Kailua Homes with Waterfront Frontage

Kailua Homes with Waterfront Frontage

Welcome to Kailua, a picturesque gem nestled on the windward coast of Oahu, Hawaii. Known for its stunning beaches, lush landscapes, and vibrant community, Kailua offers a unique blend of tranquility and adventure that captivates both residents and visitors alike. With the majestic Ko'olau Mountains as a backdrop and the azure waters of the Pacific Ocean at your doorstep, this idyllic town is a paradise for outdoor enthusiasts, families, and anyone seeking a slice of Hawaiian living.

Kailua's waterfront properties are among the most sought-after in the region, boasting breathtaking views and direct access to some of the most beautiful beaches in Hawaii. Imagine waking up to the sound of gentle waves lapping at the shore, with the sun rising over the horizon, painting the sky in hues of orange and pink. Homes with waterfront frontage in Kailua provide not just a residence, but a lifestyle—where morning swims, sunset strolls, and beach bonfires become part of your daily routine.

In addition to its natural beauty, Kailua is home to a vibrant local culture, featuring charming boutiques, delightful eateries, and a strong sense of community. The town's commitment to preserving its natural environment means that residents can enjoy a laid-back, eco-friendly lifestyle, all while being just a short drive from the bustling heart of Honolulu.

Whether you’re looking for a serene retreat or an active lifestyle, Kailua’s waterfront homes offer the perfect blend of comfort and adventure. Embrace the allure of island living and discover your dream home in this enchanting coastal paradise!

Newest Kailua Homes with Waterfront Frontage

$11,980,000
5 Beds ⋅ 5 Baths ⋅ 202613970 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Carvill Sotheby's Intl. Realty.

$3,400,000
4 Beds ⋅ 3 Baths ⋅ 202613350 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of eXp Realty.

$7,880,000
5 Beds ⋅ 4 Baths ⋅ 202613137 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of eXp Realty.

$2,625,000
5 Beds ⋅ 5 Baths ⋅ 202612304 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Arquette Properties Inc.

$4,695,000
4 Beds ⋅ 3 Baths ⋅ 202612376 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Hawaii Life.

$3,750,000
5 Beds ⋅ 4 Baths ⋅ 202612388 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of LUVA Real Estate.

$7,888,000
4 Beds ⋅ 4 Baths ⋅ 202612440 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Hawaii Modern Realty.

$7,745,000
4 Beds ⋅ 4 Baths ⋅ 202611655 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of eXp Realty.

$6,998,000
4 Beds ⋅ 5 Baths ⋅ 202610714 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Corcoran Pacific Properties.

$725,000
202610606 MLS ⋅ FS - Fee Simple Tenure
Build your Kailua dream home in a private, peaceful valley setting with 98' of canal frontage and unobstructed views of the Majestic Ko'olaus. Unit 2 of the Kihapai Ohana Residential CPR offers ~5,000 sq ft of private land in the serene Maunawili Valley, on one of the last remaining unbuilt parcels in Kailua. The property lives larger thanks to adjacent City & County buffer land along the waterway, enhancing privacy and connection to nature - you've got to visit and experience for yourself. Set back from the street for privacy yet conveniently located for construction, the lot allows creative site planning and potential two-lot assemblage (1+2 or 2+3). Utilities are nearby, and as one of the first two homes built, Unit 2 is fully SMA-exempt, streamlining permitting. Units 1, 2, and 3 may be purchased individually or together, offering a rare opportunity to live in a private, nature-filled landscape with the timeless spirit of Hawaii.

221 Kihapai Street Unit 2, Kailua

Listing courtesy of Hawaii Life.

$5,280,000
3 Beds ⋅ 2 Baths ⋅ 202610235 MLS ⋅ FS - Fee Simple Tenure ⋅ 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

Listing courtesy of Coldwell Banker Island Prop.

$17,500,000
4 Beds ⋅ 5 Baths ⋅ 202609316 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Coldwell Banker Realty.

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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.