Kailua Town Homes with Canal Frontage

Welcome to Kailua Town, a picturesque gem nestled on the windward coast of Oahu, Hawaii. Known for its stunning beaches and vibrant community, Kailua offers a unique blend of laid-back island living and modern conveniences. The town is characterized by its lush landscapes, charming boutiques, and a plethora of outdoor activities, making it a perfect destination for families, retirees, and anyone seeking a slice of paradise.

One of the standout features of Kailua is its breathtaking canal frontage homes. Imagine waking up to the gentle sound of water lapping against your property and enjoying serene views right from your backyard. These canal-front homes not only provide a tranquil setting but also offer direct access to the waterways, ideal for kayaking, paddleboarding, or simply enjoying a leisurely boat ride. The interconnected canals create a peaceful ambiance and a sense of community among neighbors, fostering a lifestyle that embraces both relaxation and recreation.

In addition to the stunning waterfront properties, Kailua Town boasts a friendly atmosphere with an array of local shops, restaurants, and farmer’s markets, where you can savor fresh produce and artisanal goods. The nearby Kailua Beach Park is a favorite among residents, known for its soft sands and crystal-clear waters, perfect for swimming, sunbathing, and beach volleyball.

Whether you’re drawn to the charm of the town or the allure of canal-side living, Kailua Town offers a captivating lifestyle that truly embodies the spirit of Hawaii. Discover your dream home in this idyllic setting and experience the beauty of island life.

Newest Kailua Town Homes with Canal Frontage

$825,000

3 Beds ⋅ 2 Baths ⋅ 202616227 MLS ⋅ FS - Fee Simple Tenure ⋅ 7 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 ⋅ 24 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.