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$2,000,000
7 Beds 5 Baths 202614077 MLS FS - Fee Simple Tenure
Spacious two story Kailua Home built in 2006 as a multi-generational home. The exterior walls are concrete and the roof is covered in tile. This home sits in the perfect location between Kailua Beach, Kailua Town Center, Enchanted Lake Elementary, & Enchanted Lake Center. There are three bedrooms, two bathrooms, a living room, kitchen and laundry connection downstairs. Both downstairs bathrooms have wide doors, walk in showers and floating sinks. Upstairs there are four bedrooms (2 have walk in closets), three bathrooms, a family room, laundry connections and a wet bar. Large backyard and side yards with many fruit trees. Two car garage and ample off street parking. Solar Water Heater. This home is zoned R-5 and the land may be large enough to build a second dwelling. Check with your architect or plan maker if you would like to create a duplex and also CPR.

646 Wanaao Road, Kailua

Listing courtesy of Blue Ribbon Realty Inc.

$1,395,000
6 Beds 3 Baths 202604953 MLS FS - Fee Simple Tenure
Spacious 6-bedroom, 3-bath home approximately 1968 sq. ft. of living area in a desirable Kailua neighborhood. This versatile home features a functional floor plan with 4 bed/2 baths on the main level, and 2 bed/1 bath and wet bar on the upper level providing additional living space. Separate entries to both levels offers added flexibility for extended or multi-generational living, accommodating guests, or investment opportunities. There is also a large covered lanai perfect for relaxing or entertaining guests. With lots of space and endless potential, this home is ready for your personal updates to make it your own. Conveniently located near the heart of Kailua, with easy access to shopping, dining, schools, parks, and world-famous beaches. Don't miss this great opportunity to own a spacious home with flexible living options in one of Kailua's most sought-after communities.

664 Kihapai Street, Kailua

Listing courtesy of REMAX Hawaii.

$1,805,000
6 Beds 2 Baths 202612433 MLS FS - Fee Simple Tenure
Step into your own private tropical retreat in desirable Keolu Hills. This beautifully updated 6-bedroom, 2-bath home offers exceptional flexibility with 3 bedrooms and 1 bath upstairs and 3 bedrooms and 1 bath downstairs, each with its own entrance—ideal for multigenerational living, extended family, guests, or a variety of living arrangements. Modern upgrades blend seamlessly with the home's classic island charm and include 21 owned PV panels, a solar water heater, solar attic fan, split AC systems, laminate and tile flooring, and stainless steel appliances. The fully fenced property feels like a private botanical garden, filled with mature tropical landscaping and fruit trees. The backyard is truly a showstopper, featuring a stunning waterfall, relaxing jacuzzi, a majestic mango tree known for its delicious fruit, and an expansive covered lanai of approximately 1,000 square feet—perfect for entertaining, outdoor dining, or simply unwinding in your own island oasis. This is a rare opportunity to own a versatile home that offers the best of the Windward lifestyle, just minutes from Kailua's world famous Beach, shopping, hiking, restaurants and more.

1237 Hele Street, Kailua

Listing courtesy of Coldwell Banker Realty.

$4,250,000
8 Beds 8 Baths 202608906 MLS FS - Fee Simple Tenure
Ideally positioned on a rare, level one-acre lot in the heart of Maunawili Valley, 969 Auloa honors a peaceful,Japanese-inspired roots. The estate has undergone a COMPREHENSIVE RENOVATION, blending essential modern upgrades with high-end aesthetics. From the new 200-amp electrical and copper plumbing to the solid quartz surfaces and Toto fixtures, every detail ensures an elevated, worry-free move-in experience. Overlooking the storied paddocks of Maunawili Farms, the estate offers a front-row seat to O‘ahu’s equestrian heritage. Relax by the pristine pool, watch the horses through the tropical canopy. From sought-after Kaimana lychee and Soursop to White peach and Apple bananas, this property is a fruit lover’s paradise. Enjoy papayas for breakfast, fresh tangerines and lemons for a refreshing drink, or gather avocados, coconuts, and mangoes for an evening meal. With multiple living wings and expansive land, it is perfectly suited for customized multi-generational living, diverse income-generating ventures, or a private estate tailored to your specific lifestyle. The main floor has 3 bedrooms and 2.5 bathrooms. The first level is accessed by an outside staircase, 3 beds, 2 baths.

969 Auloa Road, Kailua

Listing courtesy of Compass.

$1,880,000
8 Beds 8 Baths 202610511 MLS FS - Fee Simple Tenure
Welcome to 609 Olomana Street, a newer-built residence in the highly desirable Coconut Grove neighborhood of Kailua. Constructed in 2022 this expansive property offers 8 bedrooms, 6 full bathrooms, and 2 half bathrooms, including a permitted Accessory Dwelling Unit (ADU) —providing exceptional flexibility for multigenerational living, guest accommodations, or potential rental income. The home features approximately 2,960 square feet of living area on a level 5,000-square-foot lot, with split air conditioning throughout for year-round comfort. Modern finishes, and a functional floor plan create an inviting environment for both everyday living and entertaining. Outside, the paved frontage provides ample parking. Ideally located just minutes from Kailua's world-famous beaches, shopping, dining, schools, parks, and recreation, this property offers the perfect combination of island lifestyle and investment potential. Pictures uploaded completed right after construction in 2022. (2) HECO Electric meters.

609 Olomana Street, Kailua

Listing courtesy of Island Life Homes.

$2,249,000
7 Beds 5 Baths 202610167 MLS FS - Fee Simple Tenure
$200k PRICE REDUCTION! Now listed at $2,249,000! Move-in ready and ideal for multi-generational living, Maunawili’s 1031 Lunaai Place is a rare Kailua gem! Lovingly maintained by the original owners, this spacious home offers 7 bedrooms and 4.5 baths with flexible living spaces throughout. The main level features 4 bedrooms, 2 baths, a large living room, family room, dining area, and a generous kitchen. Upstairs, connected by an interior staircase, are 3 additional bedrooms, 1.5 baths, and a spacious family/rec room—perfect for extended family or guests. Both upper and lower levels include separate washer/dryer areas. This homes has a wonderful pool, ready memories to be made! Past the carport, a permitted 4th bathroom and bonus area with separate entrance adding even more versatility. Conveniently located with easy access to the Pali Hwy and/or H-3, making your commute to any of Oahu’s military bases, medical centers, finance district or University of Hawaii, in any direction is about 30 min! Let’s not forget, Kailua Town, with amazing shops, eateries and its famous beaches are also just 10 min. away! Find your favorite realtor TODAY and let’s get started!

1031 Lunaai Place, Kailua

Listing courtesy of Hawaii Modern Realty.

$4,925,000
7 Beds 7 Baths 202610108 MLS FS - Fee Simple Tenure
The most extraordinary remodel transformation you’ll ever see! This stunning 7 bedroom, 6.5 bath residence spans over 6,000 square feet on a generous 14,125-square-foot lot, just a short stroll from Kailua’s iconic 3 mile sandy beach. Completely reimagined, the home feels brand new, fresh, modern, and thoughtfully designed for today’s island lifestyle. Two expansive primary suites anchor the home, each featuring spa-level amenities with private saunas, oversized walk-in showers, washer/dryer's and luxurious soaking tubs. A large rumpus room offers the perfect retreat for the little’s or additional entertaining, while the yard is surrounded by new areka palms that will give total privacy in the near future and a prized mango tree. Plenty of room for a pool too. The kitchen is a showpiece, centered around a 14-foot quartzite island, complemented by striking windows, doors, stone flooring, and two architectural staircases. A rare 2,000-square-foot rooftop deck delivers flexibility for entertaining or relaxing under the stars. Additional highlights include an au-pair suite with kitchenette, a stunning porte-cochère, and an unbeatable location close to the heart of Kailua.

125 N Kalaheo Avenue, Kailua

Listing courtesy of eXp Realty.

$3,150,000
6 Beds 4 Baths 202608800 MLS FS - Fee Simple Tenure
Rarely available in Kailua Estates, 244 Awakea Rd is a beautifully remodeled plantation-style property on a spacious 10,000 sq ft lot just a short stroll to Kailua Beach and minutes to Kailua Town. Fully renovated in 2019, the property offers approximately 3,150 sq ft of total living space with a versatile multi-dwelling layout ideal for investors, multi-generational living, or those seeking flexible income potential. The main home features 3 bedrooms, 2 bathrooms plus a den, with vaulted ceilings, hardwood flooring, a walk-in pantry, and seamless indoor-outdoor living. In addition, the property includes a spacious 1-bedroom cottage with high ceilings and a separate 2-bedroom, 1-bath ADU, both beautifully designed and tenant occupied with strong income potential. A dedicated storage and yoga room adds additional flexibility for wellness, workspace, or lifestyle use. Located in one of Kailua’s most desirable beachside neighborhoods, enjoy easy access to Kailua and Lanikai beaches, Kalapawai Market, and local shops and dining. A rare opportunity to own a flexible compound in a prime location offering both lifestyle and income potential.

244 Awakea Road, Kailua

Listing courtesy of Compass.

$2,490,000
6 Beds 4 Baths 202608541 MLS FS - Fee Simple Tenure
Motivated seller willing to review all offers!!! Welcome to Keolu Hills offering sweeping views of the Ko’olau Mountains! Meticulously maintained 6 bedrooms, 4 full baths, and large bonus room in the back. Featuring a heated built-in swimming pool, 43 PV panels on HECO’s NEM agreement, 9 split AC systems, full alarm system with cameras. The layout offers flexibility of main living on the 1st floor having 5 bedrooms, and the 6th bedroom is a private studio/office on the 2nd floor. This is a large house with 3,536 square feet of living space inside, huge lot size of 9,000 square feet, carport for 2 cars, extended driveway for 3 additional vehicles. Image yourself floating in the heated swimming pool, watching the sunset glimmering off the Ko’olau mountains. Located just minutes from Enchanted Lake Shopping Center, Kailua Town, and only 3 miles to world-famous Kailua Beach, this property combines convenience with privacy. Set back from the road and surrounded by tropical beauty, this home is the perfect Kailua retreat. MatterPort virtual walk through available in link under main picture.

1315 Kupau Street, Kailua

Listing courtesy of Coldwell Banker Realty.

$2,188,000
6 Beds 4 Baths 202605300 MLS FS - Fee Simple Tenure
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

Listing courtesy of Corcoran Pacific Properties.

$2,495,000
9 Beds 4 Baths 202605514 MLS FS - Fee Simple Tenure
Elegant 5-year-old home offering exceptional investment potential and flexible multigenerational living. This spacious property features a two-level main home with an attached ADU, a 2-car garage, and parking for up to 9 cars. Currently operated as a 30–90 day rental. The private ADU includes a full kitchen and living/dining area—ideal for rental income or extended family. The main home offers separate living spaces on each level. Upstairs includes the primary kitchen, great room, 2 lanais, and 4 bedrooms/2 baths (one used as an office). Downstairs features a family room with dining area, kitchenette, 3 bedrooms/1 bath, and 2 small yards with a covered lanai. The ohana provides additional privacy with its own full kitchen, great room, 2 bedrooms/1 bath, and a fenced yard. All rooms offer split A/C, ceiling fans, and large windows for natural light and breezes. Three private living areas, each with separate entrances and laundry. Fully furnished, turnkey, with five years of strong rental history. Please do not disturb tenants.

451 Lanae Way, Kailua

Listing courtesy of OahuRE.com.

$4,350,000
6 Beds 4 Baths 202525771 MLS FS - Fee Simple Tenure
Discover the perfect blend of lifestyle, comfort, and value at 1251 Kainui Drive—an exceptional canal-front retreat situated along an established, palm tree-lined street in North Kailua. Fully renovated in 2026 & move-in ready, the spacious single-level main residence offers 4 beds, 3 baths, and over 3000 SF of beautifully designed living space with soaring ceilings, high-end finishes, and an effortless flow. New standing seam roof, net-metered PV & split AC. The kitchen is the heart of the home, featuring a grand island and luxurious, durable Taj Mahal quartzite countertops, ceiling-high cabinetry, premium appliances, a butler’s pantry, dedicated dining area and a charming breakfast nook. Covered and open lanais connect the living areas to landscaped grounds and a peaceful canal with ocean access—perfect for paddling from your backyard. Room to build your dream pool! A dedicated laundry room, 2-car garage, & ample storage provide everyday ease. The 2-bed, 1-bath ADU adds ~800 SF for multi-generational living, guests or rental flexibility. This desirable location is just two blocks from the beach and provides easy access to Kailua Town, top schools, and freeways for easy commuting.

1251 Kainui Drive, Kailua

Listing courtesy of Compass.

$31,000,000
9 Beds 10 Baths 202600075 MLS FS - Fee Simple Tenure
The Mokulua Estate is a breathtaking oceanfront sanctuary set within the prestigious Lanikai neighborhood. This exceptional property offers unobstructed views of the Mokulua Islands from nearly every vantage point. With over 150 linear feet of ocean frontage and a private gated entrance, the estate provides an ideal blend of seclusion, security, and harmony with its natural surroundings. Encompassing more than 10,000 square feet of refined indoor/outdoor living space, this state-of-the-art residence, designed by award winning architect Jim Jennings showcases dramatic ocean and mountain vistas throughout. A guest house and caretaker’s quarters ensure ample accommodation for family and guests. Direct ocean access from the backyard invites an active island lifestyle, from swimming and snorkeling to kayaking, surfing, fishing, or simply relaxing by the pool in your own tropical paradise. This is a rare, Once-In-A-Lifetime offering you won’t want to miss!!

1240 Mokulua Drive, Kailua

Listing courtesy of List Sotheby's Int'l Realty.

$18,880,000
12 Beds 16 Baths 202520168 MLS FS - Fee Simple Tenure
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

Listing courtesy of REMAX Hawaii.

$50,000,000
12 Beds 15 Baths 202327941 MLS FS - Fee Simple Tenure
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.

508 N Kalaheo Avenue, Kailua

Listing courtesy of Compass.

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.