Kailua Estates Real Estate

Welcome to Kailua Estates, a hidden gem nestled on the picturesque windward coast of Oahu, Hawaii. This charming neighborhood is renowned for its stunning natural beauty, friendly community spirit, and a lifestyle that embodies the essence of island living.

Kailua Estates boasts a unique blend of lush landscapes and serene beaches, making it an ideal haven for families, retirees, and anyone seeking a tranquil escape. The area is characterized by its spacious homes, many of which feature breathtaking views of the majestic Ko'olau Mountains and the sparkling turquoise waters of Kailua Bay. With tree-lined streets and well-maintained parks, Kailua Estates offers a peaceful atmosphere that invites leisurely strolls and outdoor activities.

The neighborhood is conveniently located just a short drive from Kailua Town, where residents can enjoy a vibrant selection of local shops, cafes, and restaurants. From artisanal coffee to fresh seafood, the culinary scene here is as diverse as it is delicious. For those who love the great outdoors, Kailua is famous for its stunning beaches, including the iconic Lanikai Beach, known for its soft, white sands and crystal-clear waters perfect for swimming, kayaking, and paddleboarding.

Community events and a strong sense of togetherness are hallmarks of Kailua Estates. Whether it’s a neighborhood potluck, a beach cleanup, or a local farmers' market, there’s always something happening that brings residents together.

Experience the charm of Kailua Estates, where the beauty of nature meets the warmth of community, creating a truly idyllic place to call home.

Newest Listings in Kailua Estates

$2,395,000

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

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

Listing courtesy of Compass.

$2,650,000

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

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

Listing courtesy of Compass.

$3,150,000

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

Rarely available in Kailua Estates, 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 to Kailua Town. Fully renovated in 2019, the property offers approximately 3,150 sq ft of total living space with a versatile multi-dwelling layout ideal for investors, multi-generational living, or those seeking flexible income potential. The main home features 3 bedrooms, 2 bathrooms plus a den, with vaulted ceilings, hardwood flooring, a walk-in pantry, and seamless indoor-outdoor living. In addition, the property includes a spacious 1-bedroom cottage with high ceilings and a separate 2-bedroom, 1-bath ADU, both beautifully designed and tenant occupied with strong income potential. A dedicated storage and yoga room adds additional flexibility for wellness, workspace, or lifestyle use. Located in one of Kailua’s most desirable beachside neighborhoods, enjoy easy access to Kailua and Lanikai beaches, Kalapawai Market, and local shops and dining. A rare opportunity to own a flexible compound in a prime location offering both lifestyle and income potential.

244 Awakea Road, Kailua

Listing courtesy of Compass.

$4,098,000

5 Beds ⋅ 4 Baths ⋅ 202608270 MLS ⋅ FS - Fee Simple Tenure

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

Listing courtesy of Corcoran Pacific Properties.

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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.