Best Oahu Neighborhoods Pt 4: Kailua & Lanikai

Kailua (in Hawaiian means “two seas” or “two currents”). . . is a laid-back, beach town considered one of the most desirable places to live on O’ahu by us locals and definitely a favorite for tourists. It is located about 12 miles northeast of Honolulu on the Windward side of O’ahu. Adjacent to it, you have the highly desirable neighborhood of Lanikai with one of the highest-rated beaches in the world. So whether you are just looking for a great spot to relax for an afternoon or are searching for an excellent neighborhood to buy a new home on O’ahu, I highly recommend you consider Kailua and Lanikai. Take a look here for a quick video tour.


An archeological report determined that the Kailua area was first settled around 500 A.D. These early Hawaiians lived along the ocean as well as the marsh slopes surrounding the Kawainui Marsh. In the 16th Century, Kailua became a popular destination for the Ali’i (chief or chiefess) and was quite populated prior to the arrival of Captain Cook.

It depends on who you ask, but many believe the most historic event that occurred in Kailua and the Windward side of Oahu was in 1795. It was this year when King Kamehameha conquered O’ahu and achieved his goal of uniting the Hawaiian Islands.  As a reward to the warriors and chiefs who helped him, he granted them large areas of surrounding land. Over the years, these lands were used for growing taro, rice, sugarcane, and eventually primarily for raising cattle.

At the start of the 1940s, Kailua was a quaint, quiet town with only about 1,000 residents. However, the onset of WWII had a tremendous impact on Kailua that resonates still today. Kaneohe Ranch sold land to the US Military to expand the Navy Base (now known as Marine Corps Base Hawaii) and the Army’s Fort Hase. In 1942, Kaneohe Ranch closed its remaining cattle raising operations, and the owner, Harold K.L. Castle, donated a large portion of the and for churches, schools, and a new hospital, which bears his name, Castle Medical Center. By the end of the war, population was approximately 4,000. Today, the population for Kailua and Lanikai exceeds 50,000.

Current Day

Over the years, Kailua has seen significant changes in demographics as well as development and has become a major tourist destination. These days, only about 4% of residents are local Hawaiians — compared to about 10% on O’ahu as a whole. Some of the local businesses have been replaced by chain stores from the mainland, but there are still numerous independent stores and restaurants that offer quality products and tasty food. And although Kailua and Lanikai have turned into major tourist attractions, recent enforcement of illegal vacation rentals has had some impact on reducing crowds. And since there are no sprawling resorts or hotels in the area, Kailua and Lanikai still offer a relaxing and quaint vibe in many ways.

What makes Kailua and Lanikai so desirable?

The Beaches . . . Soft Sand, Anyone?

Being that I love a warm ocean and a sandy beach, you might think I’m biased if I say the beaches are the biggest reason Kailua and Lanikai are so desirable. But don’t just trust me — ask any of the millions of people who have visited and rate them as 2 of the best beaches in the world. Personally, I prefer Kailua over Lanikai as it spans approximately 2.5 miles long, and it is fairly easy to find a quiet spot to relax. And both Kailua and Lanikai are very “swimmer-friendly” beaches (though always have respect for the ocean regardless of where you swim).

Kailua Town

The central commercial hub is known as Kailua Town. This dense area offers visitors a selection of tasty restaurants and numerous boutique shops. Down To Earth, Target, Whole Foods, Foodland, and an array of other businesses can all be conveniently found in this area. And I recommend you check out Hekili St. if you are looking for some tasty food and drinks.

Beautiful and Tranquil

The beauty and tranquility of the area is another reason Kailua and Lanikai are two of the most desirable places to live on Oahu.  I never tire of looking at the magnificent Ko’olau Mountains (actually remnants of a shield volcano). Also in Kailua you will find Kawainui Marsh (which were once royal fish ponds), the largest wetland in the state.

Kailua and Lanikai Real Estate

The most affordable single family home currently on the market is this one for $849,000. However, most single family homes sell for at least $1M. Homes in the Lanikai area often sell for a premium, and oceanfront homes command some of the highest prices on O’ahu. Median selling price for a home in Lanikai is over $3M. Here is an oceanfront estate currently on the market for $25M.

If you prefer condominium or townhome living, there are a variety of options in the area. The majority of condos and townhomes sell between $500-$800k. However, within this past year, 4 units have sold priced below $400k, and there have been 9 properties to sell above $1M — the highest selling for $1.255M.  Here is a link to condos currently for sale.

Nearby Attractions

  • Kailua Beach
  • Lanikai Beach
  • Kailua Farmers Market
  • Lanikai Pillbox
  • Surf at Castle
  • Olomana Three Peaks Trails
  • Maunawili Falls Hike
  • Grace on Growlers

If you have any questions about buying or selling real estate in Kailua or Lanikai, you are welcome to contact me at any time – 808 354-5772.  I am here to serve you.

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