Kalaheo Hillside Homes with Carport Parking Features

Welcome to Kalaheo Hillside, a hidden gem nestled in the heart of Kailua, Oahu. This enchanting neighborhood is renowned for its breathtaking views, lush landscapes, and a welcoming community spirit that makes it a perfect place to call home. With its gentle breezes and tropical ambiance, Kalaheo Hillside offers a serene escape while still being conveniently close to the vibrant amenities of Kailua town.

The homes in Kalaheo Hillside are a delightful blend of modern comfort and island charm. Many properties feature carport parking, providing convenience and protection for your vehicle from the elements. This thoughtful design element adds to the ease of living in this picturesque locale, allowing you to enjoy your home without the hassle of street parking.

As you explore the neighborhood, you'll find a variety of outdoor activities at your fingertips. From stunning beaches to hiking trails, Kalaheo Hillside is a paradise for nature lovers and adventure enthusiasts alike. The nearby Kailua Beach is perfect for sunbathing, paddleboarding, and swimming, while the lush hiking paths of the Ko’olau Mountains offer breathtaking vistas and invigorating experiences.

In addition to its natural beauty, Kalaheo Hillside boasts a close-knit community, with friendly neighbors and local events that foster connections. Whether you're enjoying a quiet evening on your porch or mingling at a neighborhood gathering, you'll feel right at home in this idyllic setting.

Discover the charm of Kalaheo Hillside, where the beauty of Hawaii meets the comfort of community living. Your dream home awaits in this enchanting neighborhood!

Newest Kalaheo Hillside Homes with Carport 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

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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.