Kailua Town Homes with Canal Frontage

Welcome to Kailua Town, a hidden gem nestled on the picturesque windward coast of Oahu, Hawaii. Known for its stunning beaches, vibrant community, and lush landscapes, Kailua offers a unique blend of island living and small-town charm. With its laid-back atmosphere, this neighborhood is perfect for families, outdoor enthusiasts, and anyone looking to embrace the beauty of Hawaii’s natural surroundings.

One of the most sought-after features of Kailua Town is its beautiful homes with canal frontage. Imagine waking up each morning to the gentle sound of water lapping against your backyard, with breathtaking views of the lush greenery that surrounds you. These canal-front properties not only provide a serene escape but also offer direct access to kayaking, paddleboarding, and other water activities, making it an ideal spot for those who love the outdoors.

Kailua Town is also known for its vibrant local culture, with a variety of charming shops, cafes, and restaurants that reflect the island's rich heritage. Enjoy a leisurely stroll down Kailua's main street, where you can discover local artisans, indulge in delicious Hawaiian cuisine, or relax at one of the many beachside parks.

With its combination of natural beauty, community spirit, and convenient amenities, Kailua Town is a dream destination for anyone looking to invest in a slice of paradise. Experience the magic of canal-front living in Kailua, where every day feels like a vacation in your own backyard!

Newest Kailua Town Homes with Canal Frontage

$825,000

3 Beds ⋅ 2 Baths ⋅ 202616227 MLS ⋅ FS - Fee Simple Tenure ⋅ 12 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 ⋅ 29 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.