Kailua Homes with Canal Frontage

Welcome to Kailua, a picturesque town nestled on the eastern coast of Oahu, Hawaii. Renowned for its stunning beaches, lush landscapes, and vibrant community, Kailua offers a unique blend of island charm and modern living. With the majestic Ko'olau Mountains as a backdrop and the sparkling waters of the Pacific Ocean at your doorstep, it's no wonder that Kailua is often considered one of the most desirable places to call home in Hawaii.

One of the standout features of Kailua is its enchanting homes with canal frontage. Imagine waking up to the gentle sounds of water lapping against your private dock, the sun glistening off the surface as you sip your morning coffee. Canal-front properties in Kailua provide not just a beautiful view, but also a lifestyle that embraces outdoor living. Kayaking, paddleboarding, and fishing become part of your daily routine, allowing you to fully immerse yourself in the natural beauty that surrounds you.

The community of Kailua is known for its friendly atmosphere and a strong sense of belonging. With a charming downtown area filled with local shops, cafes, and restaurants, residents enjoy a laid-back lifestyle that fosters connection and camaraderie. From the pristine shores of Lanikai Beach to the vibrant parks and hiking trails, Kailua offers endless opportunities for adventure and relaxation.

Whether you're seeking a serene retreat or an active lifestyle, Kailua's canal-front homes provide the perfect backdrop for your Hawaiian dream. Discover the magic of Kailua and make it your home today!

Newest Kailua Homes with Canal Frontage

$1,350,000

4 Beds ⋅ 2 Baths ⋅ 202609502 MLS ⋅ FS - Fee Simple Tenure ⋅ 18 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 ⋅ 20 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 ⋅ 41 DOM

Contractor special and Exceptional opportunity in the heart of Waimanalo! Duplex that could be separated. 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 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 ⋅ 56 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 ⋅ 56 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 ⋅ 56 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 ⋅ 56 DOM

221 Kihapai Street Unit 2, Kailua

$4,098,000

5 Beds ⋅ 4 Baths ⋅ 202608270 MLS ⋅ FS - Fee Simple Tenure ⋅ 91 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 ⋅ 117 DOM ⋅ 75 Kihapai BLDG.

Centrally located in Kailua town 75 Kihapai #3 is the lowest priced Fee Simple unit in Kailua. Stay cool in the Saltwater Pool adjacent to the Kawainui canal. Recently renovated, this one-bedroom single level unit features a covered lanai that is gated for privacy and includes one designated parking spot. PLUS it has an exterior storage unit in the backyard along with a clothes line and covered private washing machine. Enjoy the tradewind breezes, natural lighting and the spit AC on hot summer days. 100% Hurricane Insured. 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 ⋅ 131 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 ⋅ 145 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

$895,000

202528531 MLS ⋅ FS - Fee Simple Tenure ⋅ 203 DOM

Owner financing considered. Paradise found. Estate-sized lot in private community of Maunawili Summit in Kailua. Stunning Ocean, Olomana Mountain, Golf Course, and Koolau views. Mesmerizing stargazing & moon viewing at night. The only remaining Lot available in the Maunawili Summit Development. All other lots have been taken. Act now! Tranquil & quiet, with no neighbors, mountainside of the project. Located behind a private gated entry on Lopaka Way. Centrally located with short drive to beaches and downtown Honolulu. A general contractor available to consult with. Mixed zoned lot. See photos for architectural renderings & schematics for a sample home, as well as Seller’s Explanation and Disclaimer in the attached Supplements.

Lopaka Way Unit 1, 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.