Kailua Estates Real Estate

Welcome to Kailua Estates, a hidden gem nestled in the heart of Kailua, Hawaii, on the enchanting island of Oahu. This picturesque neighborhood is renowned for its lush landscapes, stunning beaches, and a vibrant community that embodies the spirit of Aloha.

Kailua Estates offers a unique blend of tranquility and adventure, making it the perfect place for families, retirees, and anyone seeking a serene lifestyle. The area is characterized by its charming single-family homes, many of which feature spacious yards and breathtaking views of the majestic Ko'olau Mountains. The architecture reflects a delightful mix of modern designs and classic Hawaiian styles, creating a warm and inviting atmosphere.

Residents of Kailua Estates enjoy easy access to some of the island's most beautiful beaches, including the famous Kailua Beach and Lanikai Beach, both just a short drive away. These pristine shores are perfect for sunbathing, swimming, and a variety of water sports, making it a paradise for outdoor enthusiasts. The neighborhood is also home to lush parks, scenic hiking trails, and a plethora of local shops and restaurants, ensuring that all your needs are just around the corner.

Kailua Estates is not just a place to live; it's a community where neighbors become friends. With an active community association and regular local events, residents can easily connect and enjoy the vibrant culture that Kailua has to offer. From farmers' markets to art festivals, there’s always something happening in this lively neighborhood.

Discover the charm of Kailua Estates, where island living meets a close-knit community, and every day feels like a vacation. Come see for yourself why this enchanting neighborhood is the perfect place to call home!

Newest Listings in Kailua Estates

$2,395,000

4 Beds ⋅ 4 Baths ⋅ 202612015 MLS ⋅ FS - Fee Simple Tenure ⋅ 59 DOM

A brand new roof and now offered at $105,000 below original list price — your opportunity to own in Kailua just got even better! Experience the best of island living in this beautifully upgraded 4-bed/3.5-bath home featuring a legal ADU on a large, custom-landscaped lot (11,353 sq. ft.). This property offers stylish high-end finishes, an open layout, & seamless indoor-outdoor flow. The main house welcomes you with 3 bed/2.5 bathrooms. The chef's kitchen is a true delight, it boasts KraftMaid cabinets, double-wall oven & granite counters. Retreat to the primary suite with its soothing bathroom and walk-in California Closet. The custom-designed legal ADU was thoughtfully crafted with meticulous detail to provide long-term comfort and independence for the owner's parent. The huge outdoor lanai extends this living space & is ideal for extended family, guests, or rental income. Energy efficiency abounds w/ 38 owned PV panels, 2 storage batteries and 2 solar water heaters. Add'l features include a laundry room, split AC's, storage rm, covered parking for a boat, outdoor shower & a fully fenced yard w/an auto. gate for privacy. Wonderful location just min. from world-famous Kailua Beach!

409 Wanaao Road, Kailua

$2,650,000

3 Beds ⋅ 3 Baths ⋅ 202609988 MLS ⋅ FS - Fee Simple Tenure ⋅ 84 DOM

Escape to the tranquility of your private sanctuary, conveniently located within a ten-minute walk from the renowned Kailua Beach. This exquisite residence was meticulously designed for casual island entertaining and seamless indoor-outdoor living. A sparkling pool, a luxurious jacuzzi, & a verdant landscape of mature tropical vegetation create a serene and visually appealing ambiance. Nestled within the picturesque town of Kailua, this property offers unparalleled convenience, with all necessary amenities within a short bicycle ride. The tranquil neighborhood provides a peaceful retreat, while the presence of a thriving lime tree named Eileen adds a touch of local charm. Pau Hana or intimate gatherings with family and friends will create lasting memories. This is the home everyone wants to come to for every occasion! Boasting a spacious yard, expansive pool deck, and an open-floor plan that is aesthetically pleasing and easy to maintain. The apartment can be kept and collected for $2,500+ per month or used as a chic private primary suite…steps to the jacuzzi and pool for midnight swims. Masterful! Hurry over. Owned solar panels, split AC, Gas Cooking, Oversized Garage, Limes!

294 Awakea Road, Kailua

$3,150,000

6 Beds ⋅ 4 Baths ⋅ 202608800 MLS ⋅ FS - Fee Simple Tenure ⋅ 99 DOM

Now offered at a new price, 244 Awakea Rd. is a beautifully remodeled plantation-style property on a spacious 10,000 sq ft lot, just a short stroll to Kailua Beach and minutes from Kailua Town. Renovated in 2019, this unique property offers three separate living spaces with a combined 6 bedrooms, 4 bathrooms, and approximately 3,150 sqft of living area, ideal for multi-generational living, extended family, or long-term rental income. The main residence features 3 bedrooms, 2 bathrooms plus a den, vaulted ceilings, hardwood flooring, a walk-in pantry, and seamless indoor-outdoor living. The property also includes a spacious 1-bedroom cottage and a separate 2-bedroom, 1-bath ADU. The 1-bedroom cottage and 2-bedroom ADU are currently tenant occupied, generating a combined $7,600 per month in rental income. A dedicated storage/yoga room adds additional flexibility. Priced at $1,000 per sqft, below the recent Kailua Estates average of approximately $1,046 per sqft, 244 Awakea offers an exceptional combination of lifestyle, flexibility, and income potential. Enjoy easy access to Kailua and Lanikai beaches, Kalapawai Market, shopping, dining, and everything Kailua has to offer.

244 Awakea Road, 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.