Kailua Real Estate

Welcome to Kailua, a picturesque gem nestled on the windward coast of Oahu, Hawaii. Known for its stunning beaches, lush landscapes, and laid-back charm, Kailua offers a unique blend of natural beauty and vibrant community life. With the majestic Ko’olau Mountains as a backdrop and the sparkling turquoise waters of Kailua and Lanikai Beaches at your doorstep, this region is a paradise for outdoor enthusiasts and beach lovers alike.

Kailua is renowned for its soft, white sand beaches, perfect for sunbathing, swimming, and kayaking. The calm waters of Kailua Bay are ideal for water sports, while the nearby Mokulua Islands beckon adventurers for a day of exploration and snorkeling. The area's lush hiking trails, such as the popular Lanikai Pillbox Hike, provide breathtaking panoramic views that are sure to leave you in awe.

Beyond its natural allure, Kailua boasts a vibrant local culture. The town is dotted with charming boutiques, artisanal shops, and delightful eateries that showcase the flavors of Hawaii. From farm-to-table dining experiences to casual beachside cafes, there’s something to satisfy every palate. The community spirit is palpable, with local events and farmers' markets that bring residents together in celebration of their island lifestyle.

Whether you’re looking for a serene retreat or an active lifestyle, Kailua offers a welcoming atmosphere that feels like home. With its stunning landscapes, rich culture, and warm community, it’s no wonder that Kailua is one of Oahu’s most sought-after destinations. Come and experience the magic of Kailua—where paradise meets everyday living!

Newest Listings in Kailua

$1,895,000

4 Beds ⋅ 3 Baths ⋅ 202618639 MLS ⋅ FS - Fee Simple Tenure ⋅ 0 DOM

Set against the dramatic backdrop of Olomana, this charming single-level Mid-Century Modern home offers timeless character, an inviting open-concept layout, and a spacious, flat, usable lot. With 4 bedrooms and 3 baths, the home is designed for easy living with a seamless connection between indoor and outdoor spaces. Glass sliders throughout invite abundant natural light and frame the lush surroundings, while thoughtful built-ins add warmth, function, and vintage appeal. The spacious living and dining areas flow naturally into the kitchen and outdoor spaces, creating an ideal setting for everyday living and entertaining. Automatic garage doors add everyday convenience and ease. This is a rare opportunity to enjoy the beauty, character, and indoor-outdoor lifestyle of a true Hawai'i home.

1575 Ulupii Street, Kailua

$1,600,000

3 Beds ⋅ 2 Baths ⋅ 202618194 MLS ⋅ FS - Fee Simple Tenure ⋅ 0 DOM

Opportunity knocks! This Kailua home is just a short walk to the beach and offers one of the lowest prices seen in years. A rare fixer-upper opportunity in sought after Kuulei Tract—with a pool and a location just 8 houses from world-famous Kailua Beach! Bring your vision to this property, just a couple of blocks from the heart of Kailua Town and close to schools, restaurants, markets, gyms, yoga studios, and farmers markets. The park-like backyard offers plenty of room to relax and play, with a refreshing pool and patio just outside the family room and a spacious grassy area beyond. The 3 bedrooms are located on the makai side of the house are cooled by the trade winds, and the 200+ s.f. workshop is located on the mauka side of the house. Fully fenced back yard provides a safe area for kids and pets.

119 Kuulei Road, Kailua

$969,000

2 Beds ⋅ 1 Baths ⋅ 202618404 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM

Great location for this tucked away 2 bedroom 1 bath Kailua cottage. Located on a quiet lane off of Ulupaina Street where there is a wide private driveway with access for the 6 homes on the lane. Short distance to Kailua town and Kalama Beach park. The cottage location gives the feeling of a spacious lot. New paint inside and out, new luxury vinyl flooring throughout. Ready for the new buyer to add your own personal touches. Flexible CPR's and By-Laws gives you total flexibility on remodeling, adding on or rebuilding. For those Buyers looking for a home in Kailua under $1 million this is a must see! Sold as is.

315 A Ulupaina Street, Kailua

$2,495,000

5 Beds ⋅ 5 Baths ⋅ 202618299 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM

Unbeatable value for a beachside estate inside Hale Kai Surf & Racquet Club, a private 14-home community in Kailua. A private access lane leads straight to the sand at Kailua Beach. This spacious home features nearly 4,000 sq. ft. of interior space, with 5 bedrooms and 4.5 baths. Soaring ceilings, with many living areas. A brand new split AC system was installed throughout. Four bedrooms are on the main level with the primary suite on the entire upper floor, with two closets, a sunroom. Enjoy Tennis, pickleball, basketball, a sparkling pool, and a clubhouse right across from the home and included in this community. Kailua town's coffee shops and restaurants are an easy bike ride away. Bring your own ideas and make it yours. Opportunities at this price and this close to Kailua Beach don't come up often, do not miss this opportunity!

824 N Kalaheo Avenue Unit A, Kailua

$1,699,000

2 Beds ⋅ 2 Baths ⋅ 202617903 MLS ⋅ FS - Fee Simple Tenure ⋅ 3 DOM

WHERE THE KOOLAUS MEET THE SEA. MOMENTS FROM WAIMANALO BEACH. Tucked into coveted Waimanalo Beach Lots, this beautifully updated 2-bedroom, 2-bath beach cottage pairs exceptional beach proximity with a rare sense of openness. Beach access is just moments away, while the property opens to an expansive green backdrop with Waimanalo Beach Park directly behind instead of another home. Koolau views, swaying palms, and the sound of the ocean complete the setting. Beautiful natural light fills the approx. 984 sq. ft. interior, with bamboo flooring throughout and custom driftwood vaulted ceilings creating a warm, relaxed aesthetic that complements the home’s easy beachside setting. Thoughtful updates include a remodeled kitchen and baths in 2022, a 2021 roof, and solar water-heating system. Outside, the fully enclosed yard and gathering spaces offer room to relax, entertain, or return home from the beach and talk story with friends. Set within one of Oahu’s most cherished beach communities, this is an opportunity to enjoy white sand, turquoise water, and the Koolau Mountains as part of everyday life. Actual square footage and number of bedrooms/baths do not match TMK records.

41-012 Wailea Street, Waimanalo

$2,228,000

6 Beds ⋅ 4 Baths ⋅ 202618361 MLS ⋅ FS - Fee Simple Tenure ⋅ 4 DOM

Welcome to Keolu Hills offering sweeping views of the Ko’olau Mountains! Meticulously maintained 6 bedrooms, 4 full baths, private suite on the 2nd floor, and large bonus room in the back. Featuring a heated built-in swimming pool, 45 PV panels on HECO’s NEM agreement, 9 split AC systems, full alarm system with cameras. The layout offers flexibility of main living on the 1st floor having 5 bedrooms, and the 6th bedroom is a private studio on the 2nd floor with 680 square feet of living space! This is a large house with over 3,0000 square feet of living space inside, huge lot size of 9,000 square feet, carport for 2 cars, extended driveway for 3 additional vehicles. Image yourself floating in the heated swimming pool, watching the sunset glimmering off the Ko’olau mountains. Located just minutes from Enchanted Lake Shopping Center, Kailua Town, and only 3 miles to world-famous Kailua Beach, this property combines convenience with privacy. Set back from the road and surrounded by tropical beauty, this home is the perfect Kailua retreat. Active cameras on property disclosure.

1315 Kupau Street, Kailua

$8,100,000

3 Beds ⋅ 5 Baths ⋅ 202618112 MLS ⋅ FS - Fee Simple Tenure ⋅ 4 DOM

Set along an exceptional stretch of Lanikai beachfront, 914 Mokulua Drive offers direct access to white sand with 75 linear feet of ocean frontage, bordered by naupaka for a natural buffer. The home boasts sweeping views of the Windward coast, encompassing the iconic Mokulua Islands as well as Popoia Island and Mokapu beyond. Inside, the airy great room is designed to breathe, capturing ocean views and towering coconut palms across a lush grassy lawn. Three primary suites, each with an ensuite bath and walk-in closet, offer generous comfort, while a private office with an adjacent half bath provides a quiet workspace or flexible guest room. Beyond the main house, a separate studio cottage with a full bath plus workshop adds ample room to host, create, exercise, or simply spread out. Step outside for a swim, paddle, or a sunset walk, then head into Kailua town in minutes for shopping and restaurants. This is your chance to be part of Lanikai’s world-famous coastline—sun, sand, sea, and island views.

914 Mokulua Drive, Kailua

$3,490,000

5 Beds ⋅ 3 Baths ⋅ 202617667 MLS ⋅ FS - Fee Simple Tenure ⋅ 9 DOM

Exceptional value and potential in the coveted Lanikai neighborhood! Tucked away on a quiet street off the main loop, this light-filled, move-in-ready 5-bedroom, 3-bath home captures beautiful ocean and Mokulua Island views from the main living areas, kitchen, dining area and primary bedroom. Abundant windows let in tons of natural light and ocean breezes and an expansive lanai for dining and entertaining offers memorable sunrise & moonrise views. Above the detached garage, a flexible suite with full bath, Murphy bed & built-in workspace offers exceptional Mokulua views—ideal as a fifth bedroom, guest suite or private office, while showcasing the property’s incredible view potential. Shovel-ready, approved permits expand the home to 4,400+ sq ft, maximizing its ocean and Mokulua views—with the 2-year design and permitting process already complete. Enjoy privacy from the lush landscaping. A level backyard has room for a pool and is ready for your vision. The private 5-foot-wide deeded easement to Aalapapa Drive puts Lanikai’s turquoise water and white sand just 300 yards away. This home is only being offered for a limited time so don’t wait to schedule your private showing!

1342 Mokolea Drive, Kailua

$595,000

1 Beds ⋅ 1 Baths ⋅ 202617742 MLS ⋅ FS - Fee Simple Tenure ⋅ 11 DOM ⋅ Windward Passage BLDG.

Stunning views and the best of Kailua living await at Windward Passage! This inviting one-bedroom condo on the 17th floor features floor-to-ceiling windows spanning the mauka side, capturing panoramic views of the Ko'olau mountains, Olomana, and Enchanted Lake. Move-in ready with fresh interior paint and AC units to keep you cool as you enjoy the views. Built-ins provide ample storage, plus the unit comes with separate storage in the building. Enjoy extraordinary amenities including a heated saltwater pool and whirlpool, BBQ area, well-equipped gym, tennis and pickleball courts, storage for bikes and beach gear, and a beautifully remodeled clubhouse. Your dog will love the unique dog park tucked into a natural quarry beneath banyan trees. Kailua Town’s coffee shops, boutiques, restaurants, Whole Foods, and Target are close by, along with beautiful Kailua Beach. Easy access to KBAY, VA approved and pet friendly. Come for the views, stay for the lifestyle!

322 Aoloa Street Unit 1706, Kailua

$15,250,000

5 Beds ⋅ 5 Baths ⋅ 202609183 MLS ⋅ FS - Fee Simple Tenure ⋅ 11 DOM

This exceptional Lanikai beachfront estate features over half an acre of land extending from the street directly to the sand and ocean. Unlike many of the neighboring properties that sit above rock and reef, this home opens directly onto the sandy beach, offering a rare and true beachfront experience with views of the Mokulua Islands. The house is built for how people actually live. Walls of glass retract and disappear, so the kitchen, dining area, pool courtyard, and beach read as one space. The open kitchen is where people gather, sized for a crowd and opening to outdoor dining and the grill. In the ocean, at the pool, or in the cool air inside, you are never closed off from the other areas. The upstairs primary suite was designed to take full advantage of the views from your bed, sitting area, bath or the private ocean-view lanai. This is a property people can grow into and form to their lifestyle. Beyond the lawn you have the Lanikai Pillbox trailhead, Mid Pacific Country Club, and the shops and restaurants of Kailua a short drive away. The ocean is the front yard. Property is offered fully furnished and being sold turnkey.

958 Mokulua Drive, Kailua

$236,600

202617227 MLS ⋅ FS - Fee Simple Tenure ⋅ 11 DOM ⋅ Uluniu Urban BLDG.

Unique opportunity to own your own office space in central business and medical area of Kailua. Has windows for natural light into the space. Ceilings are vaulted with cedar wood which provides a very calming and serene feeling within the space.

328 Uluniu Street Unit 205, Kailua

$1,590,000

6 Beds ⋅ 3 Baths ⋅ 202617350 MLS ⋅ FS - Fee Simple Tenure ⋅ 12 DOM

“I Love Kailua” - Experience the ultimate Hawaii lifestyle in a town famous for world-renowned beaches, vibrant open markets, abundant eateries, and boutique shopping, all wrapped in a charming heritage town vibe. This newly built, move-in-ready home offers an exceptional dual-living or multi-generational layout: •Top Floor: Features 3 bedrooms and 2 bathrooms, a spacious living area, and a beautiful outdoor deck perfect for hosting gatherings with family and friends. •Ground Floor: Includes 3 bedrooms and 1 bathroom, centered around a large, open entertaining space complete with a wet bar.

839 Oneawa Street, 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.