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$2,149,000
4 Beds 2 Baths 202616975 MLS FS - Fee Simple Tenure 2 DOM
Fully remodeled in 2024, truly MOVE IN READY! Just a few blocks from Aikahi shopping center and Kailua beach! This 4 bedroom 2,020 SF home has a spacious great room, chef’s kitchen with gas range, pantry, indoor laundry room, & screened in bonus room, perfect for outdoor dining, or flex space. The primary suite is separated from the other 3 bedrooms with a custom closet and lg bathroom w/walk-in shower and freestanding tub. Step out to a sparkling pool, mature landscaping and multiple lanais. The vaulted breezeway leads to the additional bedrooms with a new custom Murphy bed in the middle bedroom. Spacious enough for a built in bar plus a home office. Louvered shutters throughout, solar shades in the kitchen, new fans and designer paint. A 24-panel owned photovoltaic system with battery storage on a new ’24 roof. All new windows and doors framing mountain and mature garden views. Split AC system throughout plus a gas range and two large propane tanks for a VERY energy efficient home! Plans to enclose the carport into a 2 car garage are in the permitting process! Minutes to military base, the beach, H-3, Pali and Likelike and a short stroll to great local schools.

340 Ilimano Street, Kailua

$4,250,000
202616607 MLS FS - Fee Simple Tenure 13 DOM
MAUNAWILI AT ITS FINEST! One Acre+ lot in the heart of the Valley. Overlooking your very own Kailua estate and the horses of Maunawili Farms. Having just undergone a COMPREHENSIVE RENOVATON and appraised at over 5 million dollars, this estate offers quite a lifestyle right here in Kailua. Just a few miles from one of the world's most beautiful beaches, minutes to Le Jardin Academy and 20 minutes to Honolulu, our location is ideal. The main part of this home is stunning, featuring an open floor plan with a well planned kitchen right in the heart of the home. Floor-to-ceiling windows, large rooms, and tall ceilings frame the mountain views. The lower floor is separate from the main home but could be connected if desired. It features 3 bedrooms and two full baths, plus a large entertainment area that is ideal for MULTIGENRATIONAL living, teenagers in their own space or a rental. VERSATILITY is key here, offering many options with this AG Land. The unpermitted Yellow cottage has an additional 3 bedrooms, 2 baths and kitchen. Enjoy a refreshing swim in the pool, with a big bowl of home grown fruits. Lots of parking for cars, toys, and entertaining. Come see us today!

969 Auloa Road, Kailua

$1,525,000
4 Beds 2 Baths 202615171 MLS FS - Fee Simple Tenure 17 DOM
Single-level 4-bedroom, 2-bath home in Olomana, Kailua, located on a quiet cul-de-sac street with minimal through traffic. Features 1,848 sq. ft. of living space on a 10,944 sq. ft. lot. Easy access to the Pali Highway and H-3 provides a quick commute to town, with Castle Medical Center and Maunawili Elementary nearby. The open, light-filled floor plan features a skylight, Saltillo tile, and luxury vinyl flooring. The kitchen has white cabinets and countertops, along with newer appliances. 24 PV panels with net metering, an energy-efficient heat pump, and upgraded 200-amp electrical service help keep utility costs down. Enclosed garage. The private backyard has no homes directly behind the property and features a well-manicured slope with mature papaya, avocado, lemon, and lime trees. A covered lanai with a remote-operated cover is ideal for entertaining, morning coffee, or evening drinks with friends. Set near the base of Mount Olomana in a quiet, established neighborhood with long-time neighbors, this is a home where you can picture holidays, birthdays, and quiet Sunday mornings. Come see how easily this inviting Olomana home could feel like your own.

1567 Uluhaku Place, Kailua

$1,495,000
3 Beds 3 Baths 202614708 MLS FS - Fee Simple Tenure 42 DOM Bluestone BLDG.
Bluestone's Kamahele Townhome - under $1.5M! Welcome to Bluestone, one of Kailua’s most private and prestigious gated communities. Set on nearly 50 acres of lush grounds fronting Mid-Pacific Country Club and surrounded by preservation land, this 3-bedroom, 2.5-bath townhome offers rare privacy, sweeping golf course, Ko‘olau mountain, and sunset views, plus an attached full-size garage and driveway parking for two additional vehicles. Three covered lanais capture cooling trade winds and provide seamless indoor-outdoor living. Bluestone residents enjoy resort-style amenities including a pool, whirlpool, BBQ areas, recreation spaces, tennis/pickleball courts, sauna, and gated security with patrol. Ideally located in the hills of Kailua, just minutes from Lanikai Beach and the Pillbox hike, this is a rare opportunity to own a townhome style with attached garage in the prestigious community of Bluestone at $1,495,000 — one of the few under $1.5M. Come and see what the Bluestone community has to offer! Sold As-Is. Furniture is negotiable.

1150B Kamahele Street Unit #3002, Kailua

$645,000
1 Beds 1 Baths 202614387 MLS FS - Fee Simple Tenure 46 DOM Windward Passage BLDG.
Rarely available prestigious penthouse unit at the top of Windward Passage! Floor to ceiling windows open to a panoramic view out over Enchanted Lake & down the majestic Koolau Mountain range. You can even enjoy the colors of the sunset as the sun sinks below the mountains in the evenings. The whole apartment opens to the view, and all that window space gives you a bright airy open feel that makes the unit seem even larger than it is. The kitchen & bathroom have been upgraded. The bathroom renovation included replacing the tub with a full-size shower & brand-new vinyl plank flooring was just installed throughout. Everything is ready for you to move in & enjoy! Add to this the resort style amenities that Windward Passage has to offer including tennis courts, pickleball, a racquetball court, swimming pool, whirlpool, BBQ areas, dog park, fitness center with saunas, storage areas for surfboards & bicycles & additional storage for each unit. Plus, a can't beat location right in Kailua Town with easy access to shopping, restaurants, the open markets and so much more with Kailua Beach just moments away. What more could you ask for? This is just what you've been waiting for!

322 Aoloa Street Unit PH8, Kailua

$1,870,000
4 Beds 4 Baths 202613694 MLS FS - Fee Simple Tenure 57 DOM
Discover this beautifully upgraded and well-cared-for 4-bedroom, 3.5-bath home, ideally situated on a desirable corner lot with only two neighboring properties and striking views of the Koolau Mountains. The flexible floor plan includes a separate-entry, one-bedroom with a wet bar, full bathroom, dining space, and private lanai—ideal for guests, a home office, or private living area. At the heart of the home is a spacious, thoughtfully designed kitchen featuring a bay window overlooking a peaceful garden retreat with a waterfall pond. A large covered lanai creates a wonderful setting for outdoor dining, entertaining, or simply enjoying Kailua’s relaxed island lifestyle. The inviting, gated entry is surrounded by mature tropical landscaping, including citrus and fig trees, heliconia, palms, and other lush plantings. Additional features include a fully fenced backyard, solar water heater, workshop, and two storage sheds. Offering privacy, versatility, mountain views, and beautifully landscaped outdoor spaces, this special property is ready to welcome its next owner.

1308 Kuuna Street, Kailua

$1,350,000
4 Beds 2 Baths 202609502 MLS FS - Fee Simple Tenure 64 DOM
Wake up to stunning, unobstructed views of the majestic Olomana mountain range from this property brimming with potential. This home presents a rare opportunity to renovate, restore, or create a space tailored to your vision in one of Kailua's most desirable locations. Featuring a flexible floor plan and ample outdoor space, this property is ready for its next chapter. Whether you're looking to undertake a full renovation or make improvements over time, the possibilities are endless. Enjoy convenient access to shopping, dining, beaches, parks, and the scenic Kawainui Marsh Trail, offering opportunities to experience one of O?ahu's most unique natural landscapes. The property is being sold in its present condition. Interior square footage may differ from tax records. Buyers are strongly encouraged to perform their own due diligence regarding the property's condition, improvements, permits, square footage, and all other material facts they deem important to their purchase.

319 Kihapai Street Unit C, Kailua

$925,000
3 Beds 2 Baths 202608120 MLS FS - Fee Simple Tenure 103 DOM Windward Harbour BLDG.
Wake up to breathtaking mountain views and end your day on your own private rooftop lanai. This rare, 3-bedroom 2-bathroom gem at Windward Harbor blends modern Kailua elegance with resort-style amenities. This is island living at its finest. From the floor-to-ceiling windows that bathe the open-concept of indoor and outdoor living space with a screened in lanai to enjoy the tropical water features and landscapes. The Primary Suite is located downstairs with a large walk in closet and shower and two bedrooms plus full bathroom upstairs. Enjoy two covered side by side parking right at the walk way for easy entry. Conveniently located in the heart of Kailua Beach Town, Whether you're strolling to Kailua Town for your morning coffee or hitting the sands of world-famous Kailua Beach, this isn't just a condo—it’s your personal sanctuary. Gated Community with amenities including an on-site manager, pool, jacuzzi, sauna, BBQ, car wash, Pickleball and Tennis courts. This is a pet-friendly building!

1030 Aoloa Place Unit 2/302B, Kailua

$1,659,000
4 Beds 2 Baths 202612545 MLS FS - Fee Simple Tenure 73 DOM
Desirable Keolu Hills ~ Your Opportunity Awaits! Discover the potential in this spacious single-level 4-bedroom, 2-bath home, ready for your personal touches. Designed for both comfort and functionality, this home offers generous living spaces and a versatile layout perfect for everyday living. Inside, enjoy an open-concept design featuring a den/office area, dining space, and a large family room - ideal for gatherings and relaxation. The main living areas are enhanced with Koa-style luxury vinyl flooring and travertine tile, while the kitchen showcases granite countertops and abundant cabinetry. Step outside and unwind in your private backyard oasis, or take advantage of the upper terraced lot, leading to a viewing deck with breathtaking panoramic views of Kailua Beach, Waimanalo, and Rabbit Island. Conveniently located just minutes from shopping, dining, schools, and world-renowned beaches, this home offers both lifestyle and location. Don’t miss this incredible opportunity!

1494 Kina Street, Kailua

$4,250,000
8 Beds 8 Baths 202608906 MLS FS - Fee Simple Tenure 81 DOM
MAUNAWILI AT ITS FINEST! One Acre+ lot in the heart of the Valley. Overlooking your very own Kailua estate and the horses of Maunawili Farms. Having just undergone a COMPREHENSIVE RENOVATON and appraised at over 5 million dollars, this estate offers quite a lifestyle right here in Kailua. Just a few miles from one of the world's most beautiful beaches, minutes to Le Jardin Academy and 20 minutes to Honolulu, our location is ideal. The main part of this home is stunning, featuring an open floor plan with a well planned kitchen right in the heart of the home. Floor-to-ceiling windows, large rooms, and tall ceilings frame the mountain views. The lower floor is separate from the main home but could be connected if desired. It features 3 bedrooms and two full baths, plus a large entertainment area that is ideal for MULTIGENRATIONAL living, teenagers in their own space or a rental. VERSATILITY is key here, offering many options with this AG Land. The unpermitted Yellow cottage has an additional 3 bedrooms, 2 baths and kitchen. Enjoy a refreshing swim in the pool, with a big bowl of home grown fruits. Lots of parking for cars, toys, and entertaining. Come see us today!

969 Auloa Road, Kailua

$2,325,000
4 Beds 4 Baths 202612015 MLS FS - Fee Simple Tenure 83 DOM
Back on the market and now offered at $174,000 below original list price — your opportunity to own in Kailua just got better! Our seller has made new improvements to make this home shine! 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. 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 landscaped yard w/an auto. gate for privacy. Wonderful location just min. from world-famous Kailua Beach!

409 Wanaao Road, Kailua

$640,000
1 Beds 1 Baths 202611276 MLS FS - Fee Simple Tenure 85 DOM Windward Passage BLDG.
Rare high-floor one-bedroom unit with breathtaking views of Enchanted Lake, the Ko'olau Mountains and Kailua Town. Remodeled in 2025 with vinyl luxury flooring throughout, along with updated appliances, cabinets, countertops, lighting, and fixtures. Light and bright, the unit features floor to-ceiling windows that showcase the expansive views. Evening views are spectacular with gorgeous colorful skies as the sun sets behind the mountains. No popcorn ceilings, two window A/C units, an in-unit washer and dryer, and one covered assigned parking stall. Amenities include a heated saltwater pool, spa, sauna, BBQ area, dog park, tennis and pickleball courts, guest parking, 24-hr. security, fitness center, EV charger on property, kayak and surfboard racks, plus storage. Conveniently located in the heart of Kailua, the building is close to Kailua Beach, Whole Foods, Target, restaurants, and shops. Pet-friendly and ideally situated to enjoy everything Kailua has to offer!

322 Aoloa Street Unit 1708, Kailua

$1,450,000
3 Beds 3 Baths 202607704 MLS FS - Fee Simple Tenure 106 DOM Windsurfer BLDG.
Experience the quintessential Kailua LIFESTYLE at The WINDSURFER, a boutique 10-unit townhome community situated directly across from Kailua Beach. LOCATION. This part of Kailua Beach has Oahu's BEST KITESURFING; it's heaven! The Windsurfers Unit #4 Is the Special Unit that sits right on the lily pond, a happy and serene spot to reflect the days activities.  This RARELY AVAILABLE residence features a freshly painted interior, loft, new washer and dryer, and updated kitchen and bathrooms from a 2018 renovation. The versatile layout can accommodate either three bedrooms, or two bedrooms with a flex space and a half bath. The large tiled private patio offers many opportunities, entertaining, dining, outdoor living room and is has a lighted walk in storage closet for bikes, tools, and equipment. 2 reserved and excellent parking spaces right outside your door and guest parking is available for your friends. Most importantly ... Yes, PET FRIENDLY! Located just steps from world-class windsurfing, Kalapawai Market, and BUZZ'S Steakhouse, this serene retreat offers a welcome escape from the bustle of Honolulu.  CALL today to learn all about the outstanding lifestyle at the Windsurfer!

445 Kawailoa Road Unit 4, Kailua

$4,925,000
7 Beds 7 Baths 202610108 MLS FS - Fee Simple Tenure 112 DOM
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

$2,150,000
4 Beds 4 Baths 202609261 MLS FS - Fee Simple Tenure 121 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

$4,350,000
6 Beds 4 Baths 202525771 MLS FS - Fee Simple Tenure 191 DOM
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

$50,000,000
12 Beds 15 Baths 202327941 MLS FS - Fee Simple Tenure 1001 DOM
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

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.