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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.

$2,050,000
4 Beds ⋅ 3 Baths ⋅ 202614180 MLS ⋅ FS - Fee Simple Tenure
Relax and enjoy your slice of paradise just blocks from world famous Kailua beaches. There are cool tropical tradewinds for this brand new construction 4 bedroom 3 bath detached single family home with a brand new swimming pool and covered lanai. Enjoy an active beach, hiking and biking lifestyle with great restaurants and shopping right down the road. There is an open floor plan. High quality construction with lovely finishes throughout including quartz countertops, stainless steel appliances with durable ceramic tile and vinyl flooring. Split AC throughout and a 220 outlet for your electric car.

240 Kalama Street, Kailua

Listing courtesy of eXp Realty.

$2,750,000
5 Beds ⋅ 5 Baths ⋅ 202613874 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Koi Realty.

$2,050,000
4 Beds ⋅ 2 Baths ⋅ 202613001 MLS ⋅ FS - Fee Simple Tenure
Gorgeous, rare and turnkey single-level home in the desirable Enchanted Lake neighborhood of Kailua. The open-concept floor plan is complemented by split A/C throughout, a new roof, and picturesque Ko'olau Mountain views. Designed to embrace Hawaii's indoor-outdoor lifestyle, the backyard serves as a seamless extension of the home, featuring a tiled swimming pool with a rooftop solar pool heating system, covered lanai, built-in BBQ, wood-fired pizza oven, and generous outdoor living areas, complemented by a Sonos outdoor sound system, creating the perfect setting for al fresco dining, poolside gatherings, or movie nights under the stars. Ideally located just minutes from Kailua Town, shopping, dining, parks, and Kailua's renowned beaches. First Open House this Sunday 7/19/2026 from 2-5pm!

1127 Lauloa Street, Kailua

Listing courtesy of Coldwell Banker Realty.

$2,625,000
5 Beds ⋅ 5 Baths ⋅ 202612304 MLS ⋅ FS - Fee Simple Tenure
Rare opportunity to own a canal front home on a nearly 10,000 sq. ft. R-5 zoned lot with a legal ‘ohana unit, each with its own utility meters, complete with pool & spa.  Tucked along the peaceful cul-de-sac end of Kainui Drive, locally known as “Duck Road.”  The spacious single-level main home features three generously sized bedrooms with new carpeting, three bathrooms, a dedicated study and bright living and dining areas that flow seamlessly into an enclosed lanai. A large recreation room or studio complete with a kitchenette, bathroom, private entrance, and its own courtyard provides additional flexibility for guests, home office or extended family. Upstairs, the 800 sq ft 'ohana unit (823 Kainui Dr) features two bedrooms, one bathroom, and a covered lanai. Recent upgrades include a new roof on the main home and a freshly re-plastered pool.  Take in stunning sunsets over the Ko'olau Mountains from the multiple outdoor areas, relax in the pool and spa, or enjoy a paddle or boat out to Kailua Bay. This unique property offers flexibility and is ideal for multigenerational living, generating rental income, or both. The possibilities are truly endless.

821 Kainui Drive, Kailua

Listing courtesy of Arquette Properties Inc.

$2,450,000
4 Beds ⋅ 3 Baths ⋅ 202612934 MLS ⋅ FS - Fee Simple Tenure
Live at the top of Keolu Summit in Hillcrest with 180 degree views of the Koolau mountains, Olomana peaks, Enchanted Lake, and Kailua Bay. A stunning viewscape captured from your wrap around lanais and large picture windows framed by high vaulted ceilings. The open layout of the home embraces the essence of Hawaiian living with modern finishings and covered ipe wood lanais offering you a variety of settings for entertaining and indoor/outdoor living. The main house provides a large primary bedroom with an en suite bath, a spacious second bedroom, and a third bedroom or office. The separate cottage with full bath and kitchenette has equally captivating views with a large lanai. The resort-like blue tiled pool with spa and water feature is surrounded by lush tropical landscaping providing beauty and privacy. Features an owned PV system, 2-car enclosed garage, and adjacent workshop/storage. There are 2 dedicated parking stalls along the private road for guests. This cul-de-sac location places you at the high point of the Summit bordered by conservation land. Minutes to the white sandy beaches of Kailua and Waimanalo and the trendy shops and restaurants of Kailua Town.

1461 Aunauna Street, Kailua

Listing courtesy of Coldwell Banker Island Prop.

$2,300,000
4 Beds ⋅ 3 Baths ⋅ 202611972 MLS ⋅ FS - Fee Simple Tenure
Tucked onto one of Kalaheo Hillside's most sought-after streets, 445 Iliwahi Loop is a fully reimagined 4-bed, 3-bath retreat blending timeless island architecture with a clean, considered renovation — vaulted ceilings, an open great room flowing to covered lanais, and walls of glass framing the pool, gardens and fountains. This generous lot sits against the conservation hillside adding to the peace and quiet of this location. The chef's kitchen pairs a Viking range and Sub-Zero refrigeration w/a generous island open to the dining & living areas. Two primary suites suit multigenerational living or a guest wing, the spa-inspired primary bath w/a soaking tub and oversized shower. Two additional bedrooms w/shared bath PLUS 2 office/flex rooms Outside is your own resort: a sparkling pool (plus spa hookup), mature landscaping, a garden gazebo and covered lanai seating for golden-hour gatherings. NEM metering, 2 Tesla Powerwalls, + a new GACO roof! Freshly painted inside & out, new flooring, lighting & fans throughout. Minutes to Kailua Beach, a short hop to Marine Corps Base Hawaii, and moments from H-3, Pali and Likelike — with Aikahi Shopping Center and dining close at hand.

445 Iliwahi Loop, Kailua

Listing courtesy of eXp Realty.

$2,395,000
4 Beds ⋅ 4 Baths ⋅ 202612015 MLS ⋅ FS - Fee Simple Tenure
A brand new roof and now offered at $105,000 below original list price — your opportunity to own in Kailua just got even better! Experience the best of island living in this beautifully upgraded 4-bed/3.5-bath home featuring a legal ADU on a large, custom-landscaped lot (11,353 sq. ft.). This property offers stylish high-end finishes, an open layout, & seamless indoor-outdoor flow. The main house welcomes you with 3 bed/2.5 bathrooms. The chef's kitchen is a true delight, it boasts KraftMaid cabinets, double-wall oven & granite counters. Retreat to the primary suite with its soothing bathroom and walk-in California Closet. The custom-designed legal ADU was thoughtfully crafted with meticulous detail to provide long-term comfort and independence for the owner's parent. The huge outdoor lanai extends this living space & is ideal for extended family, guests, or rental income. Energy efficiency abounds w/ 38 owned PV panels, 2 storage batteries and 2 solar water heaters. Add'l features include a laundry room, split AC's, storage rm, covered parking for a boat, outdoor shower & a fully fenced yard w/an auto. gate for privacy. Wonderful location just min. from world-famous Kailua Beach!

409 Wanaao Road, Kailua

Listing courtesy of Compass.

$2,195,000
4 Beds ⋅ 3 Baths ⋅ 202611702 MLS ⋅ FS - Fee Simple Tenure
Live the Kalua Lifestyle! Located in the desirable Kalama Tract neighborhood of Kailua within a short distance of Beautiful Kailua Beach and Kailua Town that offers a multitude of shopping and dining choices. This desirable single level, spacious 4 bedroom / 3 bath home with an enclosed 2 car garage has a newer roof and remodeling was done within the past few years. Located near schools, the public District Park, public Library, H-3 and the Pali Highway for an easy commute to Honolulu and a short distance to Marine Corps Base Hawaii (MCBH). The generous sized lot of 12,500 square feet is really something special and offers many possibilities for the new homeowners! The yard is enclosed if you have children or pets. The home is being sold "As Is". Don't miss this special home!

176 Kuulei Road, Kailua

Listing courtesy of Hawaii Modern Realty.

$2,600,000
4 Beds ⋅ 2 Baths ⋅ 202607969 MLS ⋅ FS - Fee Simple Tenure
You will love this location in Lanikai where an active lifestyle awaits you. One block to beach access where swimming, windsurfing, paddling are yours to enjoy every day. In the other direction is the entrance to Lanikai trail and Midpac Golf Course and Country Club. Impressive lava rock wall encloses a 4-bedroom home with enclosed porch addition and large deck overlooking an expansive yard. Build your dream multilevel home with 2 street entrances and potential view of Mokulua Islands and ocean.

150 Kaelepulu Drive, Kailua

Listing courtesy of Coldwell Banker Realty.

$2,800,000
202610761 MLS ⋅ FS - Fee Simple Tenure
Rare opportunity to be the owner of a fee-simple, business zoned property in desirable Kailua. Centrally located in the heart of Kailua Town, with lots of foot traffic and drive-by traffic for high visibility. Perfect for the savvy investor, or do as the current owner and rent out 2 of the 3 units while you run your business out of the third. Current tenants on month-to-month and would like to stay. Owner's unit is vacant and easy to show. Great opportunity to get out from under the rising rents of Kailua and build equity while you build your business!

45 Hoolai Street, Kailua

Listing courtesy of Coldwell Banker Realty.

$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.

$2,650,000
3 Beds ⋅ 3 Baths ⋅ 202609988 MLS ⋅ FS - Fee Simple Tenure
Escape to the tranquility of your private sanctuary, conveniently located within a ten-minute walk from the renowned Kailua Beach. This exquisite residence was meticulously designed for casual island entertaining and seamless indoor-outdoor living. A sparkling pool, a luxurious jacuzzi, & a verdant landscape of mature tropical vegetation create a serene and visually appealing ambiance. Nestled within the picturesque town of Kailua, this property offers unparalleled convenience, with all necessary amenities within a short bicycle ride. The tranquil neighborhood provides a peaceful retreat, while the presence of a thriving lime tree named Eileen adds a touch of local charm. Pau Hana or intimate gatherings with family and friends will create lasting memories. This is the home everyone wants to come to for every occasion! Boasting a spacious yard, expansive pool deck, and an open-floor plan that is aesthetically pleasing and easy to maintain. The apartment can be kept and collected for $2,500+ per month or used as a chic private primary suite…steps to the jacuzzi and pool for midnight swims. Masterful! Hurry over. Owned solar panels, split AC, Gas Cooking, Oversized Garage, Limes!

294 Awakea Road, Kailua

Listing courtesy of Compass.

$2,099,500
4 Beds ⋅ 3 Baths ⋅ 202609203 MLS ⋅ FS - Fee Simple Tenure
Welcome home to beautiful Maunawili! Tucked away on a quiet cul-de-sac and surrounded by lush greenery, this beautifully renovated home is stunning with Ko’olau mountain views that capture the essence of Windward living. Inside, enjoy a spacious open-concept layout with soaring high ceilings, creating a bright and airy feel throughout. The home features luxury vinyl flooring, split AC units in every room, and a modern kitchen with quartz countertops, a large waterfall island, and new appliances, perfect for everyday living and entertaining. The main level offers 3 bedrooms and 2 bathrooms, with the primary bedroom located on the lower level, while the upstairs includes a separate 1-bedroom, 1-bath living area, ideal for extended family or guests. Step outside to a large Trex deck overlooking a private, lush backyard, perfect for relaxing or hosting while taking in the surrounding greenery. A rare opportunity to own a move-in ready home in highly desirable Maunawili.

1287 Puualoha Street, Kailua

Listing courtesy of REMAX Hawaii.

$2,599,000
5 Beds ⋅ 3 Baths ⋅ 202609140 MLS ⋅ FS - Fee Simple Tenure
One of Kailua's most sought-after neighborhoods. This lovely home comes with 5 bedrooms and 3 baths, a 3035 square foot home located on a cul-de-sac just a 10-minute, half-mile walk to Kailua Beach and minutes to Kailua town, shops, restaurants, boutiques, coffee shops, farmers' markets, schools, and parks. The main house on the lower level is 3 bedrooms, 2 baths, with 2 covered outdoor lanai areas, plus an upstairs 2 bedrooms, 1 bath with a separate entrance with mountain view. Includes a 2-car garage, situated on a large, level 10,000+ square foot lot.

260 Kuukama Street, Kailua

Listing courtesy of OahuRE.com.

$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.

$2,700,000
5 Beds ⋅ 3 Baths ⋅ 202606811 MLS ⋅ FS - Fee Simple Tenure
Two blocks from turquoise water and best strip of sandy beach for miles, nestled between Kailua Beach and Lanikai, this classic Hawaiian style home offers the perfect balance of privacy and effortless indoor-outdoor living. High wood beam ceilings with rich detail and open-concept layout invites natural light and garden views throughout. Walls of windows perfectly frame a backdrop that is connected to nature. The spacious living area flows seamlessly to 2 covered lanais—perfect for entertaining or relaxing. The kitchen features wood cabinetry, large island, bar seating, new appliances, and warm finishes that complement the island aesthetic. It’s a retreat designed with both style and ease in mind, while the surrounding landscape creates a peaceful, resort-like setting. Minutes from famous beaches, parks, and charming shops and cafes of Kailua, this home delivers a lifestyle of morning beach walks, sunset paddles, and the quiet luxury of island living. The main home is spacious with 3 beds and 2 baths. Enjoy a separate, private entry, ample 800+sf rec area, with wet bar, bath, and second laundry, to be used for recreation, artist studio, exercise space, caretaker or guest area.

151 Alala Road, Kailua

Listing courtesy of Coldwell Banker Realty.

$2,195,000
5 Beds ⋅ 3 Baths ⋅ 202607327 MLS ⋅ FS - Fee Simple Tenure
Recently reintroduced to the market, this spacious 5-bedroom, 3-bath single-family home sits on a large, level lot in the desirable Kailua neighborhood. Its thoughtful layout provides flexibility for multi-generational living, home offices, or extra space. Enjoy a seamless indoor-outdoor flow with a generous yard, ideal for entertaining or future expansion. Conveniently located near schools, shopping, and beaches, this is a rare chance to own a well-sized home with room to grow in one of Oahu’s most sought-after communities. Move-in ready and available for purchase "as is."

1091 Alahaki Street, Kailua

Listing courtesy of HB Homes INC.

$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.

$2,188,000
202605301 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. 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.

$2,125,000
4 Beds ⋅ 3 Baths ⋅ 202525463 MLS ⋅ FS - Fee Simple Tenure
This beautiful home provides the perfect blend of Security, Privacy & TONS of space!! The 3/2 Main floor features a deck, large living room transitioning into chefs kitchen w/ island & walk-in pantry + a family room w/ wet bar & laundry room w/ extra storage. Main bedroom includes a tasteful en-suite bathroom & walk-in closet. Outside is a landscaped, fully fenced yard, & a covered patio w/ utility sink. Upstairs living area is substantial & unique. It includes a large office leading to the huge ~750 sqft. bedroom with its own entertainment area & oversized walk-in closet. The bathroom includes dual sinks, vanity, linen closet & open format shower. Sliding doors lead to the fully enclosed ~280 sq. ft. private deck. Truly a one of a kind space. There is a 2 car garage with workshop space & storage, and a total of 5 parking (1 for boat/jet skis). Original construction was done with post tension slabs to ensure structural stability. The home also includes an insulated attic, 4 split ac units, 40 owned PV panels, 3 Tesla batteries & Tesla power charger. Pre-listing Home inspection completed 8/28/2025 with no major findings.

1386 Nanialii Street, Kailua

Listing courtesy of Real Broker.

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.