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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508 Kalaheo Ave Beachside,  ,Hi 96734 - Photo
$50,000,000
12 bd | 14 ba | 12,005 sqft
Home For sale
508 N Kalaheo Ave, Kailua, HI, 96734
Unparalleled, the Mele Komo Beachfront Estate located on the pristine shores of Kailua Beach, offers the most discerning connoisseur the ultimate in coastal living. With an impressive 12 beds and 13 baths, this 12,005 square-foot architectural marvel was meticulously designed prioritizing enjoyment with 9 ocean facing bedrooms and 11 private lanais. At 2.2-acres it's the largest residential lot on the Kailua Beachfront. The Primary Hale, boasting 6 beds and 6.5 baths within 5,835 sqft, and the Guest Hale, a companion masterpiece with 6 beds and 6.5 baths spanning 6,170 sqft, offer unparalleled living spaces designed with the perfect combination of luxury comforts and Hawaiian detail. Indulge in resort-style living with a 96,000 gallon pool showcasing a waterfall, slide, jacuzzi, and a private grotto. The 2,000 sqft Pool Cabana with a full kitchen, full bath, spacious loft, and laundry facilities adds an extra touch of convenience and comfort. Mele Komo provides the utmost in privacy and efficiency, featuring 94 photovoltaic panels, privately owned beach access, and stunning views of the famed Mokulua Islands. A unique opportunity to own a true jewel of the Hawaiian coastline.
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572C N Kalaheo Ave Beachside,  ,Hi 96734 - Photo
$18,880,000
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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200 Kalaheo Ave Beachside,  ,Hi 96734 - Photo
$17,500,000
4 bd | 4,062 sqft
Home For sale
200 S Kalaheo Ave, Kailua, HI, 96734
AMAZING NEW PRICE! 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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110 Kalaheo Ave Beachside,  ,Hi 96734 - Photo
$4,850,000
5 bd | 3,329 sqft
Home For sale
110 N Kalaheo Ave unit A, Kailua, HI, 96734
Tucked along a quiet lane in coveted Beachside Kalaheo, this LEED Gold–certified residence captures a rare balance of timeless island architecture and forward-thinking design. Built in 2014 by Mokulua High Performance Builders, the 5-bedroom, 3.5-bath home reflects a commitment to quality, comfort, and sustainability—showcasing rich hardwood floors, detailed millwork, and soaring 9-foot ceilings that create warm, understated elegance. Sunlight and tradewinds flow through open living spaces anchored by a beautifully appointed kitchen, while upstairs ocean views frame a serene primary retreat and flexible additional bedrooms. A semi-detached 1BR/1BA cottage with private entrance adds versatility for guests or extended family. Owned photovoltaic panels with Tesla Powerwall support efficient island living. Mere steps from Kailua Beach, where morning swims and sandy feet at sunset become part of daily life, this newer custom home offers a rare opportunity to experience refined coastal living.
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49 Pilipu Place Beachside,  ,Hi 96734 - Photo
$3,850,000
6 bd | 2,682 sqft
Home For sale
49 Pilipu Place, Kailua, HI, 96734
$125K Price Improvement! Designed w/ elegance & functionality, this expansive 6 bdrm, 4.5-bath home goes above & beyond to capture the magic & luxuries of Kailua beach living. Walk out your private gate & a quick stroll down the path leads you to the iconic white sand of Kailua Beach. Go for a surf, then freshen up in your outdoor shower & start your day! In the eve, swim laps in your pool, then reward yourself w/ a soak in the hot tub under a star filled sky to the sound of palm fronds in the breeze, mesmerized by the flickering flame of tiki torches. The thoughtful layout of this home is versatile for entertaining guests, or multi generational living. The main house of 4 bdrms & 2.5 baths, while guest cottage can be utilized as 2 studio guest suites or used as 1 bdrm, 2 bath for potential rental income. For culinary enthusiasts, this home boasts a chef's kitchen, complete w/ Thermador refrigerator & dbl oven gas range. Cook delicious feasts & host large gatherings w/ ease. True Hawai’i living happens outdoors & this home’s lanai offers exactly that. Whether hosting al fresco family dinners, or watching the game, the lanai exudes the essence of Hawaiian hospitality & charm.
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32 Pilipu Place Beachside,  ,Hi 96734 - Photo
$3,600,000
4 bd | 2,970 sqft
Home For sale
32 Pilipu Place unit A, Kailua, HI, 96734
Welcome to your beachside paradise—just one lot from the ocean and directly next to the beach pathway on a quiet cul-de-sac. This lovingly maintained and upgraded 4-bedroom, 2-bath home offers 2,970 sq. ft. of living space on a 7,194 sq. ft. lot, blending comfort, space, and the ultimate island lifestyle. The open-concept design features a spacious great room, separate family room, and an expansive kitchen with island cooktop, granite countertops, gas stove, and double ovens—perfect for gathering with family and friends. A versatile loft adds flexible space for an office, media room, or guest retreat, with abundant storage throughout. Enjoy 918 sq. ft. Lanai that invites seamless indoor-outdoor living, overlooking a large backyard filled with lush tropical landscaping for a tranquil Hawaiian retreat. Rinse off after the beach in your outdoor shower, host with ease thanks to extra guest parking, and relax in comfort with Mitsubishi split A/C units and PV panels for energy efficiency. Moments from dining, shopping, and everyday conveniences—and seconds from your favorite beach activities—this is more than a home, it’s the Beachside Kailua Dream you’ve been waiting for.
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824 Kalaheo Ave Beachside,  ,Hi 96734 - Photo
$2,995,000
5 bd | 3,958 sqft
Home For sale
824 N Kalaheo Ave unit A, Kailua, HI, 96734
Enjoy the beachside lifestyle near world-famous Kailua Beach, just eight homes away – without the oceanfront premium. Set within the private 14-home Hale Kai Surf & Racquet Club, this expansive beachside estate offers 5 bedrooms, 4.5 baths and 3,958 interior sqft, providing a rare combination of privacy and generous living space, with a community private lane offering direct access to Kailua’s sandy beach. The main level features four bedrooms, three full baths, and a powder room, while the entire upper level is dedicated to a private primary suite with dual closets, a sunroom retreat, and access to rooftop spaces. An impressive courtyard entry leads to a grand foyer with soaring ceilings and multiple indoor-outdoor living areas designed for both entertaining and quiet enjoyment. Residents enjoy access to the community’s premier amenities, including pickleball, tennis, basketball, an upgraded pool, and clubhouse. A beautifully customized legacy home offering the dream beachside lifestyle with opportunity for personal touches. An exceptional opportunity not to be missed.
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