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485 Wanaao Road, Kailua
$3,775,000
5 Beds ⋅ 4 Baths ⋅ 202608270 MLS ⋅ FS - Fee Simple Tenure ⋅ 105 DOM
Set along the coveted waterfront canal of Kailua, this iconic property 485 Wanaao, captures the essence of modern island living with rare versatility & timeless appeal. Situated on a generous lot, the residence offers a seamless blend of indoor-outdoor living, framed by tranquil water views & lush surroundings. The main home features 4 bedrooms & 2.5 bathrooms, thoughtfully designed with soaring ceilings, & a spacious open-concept layout that fills the interior with natural light & refreshing trade winds. Clean lines, modern finishes, & refined craftsmanship create an inviting yet sophisticated atmosphere, perfect for both everyday living & entertaining. The fully legal 1-bedroom, 1-bath ADU—ideal for guests, extended family, or rental income—adding exceptional flexibility to this already remarkable offering. Expansive outdoor spaces invite you to unwind, host gatherings & enjoy peaceful waterfront setting. This home delivers a lifestyle that is both rare and deeply connected to its surroundings. Minutes from Kailua's beaches, dining and shopping. A true once-in-a-lifetime opportunity to own a signature property in one of O‘ahu’s most desirable coastal communities.

485 Wanaao Road, Kailua
337 Wanaao Road, Kailua
$3,675,000
6 Beds ⋅ 6 Baths ⋅ 202606058 MLS ⋅ FS - Fee Simple Tenure ⋅ 112 DOM
Unique home in the heart of Kailua, this beautifully remodeled luxury residence is a rare blend of striking architectural design & authentic Hawaiian charm. Thoughtfully crafted with rich lava rock accents & natural textures throughout, the home offers a warm, elevated island lifestyle that feels both refined & relaxed. The main residence features 5 spacious bedrooms & 4 bathrooms, showcasing beautiful finishes, open-concept living, & seamless indoor-outdoor flow. The chefs kitchen is a dream with a large butlers pantry. Step outside to your private oasis—an exceptional pool with a cascading waterfall & built-in jacuzzi surrounded with beautiful landscaping, creates a tranquil paradise perfect for unwinding or entertaining. The expansive covered outdoor area is designed for gathering, complete with space to barbecue, relax & even enjoy your own red light sauna. The property also includes an approved 1-bedroom, 1-bath ADU, ideal for multigenerational living, guest accommodations, or potential rental income. Whether you’re hosting unforgettable evenings under the stars or enjoying peaceful mornings surrounded by island beauty, this home captures the essence of luxury Hawaii living.

337 Wanaao Road, Kailua
126 Mahealani Place, Kailua
$2,480,000
3 Beds ⋅ 2 Baths ⋅ 202609351 MLS ⋅ FS - Fee Simple Tenure ⋅ 34 DOM
Tucked away in one of Kailua’s most desirable beachside enclaves, this 3-bed, 2-bath residence offers the rare combination of private resort-style living and effortless access to world-famous Kailua Beach. Open the back gate and enjoy a leisurely stroll to turquoise waters, powder-soft sand, and the laid-back luxury lifestyle that defines Kailua living. Designed with indoor-outdoor entertaining in mind, the home centers around a sparkling in-ground pool surrounded by a generous lounge area that creates the feel of a private tropical retreat. Inside, the residence features a bright, functional layout with thoughtful updates throughout. New windows invite natural light and garden views into the living spaces. Set within a quiet, well-kept neighborhood, the home offers a peaceful residential feel while remaining just moments from some of Kailua’s favorite local destinations such as Kalapawai Market and Island Snow for shave ice, smoothies, açaí bowls and more. Whether you envision mornings spent paddleboarding at the beach, afternoons lounging poolside in private, or evenings entertaining under the stars, this exceptional Kailua property captures the essence of elevated island living.

126 Mahealani Place, Kailua
214 Kakahiaka Street, Kailua
$2,125,000
4 Beds ⋅ 2 Baths ⋅ 202605694 MLS ⋅ FS - Fee Simple Tenure ⋅ 49 DOM
Nestled in one of Kailua’s most sought-after neighborhoods, this exceptional 4-bedroom, 2-bath residence sits on over 10,000 sq ft of land and offers the perfect blend of island elegance and everyday comfort—just moments from the beach. Thoughtfully updated, the home features a beautifully renovated kitchen with sleek quartz countertops and newly remodeled bathrooms designed with modern style in mind. Skylights throughout the home invite an abundance of natural light, creating a bright and airy ambiance. A separate living room offers a welcoming space for quiet relaxation, while the expansive family room opens seamlessly to a level, enclosed yard—ideal for entertaining, outdoor dining, and enjoying Kailua’s indoor-outdoor lifestyle. With generous space, tasteful upgrades, and an unbeatable location near the beach, this home is a rare opportunity to experience the very best of island​​‌​​​​‌​‌​​​​‌‌​​‌‌​‌‌​​‌​​​‌​‌ living.

214 Kakahiaka Street, Kailua
279 Kakahiaka Street, Kailua
$2,500,000
4 Beds ⋅ 3 Baths ⋅ 202519934 MLS ⋅ FS - Fee Simple Tenure ⋅ 51 DOM
Welcome to your Kailua retreat! This rarely available canal-front property offers a perfect blend of comfort, privacy, and island lifestyle. Located along a wide section of Ka'elepulu Stream with the 5th hole of Mid-Pacific Country Club just across the canal, the setting is truly picturesque. Start your morning with welcoming sunrises and enjoy beautiful views throughout the day. The home is single-level and thoughtfully updated with new luxury vinyl plank flooring in three bedrooms and baths and fresh interior and exterior paint. Energy efficiency is enhanced by 21 PV panels (leased) with net metering and a solar water heater. A flag driveway provides quiet seclusion, opening to beautiful grassy yards and a private boat dock for water fun. Relax or entertain on the spacious covered lanai designed for year-round enjoyment. All of this just minutes from world-famous Kailua Beach and the shopping and dining of Kailua Town. Homes on the canal side are a rare find--don't miss this opportunity to make it yours!

279 Kakahiaka Street, Kailua

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.