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Cindy Whittemore

Agent
ABR, REALTOR (S)
License Number: RS-61689
Aloha! I have been a resident of the state of Hawaii since 1959, graduating from Punahou School in Honolulu and then from the University of the Pacific in Stockton, CA with a Business degree. After having lived and worked on Oahu, Maui and Kauai, my husband Tom and I moved our family to Hawaii Island in 1989. With each island move we made, we have enjoyed the challenge and satisfaction of designing and building our own homes, as well as investing in Hawaii real estate.
 

My real estate career began in 2003 after I retired from a 30-year career in department store management at Liberty House. Working in tandem with fellow REALTOR® Gerry L. Rott, we were the original sales team for the successful Ali`i Park Place 59-unit condominium project in Kailua-Kona, after which we partnered in real estate for 19 years. With my 35 years living in West Hawaii, and over 20 years of real estate experience, I enjoy sharing my knowledge while assisting Buyers and Sellers, and both clients and friends know my reputation for excellent service, attention to organization and detail, and professionalism at all times.
 

Giving back to the community where our family lives is important to me and I am proud to support the Hawaii Community Foundation, Hawaii Island Food Basket, Kona Historical Society and Hawaii Public Radio. My professional affiliations include the National Association of REALTORS®, Hawaii Association of REALTORS®, West Hawaii Association of REALTORS®, Multiple Listing Service, and the Volcano Community Association. My leisure time centers around family activities including our grandkids, plus walking, tennis, hula, yoga, reading and traveling.
 

I look forward to assisting you with your real estate dreams, and sharing my aloha for Hawaii! Mahalo!

Coverage

Captain Cook, Holualoa, Kailua Kona, Kailua-Kona, Kamuela and Kealakekua

Recommendations

Mar 11, 2025 at 2:09 PM

Dr. Kent and Judith-Ann Nakamaru recommends Cindy Whittemore

Cindy Whittemore led us through our first property sale with confidence, knowledge and ease. We knew exactly what she wanted us to do, explained procedures well, and we never had to repeat anything! A true professional.
We will happily have her and her company help us again.
Thanks, Cindy
Aloha, Judi and Kent
Nov 8, 2024 at 10:32 AM

Brett Ritchie recommends Cindy Whittemore

I was so happy to have Cindy as our realtor, guiding us in the sale of our property. Her research and knowledge of the area was such an asset and the entire process was smooth and stress free. Would highly recommend her to anyone looking to buy or sell.
Jun 26, 2024 at 9:18 PM

Richard H. Tamiya recommends Cindy Whittemore

I have had the pleasure of being a client of Cindy Whittemore who was the listing agent for my property located in Kailua Kona. Mrs. Whittemore demonstrated her commitment to providing a wealth of information and knowledge as we prepared to list my home. Her professionalism and personal commitment were clearly apparent as she conscientiously followed through with every endeavor. Her level of commitment and sense of responsibility are reflective of a gifted and talented agent. I am certain that Cindy’s friendly, approachable demeanor and her abounding knowledge and experience were instrumental in securing a contract swiftly with all parties happily in agreement. Her dedication to every aspect of her profession will ensure continued success in all of her endeavors.
Mar 5, 2024 at 7:09 AM

Gloria Mento recommends Cindy Whittemore

I’m glad Cindy was my realtor throughout the sale of my condo. Admittedly I was at a loss on what to do first. Luckily Cindy provided guidance on required procedures and always kept me updated at very turn. Her expertise contributed to a very quick sale and, best of all, minimal mental stress for me. Sincerely I recommend Cindy to anyone who needs a realtor. She is the best.
Jun 9, 2023 at 11:28 AM

Kathleen Stutts recommends Cindy Whittemore

Cindy is a professional with Aloha. She has lived on the Big Island for a long time and knows her market very well. Cindy has listed two properties for us and handles every detail, and is always available to answer questions or concerns. Cindy has a team of professionals to stage and photograph properties to make the marketing simple and appealing. We are so great full for her ability to work with us while we were on the mainland. If you want a seamless transaction with Aloha, Cindy is your realtor. Thank You Cindy!
Mar 10, 2023 at 8:02 AM

Seth Mills recommends Cindy Whittemore

Cindy was amazing!!!!! So easy to work with and so helpful. Couldn't be more happy!!!!!
Oct 7, 2022 at 11:06 AM

Terry & Ann O'Halloran recommends Cindy Whittemore

We would give Cindy Whittemore a 10-star rating if it was available. Cindy and her partner, Gerry Rott, have represented us on several real estate transactions. She was our listing agent when we sold and represented us as a buyer, so we have had an opportunity to see first hand how she handles transactions. The first thing to know is that Cindy defines the word 'professional' in every sense. She stayed totally on top of all details, had prompt and thorough communication, ran down any questions, and provided so much additional information that helped us make informed decisions. We worked with her while on the mainland and she kept us informed about market conditions, neighborhoods, and properties. Cindy knows the Kailua-Kona area like few people do providing insights into neighborhoods, trends, history, etc. Initially, we spent time discussing what we were looking for in a house, she would send links to properties and we gave her feedback. She quickly understood what we liked and then found homes that met our criteria. With her thorough knowledge of the areas we were able to target only properties that had serious potential. It was a real pleasure working with Cindy and we are appreciative of all her efforts on our behalf. Additionally, she is a strong community supporter and you can tell that she is highly respected by other real estate agents. Mahalo Nui Loa Cindy!
Jun 21, 2022 at 5:06 PM

Robert Laird recommends Cindy Whittemore

Responsive, knowledgeable and professional. A pleasure to work with. I recommend without reservation.
May 11, 2022 at 6:22 AM

Jerry. Stutts recommends Cindy Whittemore

Cindy was awesome thru the whole process
I can’t thank her enough
Thxs
Jerry
Feb 8, 2022 at 10:11 AM

Katie Emery recommends Cindy Whittemore

Cindy was very helpful in assisting my husband and I while buying our land. We appreciated the fact that she was very prompt in responding to any and all questions/concerns we had throughout the process.
Dec 17, 2021 at 6:53 AM

Wanda Rowan recommends Cindy Whittemore

Cindy was steps ahead of the game throughout the entire process from listing to selling our home. The listing was fantastic & made for a quick sale. Her expertise was evident as we had a very smooth sale & close. Would highly recommend for anyone selling their home!
Nov 22, 2021 at 7:19 PM

Carol Jossy recommends Cindy Whittemore

Cindy kept me on track throughout the sale, reminding me of my responsibilities and basically taking all the stress out of the process. She certainly went “above and beyond” duty! I really appreciate her vast knowledge and her amazing work ethic. Will certainly call her when I have another real estate transaction and will highly recommend her to others.
Nov 8, 2021 at 9:08 AM

Alvin Bongolan recommends Cindy Whittemore

Cindy helped me though the ups and downs of searching for that right property for my needs.

When we finally got an offer accepted, her professionalism shined all the way to closing.

She will definitely make others feel secure and confident that their goals will be met with Cindy's help.

Thank You Cindy!!!
Aug 4, 2021 at 3:10 PM

Mihwa Tully recommends Cindy Whittemore

Cindy did a great job from start to finish! She was constantly on top of everything that needed to be taken care of, especially with the sellers moving up the closing date. Great personality & always ready to answer any question we had, which we had a lot, since we were first time home buyers. Thank you so much for all your help Cindy! We love our home!
Aug 2, 2021 at 8:02 AM

Luann Dodge recommends Cindy Whittemore

Cindy worked closely with her partner Gerry to provide great service. Her communication with me was professional and timely as was her follow-up. Great experience.
Jul 2, 2021 at 8:58 PM

Leslie Kissner recommends Cindy Whittemore

Cindy was very attentive to all of the details of selling a home. She kept us on track and helped us tremendously in finding the services and professionals we needed to make repairs to the home in the timeline we were under. She brought us a buyer quickly and at a great price. Cindy knows her business, she is professional and keeps her cool under pressure -all the traits you want in a great realtor.
Jun 23, 2021 at 12:11 PM

Lolly Davis recommends Cindy Whittemore

Cindy was efficient, organized, and very timely in dealing with the sale of my home. Her communication was excellent and she was very willing to research and answer any questions that I had.
Jun 14, 2021 at 7:02 PM

Wes Segawa recommends Cindy Whittemore

Looking for an experienced and trustworthy realtor? I strongly recommend Cindy! We were in the market for a home in West Hawaii and by golly, she found exactly what we were looking for and we are now enjoying the beautiful Kona Sunsets!
Jun 4, 2021 at 10:41 AM

Phyllis Segawa recommends Cindy Whittemore

We were very pleased with the service we received from Cindy Whittemore, we feel she went over and beyond assisting us with finding the perfect location and property. Keeping us informed on new postings and taking the time to show us the many properties we were interested in. Kept us informed on all the dates we needed to remember through the closing process.
We highly recommend Cindy as a Real Estate Professional. A true friend!
Jun 2, 2021 at 10:57 PM

Ramzi Mansour recommends Cindy Whittemore

I was relocated from Oahu to the big island last December 2020 to join the new mayor’s cabinet and given the tough real estate market Cindy not only was able to find me a place to purchase but also found me a place to rent!!! Much appreciated Mahalo !!!
Mar 12, 2021 at 5:19 PM

Robert Raatz recommends Cindy Whittemore

Very easy to work with and competent and efficient. Would recommend her service.
Dec 15, 2020 at 10:07 AM

Kim Richardson Luizzi recommends Cindy Whittemore

It has been a pleasure working with Cindy and she has gone out of her way to make the home buying process as easy as possible, explaining things in simple terms and making sure that I understood every step of the process. She has been very patient and kind.

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