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$925,000
3 Beds ⋅ 2 Baths ⋅ 202608120 MLS ⋅ FS - Fee Simple Tenure ⋅ 68 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
$800,000
3 Beds ⋅ 2 Baths ⋅ 202612305 MLS ⋅ FS - Fee Simple Tenure ⋅ 43 DOM ⋅ Windward Cove BLDG.
Welcome to Windward Cove—a gated community in the heart of Kailua, surrounded by 3 acres of lush tropical landscaping, koi ponds, and peaceful water features. This private 3-bedroom, 2-bath corner unit offers an open-concept layout with floor-to-ceiling windows that fill the space with natural light. Recent updates include new kitchen cabinets, quartz countertops, refrigerator, dishwasher, vinyl flooring and fresh paint throughout. Enjoy indoor-outdoor living with a spacious 395 sq. ft. rooftop deck—perfect for BBQs and entertaining. Located just 1.1 miles from Kailua Beach and close to shopping, dining, and the weekly Farmers Market. Community amenities include a pool, sauna, tennis court, on-site security, resident manager, and pet-friendly policies. Don’t miss this rare opportunity to own a peaceful retreat in one of Oahu’s most desirable neighborhoods! Assumable VA mortgage at 2.25%interest rate/ monthly payment $2100/ balance is approx $455,000.

1020 Aoloa Place Unit 311B, Kailua
$1,450,000
3 Beds ⋅ 3 Baths ⋅ 202607704 MLS ⋅ FS - Fee Simple Tenure ⋅ 71 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
$2,650,000
3 Beds ⋅ 3 Baths ⋅ 202609988 MLS ⋅ FS - Fee Simple Tenure ⋅ 73 DOM
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
$1,399,000
3 Beds ⋅ 2 Baths ⋅ 202610095 MLS ⋅ FS - Fee Simple Tenure ⋅ 79 DOM
KAILUA BLUFFS. Original owners. Single story home on huge lot with 13,105 sf of land. Tons of potential! Needs TLC and cosmetic upgrades to make it your own. The second and third bedrooms have loft areas that can be utilized for den/study. Covered lanai perfect for outdoor entertaining. Home to be sold in AS-IS Condition.

1595 Kanapuu Drive, 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
$1,498,000
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

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.