responsive, and exceptional examples of professionalism. They were attentive to all our needs from the very beginning until the last bit of the process. We truly believe that our dream home was only possible with their expert assistance. We would highly recommend working hand in hand with Tim! Mahalo!

Nov 29, 2019

I really owe the success of this entire transaction to Tim. He is truly the textbook definition of the consummate professional. Couple this with seasoned market savvy, administrative prowess and impeccable customer relations skills, I could not have hoped for a better agent to lead me through my first home buying experience. A home purchase can be a daunting task to say the least, but it was Tim's 'we're going to do this' mantra and unwavering support that pulled me through the process and allowed me to overcome my own intrinsic doubt and complete the tasks at hand. I would not hesitate to recommend Tim to anyone looking for someone to guide them through their journey to home ownership. THANK YOU SO MUCH TIM!! You really made it happen, and every time we open the front door to our new home you will be right there with us in our thoughts!

Nov 28, 2019

Tim was amazing! He made buying a home seem so much easier than I could have ever imagined! Very professional, always available and super easy to work with! I highly recommend using him!!!

Nov 27, 2019

Working with Tim was such an amazing and exciting journey. He is very personable and he takes the time to explain ever tiny detail. We weren’t worried throughout the entire process because he would always keep us updated and help us even on Sundays! There wasn’t a time we called him and he never returned our call. I will definitely work with Tim again, without a doubt. I’m so thankful to have met him and got to work with him. We are so blessed to become new home owners but we couldn’t have done it with out Tim! He pulled through for us and never failed us. We are so glad to have made an amazing friend through this process of buying our 1st home. Thank you so much Tim, I really appreciate you and all that you do.

Nov 27, 2019

We had such an amazing time working with Tim! He helped us from start to finish and is always keeping us updated with the status about everything. We are so glad to have met Tim and become such good friends with him. He’s in this industry to help people and he always but other people first. He went over and beyond to help us get the place we wanted. When we do get another place he’ll be the first person that we call. We are so blessed and honored to have Tim on our side of the court. Thank you so much Tim for everything that you did for us. We truly truly appreciate you! We are grateful to have become new homeowners and make an amazing friend in the process. Thank you again Tim!