Kailua beach side homes for sale | beachfront real estate Kailua, Hi

Kailua beach side real estate starts here! All Kailua beachside homes and beachfront properties for sale on this Windward neighborhood on Oahu.

Some other popular Kailua neighborhoods: Lanikai, Waimanalo and Enchanted Lake

About Kailua Beachside

Beachside, a neighborhood in Kailua, is comprised of short streets sandwiched between Kalaheo Avenue and beautiful Kailua Beach. This is a popular neighborhood and attracts people from all over the world to partake in the lifestyle that this neighborhood affords. The neighborhood boasts is where President Obama and his family come to vacation when visiting the islands.

The beachfront homes priced at $3 million-plus can run into the tens of millions depending on the size of the property. The homes that are off the beach can also be a multi-million dollar, while some are much more moderately priced, although it is very uncommon to see anything for less than $1million. Each beachside lane has it’s own personality and can become a close-knit community unto itself. There are many homeowners who have lived here for decades.  Residents enjoy the soft, gentle, and cooling trade winds coming off of the ocean. With most lot sizes being at a minimum 10,000 square feet, they are considered rather generous in size compared with the vast majority of single-family homes on Oahu.

One of the best parts of living in this Kailua neighborhood is being within a short stroll of Kailua Beach. Kailua Beach provides a wonderful oasis of activity. Most areas along the beach have small gentle waves just right for the smallest of swimmers. It is also one of the best places on the island for kite surfing and windsurfing. Also, it is a comfortable and easy beach to walk or run. It has become a ritual for many to walk or run the beach every day and stop and chat with neighbors and friends creating a closer community bond.

Homes in this neighborhood are also within walking distance to Kailua town. It is common sight to see residents walk or ride bicycles to the popular farmers’ markets, to go grocery shopping, the library, and other such activities that the town has offer.

We know Kailua very well. In fact, this is the town that our principal Broker, Malia Meenderman is from originally. Growing up here and having family and friends who live here gives her a unique insight into the region which she happily uses to help her clients find their new Hawaii home.

call 808-394-9779 or click to email

Kailua beachside homes for sale:

(Many Kailua houses are sold before coming on the market. Contact us and we help you find your property)

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Days On Market No Pref. < 10 < 20 < 30 < 40 < 50 60+

Min. Price $0 $165,000 $175,000 $200,000 $225,000 $250,000 $275,000 $300,000 $325,000 $350,000 $375,000 $400,000 $425,000 $450,000 $475,000 $500,000 $525,000 $550,000 $575,000 $600,000 $700,000 $800,000 $900,000 $1,000,000 $2,000,000 $3,000,000 $4,000,000 $5,000,000 $6,000,000 $7,000,000 $8,000,000 $9,000,000 $10,000,000

Max. Price Any $165,000 $175,000 $200,000 $225,000 $250,000 $275,000 $300,000 $325,000 $350,000 $375,000 $400,000 $425,000 $450,000 $475,000 $500,000 $525,000 $550,000 $575,000 $600,000 $700,000 $800,000 $900,000 1,000,000 2,000,000 3,000,000 4,000,000 5,000,000 6,000,000 7,000,000 8,000,000 9,000,000 10,000,000 11,000,000 12,000,000 13,000,000 14,000,000 15,000,000

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$27,500,000

10 bd | 9 ba | 14,834 sqft

Home For sale

145/151 Kailuana Loop, Kailua, HI, 96734

Experience the epitome of oceanfront luxury with the unveiling of this stunning oceanfront estate - Kai Moena, "The House of the Resting Sea." Given its namesake by the former property owner, Harry Rothschild of the Rothschild Banking Family. This rare and unparalleled legacy estate spans nearly 60,000 sq ft across two completely subdivided parcels along Kailua's world-famous beachfront. Revel in over 255 linear feet of pristine white sandy beach, the most expansive beachfront available on the island of Oahu, offering an idyllic setting that embodies both serenity and maximum privacy. The estate comprises two main residences totaling 10 bedrooms, 8 full baths, and 3 half baths. Rich tropical hardwood accents and textured finishes, high vaulted ceilings give a warm opulence and living spaces flow seamlessly between indoors and outdoors for maximum ease. Experience exceptional amenities such as a resort-style lagoon pool with waterfalls, fitness center, massage room, media room, and a dry sauna. A tennis/pickleball court and lush landscaping complete your private sanctuary. Seize the rare opportunity to own this prestigious estate, your personal haven on Kailua Beach.

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$25,000,000

10 bd | 13,289 sqft

Home For sale

145/151 Kailuana Loop, Kailua, HI, 96734

Experience the pinnacle of luxury living with this extraordinary beachfront estate, set on over 60,000 square feet of prime oceanfront land. As one of the largest parcels on Oahu, this prestigious property boasts over 255 linear feet of pristine, white powdery sand — the widest beach frontage in Kailua. Spanning two expansive lots, the estate offers two distinct residences with a combined total of 10 bedrooms, eight full baths, and three half baths. The primary bedroom suite is a private sanctuary with panoramic ocean views, ideal for relaxation and rejuvenation. Resort-style amenities include a lagoon-style pool with a cascading waterfall and jacuzzi, a state-of-the-art exercise room with a dry sauna, and a professionally equipped tennis court that also accommodates pickleball. Additional luxuries include a private theater room, massage treatment room, and a cozy fireplace for tranquil evenings. With its unparalleled setting, vast beachfront grounds, and world-class amenities, this one-of-a-kind legacy property offers a rare opportunity to own a private paradise in one of Hawaii’s most sought after beach communities.

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$21,000,000

4 bd | 5 ba | 4,062 sqft

Home For sale

200 S Kalaheo Ave, Kailua, HI, 96734

Experience tranquil beachfront living in one of the most pristine areas along Kailua Beach, featuring stunning ocean views from the modern kitchen, spacious living room, and primary bedroom with a private oceanfront deck. Recent renovations include stylish baths that enhance the contemporary vibe. The custom kitchen flows into a welcoming dining area, ideal for gatherings and entertaining. A cozy cottage offers guest privacy, while ample parking and a three-car garage provide convenience. A dedicated office with courtyard access creates a peaceful workspace. Enjoy the lagoon pool and waterfall spa, with the beach just steps away for swimming, paddleboarding, or relaxing. Minutes from Kailua Beach Park, Mid-Pac Country Club, and Kailua Town, this home combines luxury and convenience. Your dream island lifestyle awaits!

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$19,800,000

12 bd | 15 ba | 14,151 sqft

Home For sale

572C N Kalaheo Ave, Kailua, HI, 96734

EXCLUSIVE NEW LISTING. Welcome to this exceptional Kailua beachfront estate. This gated resort-like retreat is situated on nearly an acre of land fronting one of the most beautiful beaches in the world. With over 14,000 sq ft of sophisticated living space, the main residence is a masterpiece of design featuring a luxurious, expansive primary suite with panoramic ocean views, and an additional 9 bedrooms-each boasting a private en-suite bathroom, a spacious gym/recreation room, 2 additional full bathrooms, and 2 powder rooms. Designed to entertain in style, this private tropical oasis is complete with an outdoor pavilion and full wet bar next to a pristine pool, spa, and wading pool all set within beautifully manicured landscaping. A charming, detached 2-bedroom, 2-bathroom guest quarters and 4-car garage further complement this magnificent property. Just beyond your backyard, a white sandy beach and the sparkling blue Pacific Ocean, ideal for swimming, ocean sports, or peaceful strolls. Embrace this once-in-a-lifetime opportunity to own this prime oceanfront property.

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$19,800,000

12 bd | 14,151 sqft

Home For sale

572C N Kalaheo Ave, Kailua, HI, 96734

Welcome to this exceptional Kailua beachfront estate. This gated resort-like retreat is situated on nearly an acre of land fronting one of the most beautiful beaches in the world. With over 14,000 sq ft of sophisticated living space, the main residence is a masterpiece of design featuring a luxurious, expansive primary suite with panoramic ocean views, and an additional 9 bedrooms-each boasting a private en-suite bathroom, a spacious gym/recreation room, 2 additional full bathrooms, and 2 powder rooms. Designed to entertain in style, this private tropical oasis is complete with an outdoor pavilion and full wet bar just steps away from a pristine pool, spa, and wading pool all set within beautifully manicured landscaping. A charming, detached 2-bedroom, 2-bathroom guest quarters and three-car garage further complement this magnificent property. Just beyond your backyard, a white sandy beach and the sparkling blue Pacific Ocean, ideal for swimming, ocean sports, or peaceful strolls. Embrace this once-in-a-lifetime opportunity to own this prime oceanfront property.

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$16,800,000

7 bd | 7 ba | 5,902 sqft

Home For sale

17 Laiki Place, Kailua, HI, 96734

Welcome to 17 Laiki, now publicly available for the first time. Completed in 2022, it is one of the newest beachfront homes on Kailua Beach. Expansive and private, the home was designed as a “Modern Victorian”. The property has curated touches throughout; Parisian glass art, Murano chandeliers, and antique stained glass. Be captivated by the 180-degree ocean view of Kailua beach and the view of the Mokulua Islands of Lanikai. The property holds a 3-bedroom main house with an oceanfront living room and a large media room overlooking the pool. The large, second-story, primary suite and office are filled with unobstructed shoreline views. The Pool house with ensuite bath and the 3-bedroom 3-bath Guest House encompass the heated tile pool and spa. There is even a “Carriage House” for your sports car with a full bath and a loft above. Lastly, there is a high-ceiling, SUV-friendly, two-car garage. If you are looking for a Hawaii Beachfront home this is a must-see. Don't miss the Video, 3D tour, floorplans, and more.

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$15,800,000

6 bd | 7 ba | 5,804 sqft

Home For sale

47 Kailuana Place, Kailua, HI, 96734

Your tropical legacy estate awaits! This oceanfront retreat lies in Kailua's most prestigious gated community. Notably selected as a holiday retreat of a former US president, the residence embodies an elite level of luxury, privacy & prestige. An expansive lot with 100 linear ft of oceanfront on over 33,800 sf set between Kawainui canal & world famous Kailua bay. The ideal single level layout is infused w/ Balinese & Hawaiian influences. Luxurious interiors flow onto spacious covered lanais w/ beautiful gardens & nature infused exteriors. Enjoy a gourmet kitchen, open beam high ceilings & AC throughout, 5 sumptuously appointed ensuite bedrooms, plus 2 half-baths. Indulge in resort like amenities including a saltwater heated pool w/cascading waterfall, spa & gym. Convenience, luxury and serenity all within 14mi to Downtown Honolulu, 19mi to HNL Int'l Airport & 5 minutes to many shops, restaurants & activities of Kailua Town.

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$5,000,000 ▼ $200,000

5 bd | 5 ba | 3,914 sqft

Home For sale

133 Kailuana Place, Kailua, HI, 96734

If you're looking for a beautiful single level home close to the beach in Kailua, look no further! High end, custom finishes with a resort -style feel set this home apart. Enjoy living in one of Oahu's most sought after neighborhoods with access to world famous white sandy beach. This Kailuana home is equipped with a gourmet kitchen and 4/5 bedrooms have en-suite bathrooms. Indoor/outdoor living with a backyard that's great for entertaining.

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$4,200,000

1 bd | 1,466 sqft

Home For sale

188 N Kalaheo Ave, Kailua, HI, 96734

Rarely does an opportunity like this come to market! Situated in the sought after Kailua Beachside neighborhood, this 1/1.5 home sits on an expansive 17,000+ sf, R-10 zoned lot providing the perfect canvas for your dream development. Whether you're envisioning a private estate, a luxury retreat, or an amazing development opportunity, this property offers unparalleled potential in one of Hawaii’s most desirable locations. A short stroll from popular Kalama beach, Kailua is known for its pristine beaches, lush tropical scenery, and relaxed yet vibrant atmosphere. Just minutes away from world-class Kailua and Lanikai Beach, you’ll enjoy sun-kissed days and breathtaking sunrises. With its unbeatable location and endless possibilities, this Kailua property is a rare gem in today’s market. Contact us today for more details and to schedule a private tour of this exceptional property.

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$3,495,000 ▼ $255,000

3 bd | 2 ba | 2,046 sqft

Home For sale

144 Kaimoani Way, Kailua, HI, 96734

This custom beachside home, built in 2000 by it's current owners, is located on a tranquil cul-de-sac with private access to Kailua Beach. The open layout and ocean-view lanai create an ideal space for modern living and entertaining. Nicely laid out as a 2 bedroom the large office will also work well as a 3rd bedroom. Constructed with durable poured concrete walls and refined finishes offer a low-maintenance beach lifestyle. Located in the desirable Kailuana neighborhood and providing easy access to Kailua town and surf spots, makes this a perfect choice for those seeking a relaxed yet convenient beach lifestyle. With a surf-friendly location and proximity to H-3 for island exploration, this home offers an unparalleled opportunity for knowledgeable buyers.

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Min $165,000 $175,000 $200,000 $225,000 $250,000 $275,000 $300,000 $325,000 $350,000 $375,000 $400,000 $425,000 $450,000 $475,000 $500,000 $525,000 $550,000 $575,000 $600,000 $700,000 $800,000 $900,000 $1,000,000 $2,000,000 $3,000,000 $4,000,000 $5,000,000 $6,000,000 $7,000,000 $8,000,000 $9,000,000 $10,000,000

Max $165,000 $175,000 $200,000 $225,000 $250,000 $275,000 $300,000 $325,000 $350,000 $375,000 $400,000 $425,000 $450,000 $475,000 $500,000 $525,000 $550,000 $575,000 $600,000 $700,000 $800,000 $900,000 $1,000,000 $2,000,000 $3,000,000 $4,000,000 $5,000,000 $6,000,000 $7,000,000 $8,000,000 $9,000,000 $10,000,000

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Days On Market

No Pref. < 10 < 20 < 30 < 40 < 50 60+

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