Kalaheo Hillside Homes under $2 million

Welcome to Kalaheo Hillside, a hidden gem nestled in the picturesque town of Kailua on the beautiful island of Oahu, Hawaii. This charming neighborhood is renowned for its stunning views, lush landscapes, and a warm sense of community that makes it an ideal place to call home. With its elevated position, Kalaheo Hillside offers breathtaking vistas of the surrounding mountains and the sparkling waters of Kailua Bay, making every sunrise and sunset a mesmerizing experience.

The neighborhood boasts a diverse selection of homes, many of which are available for under $2 million. These properties range from cozy single-family homes to spacious multi-level residences, providing ample options for families, retirees, and everyone in between. Each home reflects the island's unique architectural style, often featuring open floor plans, large windows, and outdoor living spaces that seamlessly blend indoor and outdoor life.

Kalaheo Hillside is not just about beautiful homes; it is also about the vibrant lifestyle that comes with living in Kailua. Residents enjoy easy access to pristine beaches, lush hiking trails, and an array of local shops and restaurants that showcase the island's rich culture. The community is also known for its excellent schools and family-friendly atmosphere, making it a perfect choice for those looking to settle down in paradise.

Whether you’re seeking a tranquil retreat or an active lifestyle, Kalaheo Hillside offers the best of both worlds. Discover your dream home in this enchanting neighborhood, where the beauty of Hawaii awaits you!

Newest Kalaheo Hillside Homes under $2 million

$1,595,000

3 Beds ⋅ 2 Baths ⋅ 202616142 MLS ⋅ FS - Fee Simple Tenure ⋅ 38 DOM

E komo mai to this charming home in one of Kailua's most sought after neighborhoods with less than a mile walk to beautiful Castles Beach! Located on a quiet street in the award winning Aikahi school district. Recently repainted interior & new luxury vinyl flooring in all bedrooms. This lovely home is single level with open floor plan, light and bright and plenty of privacy. Indoor/outdoor living with huge lanai area and pool perfect for social gatherings and Ohana get-togethers. Move right in or have a blank canvas ready for the most discerning buyer's upgrades, with plenty of room for expansion. Enclosed, private and large rear yard with swimming pool that is regularly serviced and cleaned. There is also a separate fenced area ideal for the pups. Close to all that Kailua has to offer. Seller will consider Seller Credit towards Buyer's Closing Costs and/or Interest Rate Reduction! Home Sweet Home Hawaii. Love where you live!

453 Iliaina Street, Kailua

$1,580,000

4 Beds ⋅ 3 Baths ⋅ 202614340 MLS ⋅ FS - Fee Simple Tenure ⋅ 72 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

$1,725,000

202610580 MLS ⋅ FS - Fee Simple Tenure ⋅ 129 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

$1,725,000

3 Beds ⋅ 3 Baths ⋅ 202609716 MLS ⋅ FS - Fee Simple Tenure ⋅ 129 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.