Koolaupoko Homes under $2 million

Welcome to Koolaupoko, a picturesque neighborhood nestled on the stunning windward coast of Oahu, Hawaii. Known for its breathtaking natural beauty, Koolaupoko offers a unique blend of serene landscapes, vibrant local culture, and a close-knit community atmosphere. This idyllic region is characterized by its lush mountains, pristine beaches, and charming small-town vibe, making it a perfect place for families and individuals seeking a tranquil lifestyle while remaining connected to the vibrant pulse of Kailua.

Kailua, the heart of Koolaupoko, is renowned for its stunning beaches, including the famous Kailua Beach and Lanikai Beach, where soft sands and crystal-clear waters beckon residents to soak up the sun and enjoy outdoor activities. The area is also rich in recreational opportunities, with hiking trails that lead to breathtaking vistas and a variety of water sports available for the adventurous spirit.

For those considering a move to Koolaupoko, you’ll be pleased to know that there are beautiful homes available for under $2 million. These properties offer a range of styles and sizes, from cozy single-family homes to spacious residences perfect for entertaining. Many homes boast stunning views of the mountains or ocean, allowing residents to enjoy the natural beauty that surrounds them every day.

With its welcoming community, stunning scenery, and a variety of affordable housing options, Koolaupoko is truly a hidden gem on Oahu. Come discover the charm of this remarkable neighborhood and make it your new home!

Newest Koolaupoko Homes under $2 million

$1,250,000

3 Beds ⋅ 1 Baths ⋅ 202618566 MLS ⋅ FS - Fee Simple Tenure ⋅ 8 DOM

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 ** Some photos have been digitally enhanced for illustrative purposes. The in-ground pool shown is a conceptual rendering to illustrate potential possibilities only. No pool currently exists on the property.

398 Kaimake Loop, Kailua

$1,850,000

4 Beds ⋅ 3 Baths ⋅ 202618881 MLS ⋅ FS - Fee Simple Tenure ⋅ 10 DOM

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

$1,590,000

6 Beds ⋅ 3 Baths ⋅ 202617350 MLS ⋅ FS - Fee Simple Tenure ⋅ 27 DOM

“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

$1,395,000

4 Beds ⋅ 3 Baths ⋅ 202613595 MLS ⋅ FS - Fee Simple Tenure ⋅ 92 DOM

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

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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.