Kailua Homes under $2 million

Welcome to Kailua, a picturesque paradise nestled on the windward coast of Oahu, Hawaii. Known for its stunning beaches, lush landscapes, and vibrant community, Kailua offers an idyllic lifestyle that seamlessly blends relaxation with adventure. With its crystal-clear waters and soft, sandy shores, Kailua Beach and Lanikai Beach are perfect for sunbathing, swimming, and kayaking, making them popular spots for both locals and visitors alike.

Kailua is not just about its natural beauty; it’s also a thriving community filled with charming boutiques, delightful eateries, and local markets that reflect the rich culture of Hawaii. Whether you're strolling through the quaint downtown area or enjoying a meal at one of the local cafes, you'll find that Kailua exudes a warm and welcoming atmosphere.

For those looking to call this enchanting region home, Kailua offers a selection of beautiful properties under $2 million. These homes often feature stunning views, spacious layouts, and easy access to the beach, providing the perfect backdrop for both relaxation and recreation. From cozy single-family residences to modern townhouses, there’s something for everyone in this vibrant community.

Living in Kailua means embracing an outdoor lifestyle, with hiking trails, parks, and water activities right at your doorstep. It’s a place where you can enjoy the best of island living while being just a short drive from the bustling city of Honolulu. Come discover your dream home in Kailua and experience the magic of this Hawaiian gem for yourself!

Newest Kailua Homes under $2 million

$1,695,000

5 Beds ⋅ 3 Baths ⋅ 202618644 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM

This spacious, 5-bedroom, 3-bath home, is perfectly set up for multigenerational living and also has the potential of generating additional income. One of the larger homes, with 2,729 square feet of living space, is on a level 9,875 square foot lot, ideally located on a quiet cul-de-sac, in the established Kailua neighborhood of Olomana. Majority of the home is single-level, with one bedroom and living space upstairs. It offers a versatile floor plan, with separate entrances that are perfect for guests, investment opportunities, or a dedicated home office. The fully fenced yard and large covered lanai space provide exceptional indoor-outdoor living, with plenty of room to relax, play with pets, or entertain friends. Mature fruit trees and lush landscaping create a private, tropical setting for you to enjoy. Large carport and driveway area, along with lots of storage, and a workshop, provide lots of room for hobbies. Conveniently located just minutes from Kailua’s world-renowned beaches, shopping, dining, and schools, this home offers both comfort and flexibility, in one of O‘ahu’s most desirable communities.

1458 Uluhala Place, Kailua

$1,895,000

4 Beds ⋅ 3 Baths ⋅ 202618639 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM

Set against the dramatic backdrop of Olomana, this charming single-level Mid-Century Modern home offers timeless character, an inviting open-concept layout, and a spacious, flat, usable lot. With 4 bedrooms and 3 baths, the home is designed for easy living with a seamless connection between indoor and outdoor spaces. Glass sliders throughout invite abundant natural light and frame the lush surroundings, while thoughtful built-ins add warmth, function, and vintage appeal. The spacious living and dining areas flow naturally into the kitchen and outdoor spaces, creating an ideal setting for everyday living and entertaining. Automatic garage doors add everyday convenience and ease. This is a rare opportunity to enjoy the beauty, character, and indoor-outdoor lifestyle of a true Hawai'i home.

1575 Ulupii Street, Kailua

$1,600,000

3 Beds ⋅ 2 Baths ⋅ 202618194 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM

Opportunity knocks! This Kailua home is just a short walk to the beach and offers one of the lowest prices seen in years. A rare fixer-upper opportunity in sought after Kuulei Tract—with a pool and a location just 8 houses from world-famous Kailua Beach! Bring your vision to this property, just a couple of blocks from the heart of Kailua Town and close to schools, restaurants, markets, gyms, yoga studios, and farmers markets. The park-like backyard offers plenty of room to relax and play, with a refreshing pool and patio just outside the family room and a spacious grassy area beyond. The 3 bedrooms are located on the makai side of the house are cooled by the trade winds, and the 200+ s.f. workshop is located on the mauka side of the house. Fully fenced back yard provides a safe area for kids and pets.

119 Kuulei Road, Kailua

$969,000

2 Beds ⋅ 1 Baths ⋅ 202618404 MLS ⋅ FS - Fee Simple Tenure ⋅ 4 DOM

Great location for this tucked away 2 bedroom 1 bath Kailua cottage. Located on a quiet lane off of Ulupaina Street where there is a wide private driveway with access for the 6 homes on the lane. Short distance to Kailua town and Kalama Beach park. The cottage location gives the feeling of a spacious lot. New paint inside and out, new luxury vinyl flooring throughout. Ready for the new buyer to add your own personal touches. Flexible CPR's and By-Laws gives you total flexibility on remodeling, adding on or rebuilding. For those Buyers looking for a home in Kailua under $1 million this is a must see! Sold as is.

315 A Ulupaina Street, Kailua

$1,699,000

2 Beds ⋅ 2 Baths ⋅ 202617903 MLS ⋅ FS - Fee Simple Tenure ⋅ 5 DOM

WHERE THE KOOLAUS MEET THE SEA. MOMENTS FROM WAIMANALO BEACH. Tucked into coveted Waimanalo Beach Lots, this beautifully updated 2-bedroom, 2-bath beach cottage pairs exceptional beach proximity with a rare sense of openness. Beach access is just moments away, while the property opens to an expansive green backdrop with Waimanalo Beach Park directly behind instead of another home. Koolau views, swaying palms, and the sound of the ocean complete the setting. Beautiful natural light fills the approx. 984 sq. ft. interior, with bamboo flooring throughout and custom driftwood vaulted ceilings creating a warm, relaxed aesthetic that complements the home’s easy beachside setting. Thoughtful updates include a remodeled kitchen and baths in 2022, a 2021 roof, and solar water-heating system. Outside, the fully enclosed yard and gathering spaces offer room to relax, entertain, or return home from the beach and talk story with friends. Set within one of Oahu’s most cherished beach communities, this is an opportunity to enjoy white sand, turquoise water, and the Koolau Mountains as part of everyday life. Actual square footage and number of bedrooms/baths do not match TMK records.

41-012 Wailea Street, Waimanalo

$595,000

1 Beds ⋅ 1 Baths ⋅ 202617742 MLS ⋅ FS - Fee Simple Tenure ⋅ 13 DOM ⋅ Windward Passage BLDG.

Stunning views and the best of Kailua living await at Windward Passage! This inviting one-bedroom condo on the 17th floor features floor-to-ceiling windows spanning the mauka side, capturing panoramic views of the Ko'olau mountains, Olomana, and Enchanted Lake. Move-in ready with fresh interior paint and AC units to keep you cool as you enjoy the views. Built-ins provide ample storage, plus the unit comes with separate storage in the building. Enjoy extraordinary amenities including a heated saltwater pool and whirlpool, BBQ area, well-equipped gym, tennis and pickleball courts, storage for bikes and beach gear, and a beautifully remodeled clubhouse. Your dog will love the unique dog park tucked into a natural quarry beneath banyan trees. Kailua Town’s coffee shops, boutiques, restaurants, Whole Foods, and Target are close by, along with beautiful Kailua Beach. Easy access to KBAY, VA approved and pet friendly. Come for the views, stay for the lifestyle!

322 Aoloa Street Unit 1706, Kailua

$1,590,000

6 Beds ⋅ 3 Baths ⋅ 202617350 MLS ⋅ FS - Fee Simple Tenure ⋅ 14 DOM

“I Love Kailua” - Experience the ultimate Hawaii lifestyle in a town famous for world-renowned beaches, vibrant open markets, abundant eateries, and boutique shopping, all wrapped in a charming heritage town vibe. This newly built, move-in-ready home offers an exceptional dual-living or multi-generational layout: •Top Floor: Features 3 bedrooms and 2 bathrooms, a spacious living area, and a beautiful outdoor deck perfect for hosting gatherings with family and friends. •Ground Floor: Includes 3 bedrooms and 1 bathroom, centered around a large, open entertaining space complete with a wet bar.

839 Oneawa Street, Kailua

$615,000

2 Beds ⋅ 2 Baths ⋅ 202617681 MLS ⋅ FS - Fee Simple Tenure ⋅ 18 DOM ⋅ Hale Makalei BLDG.

Welcome to Hale Makalei! Rarely available 2 bedroom, 2 bath unit with covered lanai. Nice open flow with the living area and primary bedroom opening out to the covered lanai. The perfect spot to sit back, relax and enjoy the view. Kitchen completely remodeled with granite counter tops and large island with bar seating that opens the kitchen to the living area. Quality vinyl plank flooring added throughout. This unit is move in ready! Wonderful location for easy access and convenience with restaurants, shops, town parties and open markets all within walking distance. Plus world renown Kailua Beach! 1 covered parking stall in gated garage. There's even a dog run for your pet and a community storage area for surfboards. This is one you need to see!

711 Wailepo Place Unit 205, Kailua

$845,000

3 Beds ⋅ 2 Baths ⋅ 202617820 MLS ⋅ FS - Fee Simple Tenure ⋅ 16 DOM ⋅ Lakeview BLDG.

Discover the comfort and convenience of Kailua living in this beautifully renovated 3-bed, 2-bath townhouse, ideal for a working professional or growing family. Fully renovated in 2026, the home has been thoughtfully refreshed from top to bottom, including the kitchen, flooring, bathrooms, appliances, and removed popcorn ceiling, creating a modern and move-in-ready living experience. As an end unit, the home offers an added sense of privacy and is tucked among lush greenery, creating a secluded atmosphere that feels like a retreat. The open-concept living area provides a welcoming space for everyday living and entertaining, while the patio extends the living space outdoors and captures the indoor-outdoor lifestyle Hawaii is known for. Multiple storage areas add valuable functionality, helping keep the home organized and comfortable. Located in a desirable neighborhood, the property also offers two parking spaces plus guest parking. With its comprehensive 2026 remodel, generous outdoor spaces, and desirable location, this is an opportunity to enjoy a brand new home while staying close to the lifestyle, community, and convenience that make Kailua such a special place to call home.

978-A Akipohe Place Unit 2A, Kailua

$1,295,000

3 Beds ⋅ 2 Baths ⋅ 202617723 MLS ⋅ FS - Fee Simple Tenure ⋅ 16 DOM

Have you been searching for your forever home to raise a young family and build lasting memories? Or maybe looking for a home to age-in-place? Look no further! Welcome to 1322 Ulupuni Street. Tucked away in a quiet neighborhood, this single-level 3 bed, 2 bath gem offers the space, flexibility, and opportunity to create the home you’ve been dreaming of or simply move-in and start living life! The vaulted ceilings in the living room create a generous, open feel, while warm wood finishes bring natural texture and island charm. Moreover, experience indoor-outdoor living with a large covered lanai, perfect for grilling or unwinding after a long day of work. Not only that, but the expansive flat yard is great for hosting and entertaining events with your favorite people. Truly making the home feel like your own personal oasis. Featuring 32 owned photovoltaic panels to help reduce electricity costs, blends everyday practicality with future possibilities. Being centrally located, your just moments away from Kailua, Town, and everything Oahu has to offer. Don’t miss out on this rare opportunity to own in one of Oahu’s most desirable communities. TMK DOES NOT MATCH ACTUAL BATHROOMS.

1322 Ulupuni Street, Kailua

$1,449,000

5 Beds ⋅ 2 Baths ⋅ 202617232 MLS ⋅ FS - Fee Simple Tenure ⋅ 18 DOM

Welcome to 1536 Kina Street — a rare opportunity to own a generously sized 5-bedroom, 2-bath single-family home in the heart of Kailua. Nestled in a great neighborhood, this property offers the perfect blend of island living and modern comfort. With an expansive layout ideal for multigenerational living or growing families, this home features flexible living spaces, a functional kitchen. The yard provides ample room for outdoor entertaining, gardening, or workshop. Conveniently located just minutes from world-renowned Kailua Beach, shopping, dining, schools, and parks — enjoy the best of Windward O‘ahu living in this desirable location. Don’t miss your chance to own a piece of paradise — schedule your private showing today! First Open House 9/20 from 2-5PM!

1536 Kina Street, Kailua

$1,725,000

6 Beds ⋅ 3 Baths ⋅ 202617501 MLS ⋅ FS - Fee Simple Tenure ⋅ 18 DOM

More Aloha, A Lot More Possibility! 5.75% VA Assumable!Welcome to this thoughtfully renovated 6+bedroom, 3-bath home offering approximately 2,100 SF of versatile living space. Currently arranged as a 3-bedroom main home plus bonus room, an attached 1-bedroom living space with bonus room, and a separate attached studio, this unique layout offers flexibility for multigenerational living, extended family, and guests. The additional living spaces may also be incorporated into the main home to create an even more expansive living arrangement. Buyer to conduct their own due diligence regarding permitted uses. Enjoy updated kitchens & baths, ceramic tile flooring, a 120 gallon water heater, 8 split ACs, and 40 solar panels plus batteries! The semi-enclosed carport lanai extends the living experience outdoors, offering a versatile space for entertaining, relaxing, storage, or additional parking. An electric gated yard provides privacy & room to garden, or simply enjoy. Near world-famous Kailua Beach and the heart of Kailua town, this move-in-ready home offers comfort, flexibility, and the relaxed island lifestyle Kailua is known for. VA assumable loan option available for qualified buyers.

650 Oneawa Street, 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.