Travel east to the Windward Coast, crossing over, or through, the Ko’olau Mountains, and shed the fast-paced city chaos and hustle. Kailua is a quiet seaside refuge that enjoys epic views of the Pacific on one side (the makai side), lush mountains on the other (the mauka side) and all with the added benefit of the magnificent, cooling trade winds! In Kailua Bay, the turquoise ocean meets a famed crescent shaped, white sand beach that will simply take your breath away.


In Kailua, you’ll meet active, laid-back locals as well as beach loving military families. Young artists, affluent professionals and wealthy retirees flock to this health conscious and eco-friendly coastal town. Water sports, such as windsurfing, are popular, and this area is very family (and dog) friendly.

Neighborhood Feel

Kailua is a small town that embodies a beachy, laid-back lifestyle. The neighborhoods typically date back to the 1960’s and are not quite as densely populated. Single-wall construction is the norm here and central air conditioning is rare, but not often needed. Living on the Windward Side, you’ll catch the breezes to economically cool your home. Homes are pricier when you go higher up in elevation, but with that comes stunning views and unobstructed breezes. There’s a Whole Foods, rumors of a Target in the works, a fantastic hospital, and tons of quaint little beach-side shops and charming strip malls with local foods and wares.

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Neighborhood Location

JBPHH – Borchers Gate
Schofield/Wheeler – Lyman Gate
Tripler AMC – Main Gate
Fort Shafter – Buckner Gate
MCBH – Front Gate
Drive Time to Gate
25 to 35* minutes
35 to 45* minutes
25 to 45* minutes
25 to 45* minutes
10 to 15* minutes
By Transit
48 minutes
2 hours
1 hour 15 minutes
60 minutes
10 minutes

Neighborhood Info

Kailua - Marine Corps Base Hawaii, HI - gomillie.com

Points of Interest

Nuuanu Pali Lookout

Lanikai Beach

Kailua Beach Park

Kailua Town

Pillbox Hike

Big Plus

Kailua is only a ten minute drive to Marine Corps Base Hawaii and easy commute to Joint Base Pearl Harbor-Hickam on the H3, which is much less-congested than the H1.

Being on the Windward Side, you’ll have the trade winds to keep you cool. Open those windows and live as high up as you can to take full advantage of nature’s air conditioning!

Kailua is a thriving beach town with trendy shops, local restaurants and small town character. An upscale grocer, farmer’s market, amazing pastry and coffee shops and talented local artisans’ studios round out the eclectic commercial offerings.

Things to Consider

Be prepared for sticker shock. You’ll be hard pressed to find a single family home under $800,000 in Kailua, and that’s the fixer-upper rate.

The Windward Side sees more rain, though light, than the Leeward Side. The systems move in and are blocked by the Ko’olau Mountain Range on the western border of Kailua. However, with the rain comes super green landscapes with exotic flora and lush mountainsides.

How’s the Market?

The median home value is $942,000 according to the Zillow Home Value Index.

Home Values are forecasted to increase by 1.7% in the coming year.

According to Zillow’s Rental Index, the median rental rate for single-family homes in Kailua is $3,299.

School Scoop

Kailua contains 16 schools. One of the best schools is Kalaheo High School, which has a rating of 10 according to GreatSchools.org.

Hawaii is the only state with a unified school system, meaning all taxes are distributed to the schools at the state level and schools are not grouped into districts.  

When looking at Oahu’s test scores and GreatSchools.org ratings, we advise you to look at the entire picture. Hawaiian public schools are evaluated based on Common Core standards, but many areas suffer a fairly large achievement gap due to socioeconomic disparities, despite offering a better quality education than the ratings imply. Many spouses report that the rankings don’t always reflect a school’s quality of education, so we encourage you to talk to friends, or Scouts, about specific schools.

Geographic Exemptions (GE’s) are available if you wish for your child to attend a different school from where your family is zoned, but these are granted on a space available basis and are at the principal’s discretion. Keep in mind – if your child attends a school while in a temporary lodging facility, he/she will have to move schools when you move out of the TLF if your new home is zoned to a different school. You may apply for a GE, but it isn’t guaranteed. Priority goes to those zoned to a failing school (based on No Child Left Behind standards), children of teachers at the school, and children who already have siblings at the school.

Highlighted Areas