Kailua Town Real Estate

Kailua Town Real Estate

Welcome to Kailua Town, a picturesque gem nestled on the windward coast of Oahu, Hawaii. This vibrant neighborhood is renowned for its stunning natural beauty, laid-back atmosphere, and a strong sense of community. With its pristine beaches, lush mountains, and friendly locals, Kailua offers a unique blend of island living that is both tranquil and invigorating.

Kailua Town is home to the famous Kailua Beach, often ranked among the best beaches in the world. Here, residents and visitors alike can enjoy sunbathing on soft, white sands, swimming in crystal-clear waters, and engaging in a variety of water sports like kayaking and paddleboarding. The nearby Lanikai Beach, with its breathtaking views of the Mokulua Islands, is just a short bike ride away, making it a favorite spot for both relaxation and adventure.

The town itself boasts a charming mix of local boutiques, cafes, and restaurants that reflect the island's rich culture and culinary diversity. From delicious poke bowls to fresh acai smoothies, there's something to satisfy every palate. The Kailua Farmers Market, held weekly, showcases the best of local produce and artisanal goods, fostering a strong community spirit.

Families are drawn to Kailua for its excellent schools and safe, welcoming neighborhoods. The area is also perfect for outdoor enthusiasts, with numerous hiking trails, parks, and recreational facilities available to explore.

In Kailua Town, you’ll find a lifestyle that embraces the beauty of nature, the warmth of community, and the spirit of aloha. Whether you're looking to settle down or simply visit, Kailua offers an unforgettable experience that captures the heart of Hawaii.

Newest Listings in Kailua Town

$855,000
3 Beds ⋅ 3 Baths ⋅ 202613359 MLS ⋅ FS - Fee Simple Tenure ⋅ 7 DOM ⋅ Gardenia Manor BLDG.
Both welcoming and thoughtfully designed this generously sized, two-story condo offers incredible indoor / outdoor living spaces, a vaulted ceiling fills the room with natural light and creates an airy atmosphere. Well-designed floor plan places all bedrooms upstairs, along with the washer and dryer for added convenience, while a half bath on the main level is ideal for guests. Vinyl laminate flooring, lots of storage, a beautiful updated kitchen and two covered parking are just some of the items this condo offers. Ideally located just minutes from shopping, dining, and Kailua's beaches, you'll love having everything you need close to home. When you're not out exploring, enjoy the community pool, BBQ and recreation area - a perfect bonus to living in Gardenia Manor. Whether you're searching for your first home, a place to downsize, or an investment in one of Hawaii's most desirable locations, this inviting condo offers the perfect place to call home.

333 Aoloa Street Unit 318, Kailua
$825,000
3 Beds ⋅ 2 Baths ⋅ 202616227 MLS ⋅ FS - Fee Simple Tenure ⋅ 8 DOM ⋅ Windward Harbour BLDG.
Experience the best of island living at Windward Harbour in the heart of Kailua. Perfectly located within walking distance from shopping, restaurants, farmers markets, and the world-renowned Kailua and Lanikai beaches, this spacious ground-floor 3-bedroom, 2-bath residence offers the ideal blend of comfort and convenience. The open-concept floor plan provides a welcoming space for living and entertaining, while newly refinished bamboo flooring and fresh interior paint create a bright, move-in-ready feel. The bedrooms feature built-in closets and the floor-to-ceiling windows fill the home with natural light while showcasing peaceful garden views from your private lanai. Windward Harbour is a secure, pet-friendly community featuring resort-style amenities, including a swimming pool, hot tub, sauna, tennis courts, ping-pong, BBQ areas, a recreation room, and a dog run. Enjoy the perfect balance of tranquil living and easy access to everything Kailua has to offer.

1030 Aoloa Place Unit 5105B, Kailua
$755,000
3 Beds ⋅ 2 Baths ⋅ 202616240 MLS ⋅ FS - Fee Simple Tenure ⋅ 11 DOM ⋅ Windward Harbour BLDG.
Welcome to Windward Harbour, a gated tropical oasis in the heart of beautiful Kailua! This spacious 3-bedroom, 2-bath condo offers the perfect opportunity to create your own dream retreat just minutes from world-famous Kailua Beach. Surrounded by lush tropical landscaping, tranquil koi ponds, garden views, and a peaceful man-made pond, the property offers a serene setting enhanced by the soothing sound of a beautiful water feature. While the interior is ready for some updating, its blank-slate appeal allows you to bring your vision to life and create a home that truly reflects your style. Enjoy Windward Harbour amenities including a sparkling pool and tennis courts, all within a private gated community. Ideally located near Kailua Beach, grocery stores, Target, UFC Gym, restaurants, boutiques, and the charming local shops that make Kailua so desirable. Whether you’re looking for a full-time residence or tropical retreat, this is your opportunity to create your dream home in paradise!

1030 Aoloa Place Unit 212B, Kailua
$729,000
1 Beds ⋅ 1 Baths ⋅ 202616213 MLS ⋅ FS - Fee Simple Tenure ⋅ 16 DOM ⋅ 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
$859,000
3 Beds ⋅ 2 Baths ⋅ 202614735 MLS ⋅ FS - Fee Simple Tenure ⋅ 21 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
$895,000
3 Beds ⋅ 2 Baths ⋅ 202615666 MLS ⋅ FS - Fee Simple Tenure ⋅ 25 DOM ⋅ Windward Cove BLDG.
Welcome to this beautifully renovated 3 bedroom/2 bath residence at Windward Cove, a gated community in the heart of Kailua that’s surrounded by koi ponds, lush landscaping and tranquil water features. Inside, you’ll find a fully upgraded kitchen with waterfall quartz countertops and appliances, new primary bath vanity, new split AC’s, fresh interior paint and luxury vinyl floors throughout. Expansive floor-to-ceiling windows fill the unit with natural light and peaceful garden views, creating the feeling of living in your own private tropical retreat. This top floor unit also comes with a spacious private rooftop balcony with beautiful Koolau mountain and treetop views, perfect for relaxing and entertaining. Set on 3 acres of tropical grounds, Windward Cove offers resort-style amenities including a swimming pool, hot tub, sauna, tennis and pickleball courts, pool, barbeque areas, bike and surfboard racks and a private storage locker. Located minutes away from world-famous Kailua beach and popular restaurants, come see what makes this complex in Kailua so special. 2 photos are virtually staged(enhanced).

1020 Aoloa Place Unit 404A, Kailua
$570,000
2 Beds ⋅ 2 Baths ⋅ 202612915 MLS ⋅ FS - Fee Simple Tenure ⋅ 29 DOM ⋅ Koolau Vista BLDG.
Welcome home to this adorable 2-bedroom, 1.5-bath condo offering the perfect blend of comfort and convenience in desirable Kailua. The thoughtfully designed first floor features a spacious living area, a great kitchen with plenty of storage, and a convenient half bath for guests. Upstairs, you'll find two comfortable bedrooms, a full bathroom, and an in-unit laundry area, providing both privacy and everyday convenience. Ideally situated in the heart of Kailua, you'll enjoy the convenience of nearby shopping, dining, parks, schools, and everything that makes this vibrant community so special. Two parking spaces and a storage unit are a plus. Whether you're searching for your first home, looking to simplify your lifestyle, or seeking a wonderful investment opportunity, this delightful condo is ready to welcome you home.

350 Aoloa Street Unit C224, Kailua
$550,000
2 Beds ⋅ 2 Baths ⋅ 202615437 MLS ⋅ FS - Fee Simple Tenure ⋅ 32 DOM ⋅ Poinciana Manor BLDG.
Best value in Poinciana Manor! Bright and breezy top-floor end unit featuring peaceful garden views, cathedral ceiling, and two private lanais. This unit includes two covered parking stalls and a remodeled kitchen, while offering the opportunity to customize the rest to your personal style. Conveniently located in the heart of Kailua, close to shopping, dining, schools, and beaches. Poinciana Manor offers beautifully maintained grounds with a pond, water features, swimming pool, recreation and BBQ areas, plus guest parking. Property is being sold AS-IS. Unit is currently unstaged and includes no appliances except for a dishwasher. Photos shown are from the prior listing.

1015 Aoloa Place Unit 437, Kailua
$690,000
2 Beds ⋅ 2 Baths ⋅ 202614286 MLS ⋅ FS - Fee Simple Tenure ⋅ 46 DOM ⋅ Poinciana Manor BLDG.
Experience the best of Kailua living! This beautifully updated 959 sq ft unit offers a modern kitchen with updated cabinets & countertops, updated bathroom vanities, and stainless steel appliances. Enjoy the convenience of a full-size washer and dryer, fresh paint throughout, newly installed luxury vinyl plank flooring, contemporary light fixtures, and a brand-new ceiling fan. The unit also includes two side-by-side covered parking stalls and a spacious 266 sq ft lanai, providing added privacy with an exterior-facing view. Located in the heart of Kailua, you're just steps away from boutique shops, local restaurants, cafes, bookstores, grocery stores, and the world-renowned Kailua Beach. The complex boasts fantastic amenities such as a saltwater pool, BBQ areas, gazebos, a kids’ playground, a koi pond, bike/surfboard storage, guest parking, on-site security, and a resident manager. The complex is fully insured and pet-friendly making it an excellent place to call home!

1015 Aoloa Place Unit 247, Kailua
$645,000
1 Beds ⋅ 1 Baths ⋅ 202614387 MLS ⋅ FS - Fee Simple Tenure ⋅ 46 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
$689,999
2 Beds ⋅ 2 Baths ⋅ 202613910 MLS ⋅ FS - Fee Simple Tenure ⋅ 50 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
$699,999
2 Beds ⋅ 2 Baths ⋅ 202611451 MLS ⋅ FS - Fee Simple Tenure ⋅ 53 DOM ⋅ Poinciana Manor BLDG.
Finally, a top floor unit at Poinciana Manor with a fully renovated, open concept kitchen and living room. No neighbor above, and a ceiling that clears 20 feet at the peak. The kitchen and living room wall came down years ago, done professionally with an engineer's letter on file. The kitchen carries it forward: quartz counters, shaker cabinets to the ceiling with crown molding, and all BRAND new (July 2026) stainless appliances in the kitchen, french door fridge, slide in range, microwave hood, dishwasher. The primary bath has a double vanity and separate walk in shower with new fixtures. Fresh paint runs through the living areas, plus new cabinet handles and an LG stacked washer and dryer. The 82 square foot lanai adds real outdoor space. Two covered stalls, side by side, no stacking. A tree blocks the sightline to the neighboring unit for extra privacy. Grounds include a pool and picnic pavilion, and Kailua adds postcard beaches and trade winds a short distance from home. Ask your agent about an assumable VA loan option for qualified veterans ONLY (2.25% interest rate, $428,556.14 balance, P&I $2,057.30). Check out our Open House Saturday, July 26th, 2-4PM.

1015 Aoloa Place Unit 451, 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.