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865 N Kalaheo Avenue, Kailua
$4,900,000
202616097 MLS ⋅ FS - Fee Simple Tenure ⋅ 18 DOM
This rare 27,725 sq. ft. estate property has fabulous mountain views over the wide canal, in a prime Kailua location one street from the beach. Enjoy over 295 ft of direct waterfront canal living! Kayak, SUP right from your yard. The layout gives you incredible flexibility, featuring multiple suites within a spacious compound. The original single-level 3-bedroom/2-bath home opens to a green yard along the waterfront, flanked by two 2-bedroom/1-bath wings with private entrances and ample parking. A breezeway carport connects to another living area with 3 bedrooms/2.5-baths upstairs opening to a gorgeous view lanai. On the ground level is a two-car enclosed garage and workshop plus a 1-bd/1-bath wing. The property has been well-kept and maintained over the years by one family. Everything Kailua has to offer is convenient to this estate including the canal, beach, restaurants and businesses, shopping centers, the Pali and H-3. 117 owned PV panels and EV Charger too! Don’t miss this one-of-a-kind opportunity!

865 N Kalaheo Avenue, Kailua
865 N Kalaheo Avenue, Kailua
$4,900,000
11 Beds ⋅ 8 Baths ⋅ 202616094 MLS ⋅ FS - Fee Simple Tenure ⋅ 18 DOM
This rare 27,725 sq. ft. estate property has fabulous mountain views over the wide canal, in a prime Kailua location one street from the beach. Enjoy over 295 ft of direct waterfront canal living! Kayak, SUP right from your yard. The layout gives you incredible flexibility, featuring multiple suites within a spacious compound. The original single-level 3-bedroom/2-bath home opens to a green yard along the waterfront, flanked by two 2-bedroom/1-bath wings with private entrances and ample parking. A breezeway carport connects to another living area with 3 bedrooms/2.5-baths upstairs opening to a gorgeous view lanai. On the ground level is a two-car enclosed garage and workshop plus a 1-bd/1-bath wing. The property has been well-kept and maintained over the years by one family. Everything Kailua has to offer is convenient to this estate including the canal, beach, restaurants and businesses, shopping centers, the Pali and H-3. 117 owned PV panels and EV Charger too! Don’t miss this one-of-a-kind opportunity!

865 N Kalaheo Avenue, Kailua
1030 Aoloa Place Unit 5105B, Kailua
$825,000
3 Beds ⋅ 2 Baths ⋅ 202616227 MLS ⋅ FS - Fee Simple Tenure ⋅ 31 DOM ⋅ Windward Harbour BLDG.
Experience the best of island living at Windward Harbour in the heart of Kailua. Perfectly located within walking distance from shopping, restaurants, farmers markets, and the world-renowned Kailua and Lanikai beaches, this spacious ground-floor 3-bedroom, 2-bath residence offers the ideal blend of comfort and convenience. The open-concept floor plan provides a welcoming space for living and entertaining, while newly refinished bamboo flooring and fresh interior paint create a bright, move-in-ready feel. The bedrooms feature built-in closets and the floor-to-ceiling windows fill the home with natural light while showcasing peaceful garden views from your private lanai. Windward Harbour is a secure, pet-friendly community featuring resort-style amenities, including a swimming pool, hot tub, sauna, tennis courts, ping-pong, BBQ areas, a recreation room, and a dog run. Enjoy the perfect balance of tranquil living and easy access to everything Kailua has to offer.

1030 Aoloa Place Unit 5105B, Kailua
445 Keolu Drive, Kailua
$2,199,000
3 Beds ⋅ 3 Baths ⋅ 202615714 MLS ⋅ FS - Fee Simple Tenure ⋅ 48 DOM
Beautiful, sweeping views of Enchanted Lake and Kaelepulu wetlands from your elegantly remodeled open concept living, dining, & gourmet kitchen. Large glass doors open onto your huge covered deck surrounded by lush lakefront lawns, perfect for indoor/outdoor entertaining, or quiet rest. Contemporary, easy care plank ceramic tile flows throughout the home. The high performance kitchen design and quality appliances are a chef’s delight. Featuring a ground floor bedroom and full bath, a large upstairs primary suite with a huge walk-in closet and resort style bath with dual rain showers, split system and recessed ceiling ACs, an oversized garage with high ceilings and plenty of storage, an owned Photovoltaic system, and more! Fully fenced, attractively landscaped, and just a block to desirable Kaelepulu elementary school and park. Easy access to Kailua town’s vibrant fine dining, entertainment, and shopping district. Assumable VA loan at 2.25% interest with substitution of eligibility. A rare chance for waterfront living so call for your private showing today.

445 Keolu Drive, Kailua
75 Kihapai Street Unit 5, Kailua
$399,500
1 Beds ⋅ 1 Baths ⋅ 202614348 MLS ⋅ FS - Fee Simple Tenure ⋅ 69 DOM ⋅ 75 Kihapai BLDG.
Welcome home! Conveniently located one bedroom, one bath condo walking distance to Kailua town's shops and restaurants, and a few minutes bike ride or drive to beautiful Kailua Beach. The condo is move in ready, newly painted with new refrigerator, range, kitchen counters, and mirror closet doors. Other amenities include tile floors, a gated lanai, window a/c in the bedroom, plus hook-ups for a washer and dryer. This unit has easy access to the assigned parking stall and pool on the ground floor. Enjoy a swim in the condo pool while you watch the wildlife of Kawainui Marsh. Come make 75 Kihapai Street unit 5 your new home!

75 Kihapai Street Unit 5, Kailua
319 Kihapai Street Unit C, Kailua
$1,350,000
4 Beds ⋅ 2 Baths ⋅ 202609502 MLS ⋅ FS - Fee Simple Tenure ⋅ 87 DOM
Wake up to stunning, unobstructed views of the majestic Olomana mountain range from this property brimming with potential. This home presents a rare opportunity to renovate, restore, or create a space tailored to your vision in one of Kailua's most desirable locations. Featuring a flexible floor plan and ample outdoor space, this property is ready for its next chapter. Whether you're looking to undertake a full renovation or make improvements over time, the possibilities are endless. Enjoy convenient access to shopping, dining, beaches, parks, and the scenic Kawainui Marsh Trail, offering opportunities to experience one of O?ahu's most unique natural landscapes. The property is being sold in its present condition. Interior square footage may differ from tax records. Buyers are strongly encouraged to perform their own due diligence regarding the property's condition, improvements, permits, square footage, and all other material facts they deem important to their purchase.

319 Kihapai Street Unit C, Kailua
821 Kainui Drive, Kailua
$2,500,000
5 Beds ⋅ 5 Baths ⋅ 202612304 MLS ⋅ FS - Fee Simple Tenure ⋅ 89 DOM
Rare opportunity to own a canal front home on a nearly 10,000 sq. ft. R-5 zoned lot with a legal ‘ohana unit, each with its own utility meters, complete with pool & spa.  Tucked along the peaceful cul-de-sac end of Kainui Drive, locally known as “Duck Road.”  The spacious single-level main home features three generously sized bedrooms with new carpeting, three bathrooms, a dedicated study and bright living and dining areas that flow seamlessly into an enclosed lanai. A large recreation room or studio complete with a kitchenette, bathroom, private entrance, and its own courtyard provides additional flexibility for guests, home office or extended family. Upstairs, the 800 sq ft 'ohana unit (823 Kainui Dr) features two bedrooms, one bathroom, and a covered lanai. Recent upgrades include a new roof on the main home and a freshly re-plastered pool.  Take in stunning sunsets over the Ko'olau Mountains from the multiple outdoor areas, relax in the pool and spa, or enjoy a paddle or boat out to Kailua Bay. This unique property offers flexibility and is ideal for multigenerational living, generating rental income, or both. The possibilities are truly endless.

821 Kainui Drive, Kailua
41-569 Inoaole Street, Waimanalo
$725,000
3 Beds ⋅ 2 Baths ⋅ 202611171 MLS ⋅ FS - Fee Simple Tenure ⋅ 110 DOM
Contractor special and Exceptional opportunity in the heart of Waimanalo! Set on a 6,777 sq ft lot with a tiny association fee, this attached single family home is ready for a buyer to create something special, whether it's a complete renovation or brand-new custom residence, the possibilities are plentiful. The existing structure was originally configured as a 3 bedroom, 1 1/2 bath home, and is in need of significant repairs. Additions have been made over the years, including a large living room plus a covered deck and another attached room on the backside. There is a new roof and gutters were added on the front portion of the home, but the property had extensive water damage from the Kona Low storm. Offered strictly As Is, Where Is, and with all its contents, it is priced less than current land value. This property is best suited for investors, builders, contractors, or buyers seeking a project. Enjoy the beauty and charm of Waimanalo, with its world-famous beaches, and the majestic Ko'olau mountain range in the background.

41-569 Inoaole Street, Waimanalo
75 Kihapai Street Unit 3, Kailua
$412,500
1 Beds ⋅ 1 Baths ⋅ 202606606 MLS ⋅ FS - Fee Simple Tenure ⋅ 186 DOM ⋅ 75 Kihapai BLDG.
Recently renovated, this one-bedroom single level unit on the ground floor features a covered lanai that is gated for privacy and includes one designated parking spot. In addition to a new split AC, flooring, kitchen countertops and cabinets, bathroom shower and shelving, during the renovation the water lines and vent/sewer stacks were upgraded. PLUS it has an exterior storage unit in the backyard along with a clothesline and washing machine.  Enjoy the trade wind breezes and natural lighting. Stay cool in the Saltwater pool on hot summer days. Furnishings included. Tenant would like to stay on.  VA Approved.

75 Kihapai Street Unit 3, Kailua
1251 Kainui Drive, Kailua
$4,350,000
6 Beds ⋅ 4 Baths ⋅ 202525771 MLS ⋅ FS - Fee Simple Tenure ⋅ 214 DOM
Discover the perfect blend of lifestyle, comfort, and value at 1251 Kainui Drive—an exceptional canal-front retreat situated along an established, palm tree-lined street in North Kailua. Fully renovated in 2026 & move-in ready, the spacious single-level main residence offers 4 beds, 3 baths, and over 3000 SF of beautifully designed living space with soaring ceilings, high-end finishes, and an effortless flow. New standing seam roof, net-metered PV & split AC. The kitchen is the heart of the home, featuring a grand island and luxurious, durable Taj Mahal quartzite countertops, ceiling-high cabinetry, premium appliances, a butler’s pantry, dedicated dining area and a charming breakfast nook. Covered and open lanais connect the living areas to landscaped grounds and a peaceful canal with ocean access—perfect for paddling from your backyard. Room to build your dream pool! A dedicated laundry room, 2-car garage, & ample storage provide everyday ease. The 2-bed, 1-bath ADU adds ~800 SF for multi-generational living, guests or rental flexibility. This desirable location is just two blocks from the beach and provides easy access to Kailua Town, top schools, and freeways for easy commuting.

1251 Kainui Drive, 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.