Kalaheo Hillside Homes with Steep Slope Lot Features

Welcome to Kalaheo Hillside, a picturesque neighborhood nestled in the heart of Kailua, Oahu. Known for its breathtaking views and serene ambiance, this charming community offers a unique blend of natural beauty and suburban tranquility. Surrounded by lush greenery and the majestic Ko’olau Mountains, Kalaheo Hillside is a paradise for outdoor enthusiasts and those seeking a peaceful retreat from the hustle and bustle of city life.

One of the standout features of this neighborhood is its homes with steep slope lot characteristics. These properties not only provide stunning panoramic vistas of the ocean and mountains but also create an inviting atmosphere that encourages outdoor living. Picture yourself sipping your morning coffee on a spacious deck, surrounded by the gentle sounds of nature, or hosting a sunset barbecue with friends while taking in the mesmerizing views that only Kalaheo Hillside can offer.

The community is also conveniently located near Kailua’s vibrant town center, where you can explore a variety of local shops, restaurants, and cafes, as well as the pristine beaches that Oahu is famous for. Whether you’re into hiking, surfing, or simply enjoying a leisurely stroll along the shore, this neighborhood has something for everyone.

Kalaheo Hillside is not just a place to live; it’s a lifestyle. With its unique homes and stunning landscapes, you’ll find yourself captivated by the charm and warmth that this community exudes. Come discover your dream home in this idyllic slice of paradise!

Newest Kalaheo Hillside Homes with Steep Slope Lot Features

$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.