Kailua Homes with Pool Community Features

Welcome to Kailua, a picturesque gem nestled on the eastern coast of Oahu, Hawaii. Known for its stunning beaches, lush landscapes, and a vibrant local culture, Kailua offers a unique blend of relaxation and adventure. The town is famed for its pristine white-sand beaches, such as Lanikai and Kailua Beach, where residents and visitors alike can enjoy swimming, kayaking, and paddleboarding in the crystal-clear waters. Surrounded by the breathtaking Ko'olau Mountain Range, Kailua is a haven for outdoor enthusiasts, offering hiking trails that reward with sweeping views of the coastline.

Kailua is not just about natural beauty; it boasts a charming community atmosphere with an array of boutique shops, delightful cafes, and local eateries that showcase the island's rich culinary scene. The town also hosts various cultural events throughout the year, making it easy to connect with neighbors and embrace the spirit of Aloha.

For those seeking a home in this idyllic setting, Kailua presents an enticing selection of properties, particularly in homes with pool community features. Imagine unwinding in your own private oasis, surrounded by lush tropical landscaping, where you can bask in the sun or enjoy a refreshing dip at your leisure. These homes often come equipped with spacious outdoor living areas, perfect for entertaining family and friends or simply enjoying the tranquil Hawaiian lifestyle.

Living in Kailua means embracing a harmonious blend of natural beauty, community spirit, and luxurious living. Discover your dream home in this enchanting town, where every day feels like a vacation in paradise.

Newest Kailua Homes with Pool Community Features

$399,500

1 Beds ⋅ 1 Baths ⋅ 202614348 MLS ⋅ FS - Fee Simple Tenure ⋅ 15 DOM ⋅ 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

$645,000

1 Beds ⋅ 1 Baths ⋅ 202614387 MLS ⋅ FS - Fee Simple Tenure ⋅ 15 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

$699,000

2 Beds ⋅ 2 Baths ⋅ 202613910 MLS ⋅ FS - Fee Simple Tenure ⋅ 19 DOM ⋅ Poinciana Manor BLDG.

Welcome home to easy Kailua living at Poinciana Manor. This inviting 2-bedroom, 2-bath condo features LVP and tile flooring, an in-unit washer and dryer, additional storage, and two assigned parking stalls. Positioned on the windward side of the building, the unit enjoys refreshing trade wind breezes, beautiful sunrises, and views toward the Lanikai Pillbox. The pet-friendly, low-rise community offers a refreshing pool, BBQ areas, clubhouse, and recreation area—perfect for relaxing or entertaining.

1015 Aoloa Place Unit 340, Kailua

$660,000

1 Beds ⋅ 1 Baths ⋅ 202613708 MLS ⋅ FS - Fee Simple Tenure ⋅ 27 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 ⋅ 30 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

$925,000

3 Beds ⋅ 2 Baths ⋅ 202608120 MLS ⋅ FS - Fee Simple Tenure ⋅ 72 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 ⋅ 47 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

$619,000

2 Beds ⋅ 2 Baths ⋅ 202609776 MLS ⋅ FS - Fee Simple Tenure ⋅ 49 DOM ⋅ Poinciana Manor BLDG.

This Poinciana Manor unit is a spacious blank slate awaiting your personally chosen upgrades, on your timeline. Excellent location in the building, with views of the open courtyard, garden, and koi pond. Enjoy peace and quiet, the faint sound of birds, and a trickling fountain. The open, flowing layout has tropical terracotta tile from kitchen to dining to living to covered lanai to open lanai; the hallway and baths have same tile as well. Two covered parking stalls, storage closet in parking area, easy entry and elevator access, bike and surfboard storage, security, plenty guest parking, car wash area... all features of great convenience that enhance your everyday living! Lovely walking pathways, lush lawn courtyard, picnic areas, and nice pool round out the features to enjoy. Cabinets are original, offering more than adequate storage. The full-size washer/dryer and dishwasher are newer. This is a home to enjoy, experience, and feel everything out while you decide if you want to just decorate or remodel. Enjoy the beach-town lifestyle Kailua offers, a few blocks from beaches, dining, shopping, for an affordable price in a well-managed development. Seller is offering credits.

1015 Aoloa Place Unit 219, Kailua

$674,000

2 Beds ⋅ 2 Baths ⋅ 202611825 MLS ⋅ FS - Fee Simple Tenure ⋅ 53 DOM ⋅ Poinciana Manor BLDG.

New Price & Now Available with a 3.125% VA Assumable Interest Rate! – Incredible Value in the Heart of Kailua! Move-in ready and priced to sell, this 2-bedroom, 2-bath condo in Poinciana Manor offers the perfect blend of comfort, convenience, and island living. Enjoy luxury vinyl plank flooring throughout the main living areas, updated bathroom vanities and countertops, AC throughout, and a kitchen with stainless steel appliances. Relax on your private, covered lanai surrounded by bamboo landscaping with beautiful Ko'olau mountain views. Additional highlights include two side-by-side covered parking stalls, a dedicated storage locker, and in-unit washer/dryer. Just minutes from world-famous Kailua Beach, shopping, dining, and everything Kailua has to offer. Don't miss this opportunity to own one of Kailua's best values! (As of 8/5/26: 3.125% interest rate, $461,303.51 remaining balance, P&I: $2,491.42/month)

1015 Aoloa Place Unit 335, Kailua

$640,000

1 Beds ⋅ 1 Baths ⋅ 202611276 MLS ⋅ FS - Fee Simple Tenure ⋅ 54 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

$739,000

2 Beds ⋅ 2 Baths ⋅ 202611566 MLS ⋅ FS - Fee Simple Tenure ⋅ 56 DOM ⋅ Aikahi Gardens BLDG.

Aikahi Gardens spacious 2 bedroom 1.5 bath unit with 2 parking stalls in front of unit, plenty of guest parking and a large beautifully titled courtyard area. Recent upgrades include finnished stairway to 2nd floor and wood flooring in living room. Unit is well maintained, light and airy. Close to KMCAS, Aikahi Elementary School and shopping center. Great access to H-3, Kailua Beach and all the stores and restaurantss in the Kailua area.

134 Noke Street Unit 602, Kailua

$859,000

3 Beds ⋅ 2 Baths ⋅ 202608782 MLS ⋅ FS - Fee Simple Tenure ⋅ 92 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

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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.