Kalaheo Hillside Homes with Cottage Style

Welcome to Kalaheo Hillside, a hidden gem nestled in the heart of Kailua, Oahu. This enchanting neighborhood is renowned for its breathtaking views, lush greenery, and a warm, inviting atmosphere that makes it a perfect place to call home. With its elevated position, residents enjoy stunning panoramas of the Pacific Ocean and the majestic Koolau Mountains, creating a serene backdrop for everyday life.

Kalaheo Hillside is characterized by its charming cottage-style homes, which exude a unique blend of island charm and modern comfort. These delightful abodes often feature open floor plans, cozy living spaces, and beautifully landscaped yards that invite you to enjoy the outdoors. Imagine sipping your morning coffee on a sun-drenched porch or hosting a family barbecue in your private garden—this is the lifestyle that awaits you in Kalaheo Hillside.

The community is not only picturesque but also conveniently located near Kailua's vibrant town center. Residents can easily access an array of boutique shops, local eateries, and stunning beaches, including the famous Kailua and Lanikai beaches, just a short drive away. For those who enjoy an active lifestyle, the neighborhood offers numerous hiking trails, parks, and recreational facilities, ensuring that there is always something to do.

Whether you're looking for a peaceful retreat or a vibrant community, Kalaheo Hillside offers the perfect blend of both. Explore the charm of cottage-style living in this idyllic Hawaiian neighborhood and discover why so many are drawn to call this place home.

Newest Kalaheo Hillside Homes with Cottage Style

$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

3 Beds ⋅ 3 Baths ⋅ 202609716 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! 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. Split ACs in each room. PV panels on net metering.

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.