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Koolaupoko Home Search

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Koolaupoko Real Estate

Neighborhood Information about Koolaupoko: Koolaupoko is on the northwestern end of Kailua between North Kalaheo Ave. and Maunawili Stream. It's also across the canal from Kalaheo Hillside. One of the better known roads in Koolaupoko is Kainui Drive, which is also known as "Duck Lane" or "Duck Road" as it's been common to see ducks on median strip. Outside of easy access to H-3 Highway via Mokapu Blvd., one of the other perks for those lucky enough is to live on the canal in Koolaupoko. From there, you can take a canoe, kayak or SUP out to the ocean. It's a great lifestyle!

Most of the original homes in Koolaupoko were built in the 1950's and were wood framed single wall construction. Most of the neighborhood is comprised of detached single family homes, however there's a section of attached CPR duplex style dwellings along Kaipii St. There's also a small condo project in Koolaupoko named Kainui Estate. 

Koolaupoko homes on the market are features below. Let us know if you have any questions about any. In the event you need help buying or selling in Koolaupoko, we can help with that as well. Contact us for more info.

Koolaupoko Home Listings

865 N Kalaheo Avenue, Kailua image
865 N Kalaheo Avenue, Kailua $4,900,000

This rare 27,725 sq. ft. estate property has fabulous mountain views over the wide canal, in a prime Kailua location one street from the beach. Enjoy over 295 ft of direc...

  • 202616097 MLS
  • FS - Fee Simple Tenure
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty.

865 N Kalaheo Avenue, Kailua image
865 N Kalaheo Avenue, Kailua $4,900,000

This rare 27,725 sq. ft. estate property has fabulous mountain views over the wide canal, in a prime Kailua location one street from the beach. Enjoy over 295 ft of direc...

  • 11 Beds
  • 8 Baths
  • 202616094 MLS
  • FS - Fee Simple Tenure
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty.

1251 Kainui Drive, Kailua image
1251 Kainui Drive, Kailua $4,350,000

Discover the perfect blend of lifestyle, comfort, and value at 1251 Kainui Drive—an exceptional canal-front retreat situated along an established, palm tree-lined street ...

  • 6 Beds
  • 4 Baths
  • 202525771 MLS
  • FS - Fee Simple Tenure
Courtesy of Compass

Listing courtesy of Compass.

445 Kaimake Loop, Kailua image
445 Kaimake Loop, Kailua $2,995,000

Brand new construction meets modern island luxury in highly coveted Kailua. This stunning, meticulously designed home with 3,579 sq ft. of living offers the ultimate in s...

  • 6 Beds
  • 4 Baths
  • 202619508 MLS
  • FS - Fee Simple Tenure
Courtesy of MG Hawaii Realty, LLC

Listing courtesy of MG Hawaii Realty, LLC.

636 Kaiemi Street Unit A, Kailua image
636 Kaiemi Street Unit A, Kailua $1,850,000

Located in the Koolaupoku neighborhood, on a quiet street - 4 bedrooms, 3 bathrooms. Single Level open concept home with covered patio. Full street facing property with 2...

  • 4 Beds
  • 3 Baths
  • 202618881 MLS
  • FS - Fee Simple Tenure
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty.

839 Oneawa Street, Kailua image
839 Oneawa Street, Kailua $1,590,000

“I Love Kailua” - Experience the ultimate Hawaii lifestyle in a town famous for world-renowned beaches, vibrant open markets, abundant eateries, and boutique shopping, a...

  • 6 Beds
  • 3 Baths
  • 202617350 MLS
  • FS - Fee Simple Tenure
Courtesy of Engel & Volkers Honolulu

Listing courtesy of Engel & Volkers Honolulu.

433 Kaimake Loop Unit A, Kailua image
433 Kaimake Loop Unit A, Kailua $1,395,000 ▼

Lowest-Priced Home in Ko'olaupoko! SELLER SAYS, "SELL!" Don't miss this incredible opportunity to own a home on a quiet, private loop in the heart of Kailua! This single-...

  • 4 Beds
  • 3 Baths
  • 202613595 MLS
  • FS - Fee Simple Tenure
Courtesy of Corcoran Pacific Properties

Listing courtesy of Corcoran Pacific Properties.

398 Kaimake Loop, Kailua image
398 Kaimake Loop, Kailua $1,250,000

A rare opportunity in a desirable Kailua location! Just minutes from Kailua Beach and a short stroll to Kalaheo Neighborhood Park, this property offers the chance to crea...

  • 3 Beds
  • 1 Baths
  • 202618566 MLS
  • FS - Fee Simple Tenure
Courtesy of Homes of Hawai'i Real Estate

Listing courtesy of Homes of Hawai'i Real Estate.

Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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