Kailua Estates Homes with Fee Simple Land tenure

Welcome to Kailua Estates, a picturesque neighborhood nestled in the heart of Kailua, Hawaii, on the stunning island of Oahu. Known for its breathtaking beaches and lush landscapes, Kailua Estates offers a perfect blend of tranquility and vibrant island life. This charming community is not just a place to live; it's a lifestyle that embraces the beauty of nature and the warmth of Hawaiian culture.

Kailua Estates boasts a variety of well-designed homes, many of which come with Fee Simple land tenure. This means that homeowners have full ownership of both their property and the land it sits on, providing a sense of security and permanence that is highly sought after in today’s real estate market. Imagine waking up each morning in your own slice of paradise, surrounded by swaying palm trees and the soothing sound of ocean waves.

The neighborhood is conveniently located just a short distance from Kailua's famous beaches, including the stunning Lanikai Beach, known for its turquoise waters and powdery white sand. Residents enjoy easy access to local shops, cafes, and restaurants, offering a taste of the vibrant community spirit that Kailua is known for. Outdoor enthusiasts will revel in the numerous hiking trails and parks nearby, perfect for weekend adventures or leisurely strolls.

Whether you are looking for a family home, a vacation retreat, or an investment property, Kailua Estates provides a unique opportunity to experience the best of island living. Embrace the aloha spirit and make Kailua Estates your new home today!

Newest Kailua Estates Homes with Fee Simple Land tenure

$2,395,000

4 Beds ⋅ 4 Baths ⋅ 202612015 MLS ⋅ FS - Fee Simple Tenure ⋅ 48 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 ⋅ 73 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 ⋅ 88 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

$4,098,000

5 Beds ⋅ 4 Baths ⋅ 202608270 MLS ⋅ FS - Fee Simple Tenure ⋅ 102 DOM

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

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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.