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$2,099,500
4 Beds ⋅ 3 Baths ⋅ 202609203 MLS ⋅ FS - Fee Simple Tenure ⋅ 86 DOM
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
$17,500,000
4 Beds ⋅ 5 Baths ⋅ 202609316 MLS ⋅ FS - Fee Simple Tenure ⋅ 88 DOM
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
$859,000
3 Beds ⋅ 2 Baths ⋅ 202608782 MLS ⋅ FS - Fee Simple Tenure ⋅ 88 DOM ⋅ Windward Passage BLDG.
Completely renovated from top to bottom! Freshly painted throughout! No popcorn ceilings! New vinyl flooring throughout. New tile on the lanai. New kitchen cabinets, appliances and lighting. New bathroom vanities, mirrors and lighting. This cool side of the building has wonderful windward breezes. Peek-a-boo ocean view. 3 new AC units. This beautiful Kailua condo has everything you could need: tennis courts, BBQ area, onsite dog park, salt water pool, spa, bike/ surfboard /kayak racks, fitness room, racquetball, and gorgeous views of Kailua. Close to Kailua Town with shopping galore and numerous restaurants. Don't forget world famous Kailua Beach just moments away.

322 Aoloa Street Unit 611, Kailua
$1,200,000
3 Beds ⋅ 2 Baths ⋅ 202608964 MLS ⋅ FS - Fee Simple Tenure ⋅ 88 DOM
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
$3,150,000
6 Beds ⋅ 4 Baths ⋅ 202608800 MLS ⋅ FS - Fee Simple Tenure ⋅ 88 DOM
Now offered at a new price, 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 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 of living area, 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, a walk-in pantry, and seamless indoor-outdoor living. The property also includes a spacious 1-bedroom cottage and a separate 2-bedroom, 1-bath ADU. The 1-bedroom cottage and 2-bedroom ADU are currently tenant occupied, generating a combined $7,600 per month in rental income. A dedicated storage/yoga room adds additional flexibility. Priced at $1,000 per sqft, below the recent Kailua Estates average of approximately $1,046 per sqft, 244 Awakea offers an exceptional combination of lifestyle, flexibility, and income potential. Enjoy easy access to Kailua and Lanikai beaches, Kalapawai Market, shopping, dining, and everything Kailua has to offer.

244 Awakea Road, Kailua
$700,000
2 Beds ⋅ 2 Baths ⋅ 202609173 MLS ⋅ FS - Fee Simple Tenure ⋅ 90 DOM ⋅ Hokulani In Kailua BLDG.
Wonderful 2 Bedroom 2 Bath at Hokulani in Kailua! Covered Parking Space and ample guest parking! High, vaulted ceilings, laminate floors, and a bright kitchen with Corian counter tops. No one above you! Both baths have upgraded vanities and ceramic tile flooring. Covered Lanai. The Hokulani recently installed new windows and sliding doors and are now completing a parking cover renovation. Nestled with a park-like setting and gazebo. Located in the heart of Kailua conveniently located near restaurants, Whole Foods, Foodland, Target, Coffee Shops, the Post Office and world-famous Kailua Beach!

355 Aoloa Street Unit G205, Kailua
$2,599,000
5 Beds ⋅ 3 Baths ⋅ 202609140 MLS ⋅ FS - Fee Simple Tenure ⋅ 91 DOM
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
$2,490,000
6 Beds ⋅ 4 Baths ⋅ 202608541 MLS ⋅ FS - Fee Simple Tenure ⋅ 93 DOM
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, 45 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
$2,790,000
202608942 MLS ⋅ FS - Fee Simple Tenure ⋅ 94 DOM
Rare opportunity with great potentials, for either own family living or rental investment, easy to afford mortgage! Located only a few houses away from world-famous Waimanalo white sand beach! Ideal for own living to enjoy lots of space in highly desirable beach neighborhood. 5704sf living space, 6 private entrances on 11,250sf lot. This 2-story house, 3811sf was newly built in 2015. Plus 1-story Ohana unit, 1893sf. This gated & spacious property offers 11 bedrooms, 8 full bathrooms, idyllic office space. Stunning, unobstructed Ko’olaumountain views. Total of 2 kitchens, 2 wet bars and plus. Huge sizes for all living rooms, kitchens, bedrooms, etc. 11ft tall ceiling for main living room; 9ft tall for other areas. Tons of upgrades: lanai, auto metal gate, natural stones, metal roof, solid wood cabinets & double-door entries, hardwood floor, granite & quartz countertops, Quartz staircase, etc. If for rental, since so close to beach, high rental demands paying good price to generate good incomes.

41-51 Hinalea Street, Waimanalo
$2,790,000
11 Beds ⋅ 8 Baths ⋅ 202608921 MLS ⋅ FS - Fee Simple Tenure ⋅ 94 DOM
Rare opportunity with great potentials, for either own family living or rental investment, easy to afford mortgage! Located only a few houses away from world-famous Waimanalo white sand beach! Ideal for own living to enjoy lots of space in highly desirable beach neighborhood. 5704sf living space, 6 private entrances on 11,250sf lot. This 2-story house, 3811sf was newly built in 2015. Plus 1-story Ohana unit, 1893sf. This gated & spacious property offers 11 bedrooms, 8 full bathrooms, idyllic office space. Stunning, unobstructed Ko’olaumountain views. Total of 2 kitchens, 2 wet bars and plus. Huge sizes for all living rooms, kitchens, bedrooms, etc. 11ft tall ceiling for main living room; 9ft tall for other areas. Tons of upgrades: lanai, auto metal gate, natural stones, metal roof, solid wood cabinets & double-door entries, hardwood floor, granite & quartz countertops, Quartz staircase, etc. If for rental, since so close to beach, high rental demands paying good price to generate good incomes.

41-51 Hinalea Street, Waimanalo
$2,700,000
5 Beds ⋅ 3 Baths ⋅ 202606811 MLS ⋅ FS - Fee Simple Tenure ⋅ 95 DOM
Steps away from turquoise water and the best strip of sandy beach for miles, nestled between Kailua and Lanikai beaches, this classic Hawaiian style home has high ceilings, an open concept layout, and offers the perfect balance of privacy and effortless indoor-outdoor living. Open wood beam ceilings, and windows galore allow natural light and views that bring the outdoors in, perfectly framing a backdrop connected to nature. The spacious living area flows seamlessly to 2 covered lanais, both with ceiling fans and lighting, 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, 800+sf garage converted rec area, with wet bar, full bath, and 2nd laundry. Must see!

151 Alala Road, Kailua
$569,000
2 Beds ⋅ 2 Baths ⋅ 202608729 MLS ⋅ FS - Fee Simple Tenure ⋅ 99 DOM ⋅ Koolau Vista BLDG.
Koolau Vista - Move In Ready! Priced to sell! Great for First Time Buyer or Investor! Live in the Heart of Kailua Town! Minutes to Shopping, Dining, Beaches. Two Bedroom, 1.5 Bath Split Level Townhome. with One Covered Parking Stall. Vacant - Easy to Show! Being Sold As-Is.

350 Aoloa Street Unit C214, Kailua
$4,098,000
5 Beds ⋅ 4 Baths ⋅ 202608270 MLS ⋅ FS - Fee Simple Tenure ⋅ 102 DOM
Set along the coveted waterfront canal of Kailua, this iconic property 485 Wanaao, captures the essence of modern island living with rare versatility & timeless appeal. Situated on a generous lot, the residence offers a seamless blend of indoor-outdoor living, framed by tranquil water views & lush surroundings. The main home features 4 bedrooms & 2.5 bathrooms, thoughtfully designed with soaring ceilings, & a spacious open-concept layout that fills the interior with natural light & refreshing trade winds. Clean lines, modern finishes, & refined craftsmanship create an inviting yet sophisticated atmosphere, perfect for both everyday living & entertaining. The fully legal 1-bedroom, 1-bath ADU—ideal for guests, extended family, or rental income—adding exceptional flexibility to this already remarkable offering. Expansive outdoor spaces invite you to unwind, host gatherings & enjoy peaceful waterfront setting. This home delivers a lifestyle that is both rare and deeply connected to its surroundings. Minutes from Kailua's beaches, dining and shopping. A true once-in-a-lifetime opportunity to own a signature property in one of O‘ahu’s most desirable coastal communities.

485 Wanaao Road, Kailua
$1,798,000
5 Beds ⋅ 3 Baths ⋅ 202608144 MLS ⋅ FS - Fee Simple Tenure ⋅ 105 DOM
With stunning upgrades in the last year,, this five bedroom home located in Kailua Bluffs has unobstructed views of the Olomana peaks, a private greenbelt backdrop, and no rear neighbors — just mountain, sky, and quiet. Inside, the home has been updated with care: fully renovated kitchen with new cabinets, countertops, appliances, and flooring. Updated bathrooms. New paint, baseboards, and canned lighting and fixtures throughout. New HVAC system with whole-home AC, including a new split system addition. It's move-in ready and thoughtfully done. The layout is flexible — two bedrooms and a full bath on the main level for multi-generational living, guests, or a home office. Soaring ceilings and an open-concept living area flow to a spacious covered patio, making indoor-outdoor living effortless. Outside, a level, private backyard with mature pomelo, avocado, and bilimbi trees. Morning light, evening breeze, and the kind of view you don't get tired of. 49 owned solar panels with two large battery banks keep energy costs low. This is a rare opportunity in one of Kailua's most sought-after neighborhoods.

1614 Paukiki Street, Kailua
$1,498,000
3 Beds ⋅ 3 Baths ⋅ 202607772 MLS ⋅ FS - Fee Simple Tenure ⋅ 107 DOM
Welcome home to this wonderful two story home that features 3 bedrooms and 2 1/2 bathrooms located in the highly desirable Kailua Bluffs neighborhood. Home features an open living area with soaring vaulted ceilings. Large covered patio located in back of home is perfect for BBQ with family and friends. Spacious primary bedroom with en suite bathroom. 2nd, 3rd bedrooms and 2nd bathroom is on the second floor. Half bathroom is located on the 1st floor. Just minutes away from world famous beaches, shops, dining and outdoor adventures. Don't miss this opportunity!

1479 Kanapuu Drive, Kailua
$1,029,000
2 Beds ⋅ 2 Baths ⋅ 202606264 MLS ⋅ FS - Fee Simple Tenure ⋅ 109 DOM ⋅ Ka Malanai At Kailua BLDG.
MAJOR PRICE IMPROVEMENT! Here's your opportunity to secure a below-market VA loan at 2.25%! And the best part? It's open to both VA & non-VA buyers*!!! Approximate loan balance of $582K and monthly P&I of $2557, the interest savings and lower monthly payments offer a unique chance to live in one the most desired neighborhoods on O‘ahu in the heart of Kailua Town! Enjoy the island lifestyle without compromising modern conveniences - from world-class beaches to all your everyday needs i.e. shopping, dining, entertainment, and fitness centers - all while benefiting from the long-term cost savings! Price is what you pay upfront, cost is what you pay over time and this home arguably offers the greatest value! Move-in ready with fresh interior paint, NEW vinyl flooring in the bedrooms, and a NEW dishwasher and just awaiting your personal touches! Contact your agent to schedule a showing today! *Subject to lender & VA approval.

437 Kailua Road Unit 6102, Kailua
$854,000
3 Beds ⋅ 2 Baths ⋅ 202607270 MLS ⋅ FS - Fee Simple Tenure ⋅ 109 DOM ⋅ Lakeview BLDG.
Welcome to one of the few 3-bedroom, 2-full bathroom homes available in the highly desirable Lakeview townhomes in Kailua’s Enchanted Lake. This well-maintained unit offers a functional layout with thoughtful updates throughout, including new window screens and blinds, updated bathroom sinks, refreshed kitchen cabinetry, and a new dishwasher. The split AC system has been improved with the condenser relocated below the home, creating additional usable lanai space ideal for relaxing or entertaining. The second floor unfolds into a private primary retreat, where the primary bedroom and bathroom are tucked away from the rest of the home with serene tree views. Enjoy one of the rare full lake view units in this community, with beautiful lake views and the added bonus of fireworks on the Fourth of July and New Year’s. Located just minutes from Kailua Town, beaches, and nearby schools, this home offers both convenience and a lifestyle that makes living on O'ahu truly special.

1237 Akipohe Street Unit 4C, Kailua
$3,495,000
3 Beds ⋅ 1 Baths ⋅ 202607560 MLS ⋅ FS - Fee Simple Tenure ⋅ 113 DOM
Prime Lanikai Location and Large, Level Land. This lot is 40% larger than a standard Lanikai lot and it’s just yards from the best of Lanikai’s sandy beach. New concrete block perimeter wall built by First Choice Concrete. Newly updated original 1930’s Cottage, currently tenant occupied. Collect rent while you finalize your building plans. This is the canvas to make your Lanikai dream a reality. (Property taxes can be significantly lower for owner-occupant)

119 Kuailima Drive, Kailua
$1,350,000
3 Beds ⋅ 3 Baths ⋅ 202607472 MLS ⋅ FS - Fee Simple Tenure ⋅ 114 DOM ⋅ Bluestone BLDG.
Enjoy sweeping, unobstructed views of the golf course, majestic mountains, and a hint of ocean from the highly desirable Lanikai side of Bluestone. This well-maintained residence offers a kitchen with granite countertops, a stylish bathroom, and thoughtfully designed vinyl windows that bring in natural light and enhance overall comfort. A skylight further elevates the interior, filling the space with brightness and creating a warm, open atmosphere. Ideally situated near beautiful beaches, shopping, and dining, this home delivers both convenience and the best of island living. A strong investment opportunity with excellent rental appeal in a highly sought-after community.

319 Kaelepulu Drive Unit 202, Kailua
$2,195,000
5 Beds ⋅ 3 Baths ⋅ 202607327 MLS ⋅ FS - Fee Simple Tenure ⋅ 118 DOM
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
$412,500
1 Beds ⋅ 1 Baths ⋅ 202606606 MLS ⋅ FS - Fee Simple Tenure ⋅ 128 DOM ⋅ 75 Kihapai BLDG.
Recently renovated, this one-bedroom single level unit on the ground floor features a covered lanai that is gated for privacy and includes one designated parking spot. In addition to a new split AC, flooring, kitchen countertops and cabinets, bathroom shower and shelving, during the renovation the water lines and vent/sewer stacks were upgraded. PLUS it has an exterior storage unit in the backyard along with a clothesline and washing machine.  Enjoy the trade wind breezes and natural lighting. Stay cool in the Saltwater pool on hot summer days. Furnishings included. Tenant would like to stay on.  VA Approved.

75 Kihapai Street Unit 3, Kailua
$10,500,000
202606637 MLS ⋅ FS - Fee Simple Tenure ⋅ 129 DOM
Value-add, multi-tenant retail center in beautiful Waimanalo. Sale includes both TMK 1-4-1-009: 275 & 278. Two contiguous fee simple parcels (~ 2.2 acres) currently under a Master Ground Lease that will expire on 12/14/2026. Approximately 36,000 square feet of leasable area including 6,300 sq. ft. of second floor offices and 95 parking stalls. Approximately 65% occupied. Call Listor for more info. Buyer to do their own due diligence and verify all information. Please do not disturb the tenants.

41-1537 Kalanianaole Highway, Waimanalo
$649,000
2 Beds ⋅ 2 Baths ⋅ 202605842 MLS ⋅ FS - Fee Simple Tenure ⋅ 136 DOM ⋅ Windward Passage BLDG.
Enjoy island living in this beautifully situated 2-bedroom, 2-bath condo in the heart of Kailua. Offering 956 sq ft of interior space plus a generous 92 sq ft lanai, this residence features floor-to-ceiling windows that fill the home with natural light and capture an indoor-outdoor lifestyle. The well-maintained, pet-friendly building offers a full suite of amenities including a pool, fitness center, tennis courts, storage, bike and surf racks, on-site manager, security, and fire sprinklers. Added convenience with in-unit washer/dryer. Ideally located just minutes from shopping, dining, and world-famous beaches, this is an exceptional opportunity to enjoy the best of Kailua living.

322 Aoloa Street Unit 309, Kailua
$3,880,000
3 Beds ⋅ 3 Baths ⋅ 202605289 MLS ⋅ FS - Fee Simple Tenure ⋅ 142 DOM
Your dream waterfront Kailua residence. This hidden jewel fronting Kawainui Canal with access to the ocean offers an exceptional blend of contemporary design and Kama‘aina elegance. Architecturally designed and tastefully refreshed, this 3 bdrm, 2.5 ba residence with 3,291 sq ft of living space offers vaulted ceilings (which elevate the sense of space and natural light), fresh interior/exterior paint, vinyl plank flooring, new carpet, and an open chef’s kitchen featuring custom cabinetry, quartz countertops, and a spacious 10’ island. An expansive primary suite overlooks the pool deck with canal and majestic Ko’olau Mountain views. Designed for effortless indoor/outdoor living, there are multiple lanais along with a swimming pool—ideal for entertaining and everyday relaxation. Lush landscaping on the 14,866 sq ft lot enhances the already tranquil setting. The cul-de-sac location maximizes the already private location. An owned photovoltaic system with a net metering agreement adds energy efficiency. Just minutes from Kailua’s beaches, shopping, and dining, this home offers elevated island living in one of Oahu’s most desirable neighborhoods.

1110 Ilikala Place, Kailua
$2,188,000
6 Beds ⋅ 4 Baths ⋅ 202605300 MLS ⋅ FS - Fee Simple Tenure ⋅ 144 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 ⋅ 144 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
$2,495,000
9 Beds ⋅ 4 Baths ⋅ 202605514 MLS ⋅ FS - Fee Simple Tenure ⋅ 147 DOM
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
$795,000
2 Beds ⋅ 2 Baths ⋅ 202528258 MLS ⋅ FS - Fee Simple Tenure ⋅ 153 DOM ⋅ Windward Passage BLDG.
A gorgeous, breezy light-filled space is yours with this remodeled 2 BR/2 Full BA condo in the premiere Windward Passage building. Features include a tree-top view, smooth/no-popcorn ceiling, fresh paint, new lighting & fans, & new primary bedroom carpet. Oak cabinets & granite counters with a breakfast bar, complement the expanded kitchen area. This condo has great storage & includes a separate exterior locker, as well as common spaces for surfboard, bike, & kayak storage. Building amenities are many: on-site manager, 24/7 security, pool, spa, fitness center, dog park, recreation area near pool, recreation/party room, & even tennis & pickle ball courts. The Windward Passage plumbing project is also complete, meaning new toilets, as well as new drain & supply lines, & shut-off valves for all units in building. Garage spalling project ongoing & near completion. This building is very well-maintained & already includes sprinklers & other fire safety measures. Pet friendly & the minimum rental period is 6 mo. The building is ideally located in the center of Kailua, within a mile of Kailua Beach & just a few blocks to shopping (Target/Whole Foods/Safeway etc.) & many restaurants.

322 Aoloa Street Unit 505, Kailua
$1,075,000
2 Beds ⋅ 2 Baths ⋅ 202600852 MLS ⋅ FS - Fee Simple Tenure ⋅ 156 DOM ⋅ Ka Malanai At Kailua BLDG.
Experience the convenience and charm of life in the heart of Kailua with a rare feature that sets this home apart: THREE assigned parking stalls. A true rarity in Kailua, the additional stall offers flexibility for multiple vehicles, visiting guests, or even potential rental income by leasing the extra stall to another resident. Moments from world-famous beaches, popular dining, shopping, cafes, and everyday essentials, this beautifully maintained 2-bed/2-bath condo offers an exceptional opportunity to enjoy one of Oahu's most desirable communities. Built in 2017, this modern residence combines comfort and style with central AC, stainless steel appliances, and a bright open-concept layout that extends seamlessly to a spacious covered lanai. The generous primary suite serves as a private retreat, featuring a walk-in closet and a spa-inspired bath with a separate soaking tub. Ka Malanai offers beautifully landscaped courtyards, BBQ areas, gathering spaces, and secure bike, surfboard, and kayak storage. Conveniently located near Kailua Beach Park, Kailua District Park, Whole Foods, Target, and the many shops, restaurants, & services that make Kailua such a special place to call home.

409 Kailua Road Unit 7106, Kailua
$4,350,000
6 Beds ⋅ 4 Baths ⋅ 202525771 MLS ⋅ FS - Fee Simple Tenure ⋅ 156 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

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.