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472 A N Kainalu Drive, Kailua
$3,600,000
4 Beds ⋅ 6 Baths ⋅ 202517832 MLS ⋅ FS - Fee Simple Tenure ⋅ 85 DOM
Completed in 2022, this custom home blends high-end finishes with thoughtful design in a prime Kailua location. The main living area features vaulted ceilings and opens to the pool, spa, wet bar, and yard through expansive Fleetwood doors, creating a seamless indoor-outdoor flow. The home offers three en suite bedrooms, a full pool bath with direct access to the outdoor wet bar, a separate guest half bath, a large laundry room, and a walk-in pantry. A private-entry upstairs studio provides flexible space for guests or work. Quietly tucked down a gated flag lot, this property offers privacy, security, and a short walk to Kailua Beach—making it a rare opportunity for newer construction in one of Kailua’s most sought-after neighborhoods.

472 A N Kainalu Drive, Kailua

435 N Kalaheo Avenue, Kailua
$3,200,000
4 Beds ⋅ 4 Baths ⋅ 202525722 MLS ⋅ FS - Fee Simple Tenure ⋅ 42 DOM
Island Living at its best — Just One Block from Kailua Beach on the corner of Palapu Street. Step into this one-of-a-kind 4-bedroom, 3.5-bath contemporary island home featuring vaulted ceilings and 2,936 sq.ft. of bright, open living space, all enclosed on a 10,000 sq.ft. lot. Relax or entertain around your solar-heated pool with both covered and open lanais—perfect for seamless indoor/outdoor living. This property includes a 3-bedroom, 2.5 bath main home, with most living areas on the main level. The private upstairs primary suite offers a peaceful, ensuite retreat away from the main living spaces. In addition, there is an attached 1-bedroom, 1 bath with a kitchen that can be used as a rental or mother-in-law suite. Move-in ready with 30 owned PV panels (NET metering), split ACs in every room, luxury vinyl plank flooring, an upgraded kitchen, motorized blinds, updated lighting, and more. Additional highlights include two laundry areas, an attached workshop/storage room, a garage, and extra parking. Located in highly sought-after Kailua, close to dining, shopping, and endless watersports—this home delivers comfort, flexibility, and modern island style. Your Kailua oasis awaits!

435 N Kalaheo Avenue, Kailua

160 Ulupa Street, Kailua
$3,183,000
3 Beds ⋅ 4 Baths ⋅ 202524938 MLS ⋅ FS - Fee Simple Tenure ⋅ 51 DOM
Discover a truly distinctive Hawaiian residence that captures iconic charm and exceptional curb appeal. Surrounded by beautifully landscaped grounds and mature fruit trees, this well-known Kailua gem awaits its next chapter. The expansive front lanai invites relaxed island living and gathering—imagine watching 4th of July fireworks from the comfort of your own home. Inside, the lower level is thoughtfully designed for connection and comfort, featuring a family room that flows into the dining area and kitchen, a separate living room with built-in features offering flexible use. This level includes three bedrooms and three bathrooms, with one bedroom officially designated as a study in the plans. Upstairs, a legal Accessory Dwelling Unit (ADU) offers an open layout with a partitioned bedroom area, full bath, full kitchen, and its own private lanai—ideal for extended living flexibility. Minutes from Kalama Beach Park, enjoy easy access to Kailua’s shoreline. After a day at the beach, rinse off with the convenience of a solar-powered hot-water outdoor spigot. Complete with a three-car garage and PV this home offers a rare opportunity to own a special piece of island living.

160 Ulupa Street, Kailua

157 Makawao Street, Kailua
$2,375,000
5 Beds ⋅ 3 Baths ⋅ 202523832 MLS ⋅ FS - Fee Simple Tenure ⋅ 74 DOM
Experience the best of both worlds with this exceptional property, offering a sprawling yard and quick access to the beach. This home has been elegantly upgraded with premium materials, and you'll stay comfortable year-round with the outstanding split AC systems throughout. Featuring 5 bedrooms and 3 full bathrooms, this residence provides an ideal blend of ample living and outdoor space, set on a generous 12,716 sq ft lot. Enjoy the vast expanse of lush, flat green grass, perfect for play, alongside an outdoor open lanai for entertaining friends and family. Plus, delight in picking fresh citrus for your beverages from the yard's fruit trees. Just a short walk to the stunning Kailua Beach, this incredible home makes sunrise views, swimming, kiteboarding, surfing, and paddling effortlessly accessible!

157 Makawao Street, Kailua

176 Kuulei Road, Kailua
$1,900,000
4 Beds ⋅ 3 Baths ⋅ 202611702 MLS ⋅ FS - Fee Simple Tenure ⋅ 89 DOM
Live the Kailua Lifestyle! Located in the desirable Kalama Tract neighborhood of Kailua within a short distance of Beautiful Kailua Beach and Kailua Town that offers a multitude of shopping and dining choices. This desirable single level, spacious 4 bedroom / 3 bath home with an enclosed 2 car garage has a newer roof and remodeling was done within the past few years. Located near schools, the public District Park, public Library, H-3 and the Pali Highway for an easy commute to Honolulu and a short distance to Marine Corps Base Hawaii (MCBH). The generous sized lot of 12,500 square feet is really something special and offers many possibilities for the new homeowners! The yard is enclosed if you have children or pets. The home is being sold "As Is". Don't miss this special home!

176 Kuulei Road, Kailua

661 N Kainalu Drive, Kailua
$1,725,000
3 Beds ⋅ 2 Baths ⋅ 202601947 MLS ⋅ FS - Fee Simple Tenure ⋅ 77 DOM
Located just moments from the white sands of Kailua Beach, this charming corner-lot home is the perfect foundation for your family’s forever retreat. Freshly painted tongue and groove walls with brand-new bedroom carpeting, this single-level residence allows you to settle in comfortably while you begin customizing and modernizing each space to your unique taste. Or embrace it and live in it as is. but whichever you decide don't miss this incredible opportunity. The home balances its original "old-world" character with oversized original windows in the bedrooms, an expansive living area with bamboo flooring and a wall of sliding doors leading out to the front courtyard. Outside, the generous corner lot offers incredible flexibility—whether you dream of building an ADU for guest, rental, or extended family or creating a lush oasis with a pool for entertaining and relaxing. Situated in an active community where walking and biking are the norm, you’ll enjoy a front-row seat to the local 4th of July parade and seamless commutes via the H-3. Being close to schools and the Kaneohe Marine Base are also convenient.

661 N Kainalu Drive, Kailua

185 Ulupa Street, Kailua
$1,591,276
3 Beds ⋅ 2 Baths ⋅ 202606840 MLS ⋅ FS - Fee Simple Tenure ⋅ 122 DOM
ACCEPTING BACK-UP OFFERS! VA ASSUMABLE LOAN at 2.75% available for qualified buyers. Beach-close Kalama Tract home located less than two blocks from the beach and minutes to Kailua Town. This unique property showcases bold colors, artistic design elements, and a distinctive floor plan, offering a home with character and creative flair. Must see! The flexible layout features 2 bedrooms and 1 bath on the main level, plus a separate upstairs 1-bedroom, 1-bath unit with a kitchenette, for guests or extended living. Two flex spaces on the main level for an extra bedroom, office, or family room, plus a separate laundry area. Outdoor features include a saltwater pool and jacuzzi, perfect for enjoying Kailua’s relaxed lifestyle. Energy-efficient upgrades include PV panels with Tesla Powerwall, solar blankets for pool heating, and a 220V EV charging service. Approved plans and open permit already in place to build up and expand, offering a rare opportunity to add value while saving significant time and costs in the permitting process. A great opportunity to own a property with flexibility in one of Kailua’s most desirable neighborhoods. Enhanced Photos.

185 Ulupa Street, Kailua

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.