Kailua Homes with Waterfront Frontage

Welcome to Kailua, a breathtaking gem nestled on the eastern coast of Oahu, Hawaii. Known for its stunning beaches and lush landscapes, Kailua is a paradise for those seeking a serene lifestyle infused with the spirit of aloha. With its picturesque views of the Mokulua Islands and the vibrant turquoise waters of the Pacific Ocean, Kailua is not just a place to live; it’s a lifestyle to embrace.

One of the most alluring features of Kailua is its selection of homes with waterfront frontage. Imagine waking up each morning to the gentle sounds of waves lapping against the shore, with the sun rising over the horizon, painting the sky in hues of orange and pink. Waterfront properties in Kailua offer unparalleled access to the beach, making it easy to enjoy a morning swim, an afternoon of paddleboarding, or a sunset stroll along the shoreline.

Kailua is not only about its stunning natural beauty; it also boasts a vibrant community with charming local shops, delightful eateries, and a rich cultural scene. Whether you’re exploring the lush trails of the nearby Olomana Mountains or indulging in a fresh acai bowl at a local café, you’ll find that Kailua offers a perfect blend of adventure and relaxation.

For those seeking a home that harmonizes with nature, Kailua's waterfront properties provide an idyllic setting. With their breathtaking views and easy access to outdoor activities, these homes are truly a slice of paradise. Embrace the Kailua lifestyle, where every day feels like a vacation in your own backyard.

Newest Kailua Homes with Waterfront Frontage

$8,100,000

3 Beds ⋅ 5 Baths ⋅ 202618112 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 DOM

Set along an exceptional stretch of Lanikai beachfront, 914 Mokulua Drive offers direct access to white sand with 75 linear feet of ocean frontage, bordered by naupaka for a natural buffer. The home boasts sweeping views of the Windward coast, encompassing the iconic Mokulua Islands as well as Popoia Island and Mokapu beyond. Inside, the airy great room is designed to breathe, capturing ocean views and towering coconut palms across a lush grassy lawn. Three primary suites, each with an ensuite bath and walk-in closet, offer generous comfort, while a private office with an adjacent half bath provides a quiet workspace or flexible guest room. Beyond the main house, a separate studio cottage with a full bath plus workshop adds ample room to host, create, exercise, or simply spread out. Step outside for a swim, paddle, or a sunset walk, then head into Kailua town in minutes for shopping and restaurants. This is your chance to be part of Lanikai’s world-famous coastline—sun, sand, sea, and island views.

914 Mokulua Drive, Kailua

$15,250,000

5 Beds ⋅ 5 Baths ⋅ 202609183 MLS ⋅ FS - Fee Simple Tenure ⋅ 13 DOM

This exceptional Lanikai beachfront estate features over half an acre of land extending from the street directly to the sand and ocean. Unlike many of the neighboring properties that sit above rock and reef, this home opens directly onto the sandy beach, offering a rare and true beachfront experience with views of the Mokulua Islands. The house is built for how people actually live. Walls of glass retract and disappear, so the kitchen, dining area, pool courtyard, and beach read as one space. The open kitchen is where people gather, sized for a crowd and opening to outdoor dining and the grill. In the ocean, at the pool, or in the cool air inside, you are never closed off from the other areas. The upstairs primary suite was designed to take full advantage of the views from your bed, sitting area, bath or the private ocean-view lanai. This is a property people can grow into and form to their lifestyle. Beyond the lawn you have the Lanikai Pillbox trailhead, Mid Pacific Country Club, and the shops and restaurants of Kailua a short drive away. The ocean is the front yard. Property is offered fully furnished and being sold turnkey.

958 Mokulua Drive, Kailua

$4,900,000

202616097 MLS ⋅ FS - Fee Simple Tenure ⋅ 18 DOM

This rare 27,725 sq. ft. estate property has fabulous mountain views over the wide canal, in a prime Kailua location one street from the beach. Enjoy over 295 ft of direct waterfront canal living! Kayak, SUP right from your yard. The layout gives you incredible flexibility, featuring multiple suites within a spacious compound. The original single-level 3-bedroom/2-bath home opens to a green yard along the waterfront, flanked by two 2-bedroom/1-bath wings with private entrances and ample parking. A breezeway carport connects to another living area with 3 bedrooms/2.5-baths upstairs opening to a gorgeous view lanai. On the ground level is a two-car enclosed garage and workshop plus a 1-bd/1-bath wing. The property has been well-kept and maintained over the years by one family. Everything Kailua has to offer is convenient to this estate including the canal, beach, restaurants and businesses, shopping centers, the Pali and H-3. 117 owned PV panels and EV Charger too! Don’t miss this one-of-a-kind opportunity!

865 N Kalaheo Avenue, Kailua

$4,900,000

11 Beds ⋅ 8 Baths ⋅ 202616094 MLS ⋅ FS - Fee Simple Tenure ⋅ 18 DOM

865 N Kalaheo Avenue, Kailua

$2,250,000

3 Beds ⋅ 2 Baths ⋅ 202617425 MLS ⋅ FS - Fee Simple Tenure ⋅ 18 DOM

Modern Kailua living meets a peaceful natural setting in Enchanted Lake! This beautifully renovated 3-bedroom, 2-bath home features soaring ceilings and an open layout that feels bright, spacious, and inviting. Enjoy new appliances, luxury vinyl flooring, an interior washer and dryer, and split air conditioning in every room. The centerpiece is the expansive 336-square-foot deck overlooking the Enchanted Lake wetlands, an exceptional space for entertaining, outdoor dining, or relaxing while taking in the tranquil surroundings. Move-in ready and designed for effortless indoor-outdoor living.

1166 Akuila Place, Kailua

$2,199,000

3 Beds ⋅ 3 Baths ⋅ 202615714 MLS ⋅ FS - Fee Simple Tenure ⋅ 48 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

$7,805,000

5 Beds ⋅ 4 Baths ⋅ 202613137 MLS ⋅ FS - Fee Simple Tenure ⋅ 89 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 ⋅ 89 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 ⋅ 94 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 ⋅ 95 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 ⋅ 97 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 ⋅ 103 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

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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.