Kalaheo Hillside Homes with None View

Welcome to Kalaheo Hillside, a hidden gem nestled in the picturesque town of Kailua on the enchanting island of Oahu, Hawaii. This charming neighborhood is renowned for its lush landscapes, serene ambiance, and welcoming community spirit. As you meander through the winding streets, you’ll discover a delightful array of homes that blend seamlessly with the natural beauty of the surroundings.

Kalaheo Hillside offers a unique opportunity for those seeking a tranquil lifestyle without the distractions of ocean views. Here, homes are thoughtfully designed to maximize comfort and functionality, making them perfect for families, retirees, or anyone looking to embrace the laid-back Hawaiian lifestyle. The neighborhood is characterized by its spacious lots, mature trees, and beautifully manicured gardens, creating a peaceful retreat that feels worlds away from the hustle and bustle of city life.

Residents enjoy easy access to Kailua’s vibrant town center, where you can find an eclectic mix of boutiques, cafes, and eateries that showcase the local culture and culinary delights. The nearby beaches, including the famous Kailua Beach and Lanikai Beach, are just a short drive away, offering endless opportunities for sun-soaked days and outdoor adventures.

Kalaheo Hillside is not just a place to live; it’s a community where neighbors become friends and memories are made. Whether you’re sipping coffee on your lanai or enjoying a leisurely stroll through the neighborhood, you’ll quickly fall in love with the charm and warmth that Kalaheo Hillside has to offer. Come explore this delightful enclave and discover your perfect slice of paradise in Hawaii!

Newest Kalaheo Hillside Homes with None View

$1,690,000

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

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

Listing courtesy of SC Realty, LLC.

$1,590,000

3 Beds ⋅ 2 Baths ⋅ 202614057 MLS ⋅ FS - Fee Simple Tenure

Welcome home to this spacious three-bedroom, two-bathroom residence in the highly sought-after Kalaheo Hillside. Freshly painted along with other upgrades throughout, this Kailua home offers a seamless blend of modern comfort and island charm. The open-concept interior is designed for indoor-outdoor living, leading you towards the large, flat fully-enclosed backyard oasis framed by lush tropical landscaping—a perfect backdrop for weekend gatherings or quiet afternoons in the sun. Situated just a short walk Castles Beach and the convenience of Aikahi Shopping Center, this location puts everything Kailua has to offer at your fingertips. Located within the Aikahi school district and just minutes to the vibrant dining and boutique shopping of Kailua town, this property captures the relaxed, active lifestyle you’ve been looking for.

923 Mokapu Boulevard, Kailua

Listing courtesy of Compass.

$1,875,000

202610580 MLS ⋅ FS - Fee Simple Tenure

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

Listing courtesy of Homes of Hawai'i Real Estate.

$1,875,000

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

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

Listing courtesy of Homes of Hawai'i Real Estate.

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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.