Kailua Homes with Canal Frontage

Welcome to Kailua, a serene paradise nestled on the eastern coast of Oahu, Hawaii. Known for its stunning beaches, lush landscapes, and vibrant community, Kailua offers a unique blend of natural beauty and laid-back island living. With its picturesque views of the Ko'olau Mountains and the sparkling turquoise waters of the Pacific Ocean, Kailua is a haven for outdoor enthusiasts and those seeking a tranquil lifestyle.

One of the most enchanting features of this region is the availability of homes with canal frontage. These properties provide a rare opportunity to enjoy the soothing sounds of water and the gentle breeze that flows through the canals, enhancing the island experience. Imagine waking up to the sight of kayakers gliding by or enjoying a peaceful evening on your deck, watching the sunset reflect on the water's surface. Canal-front homes in Kailua are not just residences; they are gateways to a lifestyle rich in adventure and relaxation.

The community of Kailua is also known for its vibrant local culture, with charming boutiques, delightful eateries, and a strong sense of camaraderie among residents. Whether you’re exploring the stunning beaches of Lanikai or savoring a delicious meal at a local café, Kailua offers a perfect blend of leisure and recreation.

If you're considering a move to this idyllic area, homes with canal frontage in Kailua represent an unparalleled opportunity to embrace the beauty and tranquility of island life. Welcome to your dream home in Kailua, where every day feels like a vacation!

Newest Kailua Homes with Canal Frontage

$399,500

1 Beds ⋅ 1 Baths ⋅ 202614348 MLS ⋅ FS - Fee Simple Tenure ⋅ 3 DOM ⋅ 75 Kihapai BLDG.

Welcome home! Conveniently located one bedroom, one bath condo walking distance to Kailua town's shops and restaurants, and a few minutes bike ride or drive to beautiful Kailua Beach. The condo is move in ready, newly painted with new refrigerator, range, kitchen counters, and mirror closet doors. Other amenities include tile floors, a gated lanai, window a/c in the bedroom, plus hook-ups for a washer and dryer. This unit has easy access to the assigned parking stall and pool on the ground floor. Enjoy a swim in the condo pool while you watch the wildlife of Kawainui Marsh. Come make 75 Kihapai Street unit 5 your new home!

75 Kihapai Street Unit 5, Kailua

$1,350,000

4 Beds ⋅ 2 Baths ⋅ 202609502 MLS ⋅ FS - Fee Simple Tenure ⋅ 21 DOM

Wake up to stunning, unobstructed views of the majestic Olomana mountain range from this property brimming with potential. This home presents a rare opportunity to renovate, restore, or create a space tailored to your vision in one of Kailua's most desirable locations. Featuring a flexible floor plan and ample outdoor space, this property is ready for its next chapter. Whether you're looking to undertake a full renovation or make improvements over time, the possibilities are endless. Enjoy convenient access to shopping, dining, beaches, parks, and the scenic Kawainui Marsh Trail, offering opportunities to experience one of O?ahu's most unique natural landscapes. The property is being sold in its present condition. Interior square footage may differ from tax records. Buyers are strongly encouraged to perform their own due diligence regarding the property's condition, improvements, permits, square footage, and all other material facts they deem important to their purchase.

319 Kihapai Street Unit C, Kailua

$2,625,000

5 Beds ⋅ 5 Baths ⋅ 202612304 MLS ⋅ FS - Fee Simple Tenure ⋅ 23 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

$749,000

3 Beds ⋅ 2 Baths ⋅ 202611171 MLS ⋅ FS - Fee Simple Tenure ⋅ 44 DOM

Contractor special and Exceptional opportunity in the heart of Waimanalo! Set on a 6,777 sq ft lot with a tiny association fee, this attached single family home is ready for a buyer to create something special, whether it's a complete renovation or brand-new custom residence, the possibilities are plentiful. The existing structure was originally configured as a 3 bedroom, 1 1/2 bath home, and is in need of significant repairs. Additions have been made over the years, including a large living room plus a covered deck and another attached room on the backside. There is a new roof and gutters were added on the front portion of the home, but the property had extensive water damage from the Kona Low storm. Offered strictly As Is, Where Is, and with all its contents, it is priced less than current land value. This property is best suited for investors, builders, contractors, or buyers seeking a project. Enjoy the beauty and charm of Waimanalo, with its world-famous beaches, and the majestic Ko'olau mountain range in the background.

41-569 Inoaole Street, Waimanalo

$725,000

202610595 MLS ⋅ FS - Fee Simple Tenure ⋅ 59 DOM

Great New Price, now listed at $725,000. 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

$735,000

202610597 MLS ⋅ FS - Fee Simple Tenure ⋅ 59 DOM

Set within a truly magical and serene setting, Unit 3 of the Kihapai Ohana CPR Development comes with a fully approved DPP building permit for a 1,607 sq ft 4bd/2ba home with carport and covered lanai, and spectacular panoramic Ko'olau views from every bedroom. With 120' of canal frontage and direct access to the Maunawili Stream, Unit 3 lives larger with the huge City & County land buffer zone creating a rare sense of privacy and connection to nature - you've got to visit and experience it for yourself. Enjoy kayaking or paddleboarding along the gentle waterways, or simply relax while surrounded by lush greenery and dramatic mountain vistas. A full construction cost breakdown, utility trenching estimates, and site development details have been prepared by a licensed contractor who is ready to build upon close, or you can bring your own builder. All details are included in the due-diligence packet. Units 1, 2, and 3 may be purchased individually or together.

221 Kihapai Street Unit 3, Kailua

$725,000

202610604 MLS ⋅ FS - Fee Simple Tenure ⋅ 59 DOM ⋅ Na BLDG.

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

$725,000

202610606 MLS ⋅ FS - Fee Simple Tenure ⋅ 59 DOM

221 Kihapai Street Unit 2, Kailua

$4,098,000

5 Beds ⋅ 4 Baths ⋅ 202608270 MLS ⋅ FS - Fee Simple Tenure ⋅ 94 DOM

Set along the coveted waterfront canal of Kailua, this iconic property 485 Wanaao, captures the essence of modern island living with rare versatility & timeless appeal. Situated on a generous lot, the residence offers a seamless blend of indoor-outdoor living, framed by tranquil water views & lush surroundings. The main home features 4 bedrooms & 2.5 bathrooms, thoughtfully designed with soaring ceilings, & a spacious open-concept layout that fills the interior with natural light & refreshing trade winds. Clean lines, modern finishes, & refined craftsmanship create an inviting yet sophisticated atmosphere, perfect for both everyday living & entertaining. The fully legal 1-bedroom, 1-bath ADU—ideal for guests, extended family, or rental income—adding exceptional flexibility to this already remarkable offering. Expansive outdoor spaces invite you to unwind, host gatherings & enjoy peaceful waterfront setting. This home delivers a lifestyle that is both rare and deeply connected to its surroundings. Minutes from Kailua's beaches, dining and shopping. A true once-in-a-lifetime opportunity to own a signature property in one of O‘ahu’s most desirable coastal communities.

485 Wanaao Road, Kailua

$412,500

1 Beds ⋅ 1 Baths ⋅ 202606606 MLS ⋅ FS - Fee Simple Tenure ⋅ 120 DOM ⋅ 75 Kihapai BLDG.

Recently renovated, this one-bedroom single level unit on the ground floor features a covered lanai that is gated for privacy and includes one designated parking spot. In addition to a new split AC, flooring, kitchen countertops and cabinets, bathroom shower and shelving, during the renovation the water lines and vent/sewer stacks were upgraded. PLUS it has an exterior storage unit in the backyard along with a clothesline and washing machine. Enjoy the trade wind breezes and natural lighting. Stay cool in the Saltwater pool on hot summer days. Furnishings included. Tenant would like to stay on. VA Approved.

75 Kihapai Street Unit 3, Kailua

$3,880,000

3 Beds ⋅ 3 Baths ⋅ 202605289 MLS ⋅ FS - Fee Simple Tenure ⋅ 134 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 ⋅ 148 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

Start Your Search

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.