Kailua is located on the Windward side of Oahu and encompasses several smaller communites. Here you will not find any two homes exactly alike. For those of us born and raised here, it's pretty fun to figure out and to identify the original layouts within most of the homes that have been highly renovated. There are many brand new homes, but also many "original" homes that may have been built as early as the 1950s.
Cool breezes come from both the Koolau mountain range, as well as from the ocean. They make for very comfortable temperatures, and is the main reason we are called the "Windward side" of the island. While Kailua is not as "wet" as many other areas, it is also not "dry". Most mornings you will awaken to dew on the grass from light rainfall through the night, which helps to create the vibrant greenery found here.
There are many local shops and restaurants to enjoy. Whether you're strolling through our little strip mall, or heading over to Target, there's lots of places to stop in along the way. We've got Starbuck's, Brew Moon, Safeway(s), and Walgreens. Our favorite eateries include Times Coffee Shop (for their ono fried rice!), Moke's Bread & Breakfast, Buzz's Original Steakhouse, and of course our very own Cinnamon's Restaurant which is just 15' from our Kailua Office on the first floor of the Kailua Square Building on Uluniu.
If you're born and raised here it would be quite surprising to go anywhere and not run into someone you know, but that is part of the beauty of being raised in Hawaii. Newcomers are also embraced with warm aloha, and are soon to make many friends.
There is only one highrise in all of Kailua. The vast majority of homes are single-family as well as low-rise condominiums and townhomes, with our newest development being Ka Malanai. But don't get me wrong, the views from our Meridian East are most fabulous from almost any unit above the 4th floor!
Windward Oahu is also home to three of Oahu's Top 5 Beaches, including Lanikai, Kailua, and Waimanalo. It's the perfect location to enjoy the outdoors, including kayaking, surfing and bodyboarding. Other outdoor activities include biking, hiking, golf and tennis. (Pre-COVID) It is not unusual for friends to just "stop by" after work to come in the backyard, relax on the lanai, and just enjoy each other's company. What an awesome way and place to live!
Almost all of our Kailua agents live, work and play here on the Windward side! Give us a call, we'd love to share our knowledge!
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A rare opportunity to own your own commercial office space in the heart of Kailua’s central business and medical district. This fully improved business office offers appr...
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Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.