Kailua Homes under $2.5 million

Welcome to Kailua, a picturesque paradise nestled on the stunning windward coast of Oahu, Hawaii. Known for its breathtaking beaches, lush landscapes, and vibrant community, Kailua offers an idyllic lifestyle that many dream of. With its crystal-clear waters and soft, sandy shores, Lanikai and Kailua Beach are perfect for sunbathing, kayaking, and paddleboarding, making it a haven for outdoor enthusiasts and water lovers alike.

Kailua boasts a charming small-town atmosphere, complemented by a variety of local shops, cafes, and restaurants that reflect the unique Hawaiian culture. The community is renowned for its friendly residents and strong sense of belonging, making it an ideal place for families and individuals seeking a welcoming environment. With an array of parks, hiking trails, and recreational activities, residents can enjoy the great outdoors while soaking in the stunning natural beauty that surrounds them.

For those looking to invest in this tropical oasis, you’ll be pleased to know that Kailua offers a variety of homes under $2.5 million. From cozy single-family residences to spacious multi-bedroom properties, there is something to suit every taste and budget. Many homes are designed to maximize the breathtaking views and embrace the island lifestyle, featuring open floor plans, lush gardens, and proximity to the beach.

Discover the charm and beauty of Kailua, where your dream home awaits amidst the enchanting landscapes of Hawaii. Whether you’re seeking a permanent residence or a vacation retreat, Kailua is the perfect place to create lasting memories in paradise.

Newest Kailua Homes under $2.5 million

$1,645,000

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

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

Listing courtesy of Coldwell Banker Realty.

$1,200,000

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

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 Open House Thursday, Oct. 8th between 10AM - NOON. Or Our Sunday Open House 2-5 PM on the 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

Listing courtesy of At Home Hawaii LLC.

41-727 Kaaumoana Place Unit NA, Waimanalo

$665,000

3 Beds ⋅ 1 Baths ⋅ 202614425 MLS ⋅ FS - Fee Simple Tenure ⋅ 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

Listing courtesy of REMAX Hawaii.

$1,695,000

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

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

Listing courtesy of Coldwell Banker Realty.

$1,895,000

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

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

Listing courtesy of Coldwell Banker Realty.

$1,600,000

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

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

Listing courtesy of eXp Realty.

$969,000

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

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

Listing courtesy of Hawaii Modern Realty.

$2,495,000

5 Beds ⋅ 5 Baths ⋅ 202618299 MLS ⋅ FS - Fee Simple Tenure

Unbeatable value for a beachside estate inside Hale Kai Surf & Racquet Club, a private 14-home community in Kailua. A private access lane leads straight to the sand at Kailua Beach. This spacious home features nearly 4,000 sq. ft. of interior space, with 5 bedrooms and 4.5 baths. Soaring ceilings, with many living areas. A brand new split AC system was installed throughout. Four bedrooms are on the main level with the primary suite on the entire upper floor, with two closets, a sunroom. Enjoy Tennis, pickleball, basketball, a sparkling pool, and a clubhouse right across from the home and included in this community. Kailua town's coffee shops and restaurants are an easy bike ride away. Bring your own ideas and make it yours. Opportunities at this price and this close to Kailua Beach don't come up often, do not miss this opportunity!

824 N Kalaheo Avenue Unit A, Kailua

Listing courtesy of Koi Realty.

$1,699,000

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

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

Listing courtesy of Coldwell Banker Realty.

$2,228,000

6 Beds ⋅ 4 Baths ⋅ 202618361 MLS ⋅ FS - Fee Simple Tenure

Welcome to Keolu Hills offering sweeping views of the Ko’olau Mountains! Meticulously maintained 6 bedrooms, 4 full baths, private suite on the 2nd floor, and large bonus room in the back. Featuring a heated built-in swimming pool, 45 PV panels on HECO’s NEM agreement, 9 split AC systems, full alarm system with cameras. The layout offers flexibility of main living on the 1st floor having 5 bedrooms, and the 6th bedroom is a private studio on the 2nd floor with 680 square feet of living space! This is a large house with over 3,0000 square feet of living space inside, huge lot size of 9,000 square feet, carport for 2 cars, extended driveway for 3 additional vehicles. Image yourself floating in the heated swimming pool, watching the sunset glimmering off the Ko’olau mountains. Located just minutes from Enchanted Lake Shopping Center, Kailua Town, and only 3 miles to world-famous Kailua Beach, this property combines convenience with privacy. Set back from the road and surrounded by tropical beauty, this home is the perfect Kailua retreat. Active cameras on property disclosure.

1315 Kupau Street, Kailua

Listing courtesy of Coldwell Banker Realty.

$595,000

1 Beds ⋅ 1 Baths ⋅ 202617742 MLS ⋅ FS - Fee Simple Tenure ⋅ 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

Listing courtesy of eXp Realty.

$1,590,000

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

“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

Listing courtesy of Engel & Volkers Honolulu.

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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.