Kailua Homes under $2 million

Welcome to Kailua, a hidden gem on the windward coast of Oahu, Hawaii, where the lush landscape meets pristine beaches and a laid-back lifestyle. This charming town is renowned for its breathtaking views of the Ko'olau Mountains and its inviting turquoise waters, making it an idyllic haven for outdoor enthusiasts and families alike. With its friendly community vibe, Kailua boasts an array of local shops, delightful cafes, and vibrant farmers' markets that celebrate the island's rich culture and flavors.

For those seeking to plant roots in this paradise, Kailua offers a remarkable selection of homes priced under $2 million. Whether you're looking for a cozy single-family home, a modern townhouse, or a spacious property with a backyard oasis, Kailua has something to suit every taste and budget. Many of these homes feature stunning ocean views, lush gardens, and easy access to the area's renowned beaches, such as Lanikai and Kailua Beach Park.

Living in Kailua means embracing a lifestyle filled with adventure, from kayaking in the calm waters to hiking the scenic trails of the nearby mountains. The community is also known for its excellent schools and family-friendly atmosphere, making it a perfect spot for raising children.

Experience the best of island living in Kailua, where your dream home awaits. With diverse real estate options available under $2 million, now is the perfect time to explore this enchanting coastal town and discover the unique charm that Kailua has to offer.

Newest Kailua Homes under $2 million

$1,350,000

2 Beds ⋅ 1 Baths ⋅ 202615974 MLS ⋅ FS - Fee Simple Tenure ⋅ 1 DOM

Come and see!! Coconut Grove charm, completely reimagined. Fully remodeled in 2021, this thoughtfully designed home blends modern comfort with the warmth and character of island living. The kitchen features an oversized island with seating, extensive cabinetry, warm wood countertops, farmhouse sink, stainless-steel appliances, gas cooking with double ovens, statement range hood, tile backsplash and under-cabinet lighting—perfect for quiet mornings or entertaining friends. The remodeled bath features striking herringbone tile, rainfall shower, matte-black fixtures, vessel sink and warm wood cabinetry. The primary bedroom offers a beautiful natural wood accent wall, multiple windows, recessed lighting and A/C. Step outside to one of the home’s best surprises: a private tropical retreat with generous lawn, mature palms, custom wood privacy features and outdoor gathering areas. As the sun goes down, string lighting beneath the palms gives the backyard an entirely different personality.

427 Kawainui Street Unit B, Kailua

$1,125,000

3 Beds ⋅ 2 Baths ⋅ 202618584 MLS ⋅ FS - Fee Simple Tenure ⋅ 1 DOM

KAILUA COCONUT GROVE Opportunity awaits in this fee-simple 3-bedroom, 2-bath home on a 5,000 sq. ft. flag lot. Enjoy added privacy, a carport, yard space, and desirable single-level living. This home is ready for updating and offers excellent potential for renovation. Conveniently located near Kailua Town's shopping, dining, farmers markets, parks, and beautiful beaches. A great opportunity to create your dream home in one of Kailua's most sought-after neighborhoods.

554-A Auwai Street, Kailua

$1,150,000

3 Beds ⋅ 2 Baths ⋅ 202618877 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM ⋅ Ka Malanai At Kailua BLDG.

Live-Work-Play! This is the heart of Kailua with so much to offer. The Urban lifestyle and the conveniences of daily living in a three bedroom that's just minutes to Kailua beach. Modern Architecture with an open breezy floorplan and lifestyle. This beautiful luxury condo features upgraded cabinets, custom Plantation windows treatments and upgraded tile floors. Enjoy cooking in your well-appointed kitchen offering stainless GE appliances, big farm sink and elegant dine-in countertops. One of the rare Kailua condos with central air conditioning to keep cool year round. A generous sized living/dining room filled with natural light plus a covered lanai taking in the majestic mountain views. The primary suite features walk-in closet, built-ins cabinet, ensuite bathroom with double vanities plus a separate bathtub and shower. Relax in the colorful landscaped gardens with BBQ areas and walking paths. Located directly across the street from Kailua district park, swimming pool & tennis courts. Enjoy a fabulous array of shopping, dining and recreational activities nearby. A perfect blend of island living at Ka Malanai@ Kailua.

471 Kailua Road Unit 3202, Kailua

$1,850,000

4 Beds ⋅ 3 Baths ⋅ 202618881 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM

Located in the Koolaupoku neighborhood, on a quiet street - 4 bedrooms, 3 bathrooms. Single Level open concept home with covered patio. Full street facing property with 2 car carport with views of Koolau Mountains. Fenced in yard with automatic gate. Original home built in 1955. Remodeled in 1987 with new Kitchen design, Added a true primary Bedroom with bathroom, Laundry Room inside home and an Office/Craft Room. 2 split AC systems. Three AC wall units. There are 22 Photovoltaic panels that helps offset Electricity Bill with possibility of new owner hooking up a critical load panel. Warranty is transferrable to new owner. Home comes with 2 split AC systems. Walkable to Kawainui Marsh Trail. Minutes to H-3, Kailua Town and Kailua & Lanikai Beach.

636 Kaiemi Street Unit A, Kailua

$1,645,000

3 Beds ⋅ 2 Baths ⋅ 202618852 MLS ⋅ FS - Fee Simple Tenure ⋅ 3 DOM

Meet your favorite morning spot: a sun-filled living room framed by distinctive trapezoid windows, where natural light pours in and beautiful mountain views set the tone for the day. Tucked at the end of a double-ended cul-de-sac, this gracious single-level home offers comfort, privacy, and easy living. The spacious lanai is perfect for morning coffee, weekend BBQs, entertaining, or unwinding with majestic Olomana as your backdrop. Pride of ownership shines throughout, with beautifully renovated bathrooms, new appliances, tasteful lighting, and thoughtful improvements that make this home truly move-in ready. Additional features include soft-close hardware added to existing kitchen cabinetry, new vinyl gates, new interior doors, an updated electrical panel, fresh interior paint (2023), and preventative ground termite treatment (2025). Enjoy indoor-outdoor living with beaches, parks, dining, and shopping just minutes away in Kailua Town. $10,000 Seller credit toward Buyer’s closing costs.

563 Alihi Place, Kailua

$1,200,000

2 Beds ⋅ 1 Baths ⋅ 202618788 MLS ⋅ FS - Fee Simple Tenure ⋅ 3 DOM

You've dreamt about living in Kailua - in a Single Family Home with no maintenance fees and your own yard. Now is your chance to live the beach town lifestyle! Easy to see! Visit our Sunday Open House 2-5 PM on Oct. 11th. This adorable Kailua cottage has a quiet location on a private lane off of Kihapai St. It sits on a 5,000 sf lot with citrus, avocado, coconut & plumeria trees. There's room in the carport to pull foward enough to allow two tandem parking stalls. A washer/dryer is also located in the carport. Inside the home has a cute & functional kitchen, a living room with a sliding glass door leading out to a spacious yard, a full bathroom and two bedrooms.

413 Kihapai Street Unit A, Kailua

41-727 Kaaumoana Place Unit NA, Waimanalo

$665,000

3 Beds ⋅ 1 Baths ⋅ 202614425 MLS ⋅ FS - Fee Simple Tenure ⋅ 4 DOM ⋅ Waimanalo Banyan Tree BLDG.

Wonderful opportunity for this rarely available Waimanalo Banyan Tree PUD with large Fenced in courtyard/yard area off the 2-vehicle carport. Current maintenance fee's under $500 for a 3 bedroom unit!! 2-stories with bedrooms and bathrooms upstairs. Living room, dining room, kitchen, courtyard on level 1. Good, clean condition... very livable, but flooring and interior paint will probably want to be updated by new owners at some point. Washer/Dryer is in the courtyard and storage closet. Feels like a single family home! Kaaumoana Place is the last road on the right in the complex, so very private and quiet.

41-727 Kaaumoana Place Unit NA, Waimanalo

$1,695,000

5 Beds ⋅ 3 Baths ⋅ 202618644 MLS ⋅ FS - Fee Simple Tenure ⋅ 7 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 ⋅ 7 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 ⋅ 7 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 ⋅ 9 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 ⋅ 10 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

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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.