5 of Urban Honolulu’s Prettiest Streets

For when you just want to go for a scenic drive, bike, run or walk without leaving the city.


We often speak of curb appeal, the way a good first impression often sells a home quickly and for the highest price. But what about street appeal? Views, a perfect line of trees, wide open space and sidewalks, and a consistent look of quality homes all contribute to creating a street that makes you want to pull over and take a photo. We looked at some of Honolulu’s prettiest streets and what it cost to live on them.


Ferdinand Avenue

Honolulu’s Prettiest Streets - Ferdinand

Photo: Rachel Ross Bradley


Along the ‘Ewa side of the entrance to Mānoa Valley, Ferdinand Avenue is a stretch of residential street just under a mile long. It rolls gently along the hillside parallel to the valley and is dotted with large historic homes on even larger lots. While the homes are all unique, they largely have both age and upkeep in common: Homeowners on Ferdinand have taken care of their properties, many of which are on the state historic register, quite well. There are no sidewalks, but traffic is light, and children still ride their bikes in the street after school. Most homes on the road have Diamond Head and Honolulu views.  There are currently no homes for sale on Ferdinand Avenue, and in the past year three homes have sold for $1,700,000 to $2,550,000 million.


SEE ALSO: How a 6,000-Square-Foot Home in Makiki Ended Up as Part of a Mililani Estate


16th Avenue

Honolulu’s Prettiest Streets - 16th Ave

Photo: Rachel Ross Bradley


16th Avenue, where it connects Kapi‘olani Community College to Pahoa, is a little bit of old Hawai‘i. The street is wide and lined with tall trees that lean from years of consistent trade winds. There’s a nice sidewalk, Diamond Head and ocean views, and the street is lined with plantation homes of yesteryear. Even the homes that replace older ones have been built in a way that honors the feel of the neighborhood. There are currently two homes for sale on 16th Avenue, ranging from $1,050,000 to $1,825,000.


SEE ALSO: Remember When Kāhala Homes Only Cost $200,000? Now They’re $5 Million


Tantalus Drive

Honolulu’s Prettiest Streets - Tantalus

Photo: Ashley Werter


Where else can you drive from the city into the rainforest in less than five minutes? Spectacular views notwithstanding, the twisting, turning road quickly turns from residential into forest, with canopies that completely shade the street in many places. Well above the Makiki Heights neighborhood, 3 and even 4 miles up Tantalus, residences are tucked-away rim lots or deep in hidden valleys. While narrow, this drive is one of the prettiest because of the tropical rainforest. There are currently two homes for sale on Tantalus Drive, ranging in price from $1,780,000 to $2,000,000.


SEE ALSO: Your O‘ahu Neighborhood Guide: 1600 Kalākaua Avenue in Honolulu


Kalākaua Avenue


Photo: Rachel Ross Bradley


We don’t mean the part where it’s overflowing with visitors, although it’s arguably beautiful there as well. We’re talking about the Kalākaua Avenue that starts at the natatorium and leads down through the gold coast. With a wide grassy median lined with century-old ironwood trees, the Dillingham fountain and peek-a-boo ocean views, the road through this coastline is beautiful. There are a few homes on the mauka side past the end of Kapi‘olani Park, but otherwise, this is a place for oceanfront condominiums. There are currently 27 residences available on Kalākaua Avenue, ranging from $215,000 (leasehold) to $6,800,000.


SEE ALSO: Two Kaka‘akos Have Emerged in 12 Years and New Plans for What Will Come May Change Our Skyline and Streets Yet Again


Pu‘u‘ikena Street


Photo: Reinout Van Wagtendonk


The planned neighborhood of Hawai‘i Loa Ridge boomed in the late 1980s, with Pu‘u‘ikena at the heart of it. The roads are perhaps Honolulu’s widest, with sidewalks, homes all kept up to association standards, and killer Koko Head to Diamond Head views. You’ll often even see as far as Moloka‘i or Lāna‘i when driving down the street. However, since this is a private neighborhood, you won’t be able to go for a leisurely drive. Check it out next time you hike the ridge. There are currently three homes for sale on Pu‘u‘ikena Street, ranging from $2,175,000 to $3,980,000.