Beachside Real Estate

Welcome to Beachside, a hidden gem nestled in the heart of Kailua, Oahu. Known for its stunning vistas and laid-back island lifestyle, this enchanting neighborhood is a haven for those seeking both adventure and tranquility.

Beachside boasts some of the most picturesque beaches on the island, with soft, powdery sands and crystal-clear waters that invite residents and visitors alike to bask in the sun or take a refreshing dip. Kailua Beach Park and Lanikai Beach are just a stone's throw away, offering endless opportunities for swimming, kayaking, and paddleboarding. The gentle trade winds make this area a favorite for windsurfing and kitesurfing enthusiasts, ensuring that the thrill of the ocean is never far from your doorstep.

Beyond the beach, Beachside is rich in community spirit. The neighborhood is dotted with charming cafes, local boutiques, and farmers' markets, where you can savor fresh, locally sourced produce and handmade goods. The friendly atmosphere fosters a sense of belonging, making it easy to connect with neighbors and enjoy the vibrant local culture.

For families, Beachside offers access to excellent schools and safe parks, creating a nurturing environment for children to grow and thrive. Outdoor enthusiasts will appreciate the nearby hiking trails, such as the stunning Makapu’u Lighthouse Trail, which rewards hikers with breathtaking panoramic views of the coastline.

Whether you’re looking to unwind on the beach, explore the lush landscapes, or immerse yourself in the local culture, Beachside in Kailua is the perfect place to call home. Embrace the spirit of Aloha and discover the idyllic lifestyle that awaits you in this coastal paradise!

Newest Listings in Beachside

$3,300,000

4 Beds ⋅ 3 Baths ⋅ 202615672 MLS ⋅ FS - Fee Simple Tenure ⋅ 0 DOM

First time on the market in over 50 years! Discover the rare opportunity to own a 2,396 sq ft Kailua Beachside home in the highly desirable Kailuana Place neighborhood. Built in 1970, this 4-bedroom, 2.75-bath home sits on a generous 1/3-acre lot, just a short stroll to private beach access at the famous “Castles” surf break—close enough to hear when the surf is up! Three distinct yard areas, including two fully fenced spaces, create a sense of privacy and room to spread out. A uniquely shaped pool and surrounding yard offer the perfect setting for entertaining or cooling off on warm days. Inside, travertine floors complement a chef’s kitchen featuring granite countertops, Brazilian mahogany cabinetry, and abundant built-in storage. The spacious primary suite offers plenty of closet space. Multiple living areas include a comfortable family room with dining space, a formal dining room, and a spacious formal living room that can be converted into a home gym, office, or both! The oversized 20’ x 20’ two-car garage provides extra storage, while a separate 10’ x 10’ utility room offers additional workspace and storage. A rare Kailua Beachside opportunity priced to sell.

117 Kailuana Place, Kailua

$3,995,000

4 Beds ⋅ 3 Baths ⋅ 202615408 MLS ⋅ FS - Fee Simple Tenure ⋅ 7 DOM

Just 3 houses from the beach, this immaculate three-story, 4-bedroom, 2.5-bath home offers direct ocean views & a rare opportunity to live just steps from the sand. A private deeded lane leads directly to FlagPoles Beach, the widest stretch of sand on Kailua Bay, offering an exceptional setting for swimming, beach walks, paddling, surfing, kitesurfing, & relaxed days by the ocean. Perched on a hill & exposed to cooling sea breezes, the home stays naturally comfortable year-round. Bathed in beautiful natural light, the interior feels bright & welcoming. Freshly painted inside & out, it features new light fixtures, ceiling fans, & appliances for a clean, fresh, move-in-ready feel. The flexible floor plan offers options for separate living spaces, ideal for multi-generational living, guests, a home office, or added privacy. A spacious 2-car garage provides excellent parking & storage. The 10,000 sq ft lot is framed by lush landscaping & towering palm trees. Ask agent about the home potentially coming w/ approved permitted plans for an ADU, pool, & main-home expansion, bringing the total living area to more than 5,000 sq ft. A rare Kailua beachside opportunity you won’t want to miss!

110 N Kalaheo Avenue Unit B, Kailua

$2,980,000

4 Beds ⋅ 2 Baths ⋅ 202612669 MLS ⋅ FS - Fee Simple Tenure ⋅ 10 DOM

Rare opportunity to own in the Kailua Beachside neighborhood of Kainalu Park w/private beach access! Enjoy the best of island-style living in this single-level home located just minutes from Kailua Beach & popular “Castles” surf spot. This spacious home features 4 beds/2 baths plus a large bonus room ideal for family/dining area, home office, playroom or potential extra bedroom. Situated on a generous 11,800 sqft lot, the large backyard & covered lanai provide plenty of room to create your own tropical retreat w/lush landscaping, outdoor living, and a pool. Lovingly cared for & well maintained, this home was updated around 1995 & has been improved as needed over the years. It has great bones & provides the perfect opportunity to add your own personal touches while enjoying the coveted Kailua Beach lifestyle. Major improvements include a new roof in 2017 & new luxury vinyl flooring throughout in 2022. Conveniently located near Kailua Town, Aikahi Shopping Center, schools, restaurants, shops & everyday amenities. Currently tenant occupied but moving out 8/16/26. Private showings only. Vacant photos taken in 2022 prior to tenant occupancy & have been enhanced/virtually staged.

162 Kailuana Loop, Kailua

$11,980,000

5 Beds ⋅ 5 Baths ⋅ 202613970 MLS ⋅ FS - Fee Simple Tenure ⋅ 29 DOM

Completed in 2022, this classic beachfront home was redesigned into a spacious, modern property. 21 Kalaka's unique elevation offers commanding views and privacy; features true beachfront connoisseurs will value. Built by Mokulua High-Performance Builder, it delivers a sleek, elegant take on beachside living. The central open living area flows naturally to the ocean and pool, surrounded by five bedrooms (four en suite) plus a pool room. A breakfast bar and separate guest wing provide privacy and space for extended family. Exceptional craftsmanship, premium materials, and a refined floor plan make this property Kailua Beachfront’s most comprehensive offering.

21 Kalaka Place, Kailua

$2,750,000

5 Beds ⋅ 5 Baths ⋅ 202613874 MLS ⋅ FS - Fee Simple Tenure ⋅ 31 DOM

Best Value in Beachside, Kailua priced under tax assessed value! Only seven homes away from the beach without the oceanfront premium. Set within the private 14-home Hale Kai Surf & Racquet Club, this special beachside estate offers 5 bedrooms, 4.5 baths and 3,958 interior sqft. Upgraded with brand new split AC, owned photovoltaic system, generous living spaces, Main level features 4 bedrooms, 3.5 baths. The entire upstairs level is a private primary ensuite with large dual closets, a sunroom retreat, and access to multiple rooftop spaces. Impressive courtyard entry leads to a grand foyer with soaring ceilings and multiple indoor-outdoor living areas designed for both entertaining and quiet enjoyment. Hale Kai community's exclusive amenities, including an upgraded pool, repaved pickleball, tennis and basketball courts, and clubhouse, are located directly across from the home's front entrance, offering the ultimate convenience. This customized legacy home offers the dream beachside lifestyle with an invitation for personal touches. Exceptional opportunity not to be missed!

824 N Kalaheo Avenue Unit A, Kailua

$3,050,000

4 Beds ⋅ 2 Baths ⋅ 202613516 MLS ⋅ FS - Fee Simple Tenure ⋅ 32 DOM

UNBELIEVABLE $245,000 Price Adjustment! Selling below Appraised Value! One of the lowest priced Beachside Property available and one of the lowest property tax. See this retreat 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….BEACH ACCESS….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. Call for showings!

50 Kalaka Place, Kailua

$3,049,000

4 Beds ⋅ 3 Baths ⋅ 202611322 MLS ⋅ FS - Fee Simple Tenure ⋅ 69 DOM

Your beach days just got closer! Just three homes from Kailua Beach, where morning walks and barefoot afternoons become part of your everyday lifestyle. Offering 4 bedrooms, 2.5 baths, plus a flexible bonus room with its own private entrance, this home is ideal for visiting guests, extended family, or a home office. Investors will appreciate the property’s proven rental appeal. The main home has previously rented for approximately $7,800 a month, while the separate flex room generated approximately $2,300 a month, providing over $10,000 a month in prior rental income. Whether you are looking for an investment, multigenerational living or a beach home with flexibility, this property delivers. Just minutes from Kailua Town's popular restaurants, cafes, boutiques, farmers market and more. And remember- "Life is always better barefoot." Come and fall in love.

156 N Kalaheo Avenue Unit C, Kailua

$3,999,900

4 Beds ⋅ 4 Baths ⋅ 202609693 MLS ⋅ FS - Fee Simple Tenure ⋅ 74 DOM

Beautifully renovated mid-century modern Kailua beach house with room for a pool! This is the single level Beachside home everyone wants, just 5 lots from a gorgeous white sand beach, down one of Kailua's most quiet lanes. Recently expanded to 4 bedrooms, 3.5 baths, this beach home sits on a large flat lot with a beautifully landscaped yard, in one of Hawaii's most coveted neighborhoods! Featuring a brand new kitchen with Wolf appliances, custom cabinets, new tile floors, and a grand living space with soaring high ceilings. The home was just recently expanded to include a brand new primary bedroom and bathroom and a new mud room with a new butler's pantry, a new laundry room, and all new plumbing and electrical. All new Fleetwood windows and sliding doors for smooth, luxurious indoor/outdoor living. And yes there is plenty of room to install a pool! Mahiloa Pl is one of Kailua's hidden gems, on a beautiful part of Kailua beach with minimal public foot traffic. This home has been lovingly remodeled from top to bottom, and is ready for a new owner to move in!

85 Mahiloa Place, Kailua

$4,349,000

6 Beds ⋅ 5 Baths ⋅ 202610270 MLS ⋅ FS - Fee Simple Tenure ⋅ 77 DOM

Experience multi generational luxury living,just moments from famous white sand Kailua Beach with shopping and dining close by.Situated on a landscaped 11,005 sq. ft. level lot, this completely remodeled open concept, light filled property offers a residence of 7 bedrooms, 4.5 bathrooms, included is this is a 1/1 guest quarters with additional full bath. Addtionally, there are 2 finished office spaces with AC across 3,827 sq.ft. of living space.Property includes 3 car garage and secured gated entry.Luxury finishes include Modico cabinetry, quartz waterfall countertops, Italian tile, soaring ceilings and dramatic Viewrail floating staircase with LED-lit Tigerwood treads.The chef’s kitchen features dual built-in DACOR refrigerators,Bosch oven/microwave combo, Monogram cooktop, Thermador dishwasher,and butler’s pantry. Home boasts two outdoor showers, and split A/Cs throughout, Cooling skylights,LED lighting, and owned 28-panel solar system on net metering.Designed to embrace wellness-focused island luxury living, the home features a premium Sunlighten mPulse infrared sauna and Michael Phelps signature cold plunge.

6 N Kalaheo Avenue, Kailua

$5,280,000

3 Beds ⋅ 2 Baths ⋅ 202610235 MLS ⋅ FS - Fee Simple Tenure ⋅ 83 DOM ⋅ Kamaaina Beach BLDG.

KAILUA BEACH is Absolutely one of the most BREATHTAKING beachfront neighborhoods on Oahu and this property doesn't disappoint! Nestled among the palm trees with direct beach frontage, this charming 1950's cottage harkens back to a slower time in the Islands. Expansive front lawn leads to a Powder White Sand Beach with gentle rolling waves suitable for all ages. Perfect location to build a dream home, restore the existing structure or simply slow down and enjoy the property. Kama'aina Beach CPR. Sold with contents and strictly As-Is. A Rare Beachfront find at this price.

140C N Kalaheo Avenue, Kailua

$17,500,000

4 Beds ⋅ 5 Baths ⋅ 202609316 MLS ⋅ FS - Fee Simple Tenure ⋅ 99 DOM

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!

200 S Kalaheo Avenue, Kailua

$18,880,000

12 Beds ⋅ 16 Baths ⋅ 202520168 MLS ⋅ FS - Fee Simple Tenure ⋅ 340 DOM

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.

572C N Kalaheo Avenue, 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.