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$1,899,000
13 Beds ⋅ 5 Baths ⋅ 202609795 MLS ⋅ FS - Fee Simple Tenure ⋅ 132 DOM
A rare opportunity for multi-generational living in the heart of Waimanalo! This 1.1-acre property sits beneath the majestic Mount Olomana and features five single-family homes, each with its own cesspool, in varying conditions. With plenty of space and privacy, it’s perfect for extended families looking to create a shared retreat or for those wanting to renovate and make it their own. Enjoy the peaceful surroundings and the potential to build lasting memories in a truly special place. Just minutes from world-famous Waimanalo Beach and a short drive to Kailua Town, you’ll find the ideal mix of island seclusion and everyday convenience. Don’t miss this rare chance to own a legacy property in one of Oahu’s most scenic communities. Flood Zones: AEF + XS

41-1702 Kalanianaole Highway, Waimanalo

$1,825,000
3 Beds ⋅ 2 Baths ⋅ 202606901 MLS ⋅ FS - Fee Simple Tenure ⋅ 140 DOM
Live on ONE LEVEL with a very private backyard oasis complete with Pool, Jacuzzi and covered Patio! Enjoy high open-beamed ceilings throughout the home. A quality kitchen with real wood cabinets and granite countertops. Updates include a 30,000 BTU split A/C, Roof re-coating, Acasia flooring, windows, Pentair Pool Pump, new pool skimmer, a new ABS sewer line from street to house, new incoming copper water lines, ceiling fans, lighting, primary bathroom vanity, automated sprinkler system, and a large detached storage shed complete with electrical and double walled framing. Exceptional curb appeal with a six-foot lava rock wall bordering the street, landscaped front yard, stamped concrete driveway, two-car carport, and extra driveway parking. Situated on a quiet dead-end street with sidewalks, this is the ideal peaceful Kailua neighborhood if you like morning/evening walks. The shops, groceries, eateries, and a movie theaters of Enchanted Lakes shopping plaza are within walking distance. This home is a turnkey gem designed to make memories!

533 Iana Street, Kailua

$2,150,000
4 Beds ⋅ 4 Baths ⋅ 202609261 MLS ⋅ FS - Fee Simple Tenure ⋅ 138 DOM
At the end of a quiet, no-through-traffic cul-de-sac on Iana Street, this 4-bedroom, 4-bath home is surrounded by golf course and canal front homes and built around an open layout that connects the kitchen, dining, and living areas into one bright, easy-flowing space. The living room has vaulted ceilings and large Pella windows and doors that pull in natural light and tropical views. The kitchen and dining area feature double wall construction and bullnose corners, giving the space a clean, updated feel. The remodeled kitchen itself has granite counters, custom cabinetry, travertine floors, a gas cooktop, and dual sinks. A dedicated home office and a separate art studio add flexibility beyond the four bedrooms. The backyard has a saltwater pool with flagstone decking, a gazebo, and mature landscaping on a level 9,912 sq. ft. lot, with the 7th fairway of Mid-Pacific Country Club as a quiet, green backdrop. The home is equipped with 39 owned PV panels and six split A/C systems. A rare mix of open, updated living space and privacy on one of Kailua's most desirable streets.

415 Iana Street, Kailua

$2,188,000
6 Beds ⋅ 4 Baths ⋅ 202605300 MLS ⋅ FS - Fee Simple Tenure ⋅ 196 DOM
This legal multi-family property spans 10,716 sq ft and features two spacious detached homes on a quiet cul-de-sac, offering a perfect setup for multi-generational living or a savvy investment. Live in one, rent the other. The front home features luxury vinyl plank and tile flooring, with split AC units in the living room and primary bedroom. The back home is accessible via a private walkway and includes a usable lanai and a window AC. Both residences enjoy their own separate fenced yards and share a large swimming pool equipped with a removable Guardian Pool Fence, creating an ideal environment for entertaining. Designed for convenience and privacy, the homes feature separately metered electricity, and the water system is ready for sub-metering. Parking is plentiful, with a two-car garage, additional off-street parking for four cars, and ample street parking available. Located in a prime Kailua neighborhood, the property is just minutes from schools, parks, the Enchanted Lake Shopping Center, and downtown Kailua, with the beach only a short distance away.

1439 Akuleana Place, Kailua

$2,188,000
202605301 MLS ⋅ FS - Fee Simple Tenure ⋅ 196 DOM
This legal multi-family property spans 10,716 sq ft and features two spacious detached homes on a quiet cul-de-sac, offering a perfect setup for multi-generational living or a savvy investment. The front home features luxury vinyl plank and tile flooring, with split AC units in the living room and primary bedroom. The back home is accessible via a private walkway and includes a usable lanai and a window AC. Both residences enjoy their own separate fenced yards and share a large swimming pool equipped with a removable Guardian Pool Fence, creating an ideal environment for entertaining. Designed for convenience and privacy, the homes feature separately metered electricity, and the water system is ready for sub-metering. Parking is plentiful, with a two-car garage, additional off-street parking for four cars, and ample street parking available. Located in a prime Kailua neighborhood, the property is just minutes from schools, parks, the Enchanted Lake Shopping Center, and downtown Kailua, with the beach only a short distance away.

1439 Akuleana Place, Kailua

$2,750,000
5 Beds ⋅ 3 Baths ⋅ 202604504 MLS ⋅ FS - Fee Simple Tenure ⋅ 215 DOM
Welcome to the beach home of your dreams, where location and quality meet for Hawaiian-living perfection. Just a short stroll from the beach, this impeccable single-level residence offers the ultimate in relaxed seaside living. Imagine morning walks along the white sands of Waimanalo Beach, and afternoon swims in the calming blue waters. Step outside to your private backyard oasis, complete with saltwater pool, sauna, and covered entertaining areas. Adding exceptional value and versatility, a 1 bed/1bath unit with kitchenette, private outdoor space, and separate entrance is located at the rear of the home. Enjoy energy-efficiency with owned Photovoltaic panels and 3 Tesla batteries. With an ample amount of bedrooms and living spaces, you’ll have plenty of options for utilizing this home in any of the ways your heart desires. Whether you’re searching for a full-time home or a vacation getaway, this beachside gem checks every box. *Tax records differ from actual

41-046 Hihimanu Street, Waimanalo

$24,900,000
10 Beds ⋅ 9 Baths ⋅ 202525519 MLS ⋅ FS - Fee Simple Tenure ⋅ 318 DOM
Live among Hawaii's natural wonders & unsurpassed beauty at this extraordinary Pahonu Beach estate. Spanning nearly 1 acre, this oceanfront property includes 152 linear feet along the Pacific Ocean. Nestled in a private, gated location, the 2 lot compound offers over 8600 sq ft of living area in its main house, guest house, cottage, and studio. Expansive lawns provide mesmerizing views across the ocean to Manama (Rabbit) Island and stunning vistas of the Koolau Mountains. The main house completed in 2022, sets a new standard of quality craftsmanship. Exceptional design, flawlessly executed using premium materials, creates a luxurious, beautiful, and comfortable home. Floor to ceiling sliding glass doors span the oceanfront side, providing spectacular views of the lush landscaping and ocean. The gourmet kitchen includes top of the line appliances, custom walnut cabinetry, and a disappearing pantry consistent with its sleek, modern design. Next door includes a 3BR oceanfront guest house, 2BR cottage and studio. This irreplaceable compound offers its next owner an opportunity to enjoy a spectacular lifestyle with family and friends in a magnificent oceanfront setting.

41-471 Kalanianaole Highway, Waimanalo

$5,388,000
202510044 MLS ⋅ FS - Fee Simple Tenure ⋅ 531 DOM
PRICE REDUCTION! 5.5% cap rate on current income! This exceptional property offers 10 apartment units and 2 ground floor retail units in prestigious Kailua. The building was majorly renovated inside and outside including replacement of all utilities, new silicone waterproof roof and commercial grade gutter systems, all new stainless steel appliances, flooring, interiors, fencing and painting. All apartment units have dual-pane glass vinyl windows and balcony sliding doors, LED lighting, split AC units in bedrooms and living rooms, and individual full-size stacked LG washer-dryers located on the balconies. The 2 retail spaces benefit from a high visibility location in this upscale retail corridor. In addition to abundant street parking in the immediate area, there are 7 covered parking stalls. Located just moments from Whole Foods Market and Kailua Beach. This is a trophy, renovated asset in an incredibly desirable submarket where investment properties are rarely available for sale and could be “turnkey” for a buyer. The apartments and retails units have been split into separate TMKs (1-4-3-31-27-1 & -2) for lower property tax rates.

54 Maluniu Avenue, Kailua

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.