Kailua Homes with Waterfront Frontage

Welcome to Kailua, Hawaii – a hidden gem nestled on the windward coast of Oahu. Known for its stunning beaches, lush landscapes, and vibrant community, Kailua offers a unique blend of island living and the comforts of home. With its breathtaking views of the Pacific Ocean and the majestic Ko'olau Mountains, this enchanting town is a paradise for those seeking a serene lifestyle.

One of the most alluring features of Kailua is its waterfront properties. Imagine waking up to the soothing sounds of the waves and the gentle ocean breeze, all from the comfort of your own home. The homes with waterfront frontage in Kailua provide not just a residence, but a lifestyle marked by tranquility and natural beauty. These properties often boast expansive views, private beach access, and outdoor spaces perfect for entertaining or simply enjoying the sunset.

Kailua is also rich in outdoor activities. Residents can indulge in kayaking, paddleboarding, or simply lounging on the pristine sands of Kailua Beach and Lanikai Beach. The nearby hiking trails offer breathtaking vistas and a chance to immerse oneself in Hawaii’s unique flora and fauna.

The community spirit in Kailua is palpable, with local farmers' markets, boutique shops, and a variety of dining options that celebrate the island's culinary diversity. Whether you’re looking for a family home, a vacation retreat, or an investment opportunity, Kailua’s waterfront properties are an invitation to experience the best of island living. Discover your slice of paradise in Kailua today!

Newest Kailua Homes with Waterfront Frontage

$2,199,000

3 Beds ⋅ 3 Baths ⋅ 202615714 MLS ⋅ FS - Fee Simple Tenure ⋅ 26 DOM

Beautiful, sweeping views of Enchanted Lake and Kaelepulu wetlands from your elegantly remodeled open concept living, dining, & gourmet kitchen. Large glass doors open onto your huge covered deck surrounded by lush lakefront lawns, perfect for indoor/outdoor entertaining, or quiet rest. Contemporary, easy care plank ceramic tile flows throughout the home. The high performance kitchen design and quality appliances are a chef’s delight. Featuring a ground floor bedroom and full bath, a large upstairs primary suite with a huge walk-in closet and resort style bath with dual rain showers, split system and recessed ceiling ACs, an oversized garage with high ceilings and plenty of storage, an owned Photovoltaic system, and more! Fully fenced, attractively landscaped, and just a block to desirable Kaelepulu elementary school and park. Easy access to Kailua town’s vibrant fine dining, entertainment, and shopping district. Assumable VA loan at 2.25% interest with substitution of eligibility. A rare chance for waterfront living so call for your private showing today.

445 Keolu Drive, Kailua

$7,855,000

5 Beds ⋅ 4 Baths ⋅ 202613137 MLS ⋅ FS - Fee Simple Tenure ⋅ 67 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 ⋅ 67 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

$4,200,000

4 Beds ⋅ 3 Baths ⋅ 202612376 MLS ⋅ FS - Fee Simple Tenure ⋅ 72 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

$3,550,000

5 Beds ⋅ 4 Baths ⋅ 202612388 MLS ⋅ FS - Fee Simple Tenure ⋅ 73 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 ⋅ 75 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

$7,495,000

4 Beds ⋅ 4 Baths ⋅ 202611655 MLS ⋅ FS - Fee Simple Tenure ⋅ 81 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

$6,998,000

4 Beds ⋅ 5 Baths ⋅ 202610714 MLS ⋅ FS - Fee Simple Tenure ⋅ 102 DOM

Nestled along one of Oahu’s most coveted stretches of coastline, this exceptional beachfront residence offers a rare combination of privacy, space, and direct access to a secluded sandy beach. Enjoy breathtaking sunrise/moonrise views, "Rabbit Island", Makapuu Lighthouse, and the "Mokes", with the majestic Koolau Mountains providing a dramatic backdrop. Spanning nearly 5,000 square feet of interior living space, the home features 4 bedrooms, a large office, and 5 full bathrooms. An attached guest suite with 2 bedrooms and 2 full bathrooms provides outstanding flexibility for extended family, guests, or a private retreat. Designed to embrace Hawaii’s indoor-outdoor lifestyle, the property offers generous living spaces, abundant natural light, and a tranquil setting. Enjoy the serenity of a private beachfront enclave while remaining conveniently connected, with multiple routes providing easy access to Kailua, Hawaii Kai, Waikiki, and Honolulu International Airport. Whether entertaining, hosting family and friends, or simply enjoying the peaceful rhythm of the ocean, this rare offering delivers the privacy, convenience, and lifestyle of Hawaii beachfront living at its finest.

41-459 Kalanianaole Highway, Waimanalo

$5,280,000

3 Beds ⋅ 2 Baths ⋅ 202610235 MLS ⋅ FS - Fee Simple Tenure ⋅ 108 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 ⋅ 124 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

$4,350,000

6 Beds ⋅ 4 Baths ⋅ 202525771 MLS ⋅ FS - Fee Simple Tenure ⋅ 192 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

$24,900,000

10 Beds ⋅ 9 Baths ⋅ 202525519 MLS ⋅ FS - Fee Simple Tenure ⋅ 302 DOM

Live among Hawaii's natural wonders & unsurpassed beauty at this extraordinary Pahonu Beach estate. Spanning nearly 1 acre, this oceanfront property includes 152 linear feet along the Pacific Ocean. Nestled in a private, gated location, the 2 lot compound offers over 8600 sq ft of living area in its main house, guest house, cottage, and studio. Expansive lawns provide mesmerizing views across the ocean to Manama (Rabbit) Island and stunning vistas of the Koolau Mountains. The main house completed in 2022, sets a new standard of quality craftsmanship. Exceptional design, flawlessly executed using premium materials, creates a luxurious, beautiful, and comfortable home. Floor to ceiling sliding glass doors span the oceanfront side, providing spectacular views of the lush landscaping and ocean. The gourmet kitchen includes top of the line appliances, custom walnut cabinetry, and a disappearing pantry consistent with its sleek, modern design. Next door includes a 3BR oceanfront guest house, 2BR cottage and studio. This irreplaceable compound offers its next owner an opportunity to enjoy a spectacular lifestyle with family and friends in a magnificent oceanfront setting.

41-471 Kalanianaole Highway, Waimanalo

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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.