Kailua Estates Homes with Garden View

Welcome to Kailua Estates, a hidden gem nestled on the stunning island of Oahu, Hawaii. This charming neighborhood is a true paradise for those seeking a tranquil lifestyle surrounded by natural beauty. Known for its lush landscapes and friendly community, Kailua Estates offers a unique blend of serene living and vibrant local culture.

As you stroll through the tree-lined streets, you’ll be captivated by the picturesque homes that dot the landscape, many of which boast enchanting garden views. These properties are designed to harmonize with the island’s natural beauty, featuring lush tropical gardens that provide a serene backdrop for everyday life. Imagine waking up to the sound of birds chirping and the gentle rustle of palm trees swaying in the breeze, all while sipping your morning coffee on your private lanai.

Kailua Estates is not just about beautiful homes; it’s about a lifestyle. Residents enjoy easy access to Kailua Beach, known for its pristine sands and crystal-clear waters, perfect for swimming, paddleboarding, or simply soaking up the sun. The neighborhood is also conveniently located near charming local shops, delightful eateries, and vibrant farmers' markets, where you can savor the flavors of Hawaii.

With its welcoming community spirit, breathtaking scenery, and homes with stunning garden views, Kailua Estates is more than just a neighborhood; it’s a place where memories are made and cherished. Come discover why so many are drawn to this enchanting slice of paradise in Oahu. Your dream home awaits!

Newest Kailua Estates Homes with Garden View

$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.

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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.