Kailua Homes with Waterfront Frontage

Welcome to Kailua, a picturesque gem nestled on the eastern coast of Oahu, Hawaii. Known for its stunning beaches, vibrant community, and lush landscapes, Kailua is the perfect blend of island charm and modern living. With its crystal-clear waters and breathtaking mountain backdrops, this charming town offers an idyllic lifestyle that many dream of.

Kailua is renowned for its pristine beaches, including the famous Kailua Beach Park and Lanikai Beach, both of which are just a stone's throw away from the residential areas. The soft, powdery sands and turquoise waters create a paradise for water enthusiasts, offering activities such as kayaking, paddleboarding, and snorkeling. The warm, inviting climate allows residents to enjoy outdoor adventures year-round, making it an ideal location for families and nature lovers alike.

One of the most alluring aspects of Kailua is its waterfront properties. Homes with waterfront frontage provide unparalleled access to the ocean, allowing you to wake up to the soothing sounds of waves and breathtaking sunrises. Imagine sipping your morning coffee while watching the surf or hosting sunset gatherings on your private lanai. These homes not only offer stunning views but also a lifestyle that embraces the beauty of island living.

Kailua’s close-knit community is filled with local shops, farmers' markets, and delightful eateries, providing a vibrant atmosphere that fosters a sense of belonging. With its rich cultural heritage and commitment to preserving the natural environment, Kailua is not just a place to live—it's a lifestyle. Discover your dream home in this enchanting coastal town and experience the magic of Kailua for yourself!

Newest Kailua Homes with Waterfront Frontage

$11,980,000

5 Beds ⋅ 5 Baths ⋅ 202613970 MLS ⋅ FS - Fee Simple Tenure ⋅ 22 DOM

Completed in 2022, this classic beachfront home was redesigned into a spacious, modern property. 21 Kalaka's unique elevation offers commanding views and privacy; features true beachfront connoisseurs will value. Built by Mokulua High-Performance Builder, it delivers a sleek, elegant take on beachside living. The central open living area flows naturally to the ocean and pool, surrounded by five bedrooms (four en suite) plus a pool room. A breakfast bar and separate guest wing provide privacy and space for extended family. Exceptional craftsmanship, premium materials, and a refined floor plan make this property Kailua Beachfront’s most comprehensive offering.

21 Kalaka Place, Kailua

$3,400,000

4 Beds ⋅ 3 Baths ⋅ 202613350 MLS ⋅ FS - Fee Simple Tenure ⋅ 32 DOM

Who's ready for NEW? Rarely available, fully renovated waterfront retreat on Enchanted Lake with panoramic 180-degree lake and mountain views. All permits are closed for peace of mind. Launch your kayak from your own backyard and experience the ultimate island lifestyle. Situated on a fully fenced 10,400 sq. ft. lot, this exceptional home offers 4 bedrooms and 3 bathrooms with a versatile floor plan that lives as a 3-bedroom, 2-bath main residence plus a separate 1-bedroom, 1-bath living space. Rebuilt from the studs with new electrical, copper plumbing, two new sewer lines, insulation, Level 5 drywall, windows, doors, vaulted ceilings, luxury wide-plank flooring, custom tile finishes in all baths, and Mitsubishi split A/C throughout. The chef's kitchen features custom KraftMaid cabinetry, a walk-in pantry, and premium Thermador appliances. Outside, enjoy a new pool with dual water features, a 60+ ft. covered stamped concrete lanai, bamboo outdoor shower, lush tropical landscaping, in-ground irrigation, 18 owned PV panels, and easy access to Kailua Town, world-famous beaches, shopping, dining, parks, and schools. Live, Love, Lake Life!

1247 Kahili Street, Kailua

$7,880,000

5 Beds ⋅ 4 Baths ⋅ 202613137 MLS ⋅ FS - Fee Simple Tenure ⋅ 35 DOM

Experience one-of-a-kind oceanfront living in the heart of Lanikai. Nestled along the shoreline in one of Hawai?i's most coveted neighborhoods, this private tropical retreat captures sweeping Pacific Ocean views and offers inviting spaces designed for relaxed island living and effortless entertaining. Enjoy days by the pool, host gatherings on the spacious covered lanai, and take in the cooling trade winds, gentle surf, and frequent visits from sea turtles. The home captures sweeping Pacific Ocean views from nearly every room, with an open floor plan that maximizes natural light and creates a strong connection to the oceanfront setting. Upstairs, four vaulted-ceiling bedrooms provide comfortable retreats, including a primary suite where expansive windows frame beautiful sunrise views. A wraparound lanai extends the living space, with additional bedrooms also enjoying tranquil ocean vistas. Ideally situated just half a block from the white sands of Lanikai Beach, one block from Kailua Beach, and two blocks from Mid-Pacific Country Club, this waterfront home combines privacy, breathtaking scenery, and an unparalleled location to create the ultimate island lifestyle.

846 Mokulua Drive, Kailua

$2,500,000

5 Beds ⋅ 5 Baths ⋅ 202612304 MLS ⋅ FS - Fee Simple Tenure ⋅ 35 DOM

Rare opportunity to own a canal front home on a nearly 10,000 sq. ft. R-5 zoned lot with a legal ‘ohana unit, each with its own utility meters, complete with pool & spa. Tucked along the peaceful cul-de-sac end of Kainui Drive, locally known as “Duck Road.” The spacious single-level main home features three generously sized bedrooms with new carpeting, three bathrooms, a dedicated study and bright living and dining areas that flow seamlessly into an enclosed lanai. A large recreation room or studio complete with a kitchenette, bathroom, private entrance, and its own courtyard provides additional flexibility for guests, home office or extended family. Upstairs, the 800 sq ft 'ohana unit (823 Kainui Dr) features two bedrooms, one bathroom, and a covered lanai. Recent upgrades include a new roof on the main home and a freshly re-plastered pool. Take in stunning sunsets over the Ko'olau Mountains from the multiple outdoor areas, relax in the pool and spa, or enjoy a paddle or boat out to Kailua Bay. This unique property offers flexibility and is ideal for multigenerational living, generating rental income, or both. The possibilities are truly endless.

821 Kainui Drive, Kailua

$4,695,000

4 Beds ⋅ 3 Baths ⋅ 202612376 MLS ⋅ FS - Fee Simple Tenure ⋅ 40 DOM

Wake up to the sound of waves and the sun rising over the Pacific Ocean at this Kaimalino oceanfront retreat in Kailua. This plantation-style home with wraparound decks offers daily views of marine life and panoramic views of Kailua Bay, the Mokulua Islands, and the majestic Ko'olau Mountains. This custom-designed home was built in 1987 and has been well maintained by one owner. The four bedroom layout w/ three baths welcomes family & friends in comfort and features a bedroom/bath on the main level, 75-ft. saltwater lap pool with heated tiled spa, remodeled kitchen (2021), double-sided fireplace, 'ohi'a wood floors, plantation shutters, photovoltaic and roof (2013), gutters (2025), laundry room with utility sink. Custom wood finishes and cabinets throughout include koa, teak, cherry. Enjoy the beauty of an oceanfront setting where every day feels like a vacation with ever-changing seascapes, full moons, whale watching, and more. Sought-after Kaimalino neighborhood features underground utilities and is just minutes from Kailua Town, world-famous Kailua Beach, and nearby Turtle Beach (Baby Beach), with convenient access for kayaking and stand-up paddleboarding.

586 Kaimalino Street, Kailua

$3,750,000

5 Beds ⋅ 4 Baths ⋅ 202612388 MLS ⋅ FS - Fee Simple Tenure ⋅ 41 DOM

Set along the peaceful shoreline of a tranquil lake, this stunning five-bedroom, four-bathroom residence offers a lifestyle where every day starts and ends with views that feel like a getaway. From the moment you step inside, you'll appreciate the thoughtfully designed layout, where spacious living areas flow effortlessly together for both everyday comfort and entertaining. All rooms are very generous in size on the main level and upstairs you will find a spacious studio with a wrap-around lanai that creates endless possibilities. Outside, the magic continues - imagine spending sunny afternoons relaxing beside the sparkling pool, hosting unforgettable gatherings with the lake as your backdrop, or simply unwinding as gentle Hawaiian breezes ripple across the water. Perfectly positioned in an exceptional location, this is more than a beautiful home—it's a place where memories are made and every day feels just a little more extraordinary.

802 Pahumele Place, Kailua

$7,888,000

4 Beds ⋅ 4 Baths ⋅ 202612440 MLS ⋅ FS - Fee Simple Tenure ⋅ 43 DOM

Oceanfront elegance awaits in this exceptional Kaimalino residence, perfectly positioned to capture panoramic views of Kailua Bay, the Mokulua Islands, and the majestic Ko'olau Mountains. This stunning 4-bedroom, 3.5-bath home welcomes you with breathtaking ocean vistas from the living room, dining room, and kitchen, all flowing seamlessly to an expansive lanai and lush backyard that’s ideal for entertaining family and friends, enjoying time with pets, or simply relaxing while taking in spectacular sunrises and sunsets over one of Oahu's most coveted waterfront locations. Upstairs, the spacious primary suite features breathtaking ocean and mountain views, an ensuite bath, walk-in closet, and shared lanai with one of the additional bedrooms, perfect as a guest room or home office. Two more spacious bedrooms complete the upper level, including one with its own ensuite bath and walk-in closet, offering comfort and privacy for family or guests. Located in the highly desirable Kaimalino neighborhood, this prestigious low-key enclave offers stunning coastal scenery and is minutes from the heart of Kailua Town with its renowned beaches, boutiques, cafés, and restaurants.

611 Kaimalino Place, Kailua

$7,745,000

4 Beds ⋅ 4 Baths ⋅ 202611655 MLS ⋅ FS - Fee Simple Tenure ⋅ 49 DOM

Set on the oceanfront along the coveted Mokulua Drive in Lanikai, this timeless island retreat captures the charm and spirit of old Hawai‘i. Nestled at the peaceful end of Lanikai, the property enjoys sweeping views of the Mokulua Islands and unforgettable sunrise panoramas across the turquoise waters. Rich in character, the classic mid-century residence has been thoughtfully updated while preserving its authentic beach-house feel. The main home offers 3 bedrooms and 2.5 baths, complemented by a separate 1-bedroom, 1-bath cottage, perfect for guests or extended family. Designed for effortless indoor-outdoor living, the home opens to a world where the ocean is your backyard. Spend your days snorkeling, kayaking, canoeing, windsurfing, foiling, or fishing just steps from your back door. Surrounded by Lanikai’s powder-soft white sands, gentle trade winds, and crystal-clear waters, this special property offers a rare glimpse of Hawai‘i as it once was. Stroll or bike the neighborhood loop, greet friendly neighbors, and embrace a slower pace of life. A truly rare opportunity to own a piece of Lanikai’s cherished oceanfront legacy, where every day feels like a return to paradise.

1414 Mokulua Drive, Kailua

$5,280,000

3 Beds ⋅ 2 Baths ⋅ 202610235 MLS ⋅ FS - Fee Simple Tenure ⋅ 76 DOM ⋅ Kamaaina Beach BLDG.

KAILUA BEACH is Absolutely one of the most BREATHTAKING beachfront neighborhoods on Oahu and this property doesn't disappoint! Nestled among the palm trees with direct beach frontage, this charming 1950's cottage harkens back to a slower time in the Islands. Expansive front lawn leads to a Powder White Sand Beach with gentle rolling waves suitable for all ages. Perfect location to build a dream home, restore the existing structure or simply slow down and enjoy the property. Kama'aina Beach CPR. Sold with contents and strictly As-Is. A Rare Beachfront find at this price.

140C N Kalaheo Avenue, Kailua

$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

$3,880,000

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

$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

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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.