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$1,825,000
3 Beds 2 Baths 202606901 MLS FS - Fee Simple Tenure
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

Listing courtesy of Corcoran Pacific Properties.

$2,150,000
4 Beds 4 Baths 202609261 MLS FS - Fee Simple Tenure
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

Listing courtesy of Hawaii Modern Realty.

$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.

$17,500,000
4 Beds 5 Baths 202609316 MLS FS - Fee Simple Tenure
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

Listing courtesy of Coldwell Banker Realty.

$1,200,000
3 Beds 2 Baths 202608964 MLS FS - Fee Simple Tenure
Huge Price Reduction! Priced Well Below Tax Assessed Value! Don't miss this incredible opportunity to own in the highly desirable Enchanted Lake neighborhood of Kailua. Bring your vision and renovation ideas to transform this single-level home into the island retreat of your dreams. Featuring 3 bedrooms, 2 baths, and two spacious family rooms, there's plenty of room to create a space that fits your lifestyle. Step outside and enjoy a backyard filled with mature fruit trees, including mountain apple, starfruit, and a rare Samoan coconut tree. Beyond the property, you'll love the charm of the neighborhood, known for its boutique shopping, cozy coffee shops, and popular local restaurants. And best of all, world-famous Kailua Beach is just minutes away. This is your chance to secure a home in one of Kailua's most sought-after communities at an exceptional value. Let's talk!

889 Alahaki Street, Kailua

Listing courtesy of Engel & Volkers Honolulu.

$3,045,000
6 Beds 3 Baths 202608800 MLS FS - Fee Simple Tenure
MAJOR PRICE REDUCTION! Exceptional opportunity in a preferred location within Kailua Estates. 244 Awakea Rd is a beautifully remodeled plantation-style property on a spacious 10,000 sqft lot, just a short stroll to Kailua Beach and minutes from Kailua Town. Renovated in 2019, this unique property offers three separate living spaces with a combined 6 bedrooms, 4 bathrooms, and approximately 3,150 sqft, ideal for multi-generational living, extended family, or long-term rental income. The main residence features 3 bedrooms, 2 bathrooms plus a den, vaulted ceilings, hardwood flooring, PV and solar hot water. There is also a spacious 1-bedroom cottage and a separate 2-bedroom, 1-bath ADU, both currently tenant occupied and generating a combined $7,600/month. The ADU is separately metered and features solar hot water. A dedicated storage/yoga room adds flexibility. Now offered at $3,045,000, or $966/sqft, below the recent Kailua Estates average of approximately $1,046/sqft. Enjoy easy access to Kailua and Lanikai beaches, Kalapawai Market, Buzz's, Whole Foods, boutique shops, dining, and everything Kailua has to offer.

244 Awakea Road, Kailua

Listing courtesy of Compass.

$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.

$1,999,000
4 Beds 3 Baths 202525463 MLS FS - Fee Simple Tenure
Hands down the best value in all of Kailua at under $580/sqft for a custom built, move in ready home!!! For buyers' peace of mind, the pre-listing home inspection was completed in 2025 with minimal findings. This home presents an incredible opportunity...don't miss out!! The 3/2 main level features a deck, lg living room transitioning into chefs kitchen w/ island & walk-in pantry + family room w/ wet bar & laundry rm w/ extra storage. Main bedroom includes a tasteful en-suite bathroom & walk-in closet. Outside is a landscaped, fully fenced yard, & covered patio w/ utility sink. Upstairs living area is substantial & unique including a lg 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. There is a 2 car garage with workshop space & storage, and a total of 5 parking. 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.

1386 Nanialii Street, Kailua

Listing courtesy of Real Broker.

$1,488,000
4 Beds 3 Baths 202525520 MLS FS - Fee Simple Tenure
Tucked away in one of Kailua's most sought-after neighborhoods, this spacious 4-bedroom, 3-bathroom home presents a wonderful opportunity to create your dream home. This property features two 8-foot storage containers, a 1,232 sq ft deck with ocean & mountain views, ample parking for up to five cars or a boat, and a unique steel-frame construction with solid Styrofoam walls that deliver insulation, structural stability, and built-in termite resistance. Situated on a generous 9,410-square-foot lot, the property offers plenty of room to relax, entertain, and embrace the Kailua lifestyle. The versatile floor plan lends itself beautifully to multi-generational living or a rental opportunity, providing flexibility to suit your needs. Ideally located just minutes from world-famous Kailua Beach, charming boutiques, and favorite, local restaurants, this property offers the perfect blend of location, potential, and lifestyle. Whether you choose to refresh the current design or reimagine the space entirely, this home invites you to bring your vision to life in one of Oahu's most exceptional communities.

1459 Akamai Street, Kailua

Listing courtesy of Engel & Volkers Honolulu.

$4,150,000
4 Beds 4 Baths 202525307 MLS FS - Fee Simple Tenure
Don't miss the best value in Lanikai! Experience elevated island living in this fully renovated Lanikai retreat where luxury, privacy, and the natural beauty of Hawaii come together. Just 2 blocks from a secluded beach cove and a short paddle to the Mokulua Islands, this thoughtfully designed property captures the laid-back yet refined Lanikai lifestyle. Enter through a landscaped courtyard into a 3-bed, 3-bath main home featuring two spacious primary suites, customizable closets, and 1000+sf of open-air lanais that make indoor-outdoor living effortless. High ceilings, large sliding doors, hardwood floors, large-format tile, and custom cabinetry reflect quality at every turn. The kitchen features a generous island, sunlit dining nook, and designer finishes ideal for casual meals or entertaining. Surrounded by mature landscaping, the property offers room for a pool in either the front courtyard or the large, level backyard. A detached 1-bed, 1-bath suite with wet bar, laundry, and 1000+sf lanai above the 2-car garage offers versatility for guests or rental income—while preserving privacy for the main residence. This is a must-see property to truly appreciate the beauty and value.

223 Lanipo Drive, Kailua

Listing courtesy of Compass.

$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.

$1,440,000
5 Beds 3 Baths 202519336 MLS FS - Fee Simple Tenure
Amazing opportunity to own in Kailua! This flexible floor plan offers endless possibilities with a well-maintained 4-bedroom, 2-bath main home (currently configured as a 3/1 plus a spacious studio). An additional remodeled studio (5th bedroom), separated by the saltwater pool, enjoys treetop and mountain views of Enchanted Lake, along with cool breezes and privacy. Ideal for multigenerational living, a home office, or rental income potential. The property is fully fenced and landscaped with a sprinkler system—perfect for your fur babies! Conveniently located near world-famous Kailua beaches, parks, shops, and restaurants, with easy access to the H-3 and Pali Highway—without having to fight traffic in Kailua town. Put this home on your must-see list! Number of bedrooms differs from tax records. One or more photos have been enhanced.

1233 Keolu Drive, Kailua

Listing courtesy of Redfin Corporation.

$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.