Kailua’s Top 10+ Cul-de-Sacs

The term cul-de-sac is French in origin and means bottom of the bag or sack. However; in real estate terms, a cul-de-sac is a dead-end street with a bulb-shaped turn-around at the end – just like the bottom of a sack. A home on a cul-de-sac is the crème de la crème – a highly sought after location and we all know about location, location, location.

Cul-de-sacs and other shapes of dead ends are ideal nooks with enhanced quality of living because they have no through-traffic. No traffic equals less noise from vehicles, and safer streets. There are reports that point to a potentially lower burglary and vandalism rate because a cul-de-sac brings neighbors together and has the one-way-in and one-way-out feature. Let the children play, come out and meet your neighbors, throw a party in the cul-de-sac and enjoy the safety and quiet. The bottom line is that your property value increases when you own a home on a cul-de-sac.

Good for homebuyers, Kailua’s real estate has an abundant number of cul-de-sacs and dead ends. The dead-end streets off of Kalaheo Avenue, which parallels the ocean, almost all end at the beach. Many other neighborhood pockets are designed with loops set-off of Kailua’s main roads. Within these neighborhoods are the top ten of my favorite Kailua cul-de-sacs (with a few extra thrown in for good house-hunting measure).

Coming into Kailua from Honolulu, take a right off of the Pali Highway onto Maunawili Road. Follow Maunawili Road back in the valley and you’ll find the Maunawili neighborhood nestled under the Koolau Mountains and surrounded by agricultural lands. In a minute or two, you’ll suddenly feel like you’re in a tropical jungle, and yet, Maunawili is one of the most accessible neighborhoods to Honolulu due to its proximity to the Pali Highway and H-3.

Mauanwili Road takes you way back into the valley to the bedroom community where single-family homes range in size and architecture, yet all have the tranquility of country living. One of Hawaii Living’s favorite cul-de-sacs is Kika Street, which ends on top of a hill and showcases stunning views of Mount Olomana and the Koolau mountains. Just off of Kika Street is Kika Place, another cul-de-sac. Both streets and the area’s homes are set amongst lush tropical foliage, and benefit from the slightly cooler temperatures and underground and above-ground streams that feed into the wetlands.

Maunawili is also known for its top-rated public elementary school and close proximity to two top private schools, Le Jardin Academy and Trinity Christian. Hiking trails and a community park make this a perfect real-estate location for a family home.

Heading to the Enchanted Lake community and then toward Kailua Town, you’ll find a very long street called Iana Street, which also ends in a cul-de-sac. The street is lined with single-family ranch-style homes that backup either to the canal or Mid-Pacific Country Club’s golf course. Other loops and cul-de-sacs split off of Iana Street. One of those cul-de-sacs is Ikemaka Place. Just a few choice homes are on Ikemaka Place with backyards that open onto the Mid-Pacific golf course. Most of Ikemaka Place residents have had the privilege of shaking former President Obama’s hand when he has taken breaks from his golf games along this famous course. Due to the tiny size of this cul-de-sac and lack of homes for sale on the market, homebuyers might also want to look at real estate on Paokana Loop, Paokana Place and Paakiki Place – a trio of great looping streets and cul-de-sacs with welcoming, neighborly residents.

On the other side of the Mid-Pacific Country Club golf course is another no-throughway neighborhood with two prime cul-de-sacs: Paumakua Place, whose residents have spectacular backyard views of the golf course and Koolau Mountains and Pauahilani Place, up on the hill above Paumakua Place where homeowners enjoy stunning views of Kailua Bay.

This enclave features a variety of sizes and architecture including many larger, remodeled luxurious homes alongside well-maintained older homes. Real estate is at a premium here since Kailua Beach and Lanikai Beach are in walking distance. Families will be happy to know that this area is zoned for one of the highest-rated public elementary schools on Oahu, Kaohao Public Charter School (formerly Lanikai Elementary School). For a night out without having to drive, a favorite of locals and visitors, Buzz’s Steak House, is just down the street opposite Kailua Beach Park.

Not too far from Buzz’s and right across the canal is another prime cul-de-sac and neighborhood, Mahealani Place. The homes at the bulb-ish end of the cul-de-sac have backyard sunrise views of the canal across from Buzz’s. Easy access to the beach by foot or via the canal with your boat, Mahealani Place actually extends into the manicured Kailua Estates neighborhood, featuring well-maintained single-family homes. The homes on the oceanside of the extended portion of Mahealani Place have secured gates that lead to the beach across Kalaheo Avenue while the rest of the homes are wrapped into the looping neighborhood that features a family-oriented park and playground. Mostly ranch-style homes in a variety of sizes afford residents an easy walk to Kailua Beach or town. Directly across from this neighborhood is the world-famous shave-ice store – Island Snow.

The next group of homes, just north of Kailua Estates, is Kuulei Tract. Within the looping streets of Kuulei Tract are two cul-de-sacs: Kuumele Place and Kuuhoa Place. The unique cul-de-sacs are entered in the middle of the street by a side street, creating bulbish cul-de-sacs on both ends. Both streets offer single-family, ranch-style homes and well-maintained properties. The two cul-de-sacs are located within the middle of the Kuulei Tract creating a very safe and quiet environment. This neighborhood is also in walking distance of the beach and town. Kailua Intermediate School is nearby as is the biggest community park in the area: Kailua District Park. Kailua District Park offers tennis courts, basketball courts, swimming pool, soccer and baseball fields, and a recreation center.

Closer to the beach and between the Kuulei Tract and Kailua Estates is a tiny gem of a cul-de-sac, Puukani Place. This tiny street off of South Kalaheo Avenue would be missed if you didn’t know it existed. Less than ten beach-style houses in a variety of sizes and architectures are on this quiet, exclusive cul-de-sac with Kailua beach as their backyard or just footsteps away. Kailua’s iconic Kalapawai Market is also just a hop away by foot for any breakfast, lunch or supplies that you might need.

Making your way on South then North Kalaheo Avenue, towards Aikahi Park, you’ll find all the other public and private lanes which result in dead ends and lead to the beach. One of the most famous is Kailuana Place at the other end of Kailua Beach from Kailua Beach Park. Kailuana Place is an exclusive community of luxurious, high-end family homes. There is a small looping neighborhood beachside of Kailuana Place and then the street continues on to what local residents refer to as Castle Point with the canal offering a natural landmark to the left. Before reaching the canal are homes behind impressive gates and rock walls. Kailuana Place, a very exclusive and private road, with luxurious ocean front homes, offers stunning views of the bay. The street is also famous for hosting President Obama and his family when they would come to stay in Kailua during the holidays. Often referred to as his Winter White House, one of the homes the Obama entourage stayed in was the historic Harold Kainalu Long Castle Residence. This home is on the Hawaii Register of Historic Places, as the Harold Castle Beach Residence. Most of the other homes are of modern architecture complete with high-end amenities.

Kailuana Place ends at the point where the canal and the ocean meet. On the other side of this canal and continuing along the oceanfront is the Kaimalino neighborhood. To get there, you have to go back out of the Kailuana neighborhood and take Mokapu Boulevard to Kaimalino Street. This extremely exclusive neighborhood is filled with high-end luxury homes. The spectacular architecture is particularly noted on the cul-de-sacs of Kaimalino where it turns into a cul-de-sac and at the opposite end of Kaimalino Place. Tucked away in this elite neighborhood, all the amenities are still close by – shopping, schools and community. Even if you can’t find your dream house on Kaimalino Place or Street, try searching this neighborhood for other real estate nuggets. Milokai Street and Place are other cul-de-sacs in this neighborhood that offer homebuyers options for their dream house.

Within two miles of the vibrant business and shopping center of Kailua Town, there are multitudes of little neighborhood pockets, where residents seek quiet when they return home from their busy days. These ten cul-de-sacs are just a few of the prized cul-de-sacs of Kailua. It’s fun to explore the different neighborhoods and search out the cul-de-sacs. Each has its own personality and energy. There’s one to match yours for sure.