Kalaheo Hillside Homes with Boat Parking Features

Welcome to Kalaheo Hillside, a hidden gem nestled in the heart of Kailua, Oahu. This picturesque neighborhood boasts stunning views of the lush Ko'olau Mountains and is just a stone's throw away from the pristine beaches that make this island paradise so sought after. With its tranquil ambiance and friendly community spirit, Kalaheo Hillside is the perfect place for families, retirees, and anyone looking to embrace the laid-back Hawaiian lifestyle.

One of the standout features of homes in this charming neighborhood is the availability of boat parking. For water enthusiasts and adventure seekers, having a dedicated space for your boat is a dream come true. Imagine being able to launch your vessel at the nearby Kailua Beach or Lanikai Beach, both renowned for their crystal-clear waters and vibrant marine life. With boat parking options readily available, you can easily enjoy a day of sailing, fishing, or simply soaking up the sun on the open water.

The homes in Kalaheo Hillside are designed with comfort and convenience in mind, often featuring spacious layouts, modern amenities, and lush landscaping that complements the natural beauty of the area. Many properties also offer stunning ocean views, allowing you to wake up to breathtaking sunrises and unwind with spectacular sunsets.

Living in Kalaheo Hillside means embracing a lifestyle filled with outdoor activities, community events, and the warmth of island living. Whether you're hiking the nearby trails, exploring local shops, or enjoying a meal at one of the delightful nearby eateries, you’ll quickly find that this neighborhood is more than just a place to live—it's a place to thrive. Come discover the magic of Kalaheo Hillside and make it your home today!

Newest Kalaheo Hillside Homes with Boat Parking Features

$1,690,000

4 Beds ⋅ 3 Baths ⋅ 202614340 MLS ⋅ FS - Fee Simple Tenure ⋅ 17 DOM

Experience elevated island living in this fully remodeled, single-level home in the heart of Kailua. Renovated from top to bottom, this property feels virtually new and offers the perfect blend of modern design and everyday comfort. The home features a 3-bedroom, 2-bath main residence plus a connected 1-bedroom, 1-bath suite with a kitchenette, providing exceptional flexibility for extended family, guests, a home office, or potential rental income. Inside, a bright open-concept floor plan seamlessly connects the kitchen, living, and dining areas, creating an inviting space for both entertaining and daily living. The bedrooms feature premium DuChâteau hardwood flooring, adding warmth and an elegant finish throughout. A thoughtfully designed hidden laundry room enhances functionality while maintaining clean lines and a spacious feel. Outside, enjoy a fully fenced, oversized backyard—perfect for entertaining, pets, or relaxing in your own private retreat—along with a generous front yard that enhances the home's curb appeal. Turnkey and move-in ready, this exceptional property offers modern island living in one of Oahu's most desirable beach communities.

1225 Mokapu Boulevard, Kailua

$2,300,000

4 Beds ⋅ 3 Baths ⋅ 202611972 MLS ⋅ FS - Fee Simple Tenure ⋅ 49 DOM

Tucked onto one of Kalaheo Hillside's most sought-after streets, 445 Iliwahi Loop is a fully reimagined 4-bed, 3-bath retreat blending timeless island architecture with a clean, considered renovation — vaulted ceilings, an open great room flowing to covered lanais, and walls of glass framing the pool, gardens and fountains. This generous lot sits against the conservation hillside adding to the peace and quiet of this location. The chef's kitchen pairs a Viking range and Sub-Zero refrigeration w/a generous island open to the dining & living areas. Two primary suites suit multigenerational living or a guest wing, the spa-inspired primary bath w/a soaking tub and oversized shower. Two additional bedrooms w/shared bath PLUS 2 office/flex rooms Outside is your own resort: a sparkling pool (plus spa hookup), mature landscaping, a garden gazebo and covered lanai seating for golden-hour gatherings. NEM metering, 2 Tesla Powerwalls, + a new GACO roof! Freshly painted inside & out, new flooring, lighting & fans throughout. Minutes to Kailua Beach, a short hop to Marine Corps Base Hawaii, and moments from H-3, Pali and Likelike — with Aikahi Shopping Center and dining close at hand.

445 Iliwahi Loop, Kailua

Start Your Search

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.