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$2,395,000
4 Beds ⋅ 4 Baths ⋅ 202612015 MLS ⋅ FS - Fee Simple Tenure ⋅ 48 DOM
A brand new roof and now offered at $105,000 below original list price — your opportunity to own in Kailua just got even better! Experience the best of island living in this beautifully upgraded 4-bed/3.5-bath home featuring a legal ADU on a large, custom-landscaped lot (11,353 sq. ft.). This property offers stylish high-end finishes, an open layout, & seamless indoor-outdoor flow. The main house welcomes you with 3 bed/2.5 bathrooms. The chef's kitchen is a true delight, it boasts KraftMaid cabinets, double-wall oven & granite counters. Retreat to the primary suite with its soothing bathroom and walk-in California Closet. The custom-designed legal ADU was thoughtfully crafted with meticulous detail to provide long-term comfort and independence for the owner's parent. The huge outdoor lanai extends this living space & is ideal for extended family, guests, or rental income. Energy efficiency abounds w/ 38 owned PV panels, 2 storage batteries and 2 solar water heaters. Add'l features include a laundry room, split AC's, storage rm, covered parking for a boat, outdoor shower & a fully fenced yard w/an auto. gate for privacy. Wonderful location just min. from world-famous Kailua Beach!

409 Wanaao Road, Kailua
$2,650,000
3 Beds ⋅ 3 Baths ⋅ 202609988 MLS ⋅ FS - Fee Simple Tenure ⋅ 73 DOM
Escape to the tranquility of your private sanctuary, conveniently located within a ten-minute walk from the renowned Kailua Beach. This exquisite residence was meticulously designed for casual island entertaining and seamless indoor-outdoor living. A sparkling pool, a luxurious jacuzzi, & a verdant landscape of mature tropical vegetation create a serene and visually appealing ambiance. Nestled within the picturesque town of Kailua, this property offers unparalleled convenience, with all necessary amenities within a short bicycle ride. The tranquil neighborhood provides a peaceful retreat, while the presence of a thriving lime tree named Eileen adds a touch of local charm. Pau Hana or intimate gatherings with family and friends will create lasting memories. This is the home everyone wants to come to for every occasion! Boasting a spacious yard, expansive pool deck, and an open-floor plan that is aesthetically pleasing and easy to maintain. The apartment can be kept and collected for $2,500+ per month or used as a chic private primary suite…steps to the jacuzzi and pool for midnight swims. Masterful! Hurry over. Owned solar panels, split AC, Gas Cooking, Oversized Garage, Limes!

294 Awakea Road, Kailua
$1,399,000
3 Beds ⋅ 2 Baths ⋅ 202610095 MLS ⋅ FS - Fee Simple Tenure ⋅ 79 DOM
KAILUA BLUFFS. Original owners. Single story home on huge lot with 13,105 sf of land. Tons of potential! Needs TLC and cosmetic upgrades to make it your own. The second and third bedrooms have loft areas that can be utilized for den/study. Covered lanai perfect for outdoor entertaining. Home to be sold in AS-IS Condition.

1595 Kanapuu Drive, Kailua
$3,150,000
6 Beds ⋅ 4 Baths ⋅ 202608800 MLS ⋅ FS - Fee Simple Tenure ⋅ 88 DOM
Now offered at a new price, 244 Awakea Rd. is a beautifully remodeled plantation-style property on a spacious 10,000 sq ft lot, just a short stroll to Kailua Beach and minutes from Kailua Town. Renovated in 2019, this unique property offers three separate living spaces with a combined 6 bedrooms, 4 bathrooms, and approximately 3,150 sqft of living area, ideal for multi-generational living, extended family, or long-term rental income. The main residence features 3 bedrooms, 2 bathrooms plus a den, vaulted ceilings, hardwood flooring, a walk-in pantry, and seamless indoor-outdoor living. The property also includes a spacious 1-bedroom cottage and a separate 2-bedroom, 1-bath ADU. The 1-bedroom cottage and 2-bedroom ADU are currently tenant occupied, generating a combined $7,600 per month in rental income. A dedicated storage/yoga room adds additional flexibility. Priced at $1,000 per sqft, below the recent Kailua Estates average of approximately $1,046 per sqft, 244 Awakea offers an exceptional combination of lifestyle, flexibility, and income potential. Enjoy easy access to Kailua and Lanikai beaches, Kalapawai Market, shopping, dining, and everything Kailua has to offer.

244 Awakea Road, Kailua
$4,098,000
5 Beds ⋅ 4 Baths ⋅ 202608270 MLS ⋅ FS - Fee Simple Tenure ⋅ 102 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
$1,798,000
5 Beds ⋅ 3 Baths ⋅ 202608144 MLS ⋅ FS - Fee Simple Tenure ⋅ 105 DOM
With stunning upgrades in the last year,, this five bedroom home located in Kailua Bluffs has unobstructed views of the Olomana peaks, a private greenbelt backdrop, and no rear neighbors — just mountain, sky, and quiet. Inside, the home has been updated with care: fully renovated kitchen with new cabinets, countertops, appliances, and flooring. Updated bathrooms. New paint, baseboards, and canned lighting and fixtures throughout. New HVAC system with whole-home AC, including a new split system addition. It's move-in ready and thoughtfully done. The layout is flexible — two bedrooms and a full bath on the main level for multi-generational living, guests, or a home office. Soaring ceilings and an open-concept living area flow to a spacious covered patio, making indoor-outdoor living effortless. Outside, a level, private backyard with mature pomelo, avocado, and bilimbi trees. Morning light, evening breeze, and the kind of view you don't get tired of. 49 owned solar panels with two large battery banks keep energy costs low. This is a rare opportunity in one of Kailua's most sought-after neighborhoods.

1614 Paukiki Street, Kailua
$1,498,000
3 Beds ⋅ 3 Baths ⋅ 202607772 MLS ⋅ FS - Fee Simple Tenure ⋅ 107 DOM
Welcome home to this wonderful two story home that features 3 bedrooms and 2 1/2 bathrooms located in the highly desirable Kailua Bluffs neighborhood. Home features an open living area with soaring vaulted ceilings. Large covered patio located in back of home is perfect for BBQ with family and friends. Spacious primary bedroom with en suite bathroom. 2nd, 3rd bedrooms and 2nd bathroom is on the second floor. Half bathroom is located on the 1st floor. Just minutes away from world famous beaches, shops, dining and outdoor adventures. Don't miss this opportunity!

1479 Kanapuu Drive, Kailua
$1,488,000
4 Beds ⋅ 3 Baths ⋅ 202525520 MLS ⋅ FS - Fee Simple Tenure ⋅ 263 DOM
Tucked away in one of Kailua's most sought-after neighborhoods, this spacious 4-bedroom, 3-bathroom home presents a wonderful opportunity to create your dream home. This property features two 8-foot storage containers, a 1,232 sq ft deck with ocean & mountain views, ample parking for up to five cars or a boat, and a unique steel-frame construction with solid Styrofoam walls that deliver insulation, structural stability, and built-in termite resistance. Situated on a generous 9,410-square-foot lot, the property offers plenty of room to relax, entertain, and embrace the Kailua lifestyle. The versatile floor plan lends itself beautifully to multi-generational living or a rental opportunity, providing flexibility to suit your needs. Ideally located just minutes from world-famous Kailua Beach, charming boutiques, and favorite, local restaurants, this property offers the perfect blend of location, potential, and lifestyle. Whether you choose to refresh the current design or reimagine the space entirely, this home invites you to bring your vision to life in one of Oahu's most exceptional communities.

1459 Akamai 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.