Kailua Town Homes with Canal Frontage

Welcome to Kailua Town, a picturesque gem nestled on the eastern coast of Oahu, Hawaii. Known for its stunning beaches, lush landscapes, and vibrant community, Kailua offers a unique blend of tranquility and adventure that attracts residents and visitors alike. With its laid-back atmosphere, this charming town is perfect for those seeking a slice of paradise.

Kailua Town is renowned for its breathtaking natural beauty, featuring the iconic Lanikai Beach and the crystal-clear waters of Kailua Bay. Residents enjoy a variety of outdoor activities, from kayaking and paddleboarding to hiking the nearby Olomana Trail, which offers panoramic views of the island. The town also boasts a thriving local scene, with an array of boutique shops, delightful cafés, and farm-to-table restaurants that celebrate the flavors of Hawaii.

For those seeking a home with a unique waterfront experience, Kailua Town offers an impressive selection of canal-front properties. Imagine waking up to the gentle sounds of water lapping at your doorstep, with easy access to the serene canals that wind through the neighborhood. These homes provide an idyllic setting for boating enthusiasts and nature lovers alike, allowing residents to enjoy kayaking or paddleboarding right from their own backyard.

Kailua’s strong sense of community is evident in its numerous local events and festivals, making it a wonderful place to call home. Whether you're looking for a family-friendly environment or a peaceful retreat, Kailua Town's canal-front properties offer an exceptional lifestyle in one of Hawaii’s most sought-after locales. Embrace the charm of Kailua and discover the perfect place to create lasting memories in this tropical paradise.

Newest Kailua Town Homes with Canal Frontage

$825,000

3 Beds ⋅ 2 Baths ⋅ 202616227 MLS ⋅ FS - Fee Simple Tenure ⋅ 9 DOM ⋅ Windward Harbour BLDG.

Experience the best of island living at Windward Harbour in the heart of Kailua. Perfectly located within walking distance from shopping, restaurants, farmers markets, and the world-renowned Kailua and Lanikai beaches, this spacious ground-floor 3-bedroom, 2-bath residence offers the ideal blend of comfort and convenience. The open-concept floor plan provides a welcoming space for living and entertaining, while newly refinished bamboo flooring and fresh interior paint create a bright, move-in-ready feel. The bedrooms feature built-in closets and the floor-to-ceiling windows fill the home with natural light while showcasing peaceful garden views from your private lanai. Windward Harbour is a secure, pet-friendly community featuring resort-style amenities, including a swimming pool, hot tub, sauna, tennis courts, ping-pong, BBQ areas, a recreation room, and a dog run. Enjoy the perfect balance of tranquil living and easy access to everything Kailua has to offer.

1030 Aoloa Place Unit 5105B, Kailua

$895,000

3 Beds ⋅ 2 Baths ⋅ 202615666 MLS ⋅ FS - Fee Simple Tenure ⋅ 26 DOM ⋅ Windward Cove BLDG.

Welcome to this beautifully renovated 3 bedroom/2 bath residence at Windward Cove, a gated community in the heart of Kailua that’s surrounded by koi ponds, lush landscaping and tranquil water features. Inside, you’ll find a fully upgraded kitchen with waterfall quartz countertops and appliances, new primary bath vanity, new split AC’s, fresh interior paint and luxury vinyl floors throughout. Expansive floor-to-ceiling windows fill the unit with natural light and peaceful garden views, creating the feeling of living in your own private tropical retreat. This top floor unit also comes with a spacious private rooftop balcony with beautiful Koolau mountain and treetop views, perfect for relaxing and entertaining. Set on 3 acres of tropical grounds, Windward Cove offers resort-style amenities including a swimming pool, hot tub, sauna, tennis and pickleball courts, pool, barbeque areas, bike and surfboard racks and a private storage locker. Located minutes away from world-famous Kailua beach and popular restaurants, come see what makes this complex in Kailua so special. 2 photos are virtually staged(enhanced).

1020 Aoloa Place Unit 404A, 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.