Kailua Real Estate

Welcome to Kailua, a picturesque gem nestled on the eastern shore of Oahu, Hawaii. Known for its stunning beaches, lush landscapes, and vibrant community, Kailua offers a unique blend of island charm and modern conveniences that make it a coveted destination for both residents and visitors alike.

Kailua is renowned for its breathtaking beaches, including the famous Kailua Beach and Lanikai Beach, where soft golden sands meet crystal-clear turquoise waters. These idyllic shores provide the perfect backdrop for a variety of outdoor activities—whether you’re kayaking to the nearby Mokulua Islands, paddleboarding on the gentle waves, or simply soaking up the sun with a good book. The warm, tropical climate allows for year-round enjoyment of these natural wonders.

Beyond its stunning coastline, Kailua boasts a thriving local culture. The town is dotted with charming boutiques, artisanal shops, and delightful eateries, offering everything from fresh poke bowls to gourmet coffee. The weekly farmers' market is a must-visit, showcasing the best of local produce and handmade goods, fostering a sense of community and connection among residents.

For those seeking a family-friendly atmosphere, Kailua is home to excellent schools and numerous parks, making it an ideal place to raise children. The friendly neighborhoods are filled with a mix of quaint single-family homes and modern condos, each offering a slice of paradise.

Whether you’re looking for a serene retreat or an active lifestyle, Kailua promises an unparalleled living experience. Discover the beauty and warmth of this enchanting town, where the spirit of Aloha thrives in every corner.

Newest Listings in Kailua

$1,748,000

202617235 MLS ⋅ FS - Fee Simple Tenure ⋅ 1 DOM

Discover the true essence of country living. Positioned along one of Waimanalo's most picturesque corridors, this lot invites you to build the island home you have long imagined. Wake up each morning to dramatic mountain ridges, cool trade winds, and the peaceful ambiance of Oahu's windward side. Whether you intend to plant organic fruit trees, build a spacious multi-generational home, or design an eco-retreat, or farm this lush vacant lot provides the space and versatility to make it happen. Properties in this tight-knit agricultural and residential community are highly sought after-don't miss your chance to claim a piece of paradise. Bring your architect, your builder, and your dreams.

41-812 Kakaina Street, Waimanalo

$2,149,000

4 Beds ⋅ 2 Baths ⋅ 202616975 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM

Fully remodeled in 2024, truly MOVE IN READY! Just a few blocks from Aikahi shopping center and Kailua beach! This 4 bedroom 2,020 SF home has a spacious great room, chef’s kitchen with gas range, pantry, indoor laundry room, & screened in bonus room, perfect for outdoor dining, or flex space. The primary suite is separated from the other 3 bedrooms with a custom closet and lg bathroom w/walk-in shower and freestanding tub. Step out to a sparkling pool, mature landscaping and multiple lanais. The vaulted breezeway leads to the additional bedrooms with a new custom Murphy bed in the middle bedroom. Spacious enough for a built in bar plus a home office. Louvered shutters throughout, solar shades in the kitchen, new fans and designer paint. A 24-panel owned photovoltaic system with battery storage on a new ’24 roof. All new windows and doors framing mountain and mature garden views. Split AC system throughout plus a gas range and two large propane tanks for a VERY energy efficient home! Plans to enclose the carport into a 2 car garage are in the permitting process! Minutes to military base, the beach, H-3, Pali and Likelike and a short stroll to great local schools.

340 Ilimano Street, Kailua

$799,500

3 Beds ⋅ 2 Baths ⋅ 202617186 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM ⋅ Lakeview BLDG.

First time offered in 38 years! One of the largest Lakeview townhomes is finally available. This unit checks all the boxes for location, quiet, ease of access, new renovations, sunrise view, and great neighbor. Enjoy privacy, space, and trade winds in this 3-bed, 2-bath corner unit at Lakeview in Enchanted Lake. A wraparound lanai offers wonderful views and relaxation. The second floor enjoys views of Enchanted Lake. Updates within include fresh paint, new carpet, ceiling fans, washer/dryer, outlets and switches, interior doors and frames, closet doors, new windows and sliding glass doors. The kitchen features a farmer's sink, quality countertops, cabinetry, and generous storage. The bathrooms offer a great opportunity to create your own personal touch. The primary bedroom and bath are conveniently located on the first floor, and offer plenty of storage. A rare convenience at Lakeview, the primary parking stall is located directly in front of the unit, providing direct access to your home. Centrally located within this well-maintained, landscaped community, and close to Kailua Town, shopping, restaurants, schools, beaches, and conveniences. Pet friendly and VA approved.

1187 Akipohe Street Unit 8A, Kailua

$1,625,000

4 Beds ⋅ 2 Baths ⋅ 202617085 MLS ⋅ FS - Fee Simple Tenure ⋅ 5 DOM

Welcome to this highly desirable, single story, 4 bedroom, 2 bath home in the beautiful neighborhood of Pohakapu. Amazing new Kitchen including cabinets, countertop and appliances. The bathrooms have been designed in a luxurious manner that provides warmth and comfort. New split level air conditioning systems and ceiling fans have been installed. Conveniently located near the Pali Highway, Castle Hospital and downtown Kailua. neighborhood. The home has been freshly painted inside and out. A must see.

526 Ulumawao Street, Kailua

$1,498,000

3 Beds ⋅ 2 Baths ⋅ 202616698 MLS ⋅ FS - Fee Simple Tenure ⋅ 7 DOM

Beautifully remodeled with panoramic Koolau views. Stylishly renovated with modern finishes, this home features a bright, open-concept design with vaulted ceilings, exposed beams, warm wood accents, and a new kitchen that flows seamlessly into the living and dining areas. Large windows and doors bring in natural light while capturing the stunning, unobstructed mountain views. The living area opens to a spacious lanai, creating an ideal setting for indoor-outdoor living and entertaining, with ample land to expand if desired. A prime location on desirable Kupau Street. First available viewing September 10th.

1375 Kupau Street, Kailua

$855,000

3 Beds ⋅ 3 Baths ⋅ 202613359 MLS ⋅ FS - Fee Simple Tenure ⋅ 7 DOM ⋅ Gardenia Manor BLDG.

Both welcoming and thoughtfully designed this generously sized, two-story condo offers incredible indoor / outdoor living spaces, a vaulted ceiling fills the room with natural light and creates an airy atmosphere. Well-designed floor plan places all bedrooms upstairs, along with the washer and dryer for added convenience, while a half bath on the main level is ideal for guests. Vinyl laminate flooring, lots of storage, a beautiful updated kitchen and two covered parking are just some of the items this condo offers. Ideally located just minutes from shopping, dining, and Kailua's beaches, you'll love having everything you need close to home. When you're not out exploring, enjoy the community pool, BBQ and recreation area - a perfect bonus to living in Gardenia Manor. Whether you're searching for your first home, a place to downsize, or an investment in one of Hawaii's most desirable locations, this inviting condo offers the perfect place to call home.

333 Aoloa Street Unit 318, Kailua

$1,430,625

202616767 MLS ⋅ FS - Fee Simple Tenure ⋅ 10 DOM ⋅ Uluniu Urban BLDG.

A rare opportunity to own your own commercial office space in the heart of Kailua’s central business and medical district. This fully improved business office offers approximately 1,638 square feet of ground-level space plus an additional 651 square feet of mezzanine office space. The distinctive cedar wood building features vaulted, open ceilings, creating a warm, inviting, and calming atmosphere. The current short-term lease provides an excellent opportunity for an owner-user business to transition into the space. The thoughtfully designed office includes a kitchen and breakroom, multiple private offices, a private restroom, a computer room, a storage room and an open work area with numerous cubicles. The property also features photovoltaic solar panels, helping to offset electrical expenses. Located in a high-visibility area with strong vehicle and pedestrian traffic. This unique property offers an exceptional combination of functionality and character in one of Kailua’s most desirable commercial districts.

320 Uluniu Street Unit 3, Kailua

$2,625,000

5 Beds ⋅ 3 Baths ⋅ 202616563 MLS ⋅ FS - Fee Simple Tenure ⋅ 8 DOM

Welcome to this single-level, classic Hawaii-style home, steps from the best stretch of sandy beach for miles, nestled between Kailua and Lanikai. See the ocean from the front yard of this oversized lot! With cul-de-sac entry and plenty of parking, the home offers a sweeping open-concept layout, perfect for effortless indoor-outdoor living. Travertine flooring, open-beam wood ceilings, and windows galore welcome natural light and exquisite views, bringing nature in as a stunning backdrop. The expansive living area flows seamlessly to two covered lanais, both with ceiling fans and recessed lighting, perfect for entertaining or relaxing. The kitchen features wood cabinetry, a large island, bar seating, new appliances and warm finishes that complement the island aesthetic. New ceiling fans throughout too. Every day can feel like vacation, living in style and comfort amid landscaping that creates a peaceful, resort-like setting. Minutes from famous turquoise beaches, parks, dining, cafes, and charming Kailua shops, the spacious main home has 3 bedrooms, 2 baths and bonus room, plus an 800+sf garage conversion with private entry, used as 2 bedrooms, 1 bath, wet bar and second laundry.

151 Alala Road, Kailua

$825,000

3 Beds ⋅ 2 Baths ⋅ 202616227 MLS ⋅ FS - Fee Simple Tenure ⋅ 8 DOM ⋅ Windward Harbour BLDG.

Experience the best of island living at Windward Harbour in the heart of Kailua. Perfectly located within walking distance from shopping, restaurants, farmers markets, and the world-renowned Kailua and Lanikai beaches, this spacious ground-floor 3-bedroom, 2-bath residence offers the ideal blend of comfort and convenience. The open-concept floor plan provides a welcoming space for living and entertaining, while newly refinished bamboo flooring and fresh interior paint create a bright, move-in-ready feel. The bedrooms feature built-in closets and the floor-to-ceiling windows fill the home with natural light while showcasing peaceful garden views from your private lanai. Windward Harbour is a secure, pet-friendly community featuring resort-style amenities, including a swimming pool, hot tub, sauna, tennis courts, ping-pong, BBQ areas, a recreation room, and a dog run. Enjoy the perfect balance of tranquil living and easy access to everything Kailua has to offer.

1030 Aoloa Place Unit 5105B, Kailua

$1,360,000

3 Beds ⋅ 1 Baths ⋅ 202616680 MLS ⋅ FS - Fee Simple Tenure ⋅ 10 DOM

Nestled at the end of a private lane, this cozy 3-bed 1-bath Kailua home offers a laidback beach lifestyle + modern charm. Located on the desirable beach-side of Coconut Grove and a nice walk to the beach, this home features a spacious, updated kitchen with sleek finishes, a 13-panel owned PV system, and ample storage. The oversized + fully enclosed yard with automatic gate is the standout and a true blank canvas, providing endless potential to expand the home, build a sparkling pool, create a lush outdoor oasis, or all of the above. Perfectly situated to enjoy the best of Kailua, with Kailua beach and the endless shopping + dining options of Kailua town just a short walk away. This home serves as the ultimate base for a relaxed, active lifestyle and is a rare opportunity to secure your own piece of paradise.

324 Olomana Street Unit D, Kailua

$2,800,000

4 Beds ⋅ 2 Baths ⋅ 202616703 MLS ⋅ FS - Fee Simple Tenure ⋅ 10 DOM

See this single-level beachside residence. First time on the market showcases timeless design, private pool that perfectly captures the essence of Island living. Move-in ready with the opportunity to make thoughtful updates and create a style that’s uniquely yours! Set on a private, fee simple level 10,002 sq ft. lot, this property offers a serene oasis with mature, fruit-bearing trees—including varieties of guava, lemon, tangerines. pomegranate. Home features a newly remodeled kitchen 2020 and bathroom 2022/2023. Upgraded flooring throughout. LAND….POOL….BEACHACCESS….POTENTIAL! Four doors from private beach access to prestigious Kailua Beach. Have fun in the sand and take in the sunset!! This home is situated in a quiet lane featuring luxury estates! Enjoy the close proximity to Kailua's boutique shops and restaurants. Easy H-3 commute to either direction of the island.

50 Kalaka Place, Kailua

$755,000

3 Beds ⋅ 2 Baths ⋅ 202616240 MLS ⋅ FS - Fee Simple Tenure ⋅ 11 DOM ⋅ Windward Harbour BLDG.

Welcome to Windward Harbour, a gated tropical oasis in the heart of beautiful Kailua! This spacious 3-bedroom, 2-bath condo offers the perfect opportunity to create your own dream retreat just minutes from world-famous Kailua Beach. Surrounded by lush tropical landscaping, tranquil koi ponds, garden views, and a peaceful man-made pond, the property offers a serene setting enhanced by the soothing sound of a beautiful water feature. While the interior is ready for some updating, its blank-slate appeal allows you to bring your vision to life and create a home that truly reflects your style. Enjoy Windward Harbour amenities including a sparkling pool and tennis courts, all within a private gated community. Ideally located near Kailua Beach, grocery stores, Target, UFC Gym, restaurants, boutiques, and the charming local shops that make Kailua so desirable. Whether you’re looking for a full-time residence or tropical retreat, this is your opportunity to create your dream home in paradise!

1030 Aoloa Place Unit 212B, 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.