Koolaupoko Homes under $2.5 million

Welcome to Koolaupoko, a picturesque gem nestled on the windward side of Oahu, Hawaii. This enchanting neighborhood, located in the charming city of Kailua, offers a unique blend of natural beauty, vibrant community spirit, and a laid-back island lifestyle that is truly hard to resist.

Koolaupoko is renowned for its breathtaking landscapes, featuring lush mountains, pristine beaches, and the iconic Mokulua Islands just off the coast. Residents enjoy a myriad of outdoor activities, from hiking the scenic trails of the Koʻolau Range to paddleboarding in the crystal-clear waters of Kailua Bay. The area is also home to a variety of parks, providing ample space for family picnics, beach days, and leisurely strolls.

In addition to its stunning scenery, Koolaupoko boasts a welcoming community filled with friendly neighbors and a rich cultural heritage. The local farmers' markets, boutique shops, and delicious dining options reflect the vibrant spirit of the area, making it a perfect place to call home.

For those seeking a slice of paradise without breaking the bank, Koolaupoko offers an impressive selection of homes priced under $2.5 million. From charming single-family residences to modern ocean-view properties, there’s something for everyone. These homes not only provide comfortable living spaces but also allow residents to fully embrace the island lifestyle, with easy access to the beach and the vibrant Kailua town center.

Discover the allure of Koolaupoko, where your dream home awaits amidst the stunning backdrop of Oahu's natural beauty!

Newest Koolaupoko Homes under $2.5 million

$1,250,000

3 Beds ⋅ 1 Baths ⋅ 202618566 MLS ⋅ FS - Fee Simple Tenure

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 create something truly special. Situated on a generous 7,500 sq. ft. level lot, the property is being offered in tear-down condition, presenting an opportunity to start fresh and bring your vision to life. Bring your contractor, your ideas, and your vision. Your Kailua dream starts here! **Property to be sold strictly AS-IS. Seller will not make any repairs or provide credits **

398 Kaimake Loop, Kailua

Listing courtesy of Homes of Hawai'i Real Estate.

$1,850,000

4 Beds ⋅ 3 Baths ⋅ 202618881 MLS ⋅ FS - Fee Simple Tenure

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 car carport with views of Koolau Mountains. Fenced in yard with automatic gate. Original home built in 1955. Remodeled in 1987 with new Kitchen design, Added a true primary Bedroom with bathroom, Laundry Room inside home and an Office/Craft Room. 2 split AC systems. Three AC wall units. There are 22 Photovoltaic panels that helps offset Electricity Bill with possibility of new owner hooking up a critical load panel. Warranty is transferrable to new owner. Home comes with 2 split AC systems. Walkable to Kawainui Marsh Trail. Minutes to H-3, Kailua Town and Kailua & Lanikai Beach.

636 Kaiemi Street Unit A, Kailua

Listing courtesy of Coldwell Banker Realty.

$1,590,000

6 Beds ⋅ 3 Baths ⋅ 202617350 MLS ⋅ FS - Fee Simple Tenure

“I Love Kailua” - Experience the ultimate Hawaii lifestyle in a town famous for world-renowned beaches, vibrant open markets, abundant eateries, and boutique shopping, all wrapped in a charming heritage town vibe. This newly built, move-in-ready home offers an exceptional dual-living or multi-generational layout: •Top Floor: Features 3 bedrooms and 2 bathrooms, a spacious living area, and a beautiful outdoor deck perfect for hosting gatherings with family and friends. •Ground Floor: Includes 3 bedrooms and 1 bathroom, centered around a large, open entertaining space complete with a wet bar.

839 Oneawa Street, Kailua

Listing courtesy of Engel & Volkers Honolulu.

$1,395,000

4 Beds ⋅ 3 Baths ⋅ 202613595 MLS ⋅ FS - Fee Simple Tenure

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-level 3-bedroom, 2-bath home offers comfortable island living with a flexible layout and plenty of potential. Previous owners added a wet bar and a separate entrance to the primary suite, creating an opportunity to live in one area and rent out the other, or use the space to accommodate extended family or guests. Minimal yard work means more time to enjoy everything Kailua has to offer, including Kailua Town and the world-famous Kailua Beach. Additional features include owned solar panels to help reduce electricity costs and split A/C units throughout to keep you cool and comfortable year-round. Motivated Seller - let's make a deal! Schedule your private showing today and come see all this exceptional Kailua home has to offer!

433 Kaimake Loop Unit A, Kailua

Listing courtesy of Corcoran Pacific Properties.

$2,500,000

5 Beds ⋅ 5 Baths ⋅ 202612304 MLS ⋅ FS - Fee Simple Tenure

Rare opportunity to own a canal front home on a nearly 10,000 sq. ft. R-5 zoned lot with a legal ‘ohana unit, each with its own utility meters, complete with pool & spa. Tucked along the peaceful cul-de-sac end of Kainui Drive, locally known as “Duck Road.” The spacious single-level main home features three generously sized bedrooms with new carpeting, three bathrooms, a dedicated study and bright living and dining areas that flow seamlessly into an enclosed lanai. A large recreation room or studio complete with a kitchenette, bathroom, private entrance, and its own courtyard provides additional flexibility for guests, home office or extended family. Upstairs, the 800 sq ft 'ohana unit (823 Kainui Dr) features two bedrooms, one bathroom, and a covered lanai. Recent upgrades include a new roof on the main home and a freshly re-plastered pool. Take in stunning sunsets over the Ko'olau Mountains from the multiple outdoor areas, relax in the pool and spa, or enjoy a paddle or boat out to Kailua Bay. This unique property offers flexibility and is ideal for multigenerational living, generating rental income, or both. The possibilities are truly endless.

821 Kainui Drive, Kailua

Listing courtesy of Arquette Properties Inc.

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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.