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$17,500,000
4 Beds 5 Baths 202609316 MLS FS - Fee Simple Tenure 92 DOM
Experience tranquil beachfront living in one of the most pristine areas along Kailua Beach, featuring stunning ocean views from the modern kitchen, spacious living room, and primary bedroom with a private oceanfront deck. Recent renovations include stylish baths that enhance the contemporary vibe. The custom kitchen flows into a welcoming dining area, ideal for gatherings and entertaining. A cozy cottage offers guest privacy, while ample parking and a three-car garage provide convenience. A dedicated office with courtyard access creates a peaceful workspace. Enjoy the lagoon pool and waterfall spa, with the beach just steps away for swimming, paddleboarding, or relaxing. Minutes from Kailua Beach Park, Mid-Pac Country Club, and Kailua Town, this home combines luxury and convenience. Your dream island lifestyle awaits!

200 S Kalaheo Avenue, Kailua

$3,150,000
6 Beds 4 Baths 202608800 MLS FS - Fee Simple Tenure 92 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

$2,700,000
5 Beds 3 Baths 202606811 MLS FS - Fee Simple Tenure 99 DOM
Steps away from turquoise water and the best strip of sandy beach for miles, nestled between Kailua and Lanikai beaches, this classic Hawaiian style home has high ceilings, an open concept layout, and offers the perfect balance of privacy and effortless indoor-outdoor living. Open wood beam ceilings, and windows galore allow natural light and views that bring the outdoors in, perfectly framing a backdrop connected to nature. The spacious living area flows seamlessly to 2 covered lanais, both with ceiling fans and lighting, perfect for entertaining or relaxing. The kitchen features wood cabinetry, large island, bar seating, new appliances, and warm finishes that complement the island aesthetic. It’s a retreat designed with both style and ease in mind, while the surrounding landscape creates a peaceful, resort-like setting. Minutes from famous beaches, parks, and charming shops and cafes of Kailua, this home delivers a lifestyle of morning beach walks, sunset paddles, and the quiet luxury of island living. The main home is spacious with 3 beds and 2 baths. Enjoy a separate, private entry, 800+sf garage converted rec area, with wet bar, full bath, and 2nd laundry. Must see!

151 Alala Road, Kailua

$649,000
2 Beds 2 Baths 202605842 MLS FS - Fee Simple Tenure 140 DOM Windward Passage BLDG.
Enjoy island living in this beautifully situated 2-bedroom, 2-bath condo in the heart of Kailua. Offering 956 sq ft of interior space plus a generous 92 sq ft lanai, this residence features floor-to-ceiling windows that fill the home with natural light and capture an indoor-outdoor lifestyle. The well-maintained, pet-friendly building offers a full suite of amenities including a pool, fitness center, tennis courts, storage, bike and surf racks, on-site manager, security, and fire sprinklers. Added convenience with in-unit washer/dryer. Ideally located just minutes from shopping, dining, and world-famous beaches, this is an exceptional opportunity to enjoy the best of Kailua living.

322 Aoloa Street Unit 309, Kailua

$3,880,000
3 Beds 3 Baths 202605289 MLS FS - Fee Simple Tenure 146 DOM
Your dream waterfront Kailua residence. This hidden jewel fronting Kawainui Canal with access to the ocean offers an exceptional blend of contemporary design and Kama‘aina elegance. Architecturally designed and tastefully refreshed, this 3 bdrm, 2.5 ba residence with 3,291 sq ft of living space offers vaulted ceilings (which elevate the sense of space and natural light), fresh interior/exterior paint, vinyl plank flooring, new carpet, and an open chef’s kitchen featuring custom cabinetry, quartz countertops, and a spacious 10’ island. An expansive primary suite overlooks the pool deck with canal and majestic Ko’olau Mountain views. Designed for effortless indoor/outdoor living, there are multiple lanais along with a swimming pool—ideal for entertaining and everyday relaxation. Lush landscaping on the 14,866 sq ft lot enhances the already tranquil setting. The cul-de-sac location maximizes the already private location. An owned photovoltaic system with a net metering agreement adds energy efficiency. Just minutes from Kailua’s beaches, shopping, and dining, this home offers elevated island living in one of Oahu’s most desirable neighborhoods.

1110 Ilikala Place, Kailua

$2,495,000
9 Beds 4 Baths 202605514 MLS FS - Fee Simple Tenure 151 DOM
Elegant 5-year-old home offering exceptional investment potential and flexible multigenerational living. This spacious property features a two-level main home with an attached ADU, a 2-car garage, and parking for up to 9 cars. Currently operated as a 30–90 day rental. The private ADU includes a full kitchen and living/dining area—ideal for rental income or extended family. The main home offers separate living spaces on each level. Upstairs includes the primary kitchen, great room, 2 lanais, and 4 bedrooms/2 baths (one used as an office). Downstairs features a family room with dining area, kitchenette, 3 bedrooms/1 bath, and 2 small yards with a covered lanai. The ohana provides additional privacy with its own full kitchen, great room, 2 bedrooms/1 bath, and a fenced yard. All rooms offer split A/C, ceiling fans, and large windows for natural light and breezes. Three private living areas, each with separate entrances and laundry. Fully furnished, turnkey, with five years of strong rental history. Please do not disturb tenants.

451 Lanae Way, Kailua

$4,350,000
6 Beds 4 Baths 202525771 MLS FS - Fee Simple Tenure 160 DOM
Discover the perfect blend of lifestyle, comfort, and value at 1251 Kainui Drive—an exceptional canal-front retreat situated along an established, palm tree-lined street in North Kailua. Fully renovated in 2026 & move-in ready, the spacious single-level main residence offers 4 beds, 3 baths, and over 3000 SF of beautifully designed living space with soaring ceilings, high-end finishes, and an effortless flow. New standing seam roof, net-metered PV & split AC. The kitchen is the heart of the home, featuring a grand island and luxurious, durable Taj Mahal quartzite countertops, ceiling-high cabinetry, premium appliances, a butler’s pantry, dedicated dining area and a charming breakfast nook. Covered and open lanais connect the living areas to landscaped grounds and a peaceful canal with ocean access—perfect for paddling from your backyard. Room to build your dream pool! A dedicated laundry room, 2-car garage, & ample storage provide everyday ease. The 2-bed, 1-bath ADU adds ~800 SF for multi-generational living, guests or rental flexibility. This desirable location is just two blocks from the beach and provides easy access to Kailua Town, top schools, and freeways for easy commuting.

1251 Kainui Drive, Kailua

$650,000
2 Beds 2 Baths 202601936 MLS FS - Fee Simple Tenure 192 DOM Meridian East BLDG.
Discover a premier opportunity to own one of the few condos in Kailua Town offering true 180-degree OCEAN VISTAS. This freshly painted unit features modern light fixtures, cool tile floors and an unbeatable location close to world-famous Kailua Beach The vibrant shops and restaurants of downtown Kailua are right out your door. Enjoy unmatched convenience with Kailua District Park—featuring tennis, pickleball, a skate park and an Olympic-sized pool—only one block away. Within the building, you'll find a welcoming community complete with a lush herb garden, saltwater pool, and a covered area for social gatherings on the recreation deck. Includes a premium parking spot located directly next to the elevator for effortless access and in the gated garage you'll find bike and surfboard storage for your convenience.

14 Aulike Street Unit 904, Kailua

$695,000
2 Beds 2 Baths 202600370 MLS FS - Fee Simple Tenure 214 DOM Poinciana Manor BLDG.
Discover island living in this beautifully maintained 2 bdrm/2 bath condo at desirable Poinciana Manor in Kailua. Offering 959 sq ft of interior living space, this residence features fresh interior paint, a contemporary kitchen with stainless steel appliances, and a spacious lanai ideal for relaxing or entertaining. Enjoy the convenience of 2 covered parking stalls and a thoughtfully designed layout. Poinciana Manor offers amazing amenities including a swimming pool, BBQ area, recreation space, and an on-site resident manager. Ideally located near Kailua’s popular restaurants, shopping, and world-famous beaches, this condo combines comfort, convenience, and an exceptional lifestyle opportunity.

1015 Aoloa Place Unit 217, Kailua

$4,250,000
4 Beds 4 Baths 202527969 MLS FS - Fee Simple Tenure 241 DOM
This stunning home is ready for you to live the ultimate Hawaii paradise lifestyle in the gorgeous community of Lanikai. Do not miss the opportunity to reside in this impeccable custom-built 4 bedroom 3.5 bathroom beauty! Built brand new and finished in 2018, the upper level showcases a chef’s kitchen and an open-concept living space that seamlessly extends to a spacious lanai, offering breathtaking ocean views—ideal for hosting or simply unwinding. This home features not one, but two luxurious primary suites, each with spa-inspired bathrooms and soaring windows that flood the space with natural light. High-quality materials were used, including marble countertops and gorgeous Walnut hardwood and Travertine floors throughout. The best part is that you’re just a short five-minute stroll from the pristine sands of both Kailua Beach and Lanikai Beach!

851 Aalapapa Drive, Kailua

$4,150,000
4 Beds 4 Baths 202525307 MLS FS - Fee Simple Tenure 273 DOM
Don't miss the best value in Lanikai! Experience elevated island living in this fully renovated Lanikai retreat where luxury, privacy, and the natural beauty of Hawaii come together. Just 2 blocks from a secluded beach cove and a short paddle to the Mokulua Islands, this thoughtfully designed property captures the laid-back yet refined Lanikai lifestyle. Enter through a landscaped courtyard into a 3-bed, 3-bath main home featuring two spacious primary suites, customizable closets, and 1000+sf of open-air lanais that make indoor-outdoor living effortless. High ceilings, large sliding doors, hardwood floors, large-format tile, and custom cabinetry reflect quality at every turn. The kitchen features a generous island, sunlit dining nook, and designer finishes ideal for casual meals or entertaining. Surrounded by mature landscaping, the property offers room for a pool in either the front courtyard or the large, level backyard. A detached 1-bed, 1-bath suite with wet bar, laundry, and 1000+sf lanai above the 2-car garage offers versatility for guests or rental income—while preserving privacy for the main residence. This is a must-see property to truly appreciate the beauty and value.

223 Lanipo Drive, Kailua

$18,880,000
12 Beds 16 Baths 202520168 MLS FS - Fee Simple Tenure 333 DOM
Welcome to this exceptional Kailua beachfront estate. This gated resort-like retreat is situated on nearly an acre of land fronting one of the most beautiful beaches in the world. With over 14,000 sq ft of sophisticated living space, the main residence is a masterpiece of design featuring a luxurious, expansive primary suite with panoramic ocean views, and an additional 9 bedrooms-each boasting a private en-suite bathroom, a spacious gym/recreation room, 2 additional full bathrooms, and 2 powder rooms. Designed to entertain in style, this private tropical oasis is complete with an outdoor pavilion and full wet bar just steps away from a pristine pool, spa, and wading pool all set within beautifully manicured landscaping. A charming, detached 2-bedroom, 2-bathroom guest quarters and three-car garage further complement this magnificent property. Just beyond your backyard, a white sandy beach and the sparkling blue Pacific Ocean, ideal for swimming, ocean sports, or peaceful strolls. Embrace this once-in-a-lifetime opportunity to own this prime oceanfront property.

572C N Kalaheo Avenue, 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.