Kalaheo Hillside Homes with Other Community Features

Welcome to Kalaheo Hillside, a hidden gem nestled in the picturesque town of Kailua on the enchanting island of Oahu, Hawaii. This delightful neighborhood is known for its stunning views, lush greenery, and a sense of community that makes it a perfect place to call home. With its elevated position, Kalaheo Hillside offers breathtaking panoramic vistas of the surrounding mountains and the sparkling Pacific Ocean, creating a serene backdrop for everyday living.

The homes in Kalaheo Hillside are as diverse as the residents who inhabit them, ranging from charming single-family homes to modern architectural masterpieces. Each property is designed to maximize the natural beauty of the area, often featuring spacious yards, tropical landscaping, and outdoor living spaces that invite you to soak in the island sunshine. Many homes also boast energy-efficient features and smart home technology, catering to the eco-conscious homeowner.

Beyond the stunning residences, Kalaheo Hillside is a community that thrives on connection. Residents enjoy easy access to nearby parks, hiking trails, and pristine beaches, making it an ideal location for outdoor enthusiasts and families alike. The vibrant Kailua town center is just a short drive away, offering a delightful mix of local boutiques, cafes, and restaurants that celebrate the island's rich culture.

In Kalaheo Hillside, you’re not just buying a home; you’re investing in a lifestyle. Embrace the tranquility of island living while enjoying the warmth of a close-knit community. Discover your dream home in this enchanting neighborhood, where every day feels like a vacation in paradise.

Newest Kalaheo Hillside Homes with Other Community 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

$1,875,000

202610580 MLS ⋅ FS - Fee Simple Tenure ⋅ 74 DOM

Nestled within one of Kailua’s favorite neighborhoods, Kalaheo Hillside, 315 Iliaina Street is filled with potential and island charm. The property includes two separate structures --- a cute, detached cottage studio with a full bath and kitchenette, plus a classic home offering 3 bedrooms, 2 full baths, a great open floor plan, and a separate dining area with large windows looking out to the backyard. Much of the home remains in its original condition, including beautiful koa kitchen cabinet doors that could shine again with restoration. The spacious yard features a large in-ground pool and plenty of room to reimagine the outdoor spaces! Split ACs in each room. Owned PV panels with net metering. Just minutes from Aikahi Shopping Center, Aikahi Elementary School, Kailua’s beaches, shopping, dining opportunities, markets, and so much more! Also close to MCBH Kaneohe, H-3, and Likelike Highway access, this property combines location, flexibility, and opportunity in one of Kailua’s most convenient neighborhoods. (Also listed as MLS#202609716)

315 Iliaina Street, 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.