Kailua Homes with Kailua High School

Welcome to Kailua, a picturesque gem nestled on the windward coast of Oahu, Hawaii. Known for its stunning beaches, lush landscapes, and a tight-knit community, Kailua offers a unique blend of island living and vibrant culture. With its crystal-clear waters and soft sandy shores, Kailua Beach and Lanikai Beach are perfect for swimming, kayaking, and sunbathing, making them popular spots for both locals and visitors alike.

Kailua is not only a paradise for outdoor enthusiasts but also a thriving community that boasts an array of shops, restaurants, and local markets. The town’s charming boutiques and eateries reflect the island’s rich heritage, offering everything from fresh seafood to traditional Hawaiian cuisine. The laid-back atmosphere is complemented by the warm hospitality of its residents, making it a welcoming place to call home.

For families considering a move to Kailua, the presence of Kailua High School is a significant advantage. This well-respected institution is known for its commitment to academic excellence and a wide range of extracurricular activities. Living near Kailua High School means your children can benefit from quality education while being part of a supportive community. The school’s proximity to residential neighborhoods makes it convenient for families to enjoy a balanced lifestyle, with easy access to both education and recreational opportunities.

In Kailua, you’ll find a variety of homes that cater to diverse lifestyles, from charming single-family residences to modern oceanfront properties. Embrace the spirit of aloha and discover why Kailua is not just a place to live, but a way of life. Whether you’re looking for adventure or tranquility, Kailua is the ideal setting for your next chapter.

Newest Kailua Homes with Kailua High School

$1,499,999

3 Beds ⋅ 2 Baths ⋅ 202615210 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM

Welcome to this well-maintained, updated 3-bedroom, 2-bath single-family home tucked away on a peaceful cul-de-sac. Featuring approximately 1,692 sq ft of living space on a 6,000 sq ft lot, this home offers privacy, comfort, and a desirable indoor-outdoor lifestyle. Improvements include a remodeled kitchen with an open wall and wrap-around bar, remodeled bathrooms and flooring, five split A/C units, five ceiling fans with lights, gutters, and removal of acoustic ceilings other than the garage. The primary bedroom features a sliding glass/screen door opening to the backyard. Enjoy outdoor entertaining from the deck and gazebo, ideal for BBQs, relaxing, and gardening. The garage includes an automatic door opener, with a new garage door recently purchased. The interior was recently partially repainted for the new owners. Enjoy the quiet cul-de-sac setting with no through traffic, no rear neighbors, and a canal separating the home from neighboring properties on one side. Conveniently located near Enchanted Lakes Shopping Center, Safeway, restaurants, services, and the popular 3-mile walking/jogging route. A great opportunity to enjoy privacy and the relaxed Kailua lifestyle.

1724 Akaakoa Street, Kailua

$1,580,000

3 Beds ⋅ 2 Baths ⋅ 202612434 MLS ⋅ FS - Fee Simple Tenure ⋅ 5 DOM

NEW LISTING! Beautifully updated 3 bedroom, 2 bath single-level home with stunning Koolau mountain views in a peaceful neighborhood setting. This Enchanted Lake charmer sits on a level 7,500-sqft lot and features a newly renovated kitchen, 25 owned PV panels, and a spacious flex room that's great for guests or entertaining. Bright-and-airy living room features new tile flooring that leads to a wide-open kitchen with a welcoming breakfast bar, luxurious African Canyon granite countertops, stainless steel appliances and farmhouse sink. The primary suite includes direct backyard access and a large walk-in closet. Enjoy indoor-outdoor living from the fully fenced yard with cool trade winds, natural shade, and a plumeria tree that adds to the relaxed island ambiance. Additional upgrades include high open-beam ceilings, multiple split ACs, fresh exterior paint and an EV outlet at the spacious carport. Located in a walkable neighborhood with ample street parking and easy access to Kailua Town, Kailua Beach, Lanikai Pillbox, Mid-Pacific Country Club, schools, shopping and freeways. Don’t miss this Windward gem!

903 Alahaki Street, Kailua

$5,798,000

4 Beds ⋅ 4 Baths ⋅ 202614113 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 DOM

Special Lanikai beachside retreat just steps away from sparkling turquoise waters, with iconic Mokulua Island views just beyond the white sandy beach. This plantation-style home exudes charm, warmth, character, and offers resort-like living--swim, snorkel, sail, kayak, or paddle board, right out your door. An architect-designed gate welcomes you into lush landscaping with mango, banana trees, tropical plants, and flowers. The inviting living room w/impressive wood-vaulted ceilings and slate flooring opens through French doors to a a large covered lanai, ideal for family gatherings and entertaining. Gourmet kitchen features Thermador gas stove/convection oven, full-sized Miele freezer & refrigerator, walk-in pantry, wine refrigerator and bar area. The spacious primary suite upstairs showcases Australian eucalyptus hardwood floors, vaulted ceilings, built-in desk, wet bar, walk-in closet, wraparound lanais, and rooftop deck with Ko'olau mountain, Lanikai Pillbox, and ocean views. Enjoy early morning swims, backyard fire pit, hot/cold outdoor shower, two-car garage, & guest parking. A heavenly Lanikai property where indoor/outdoor living is a daily treat just steps from sand and sea.

1036 Mokulua Drive, Kailua

$1,795,000

5 Beds ⋅ 3 Baths ⋅ 202614738 MLS ⋅ FS - Fee Simple Tenure ⋅ 8 DOM

Come enjoy the amazing Kailua lifestyle in this spacious, 5-bedroom, 3-bath home, ideally located on a quiet cul-de-sac in the Olomana community. One of the larger homes on a generous 9,875 Sq Ft. lot, it offers a versatile floor plan, with separate entrances that are perfect for multigenerational living, extended family, or a dedicated home office. Majority of the home is single level with one bedroom and large living space upstairs. Cool breezes and lots of natural light. The fully fenced yard and huge covered lanai space provide exceptional indoor-outdoor living, with plenty of room to relax, play, and entertain. Enjoy mature fruit trees and lush landscaping that create a private, tropical setting. Large carport and driveway area, along with lots of storage and a workshop, allows for all kinds of 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

$1,928,000

3 Beds ⋅ 3 Baths ⋅ 202614109 MLS ⋅ FS - Fee Simple Tenure ⋅ 8 DOM

Great location! Don't miss this incredible opportunity to own a charming newly Completely renovated 3-bedroom, 2.5-bathroom home plus an work space in the main bedroom and a recreation room that can be use for extra living or exercise/TV room with a BBQ decking on a spacious 7677 sq ft level lot located at Enchanted lake kailua. The renovation includes new exterior and interior wall, new windows and doors, new roofing, new flooring, new cabinets and granite counter top, new appliances, new splits AC in every room, new gutter, new electric and plumbing lines and fixtures, new rock wall, new landscape and water sprinkler system etc. Enjoying beautiful mountain and lake views and the extra privacy the waterway that separates the property from its neighbors. This like new home is one of must see with endless possibilities in the big extra space in the back of the house. Enjoying peaceful living just minutes to kailua's beach, shops, and dining. Tax record not updated with the new renovation, First open house on 8/9/2026 from 2pm-5pm.

743 Akumu Street, Kailua

$988,000

3 Beds ⋅ 1 Baths ⋅ 202614578 MLS ⋅ FS - Fee Simple Tenure ⋅ 10 DOM

Rarely available corner lot. New electrcial rewiring and panel done in 2025.

1037 Kina Street, Kailua

$1,550,000

4 Beds ⋅ 2 Baths ⋅ 202614500 MLS ⋅ FS - Fee Simple Tenure ⋅ 14 DOM

Beautifully remodeled in 2009, this 4-bedroom, 2-bath home combines quality finishes with the peaceful setting of Maunawili. The light-filled, open floor plan features elegant travertine flooring throughout and a spacious primary suite with brand-new carpeting and double closets. The beautifully appointed kitchen showcases African Mahogany shaker cabinetry, granite countertops, Bosch appliances, a gas cooktop, and a wine refrigerator. Both bathrooms have been tastefully upgraded, with the primary bath featuring a new walk-in shower and the hall bath featuring custom African Mahogany cabinetry. Split A/C units provide added comfort, while the two-car carport offers convenient covered parking. Situated on an expansive 8,000+ sq. ft. lot, lush tropical landscaping creates a private, tranquil setting ideal for relaxing or entertaining. Enjoy the quiet charm of Maunawili with convenient access to Kailua Town, hiking trails, parks, and major commuter routes. A wonderful opportunity to own a beautifully maintained home in one of Windward Oahu's most desirable neighborhoods.

1176 Lunaai Street, Kailua

$1,560,000

3 Beds ⋅ 2 Baths ⋅ 202614243 MLS ⋅ FS - Fee Simple Tenure ⋅ 14 DOM

621 Palawiki Street offers move-in ready Kailua living in desirable Enchanted lake. This refreshed three-bedroom, two-bath single -level home sits on a generous 7,500 square foot lot on a quiet street with minimal through traffic. This property enjoys cooling Tradewinds, and a peaceful private retreat feeling. Inside, high beam ceilings, updated LED lighting, fresh interior paint, luxury waterproof laminate flooring, and mountain views from the living room create a bright, modern setting. The open kitchen features quartz countertops, a new sink and new stainless-steel appliances. A spacious permitted addition add flexible living space for a family room, media room, or office. Outdoors, the exterior is freshly painted. There is a large permitted covered lanai, fully fenced and landscaped yard, and a fruit-bearing mango tree. This backyard is the ideal space for relaxing or hosting gatherings. Minutes to Kailua Beach and close to Kailua Town shops, groceries, restaurants, Windward schools, Castle Medical Center, Pali Highway and H-3, this home blends comfort, convenience, and fully embraces Windward Lifestyle

621 Palawiki Street, Kailua

$2,000,000

7 Beds ⋅ 5 Baths ⋅ 202614077 MLS ⋅ FS - Fee Simple Tenure ⋅ 18 DOM

Spacious two story Kailua Home built in 2006 as a multi-generational home. The exterior walls are concrete and the roof is covered in concrete tile. This home sits in the perfect location between Kailua Beach, Kailua Town Center, Enchanted Lake Elementary, & Enchanted Lake Center. There are three bedrooms, two bathrooms, a living room, kitchen and laundry connection downstairs. Both downstairs bathrooms have wide doors, walk in showers and floating sinks. Upstairs there are four bedrooms (2 have walk in closets), three bathrooms, a family room, laundry connections and a wet bar. Large backyard and side yards with many fruit trees. Two car garage and ample off street parking. Solar Water Heater. This home is zoned R-5 and the land may be large enough to build a second dwelling. Check with your architect or plan maker if you would like to create a duplex and also CPR.

646 Wanaao Road, Kailua

$495,000

2 Beds ⋅ 1 Baths ⋅ 202614153 MLS ⋅ FS - Fee Simple Tenure ⋅ 19 DOM ⋅ 725 Kihapai Pl BLDG.

Seller relisted with HUGE Price Reduction! Don't miss this rare opportunity to own a charming 2-bedroom, 1-bath ground floor corner unit in Kailua's highly desirable Coconut Grove neighborhood. This bright and private townhome features an open-concept layout, low maintenance fees, assigned parking, and is just minutes from world-famous Kailua and Lanikai Beaches, Kailua Town's shopping and dining, H-3, the Pali Highway and Kaneohe Marine Corps Base. Whether you're a first time homebuyer, downsizing, or seeking a great investment property, this is your chance to own a piece of paradise in one of Oahu's most sought-after beach communities.

725 Kihapai Place Unit B1, Kailua

$1,985,000

4 Beds ⋅ 3 Baths ⋅ 202613204 MLS ⋅ FS - Fee Simple Tenure ⋅ 23 DOM

Discover a private sanctuary at the top of Maunawili Estates, one of Kailua’s most private neighborhoods, where old-school island charm meets some of the finest views in all of Kailua. Set on a 20,000-square-foot lot near the end of a quiet cul-de-sac and priced $234,700 below the current tax-assessed value, this distinctive 4BR/3BA home offers approximately 3,403 square feet of interior living area, plus 1,122 square feet of lanai, attic, and garage space. Custom Polynesian-inspired woodwork, handcrafted metal details, natural stone accents, curved architectural elements, and built-ins give the home character rarely found today. The light-filled main level features 3 bedrooms, 2 baths, an expansive primary suite, cooling valley breezes, and a wraparound lanai framing sweeping views of Kailua Bay, Olomana, and the Ko'olau Mountains. The flexible lower level includes a large bonus room and separate-entry 1BR/1BA apartment with private outdoor space. Terraced gardens, elevated lookout areas, 17 photovoltaic panels, a Tesla charger, two-car garage, and no rear neighbors complete this rare opportunity for a buyer ready to add personal touches and create an exceptional Kailua retreat.

1350 Lopaka Place, Kailua

$1,495,000

3 Beds ⋅ 2 Baths ⋅ 202613582 MLS ⋅ FS - Fee Simple Tenure ⋅ 28 DOM

Charming home with separate cottage. Home is updated with lovely merbau (Indonesian hardwood) floors, kitchen and bath. Main house has three bedrooms & one bath. Carport contiguous to the LR could be enclosed to increase living area by 240 sq ft. There are many leased PV panels. Large private yard has plenty of room to expand primary bedroom and add a bath. Cottage has a very private entry and its own deck and yard area. Cottage is permitted for use as additional living space to main house. Some of the photos are digitally staged. Property is located in the friendly neighborhood of Pohakupu. Kailua town and beach are a short distance away. This is a very special property.

1254 Ulupii Street, Kailua

Start Your Search

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.