For most tourists, Hawaii means staying within the gates of a resort, never seeing the neighborhoods where residents live. So when a person is transferred here, (usually to Oahu) often they have no idea where in Hawaii they will live.
Where you choose to live on Oahu will determine a lot about your lifestyle. Even though Oahu is only about 65 miles across and 111 miles around the perimeter, each section of the island has it's own personality and quirks. A demographics study of each zip code can be found here . Choose carefully where you will live, or you will find yourself stuck somewhere you really don't want to be. The commute around the island can be brutal, so it's best to talk to a resident (me) first and find out the best place for you to live.
There are several ways to break down the island, but here's a general overview from a real estate perspective:
* Town / Metro (Waikiki, downtown, St. Louis hts, Nuuanu, Manoa, Punchbowl, Makiki, etc) ~ People on Oahu call it "Town." What they mean is usually the downtown area of Honolulu, the business districts, and possibly China town. When you arrive at the airport and start heading toward Damond head (east) you are in town. Town could be Waikiki, Kaimuki, Pali, University, even Manoa. People who love to live in Town are called Townies. Most people who visit Oahu only see Town, the North Shore, and maybe Hawaii Kai if they go to Hanauma bay.
Living in Town is a little like living in L.A. It's crowded and there are about 1000 condo buildings everywhere. If you look around and all you see are high rises, you are in Town. However there are beautiful areas of town, like Manoa, Nuuanu, Pali, Dowsett, Makiki Heights, and other neighborhoods hidden from most visitors. There are wondeful neighborhoods in Honolulu, many of which you'll never see unless you know where you are going.
* The Windward side (Kailua, Kaneohe) ~ To many, the Windward side is paradise within paradise. For this reason it has some of the most expensive real estate on the island of Oahu. Some people call it the rainy side, because it seems like it rains almost every day. Thanks to all that rain, Kailua and Kaneohe (and Waimanalo) have the most lush forests and mountains on Oahu. Much of the Windward side looks a lot like Kauai's north shore, with tall green mountains and thick foliage everywhere you look.
Kailua has recently been updated, which has made the little town into a very nice place to live. With America's best beach being Kailua beachpark, it's easy to see why real estate here is in high demand. If you haven't visited Kailua town before, it should be high on your list!
Kaneohe Town has also been renovated as of 2008 with the same kind of care that Kailua has. Over the last few years it has been revived, with a new mall and downtown area. There are some wonderful homes up in the hills and down near the bay. Kaneohe bay is a giant body of water where many people like to waterski, fish, and kaya. It's also where a lot of sharks like to breed. Kaneohe has wondeful ocean and mountain views, great new and old homes, and a lively downtown area with plenty to do.
Up beyond Kaneohe is Laie, Ka'aawa (not a typo), Hauula, and a few other little towns that are very small, and very far from the big city. When I drive through those areas I am reminded of old Hawaii, and though it takes them an hour to get into Honolulu in rush hour, it's peaceful and simple. Buying real estate up here is often for people who want a second home or vacation rental, because of the remoteness. You could live up there and commute, but it would be a lot of driving. It's better suited for people who can just sit at home and enjoy the ocean views, and not worry about driving anywhere. Life in this area is slow, and it's the way Hawaii was in the old days. A beautiful relaxing community of mostly long time residents and a some vacaitioners. It's slow paced Oahu, kind of like living on Maui or Kauai. If you can handle the slowness of life, it will be wonderful.
* East Oahu (Hawaii Kai, Kahala, Aiana Haina, Diamond Head) ~ Right after you pass Diamond Head on H1, the scenery starts to change. That's because just about everything east of Diamond Head is zoned as residential real estate. That means more homes, less high rises, less condos, and a more upscale feel to the area. Hawaii Kai was the first planned community in Hawaii, and it's clear as you look around that things are more orderly than in Town. The buildings are nicer, the houses are farther apart than in Town, and the traffic is lighter.
A lot of people that work in Honolulu live in East Oahu, so sometimes the morning commute is kind of long at about 30-40 minutes, but it's nothing like the commute from the Ewa side (more later). Starting in Kahala, H1 turns into a minor 3 lane highway with stoplights. As you drive down the coast, you see multi million dollar homes perched on Hawaii Loa ridge and Aiana Haina. I think it's the best part of the island, perhaps because I live in East Oahu.
Many people moving from the Mainland chose to live in East Oahu, particularly Kahala and Hawaii Kai. This is probably because it feels most familiar to them. The size of homes, the demographics, the layout of the city - these all add to the familiar feel that mainland transplants appreciate about East Oahu, Hawaii Kai, Aina Haina, and Kahala. I'll give you a free tour of East Oahu, as long as you're going to buy a house here :)
Within Hawaii Kai, there are about 20 different neighborhoods, and many are very nicely built modern homes with all the amenities you could ask for. The average price in East Oahu is the highest in Hawaii, at around $800-900k for just a regular home. It's the cost of living in paradise.
* Ewa (Ewa, Kapolei, Makakilo) ~ Ewa is pronounced E' VA. Ewa, Kapolei, and Makakilo are the newest developed cities in Oahu, which means the homes are new, the buildings and some roads, almost everything is new. So on an island where everything gets rusted and oxidized by the sea air, the new housing can be very appealing.
People who live in Ewa typically do so because they want more house for their money, and they don't mind commuting to Honolulu. If you want a new house with more space than you can get in East Oahu or in Town, then move to Ewa. There are great new shopping centers, including a new Target as of 2009. A brand new mall will be built in 2010-2012, and there are plenty of other things to do on the West side.
The average 3 bedroom 2bath house will run you about 25-50% LESS in Ewa than in Town or East Oahu. That is why you might want to check it out.
* Leeward side (Makaha, Nanakuli, Waianae) ~ The Waianae coast is beautiful, but the homes can be a little run down, and many home owners are generally not taking care of things, and it's the longest drive in Hawaii to get from Waianae to town. However, you can buy a house in Waianae for dirt cheap compared to everywhere else in Oahu, and in the winter there is good surf. There is a beautiful golf course community up in Makaha with huge custom homes, and there are beach front homes that are pretty amazing. You can buy a large estate with an acre of land up in Makaha, with an ocean view, for about 1/4 the price of the same property in Kahala or Hawaii Kai. It's remote, some areas are run down, but you have beautiful beaches and you get so much more for your money.
* Central Oahu (Mililani, Wahiawa) ~ About half way up H2 on the way to the North Shore, you pass through Wahiawa and Mililani. Mililani is another town that has recently been built with a master plan. As such, it's layout is pretty good, with shopping and amenities for everyone. There is old and new side to Mililani, and of course new Mililani is nicer because it's new! Housing here and in Wahiawa is a little cheaper than town, so a lot of people make the commute down. It's very green up in this area, and the trees remind people of Japan a little bit. I love Mililani Mauka, where all the homes were built after about 1990, and the neighborhoods have a great feel. The schools there are also very highly praised.
Around Wahiawa and Mililani are dozens of little communities. In fact there are so many that I don't think anyone could ever keep track of them all. There are hillside homes, valley homes, flatland homes, country, city, you name it, it's there. Also, there is a large military contingent, because of the base right there in the middle of Mililani.
* Pearl City area (Pearlridge, Aiea, Halawa) ~ If you need to live near Town, but you don't want to live right in it, Pearl City and the Aiea area are a good alternative. If you can work/live in Pearl City, even better. With housing prices that are a little lower then Kailua and the East side, there are great properties for sale here. As you might suspect it's near Pearl Harbor, and if you can get a home on Halawa Hts or Aiea Hts, chances are you will have a nice view of the harbor. Some homes actually have a view all the way to Diamond Head. From Aiea, you can get a view of both ends of the island, depending on the position of your house.
The most popular local mall, Pearlridge, is the largest center of shopping, eating, and all kinds of industrial and commercial businesses. This area has easy access to all the freeways, and is about as central to Town as anything else. Also, Aloha stadium is here, where you can enjoy all kinds of events, including concerts and sports.
Houses in Aiea and Pearl City are mostly built in the 1960's to 70's, but there have been many homes built ore rebuilt in the last few years. In the oldest neighborhoods people are starting to tear down old homes and rebuild with new construction. If you can get one of these new rebuilds with a nice view, I think you'll be very satisfied.
* North Shore (Haleiwa, Sunset, Pupukea) ~ Big waves, 2 lane roads, and multi million dollar houses. Locals will call this area "country," as in, "I'm going up country." Or, "the waves in country are huge!" Life on the North Shore is different than most of the island. It's a little bit like living in Kauai or the Big Island, except that you can get to Honolulu Town in about 30 minutes with no traffic. The famous Pipeline and Waimea Bay bring giant waves in the winter, and about a million tourists with them.
If you're thinking of living up country, I hope you don't need to commute into Honolulu. While a lot of people do commute all the way from North Shore in Honolulu, it's a pretty long drive, probably around an hour. There is not much to do except surf and enjoy the ocean, or the country on the North Shore of Oahu. There are no malls, hardly any stores, no entertainment. The country side of Oahu is for surfers, local people with local jobs, vacationers, and retirees. If you can afford a second home on the north shore, you're one of the lucky ones on earth. It's beauty and tranquility are second to none. The only problem is that there is a 2 lane road that runs all the way through the country, so if there's big waves, expect tons of traffic. Living on the North Shore is a little bit like living in a small town.