Oahu Real Estate #illumedati

Hey guys, this is kind of a random post, but it’s Whatever Wednesdays, so I think it’s ok. Like I’ve said before, I recently bought a house, which I advised against in Do As I Say Not As I Do as a young attending. However, I didn’t come to that decision lightly. So today I’m going to share my opinions on Oahu Real Estate.

Oahu Real Estate

Stock Photo from: Pexels

Let’s begin…

This story begins back in 2014 when I first accepted this job in Oahu. The plan was that I was going to come out to Oahu first in April by myself and find a place to rent near work. So that’s what I did. I booked a week at the Ala Moana Hotel and rented a car. My plan was to rent something in town near my new job and near my wife’s new job.

In hindsight, what I did probably wasn’t a great idea. Trying to secure a place to live in a week with the geographic restrictions I had placed on myself in a constrained time frame is usually a recipe for disaster. However, I didn’t want to rent a place sight-unseen, nor could I could come out to Oahu more than once, all the way from Rhode Island. As such, I did the best I could with what I had.

So I started looking…

I quickly realized that in town, I would mostly be looking at renting a condo. In my mind I was planning to rent a condo for at least 3 years. Kylie would turn 1 in May, and would probably need her own room at 3 or 4 years old. Additionally, if our parents came to visit, having a 2nd bedroom would be nice. For this reason, I looked primarily at 2 bedroom condos. In retrospect, this probably wasn’t necessary since we ended up buying a house January 2016. However, hindsight is 20/20.

We ended up in a condo very close to my job and still pretty close to my wife’s future job. Also, it was already furnished, which saved us the need to buy any new furniture. However, all this convenience came at a price, as it was very expensive for rent. However, I rationalized that the convenience was worth it. It’s hard to say whether it was or not because I don’t have anywhere else to compare to.

Ok… so when did you start looking at houses?

Well, actually I started looking at neighborhoods even before we moved to Oahu. I knew that whatever rental we chose would be most likely be temporary. However, I wanted to get an idea for what all the other neighborhoods offered.

You may recall that my wife had a pretty bad commute when we were in Rhode Island, so I didn’t want her to have to deal with that anymore if possible. For this reason, I did not consider buying a house in West Oahu or North Shore.

Here are my thoughts:

Central Oahu

“Mililani to Aiea”


This is a really nice area in Oahu which I really liked. It has good public schools K-12 also with Mililani High School considered one of the better high schools.

Unfortunately, Mililani has the double-whammy of traffic in the morning. It has the same problem that Honolulu does of being 1 way in 1 way out. Mililani residents who work in town have to deal with traffic going south on H2 to the H1/H2 merge, then traffic going into town going east on H1. This is similar during the evening commute. This isn’t a huge problem for me since I work evening hours mostly, but this would have been pretty bad commute for my wife.

Nonetheless, I still considered living here as a possibility if my wife was to change jobs for some reason and be in the Central Oahu area.


This area is kind of the closest suburb to Honolulu, in my opinion. It has its own little mall and you can find nice houses within nice neighborhoods. However, even with its relatively short distance from town, the commute in the morning can still be difficult. Also, the public school system isn’t as good compared to other districts, so I would probably end up putting my kids in private school from day 1. However, if the perfect house came up, we would have considered buying in Aiea.




This area is kind of broken up into multiple smaller areas, Capitol District, Business District, Chinatown, and Waterfront. This area has very little parking available as you would expect and mostly consists of condos. While this area was pretty close to our jobs, parking was important to both my wife and I, which may be difficult to find here. Also, there were some safety concerns about this area at night. Additionally, we really wanted an actual house, rather than a condo, so we eventually crossed Downtown of our list.

Note: There are many neighborhoods I am not mentioning here, including Kaimuki, Kapahulu, Diamond Head, Waikiki, etc. However, we wanted to be slightly farther outside the center of town and the tourist areas, so we did not consider them.


I actually really like the Nuuanu area a lot too. The area is set back a little bit from the hustle/bustle of town and it has good elementary schools (Maemae and Nuuanu). There was one thing that about Nuuanu that I had a concern about though. Pali Highway runs through Nuuanu which is one the main routes to go to/from town to the Windward Side (Kailua/Kaneohe). For this reason, there aren’t many breaks in the middle of this main street to make a left turn into your neighborhood. You may be required to make U-turn, and then a right turn to get into your neighborhood depending on where you live. Now, this isn’t a huge deal, but I could imagine it might get a little annoying after awhile. Nuuanu was high on my list.


Manoa is an area kind of northeast of the middle of town. I would consider it a suburb of town, but it’s still part of Honolulu. Manoa is where the University of Hawaii, Manoa campus (main campus) is located. It also has two good public elementary schools, Noelani and Manoa. It also is cahement area for a good public high school Roosevelt High School. Fun fact, Bruno Mars went to Roosevelt High School.

The relatively well-known private school Punahou is also located in Manoa. Punahou School has become more well-known since Barack Obama is an alumnus of Punahou School. Mid-Pac and St. Francis, other private schools are also there as well. For this reason, I think the majority of people who live there do it because of the education.

The area itself is pretty nice since it has its own little Manoa Marketplace. However, it does rain a significant amount more in Manoa than probably anywhere else on the island. I kind of think of Manoa as the “Seattle of Oahu”. If it’s raining on Oahu, it’s probaly raining in Manoa. However, if it’s raining in Manoa that’s just normal. The houses here also tend to be older and need work, whereas still being pretty expensive overall. The “million dollar fixer-upper” is what you hear a lot when people talk about Manoa. Nowadays, I think it’s more like $1.1 or $1.2 million dollar fixer-upper.

However, like Nuuanu, Manoa was high on my list.


People like Kahala because most, if not all, of the land is flat and most houses come with reasonable size yards (and pools!). It’s also nice that there is a mall nearby (Kahala Mall). Additionally, while being on the outskirts of Honolulu, it’s still a reasonable drive into town. However, the houses here are significantly more expensive.

This difference will price many out of Kahala. To give you an idea, back when I was looking at houses, it was $1.5 – 2million for a “fixer-upper” in Kahala, or as they put it a “handyman’s dream”. Houses costing more than $2 million is par for the course, with many selling for $3 or $4 million, and upwards of $18 million.

The public schools in Kahala are “ok”, which are Kahala Elementary and Wilson Elementary. From my understanding, Wilson is the better of the two. It does also place you into the cachement area of Kalani High School, which is considered one of the best public high schools. However, I think a majority of the kids who live in Kahala go to private school from day 1.

I think it would be nice to live in Kahala. However, like many, I am priced out of Kahala.

Sensei’s Note: I did also briefly consider Waialae, which is the area on the north side of H1 from Kahala, as well as Wilhelmina, but I decided that driving up those hills everyday would eventually get to me, despite how nice the views can be from up there.

East Honolulu

Some realtors would disagree with me, but I believe anything east of Kahala isn’t really “Metro” anymore.

Aina Haina / Hawaii Loa Ridge / Niu Valley: (west to east)

Although technically different areas, I consider them to be the same because they are both nice suburbs just outside of Honolulu. Of the above, Hawaii Loa Ridge has a reputation for being more exclusive, and more expensive – a gated community.

Aina Haina has its own shopping center and Aina Haina Elementary school is also a good public elementary school. Aina Haina is also a cachement area of Kalani High School as well, which as I said before, is a good public high school.

However, it is important to know that east of Kahala, H1 becomes Kalanianole Highway. This runs east all the way through to Hawaii Kai and then goes northwest toward the Windward side. This is another one of those one way in one way out problems of Oahu. The further you get outside of Kahala, the more traffic you may experience during your commute to and from work.

For example, to get from Aina Haina to Downtown in a typical morning at 7:30 am may take 25-45 minutes (to go ~8 miles). However, this will increase a little as you go east to maybe 30-50 minutes for Niu Valley. You can imagine that if there was any kind of car accident, your morning commute could be more than an hour or even an hour and a half.

This becomes worse the more west your job is, for example, at Kaiser in Moanalua or at Tripler Army Medical Center. This isn’t horrible, by itself. However, it may make things difficult for picking up your kids from school or doing after-school activities, unless of course, you have help.

This area was still on my list, although I preferred Aina Haina rather than Niu Valley.

Note: There are areas on the south side of Kalanianole Highway which are very expensive: Kai Nani, Wailupe Beach, Niu Beach, and Aina Haina Beach, which of course I am priced out of.

Hawaii Kai:

I really like Hawaii Kai a lot. The thought of living on the marina with a relatively new townhouse on/near the water was a nice one. My DINK friend tried to convince me to buy here so that I could buy a boat and he could come visit me and go fishing.

However, for the reasons above, I didn’t want my wife to have to deal with the traffic.

Note: There are very expensive areas of Hawaii Kai called Paiko Lagoon and Portlock, which are right on the water, and I am priced out of.


Kailua, Kaneohe, Waimanalo


I really like Kailua a lot. I really like Lanikai Beach and the little shopping center there with a Target and a Whole Foods. My wife and I talked a lot about maybe buying a place in Kailua. However, after much deliberation, we decided that to do the drive over the Pali everyday might be difficult. Also, since I eventually wanted my kids to go to private school for high school (or maybe middle school too), eventually we decided we wanted to stay near town. There are simply more options closer to town.

Maybe when I retire I can find a nice little 1 bedroom condo in Kailua to retire to. However, like I’ve said before it will depend on where my kids are.


Kaneohe is also really nice. There are some really nice houses out there with a good amount of land because of the way it was developed. However, living in Kaneohe would require a commute across either H3 or Pali to get into town everyday for us. So for the same reasons as Kailua, we crossed Kaneohe off the list as well.


To be honest, I’m not all that familiar with Waimanalo. I have been there a few times but I didn’t really check out the real estate as I had already decided it was too far to consider buying a house out there. However, from my understanding, it’s mostly a residential area and you can get a good amount of land for your money.

So there you have it, that’s my take on Oahu Real Estate (at least the areas I considered).

Can you guess where I ended up?


Just my thoughts on the different areas to live in Oahu.

Can you guess where I ended up? Comment below!

Whatever Wednesdays Sensei


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