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$729,000
1 Beds ⋅ 1 Baths ⋅ 202616213 MLS ⋅ FS - Fee Simple Tenure ⋅ Windward Harbour BLDG.
Live above the treeline in the heart of Kailua. This top-floor corner residence at Windward Harbour pairs sweeping Ko?olau Mountain views with an exceptional indoor-outdoor lifestyle. The spacious 1-bedroom, 1-bath home offers 865 sq ft of single-level living plus a rare 440 sq ft open rooftop lanai—an incredible private retreat for morning coffee, sunset dinners, gardening, entertaining, or simply enjoying the trade winds. Floor-to-ceiling windows fill the home with natural light and frame lush garden and mountain views throughout. Updated in 2017, the residence features an ensuite bath with double sinks and in-unit laundry with washer and dryer replaced approximately 3 years ago. Fee simple and pet-friendly, with covered parking and separate storage large enough for a bicycle and kayak. Enjoy resort-style amenities including pool, hot tub/Jacuzzi, sauna, tennis court, clubhouse, BBQ areas, secured entry, and resident manager. Just minutes from Kailua Beach, Whole Foods, shops, dining, and everything that makes Kailua living so special. A rare opportunity to own a home that captures the light, views, trade winds, and effortless indoor-outdoor lifestyle Kailua is known for.

1030 Aoloa Place Unit 412A, Kailua

Listing courtesy of Compass.

$399,500
1 Beds ⋅ 1 Baths ⋅ 202614348 MLS ⋅ FS - Fee Simple Tenure ⋅ 75 Kihapai BLDG.
Welcome home! Conveniently located one bedroom, one bath condo walking distance to Kailua town's shops and restaurants, and a few minutes bike ride or drive to beautiful Kailua Beach. The condo is move in ready, newly painted with new refrigerator, range, kitchen counters, and mirror closet doors. Other amenities include tile floors, a gated lanai, window a/c in the bedroom, plus hook-ups for a washer and dryer. This unit has easy access to the assigned parking stall and pool on the ground floor. Enjoy a swim in the condo pool while you watch the wildlife of Kawainui Marsh. Come make 75 Kihapai Street unit 5 your new home!

75 Kihapai Street Unit 5, Kailua

Listing courtesy of Kailua Beach Properties LLC.

$645,000
1 Beds ⋅ 1 Baths ⋅ 202614387 MLS ⋅ FS - Fee Simple Tenure ⋅ 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

Listing courtesy of Homequest LLC.

$759,000
1 Beds ⋅ 1 Baths ⋅ 202613740 MLS ⋅ FS - Fee Simple Tenure ⋅ Ka Malanai At Kailua BLDG.
Tucked away in one of the most peaceful locations within Ka Malanai, this desirable one-bedroom residence enjoys a quiet back corner, top floor setting surrounded by lush tropical landscaping, offering exceptional privacy and a serene island atmosphere. Fresh new carpet and a bright, well-maintained interior create a welcoming space ready to enjoy, while the convenient in-unit washer and dryer make everyday living effortless. Two parking stalls provide the flexibility and convenience that are rarely found with a one-bedroom home. Perfectly positioned in the heart of Kailua, this residence offers easy access to world-famous Kailua Beach, where turquoise waters and powder-soft sand invite morning swims, paddling, and sunset strolls. Kailua Town's vibrant collection of boutiques, cafés, restaurants, grocery stores, and everyday conveniences are just moments away, creating an ideal balance of relaxation and accessibility. Nearby Kailua District Park offers tennis courts, sports fields, fitness opportunities, and community events, completing the lifestyle that makes Ka Malanai one of Kailua's most sought-after communities.

445 Kailua Road Unit 5304, Kailua

Listing courtesy of Hawaii Modern Realty.

$660,000
1 Beds ⋅ 1 Baths ⋅ 202613708 MLS ⋅ FS - Fee Simple Tenure ⋅ Windward Passage BLDG.
Welcome to Windward Passage unit #810. This one-bedroom, one bathroom, and one assigned parking stall unit was just renovated with no expense spared. Every small detail was considered in the renovation to make this unit move-in ready. The kitchen features a single-level quartz countertop and brand-new stainless steel appliances. The entire unit has brand-new luxury vinyl plank flooring. The bathroom was converted to a shower, and a GFCI outlet was added so you can install a washlet on the toilet. Brand-new board-approved AC units were installed to help keep the unit cool during the warm summertime. Windward Passage features a wide variety of amenities, including a gym, kayak/surfboard racks, pool, jacuzzi, BBQ grills, dog park, tennis/pickleball courts, and a racquetball court. Located in Kailua town, shopping and restaurants are just steps away from this condo.

322 Aoloa Street Unit 810, Kailua

Listing courtesy of Newtown Realty, Inc..

$640,000
1 Beds ⋅ 1 Baths ⋅ 202611276 MLS ⋅ FS - Fee Simple Tenure ⋅ 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

Listing courtesy of Hawaii Life.

$374,000
1 Beds ⋅ 1 Baths ⋅ 202611325 MLS ⋅ FS - Fee Simple Tenure ⋅ Windward Passage BLDG.
Welcome to Windward Passage, one of Kailua’s most established and desirable condominium residences, ideally positioned in the heart of Kailua Town. This exceptional address offers the rare combination of island ease, everyday convenience, and resort-style amenities, all just moments from world-famous Kailua Beach, boutique shopping, dining, cafés, farmers markets, and the relaxed charm that makes Kailua one of Oahu’s most beloved communities. Set within a well-known high-rise community at 322 Aoloa Street, residents enjoy an amenity-rich lifestyle with features that may include a pool, spa, fitness center, sauna, tennis/pickleball courts, BBQ areas, recreation spaces, storage options, security, and on-site management. Whether you are seeking a primary residence, island retreat, or investment opportunity, Windward Passage offers a compelling blend of location, lifestyle, and long-term appeal. Please note, some photos have been virtually staged. A wonderful opportunity to own in the heart of Kailua, where comfort, convenience, and island living come together beautifully.

322 Aoloa Street Unit 306, Kailua

Listing courtesy of First Hawaiian Realty.

$412,500
1 Beds ⋅ 1 Baths ⋅ 202606606 MLS ⋅ FS - Fee Simple Tenure ⋅ 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

Listing courtesy of Coldwell Banker Realty.

$469,999
1 Beds ⋅ 1 Baths ⋅ 202513528 MLS ⋅ FS - Fee Simple Tenure ⋅ Windward Passage BLDG.
Short sale lender has already done their Broker Price Opinion. Just need your offer. Welcome to Windward Passage in the heart of Kailua! This spacious 1-bedroom, 1-bath condo features a bright and open layout with floor to ceiling windows. Enjoy an upgraded kitchen and in-unit washer/dryer. The pet-friendly building offers top-notch amenities including a pool, tennis courts, fitness center, sauna, BBQ areas, guest parking, and 24-hour security. One covered parking stall included. Just minutes to world-famous Kailua Beach, Whole Foods, Target, restaurants, and shops. Live the Kailua lifestyle—don’t miss this opportunity!

322 Aoloa Street Unit 208, Kailua

Listing courtesy of Island Life Homes.

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.