Kailua Estates Real Estate

Welcome to Kailua Estates, a hidden gem nestled on the stunning windward coast of Oahu, Hawaii. This charming neighborhood offers a unique blend of natural beauty, vibrant community spirit, and a relaxed island lifestyle that makes it one of the most sought-after locations in Kailua.

Kailua Estates is renowned for its lush landscapes, featuring swaying palm trees, vibrant hibiscus flowers, and breathtaking views of the Ko'olau Mountains. Residents enjoy easy access to some of the most pristine beaches in Hawaii, including the famous Kailua Beach and Lanikai Beach, both perfect for sunbathing, swimming, and water sports. The gentle trade winds and warm climate make outdoor activities a year-round delight, whether you're hiking the nearby trails or kayaking in the turquoise waters.

The neighborhood fosters a strong sense of community, where friendly neighbors gather for weekend barbecues and local events. Kailua Estates is conveniently located near charming shops, delightful cafes, and excellent dining options, giving residents a taste of local culture and cuisine. The Kailua Farmers Market is a must-visit, offering fresh produce, artisanal goods, and a vibrant atmosphere every Thursday.

Families will appreciate the top-rated schools in the area, along with numerous parks and recreational facilities that cater to all ages. With its perfect blend of tranquility and convenience, Kailua Estates is not just a place to live; it’s a lifestyle. Embrace the aloha spirit and discover your dream home in this idyllic neighborhood where every day feels like a vacation.

Newest Listings in Kailua Estates

$2,325,000

4 Beds ⋅ 4 Baths ⋅ 202612015 MLS ⋅ FS - Fee Simple Tenure ⋅ 83 DOM

Back on the market and now offered at $174,000 below original list price — your opportunity to own in Kailua just got better! Our seller has made new improvements to make this home shine! 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. 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 landscaped 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 ⋅ 108 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

$3,045,000

6 Beds ⋅ 3 Baths ⋅ 202608800 MLS ⋅ FS - Fee Simple Tenure ⋅ 123 DOM

MAJOR PRICE REDUCTION! Exceptional opportunity in a preferred location within Kailua Estates. 244 Awakea Rd is a beautifully remodeled plantation-style property on a spacious 10,000 sqft 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, 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, PV and solar hot water. There is also a spacious 1-bedroom cottage and a separate 2-bedroom, 1-bath ADU, both currently tenant occupied and generating a combined $7,600/month. The ADU is separately metered and features solar hot water. A dedicated storage/yoga room adds flexibility. Now offered at $3,045,000, or $966/sqft, below the recent Kailua Estates average of approximately $1,046/sqft. Enjoy easy access to Kailua and Lanikai beaches, Kalapawai Market, Buzz's, Whole Foods, boutique shops, dining, and everything Kailua has to offer.

244 Awakea Road, Kailua

Start Your Search

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.