Kailua Homes with City View

Welcome to Kailua, a picturesque gem nestled on the eastern coast of Oahu, Hawaii. Known for its stunning beaches, lush landscapes, and vibrant community, Kailua offers a unique blend of island charm and modern conveniences. With its crystal-clear waters and soft, sandy shores, Kailua Beach and Lanikai Beach are perfect for sunbathing, kayaking, and enjoying breathtaking sunsets. The town is also home to an array of local shops, cafes, and restaurants, making it a delightful place to explore and savor the flavors of the island.

One of the most alluring features of Kailua is its diverse real estate offerings, particularly homes with magnificent city views. Imagine waking up to panoramic vistas of the vibrant Kailua town, framed by the majestic Ko'olau Mountains. These homes provide not only a stunning backdrop but also a serene atmosphere that enhances the island living experience. Whether you’re looking for a cozy bungalow or a luxurious estate, Kailua’s real estate market has something for everyone.

Living in Kailua means embracing a lifestyle that harmonizes outdoor adventures with community spirit. The area boasts numerous hiking trails, water sports, and family-friendly parks, ensuring that there’s always something to do. With its laid-back vibe and welcoming atmosphere, Kailua is not just a place to live; it’s a place to thrive. Discover your dream home with a city view in this enchanting coastal town and experience the best that island life has to offer!

Newest Kailua Homes with City View

$2,250,000

3 Beds ⋅ 3 Baths ⋅ 202615714 MLS ⋅ FS - Fee Simple Tenure ⋅ 8 DOM

Beautiful, sweeping views of Enchanted Lake and Kaelepulu wetlands from your elegantly remodeled open concept living, dining, & gourmet kitchen. Large glass doors open onto your huge covered deck surrounded by lush lakefront lawns, perfect for indoor/outdoor entertaining, or quiet rest. Contemporary, easy care plank ceramic tile flows throughout the home. The high performance kitchen design and quality appliances are a chef’s delight. Featuring a ground floor bedroom and full bath, a large upstairs primary suite with a huge walk-in closet and resort style bath with dual rain showers, split system and recessed ceiling ACs, an oversized garage with high ceilings and plenty of storage, an owned Photovoltaic system, and more! Fully fenced, attractively landscaped, and just a block to desirable Kaelepulu elementary school and park. Easy access to Kailua town’s vibrant fine dining, entertainment, and shopping district. Assumable VA loan at 2.25% interest with substitution of eligibility. A rare chance for waterfront living so call for your private showing today.

445 Keolu Drive, Kailua

$645,000

1 Beds ⋅ 1 Baths ⋅ 202614387 MLS ⋅ FS - Fee Simple Tenure ⋅ 29 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

$660,000

1 Beds ⋅ 1 Baths ⋅ 202613708 MLS ⋅ FS - Fee Simple Tenure ⋅ 41 DOM ⋅ 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

$1,650,000

2 Beds ⋅ 3 Baths ⋅ 202612833 MLS ⋅ FS - Fee Simple Tenure ⋅ 44 DOM ⋅ Bluestone BLDG.

Welcome to Bluestone – where island living meets everyday luxury! Picture yourself sipping your morning coffee or dining in the evening on your lanai while looking across acres of green and sunsets dipping behind the Ko'olau Mountain Range. Or waking up to catch a rainbow over the golf course from the comfort of bed. Maybe join a friend for a meal or round of golf at near-by Mid-Pacific Country Club. Or take advantage of the resort-like amenities that Bluestone has to offer such as tennis courts, pickle ball, salt-water pool, hot tub, sauna, or one of many other activities available to you nearby. It’s the Kailua lifestyle, beautiful Lanikai Beach, the open spaces and the scenic beauty that makes Bluestone such a fabulous place to live. Add to that list a lovely townhome in a gated community with stunning views and cooling breezes. Spacious, scenic, and serene, it’s a truly special place to call home.

1302 Kamahele Street Unit 2402, Kailua

$2,450,000

4 Beds ⋅ 3 Baths ⋅ 202612934 MLS ⋅ FS - Fee Simple Tenure ⋅ 52 DOM

Live at the top of Keolu Summit in Hillcrest with 180 degree views of the Koolau mountains, Olomana peaks, Enchanted Lake, and Kailua Bay. A stunning viewscape captured from your wrap around lanais and large picture windows framed by high vaulted ceilings. The open layout of the home embraces the essence of Hawaiian living with modern finishings and covered ipe wood lanais offering you a variety of settings for entertaining and indoor/outdoor living. The main house provides a large primary bedroom with an en suite bath, a spacious second bedroom, and a third bedroom or office. The separate cottage with full bath and kitchenette has equally captivating views with a large lanai. The resort-like blue tiled pool with spa and water feature is surrounded by lush tropical landscaping providing beauty and privacy. Features an owned PV system, 2-car enclosed garage, and adjacent workshop/storage. There are 2 dedicated parking stalls along the private road for guests. This cul-de-sac location places you at the high point of the Summit bordered by conservation land. Minutes to the white sandy beaches of Kailua and Waimanalo and the trendy shops and restaurants of Kailua Town.

1461 Aunauna Street, Kailua

$640,000

1 Beds ⋅ 1 Baths ⋅ 202611276 MLS ⋅ FS - Fee Simple Tenure ⋅ 68 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

$1,498,000

3 Beds ⋅ 3 Baths ⋅ 202607772 MLS ⋅ FS - Fee Simple Tenure ⋅ 125 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

Start Your Search

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.