The island of Oahu is a unique place. Since the entire island is considered the City and County of Honolulu, we can't divide the island up into counties or cities, so we divide the island into regions. As you can see in the picture below, the 12 regions are not exactly squares or any other shape, but divided by the topography of the island.
Unless you've driven or flown around the island a few times, it's hard to understand why the areas are divided up the way they are. But once you've seen the mountain ranges, the suburban boundaries, and natural geographical divisions, it becomes a bit more clear. In some cases a river or harbor can divide regions, such as the line between The Ewa Plain and Metro Oahu, whereas in other areas it's more based on the man made elements, such as freeways and housing tracts.
I start with Metro Oahu because this is where the majority of the action is. Downtown Honolulu sits in this region, with large buildings such as the state capital right in the heart of it. Metro Oahu consists of thousands of great homes and high rise condos interspersed with commercial and industrial buildings. Some parts of Metro Oahu are actually the ugliest on the island because of the industrial zones, but if you have to commute into town everyday, living in "town" makes life a lot easier. Just a few minutes drive out of those ugly areas and you can find yourself in a beautiful neighorhood of luxury homes.
Some of Metro Oahu feels run down and shabby, but there are also very nice areas where you can find a gem. Around Ala Moana and Kakaako there are beautiful high rise condo buildings like Hokua, Ko Olani, Kukui Plaza Moana Pacific. There might be 1000 condo buildings around town, which makes selection a difficult process if you don't know the area.
As for single family homes, there are some beautiful areas with multi million dollar homes such as Nuuanu, Alewa Heights, Manoa, Dowsett, Tantalus, Pacific Heights, Old Pali, Makiki, and Makiki Heights. In these areas you can have amazing views of the ocean and island from high hillside estates. If you have a home in Manoa, you'll be in a tropical garden setting probably on a hill, but you're still only 10 minutes from downtown. It's the best of both worlds. You will definitely pay a premium for living in Metro Oahu, because the short commute into town makes it very appealing. Basically you can live in an area like Old Pali and have everything from a tiny cottage to a giant mansion.
Pearl City consists of a few great neighborhoods like Aiea, Halawa and Halawa heights, Pearlridge, Pacific Palisades, Royal Summit, and a few others that are not so great. On the high end there are single family homes around $1million to about $1.5million. These homes are in pretty good shape but because of the location, you pay a premium and don't get as great a house as you would in say, Hawaii Kai, for the same price.
There are some great houses and neighborhoods in Pearl City, and you can get something cheap for about $450k- $500k, or spend $1.5 million in Royal Summit. There are some very good schools and veyr nice neighborhoods, and you're close to Pearlridge mall, which is a gigantic shopping center, at least at Hawaii standards. This entire area is a little older than other parts of the island, which means you have to inspect homes carefully and try to find a good value.
Diamond Head is one of the nicest and most expensive places to live on earth. With homes starting around $1.5 million and up to $20million, Diamond Head has some of the most luxurious homes in Hawaii. From Kahala to Aina Haina, from Kaimuki, Waialae Iki and Waialae Nui all the way to Hawaii Loa Ridge, properties in this region can be truly amazing, with ocean and golf course views, and the best sunsets in the world.
Even the lowest priced homes in this area are around $700k, and the average price is over a million dollars. Kahala is an incredible area with world class properties right on the beach or the golf course. Up on the hills overlooking Kahala, you can get a beautiful hillside home with panoramic views of the Pacific from Waialae Iki and Waialae Nui.
Another nice hillside neighborhood is Wilhelmina rise, with Mauna Lani Heights at the top, which requires a drive straight up a hill for about a mile. In fact it feels like you're driving straight up a giant mountain, because you are. Once you get up to the top, you'll be amazed at the grand ocean views. Homes up on these great ridges are not for those who are afraid of heights.
I think the most beautiful homes on the island are in Diamond Head, but you can't see most of them from the road. Most have high gates and plenty of security, so the only way you're going to see them is if you're invited, or if you're serious about buying one. The captains of industry live in this area in tremendous privacy. If you have to ask how much...
Hawaii Kai is my favorite part of the island. With beautiful waterways of the marina running a mile inland, many of the homes are waterfront, even though they are not on the beach. The marina canals are the only place on the island that allow you to dock a boat in front of your home, so Hawaii Kai is very popular with boat owners. Hawaii Kai was the first master planned community in Hawaii, and you can tell that the layout is more organized than other parts of the island.
This is a little less expensive region than Diamond Head, but higher priced than others West of Town. With an average home price around $800-$900k, you can get a very nice home here with an ocean view. There are also great condos available for $400-$900k with many right on the marina. Hawaii Kai is a very different feeling "city" than any other in Oahu, and you just have to see it to understand. It's mostly a bedroom community because there isn't a business district. It has some great shopping, but not much office space. Most people who live in Hawaii Kai are commuting into town about 20-40minutes each way. That's not too long by mainland standards, and it's well worth it to live in this great neighborhood. I have a page dedicated to Hawaii Kai and you should read it if you want more info.
On the windward side of Oahu is one of the most desirable regions, Kailua. This quaint beach town has everything you could want including a little shopping area to walk around in, the most beautiful beach in America, and fabulous million dollar homes on the sand. Kailua town has recently had a facelift which really helped the appeal. It also tends to be the cooler side of the island because it's usually overcast and it rains a lot. A LOT. If you don't like rain, you won't like Kailua. But the frequent rain means that everything is green, lush, and feels like the tropical Hawaii you would imagine.
Kailua homes start around $600k for a small older house, and $800k for an average 1600sqft house, and we are talking average in Hawaii standards. Unfortunately there are only a few good condo complexes in Kailua, most priced between $400k-$800k. Most of the properties in Kailua are within a mile or so to the beach, and it is truly the best beach you can find in the world.
There is a little community in Kailua called Lani Kai, which has a nice little beach retreat feel. Homes here are hit and miss. You have multi million dollar beautiful estates, and you have totally run down shacks that should be burned to the ground. In fact these two homes I described could be right next door to each other. People love Lani Kai and it's twin sister Beachside, because of the easy access to the sandy beaches and crystal blue ocean.
If you can afford Kailua, you definitely should consider it. Just about everyone loves Kailua because it's beautiful, clean, cool, and it feels like Hawaii should feel - relaxed. There is a Kailua page if you're interested.
Just north of Kailua is Kaneohe, which is kind of like Kailua's sister city. It's a bit cheaper overall than Kailua, and Kaneohe town was updated in 2008 and now it's beautiful! There are great neighborhoods in Kaneohe, and the views of Kaneohe Bay and the Koolau mountain range are available from all over the city. It is a wonderful place to live.
The small marina area allows you to dock a boat, although not right in front of your home. Kaneohe has it's own yacht club, it's own just about everything, so you don't have to leave the city often. Also there's Kaneohe Marine Corps Base, or "K-bay" as they call it, which means that there is a huge military presence there. If you can find a way to get on the base to play the golf course, do it. That means there is a steady stream of buyers and renters, which is great for the local economy.
Commuting from Kaneohe is easy because H3 runs right into town and makes for easy driving. I should mentioned that H3 is probably the most beautiful non coastal drive on the island. The highway runs through the most lush tropical rain forest on Oahu, and is perched about 100 feet above the ground. It's an amazing drive. Check out the Kaneohe page.
The North Shore of Oahu is the most famous stretch of surfing beaches on earth. Waimea, Pipeline, Sunset, Rocky Point, Velzy land, and Log Cabins, just to mention a few of the world class waves on the North Shore. While most of the visitors who come are there for the amazing surfing, North Shore real estate will amaze you too. Pupukea hills, Sunset, Haleiwa, and Kawela Bay, offer spectacular ocean view homes well into the millions. For about $1million you can buy North Shore real estate with a nice ocean view or even a beachfront home.
The North Shore of Oahu is called "country" because it really feels like you're out in the country. You wouldn't know that downtown Honolulu is just 30 minutes away. It's green most of the year, it's cooler than most of the island, it's wonderful. As long as you're not commuting into Honolulu every single day, the North shore is a great place to live. And real estate on the North Shore of Oahu is world class. Custom homes abound and if your pockets are deep enough, you'll enjoy wonderful panoramic views for miles. Sometimes on a clear day you feel like you could see Japan.
The middle of the island is called Central Oahu by the MLS, but nobody else calls it that. We call it Mililani. Mililani and Mililani Mauka are great communities with large housing tracts and lush green forests. Mililani Mauka is a master planned community with some of the best schools on the island. Somewhat more affordable than areas like Kailua and Hawaii Kai, it offers some great neighborhoods with newer homes. People like Mililani because a lot of it is newer than other areas of Oahu, which means it feels more like the mainland to some.
You can buy a nice single family home for around $600-$800k, and it will have been built in the last 10 years or so, which is pretty new for Oahu real estate. Much of the real estate in Oahu was built in the 60's, which means it's about to fall apart if it hasn't been renovated, but Mililani has the newer planned feel that many buyers are looking for.
One bonus of Mililani is that it's right on the H2, so commuting into Pearl City or Waipahu is pretty easy. I have found that a lot of people who work around Pearl Harbor or Tripler Medical Center prefer to live in Mililani for the commute and the quality of home the can get. I like Mililani because it's nice and green most of the year, and tends to stay cool because it's a little bit cloudy most of the time.
Waipio Gentry, Royal Kunia, and Waikele are areas within Waipahu with newer homes and communities that are very appealing. With prices a bit cheaper than the east side or Mililani, Waipahu has some good neighborhoods. Royal Kunia and Waipio Gentry are probably the two most desirable in terms of real estate, with planned communities and newer shopping areas.
Waikele has an outlet mall with Polo, Calvin Klein, Geoffrey Bean, Sacks, Coach, and several other nice stores. As you might imagine the area surrounding Waikele is pretty nice as a result. You can buy real estate around Waikele and Waipio gentry for much cheaper than other areas, so it's definitely worth a look.
One of the newest communities in Hawaii is Makakilo. In the past 10 years or so, new construction in Oahu has been focused in Makakilo and Ewa Beach. Dr Horton and other builders have been putting homes up in Makakilo in neighborhoods like Anuhea, Highpointe, Highlands, Palehua Heights, Royal Ridge, and Kumulani.
Makakilo sits just a bit above Ewa Beach but doesn't have nearly the traffic that Ewa has. And since it's a nice high hill, most everything in Makakilo has the potential of having a great ocean view over Barber's point. Homes can be as much as a million dollars, and you definitely get way more for your money in Makakilo than on the east or north sides of Oahu.
Makakilo real estate is often newer, bigger, and nicer than much of the other areas of Oahu. In Makakilo I have seen million dollar homes with fantastic views of the ocean, custom pools, and large lots. The commute into Honolulu is a bit long from Makakilo, it can definitely be worth it. If you want a nice newer home and you want more bang for your buck than Hawaii Kai or Kailua, or even Mililani, consider Makakilo.
On the south west side of Oahu is a very popular region called Ewa Beach or the Ewa Plain, although everyone here just calls is Ewa. It's pronounced with w short "E" and a "V" sound, like "for-ever." Ewa has some of the best affordable homes on the island, and since most of it has been built in the last 20 years, the entire area has a nice newer feel than most of the island.
A giant master planned community, Ewa has thousands of nice homes with a nice clean feel and plenty of parks and amenities. Neighborhoods such as Ocean Pointe, Ewa Gentry, Kapolei, Westloch Fairways, Soda Creek, Alii court, Carriages, Tiburon, Cypress point, and a dozen or so more, offer great newer homes in well planned layouts. What people like most about Ewa is the affordability. You get way more for your money here and the homes feel new. In fact, there is still plenty of new construction available at Ocean Pointe and the newest development, Ka Makana at Hoakalei.
With a new marina coming in a few years and a new resort and golf course, Ewa has some great future potential. The only problems are that it's a little hotter than the rest of Oahu, and the traffic can be bad during rush hours. I have driven from Ewa all the way across to Hawaii Kai in 45 minutes without traffic, but that could take 2 hours during rush hour.Check out the Ewa Beach page.
Another great option is the Kapolei area, which is a little farther but doesn't have as much traffic going into it, so it actually takes less time to commute to and from than Ewa Beach. Kapolei has even more infrastructure than Ewa, with a medical center, shopping centers, and big stores like Target and Home depot. If you can stand the commute to Town and you want a nice big newer home, consider the Ewa side, especially if you want it to feel like your mainland home. Kapolei is truly turning into a great city with all the new construction. In 2010 construction began on a huge new mall! Check out the Kapolei real estate page.
Homes are the most affordable on the Leeward coast. The commute to Honolulu Town is the longest from here. Recently Dr Horton has been building new construction in Maili, which ranges around $300-$600k, and offers great little homes up to about 2000ft. This new community, called Sea Country, has brought in a lot of new blood into Maili, and has really given the place a face lift. Over time I think the influence of this new community will bring the rest of the area sales up a bit.
Also another great secluded area that few people know about is in Makaha, called Mauna Olu Estates. This gated community has huge custom homes for under $2million, and most have sweeping ocean views for miles. The homes are built on at least an acre or so, and this truly feels like a tropical estate. The golf course that runs through the area offers year round play, and it rains a lot less out there, so it can be a great place to retire or just have a vacation getaway. The homes around Mauna Olu Estates are fantastic and they are custom large homes, so this neighborhood is a must see. You will be shocked that such a neighborhood exists when you are driving through Waianae.
Most of Waianae looks like it has been forgotten by time. It is old Hawaii in tact. There are beautiful beaches and beach front homes for much less than you can buy them for on other parts of the island.