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$1,899,000
4 Beds ⋅ 3 Baths ⋅ 202609848 MLS ⋅ FS - Fee Simple Tenure ⋅ 49 DOM
SPACE, PRIVACY & FLEXIBILITY ON A 15,373 SQ FT LOT IN MAUNAWILI. Set on a 15,373 sq ft lot in sought-after Maunawili, this beautifully updated property combines a spacious 3-bedroom, 2-bath main residence featuring hardwood flooring, split AC, double-wall construction, and a beautifully renovated primary suite with a spa-inspired bath, along with a private 1-bedroom, 1-bath living space complete with its own entrance, living room, lanai, and laundry. French doors open to a gazebo tucked just outside, creating a peaceful outdoor space to relax, gather, or enjoy the trade winds. The expansive fenced yard offers room to play, entertain, garden, and gather, while the terraced hillside above provides a unique vantage point to enjoy Olomana views. The private 1-bedroom, 1-bath living space offers an ideal setup for extended family, guests, or multigenerational living while maintaining separation from the main home. Recent improvements include a newer roof, PV with 2 Tesla Powerwalls, a new driveway, and additional updates. Conveniently located near Kailua Town, Castle Medical Center, and Pali Highway. Sq ft differs from tax records.

1002 Lunaai Street, Kailua
$3,049,000
4 Beds ⋅ 3 Baths ⋅ 202611322 MLS ⋅ FS - Fee Simple Tenure ⋅ 49 DOM
Your beach days just got closer! Just three homes from Kailua Beach, where morning walks and barefoot afternoons become part of your everyday lifestyle. Offering 4 bedrooms, 2.5 baths, plus a flexible bonus room with its own private entrance, this home is ideal for visiting guests, extended family, or a home office. Investors will appreciate the property’s proven rental appeal. The main home has previously rented for approximately $7,800 a month, while the separate flex room generated approximately $2,300 a month, providing over $10,000 a month in prior rental income. Whether you are looking for an investment, multigenerational living or a beach home with flexibility, this property delivers. Just minutes from Kailua Town's popular restaurants, cafes, boutiques, farmers market and more. And remember- "Life is always better barefoot." Come and fall in love.

156 N Kalaheo Avenue Unit C, Kailua
$3,999,900
4 Beds ⋅ 4 Baths ⋅ 202609693 MLS ⋅ FS - Fee Simple Tenure ⋅ 54 DOM
Beautifully renovated mid century modern Kailua beach house with room for a pool! This is the single level Beachside home everyone wants, just 5 lots from a gorgeous white sand beach, down one of Kailua's most quiet lanes. Recently expanded to 4 bedrooms, 3.5 baths, this beach home sits on a large flat lot with a beautifully landscaped yard, in one of Hawaii's most coveted neighborhoods! Featuring a brand new kitchen with Wolf appliances, custom cabinets, new tile floors, and a grand living space with soaring high ceilings. The home was just recently expanded to include a brand new primary bedroom and bathroom and a new mud room with a new butler's pantry, a new laundry room, and all new plumbing and electrical. All new Fleetwood windows and sliding doors for smooth, luxurious indoor/outdoor living. And yes there is plenty of room to install a pool! Mahiloa Pl is one of Kailua's hidden gems, on a beautiful part of Kailua beach with minimal public foot traffic. This home has been lovingly remodeled from top to bottom, and is ready for a new owner to move in!

85 Mahiloa Place, Kailua
$2,600,000
4 Beds ⋅ 2 Baths ⋅ 202607969 MLS ⋅ FS - Fee Simple Tenure ⋅ 57 DOM
You will love this location in Lanikai where an active lifestyle awaits you. One block to beach access where swimming, windsurfing, paddling are yours to enjoy every day. In the other direction is the entrance to Lanikai trail and Midpac Golf Course and Country Club. Impressive lava rock wall encloses a 4-bedroom home with enclosed porch addition and large deck overlooking an expansive yard. Build your dream multilevel home with 2 street entrances and potential view of Mokulua Islands and ocean.

150 Kaelepulu Drive, Kailua
$1,375,000
4 Beds ⋅ 2 Baths ⋅ 202609595 MLS ⋅ FS - Fee Simple Tenure ⋅ 75 DOM
Welcome to Enchanted Lake Estates, one of Kailua’s most sought-after neighborhoods. Situated on a desirable corner lot, this 4-bedroom, 1.5-bath single-family home offers a wonderful opportunity to own in a prime location just minutes from beaches, parks, shopping, dining, and top-rated schools. The home features a functional floor plan with comfortable living spaces, great natural light, and plenty of potential to update and personalize to your taste. The spacious yard provides ample room for outdoor entertaining, gardening, or creating your own private island retreat. Conveniently located near Kailua Town, Enchanted Lake Center, and with easy access to H-3 and MCBH, this property combines lifestyle, location, and value. Whether you’re looking for a primary residence, investment opportunity, or a home to renovate and make your own, this property is full of potential in a highly desirable community.

604 Paokano Loop, Kailua
$2,099,500
4 Beds ⋅ 3 Baths ⋅ 202609203 MLS ⋅ FS - Fee Simple Tenure ⋅ 77 DOM
Welcome home to beautiful Maunawili! Tucked away on a quiet cul-de-sac and surrounded by lush greenery, this beautifully renovated home is stunning with Ko’olau mountain views that capture the essence of Windward living. Inside, enjoy a spacious open-concept layout with soaring high ceilings, creating a bright and airy feel throughout. The home features luxury vinyl flooring, split AC units in every room, and a modern kitchen with quartz countertops, a large waterfall island, and new appliances, perfect for everyday living and entertaining. The main level offers 3 bedrooms and 2 bathrooms, with the primary bedroom located on the lower level, while the upstairs includes a separate 1-bedroom, 1-bath living area, ideal for extended family or guests. Step outside to a large Trex deck overlooking a private, lush backyard, perfect for relaxing or hosting while taking in the surrounding greenery. A rare opportunity to own a move-in ready home in highly desirable Maunawili.

1287 Puualoha Street, Kailua
$17,500,000
4 Beds ⋅ 5 Baths ⋅ 202609316 MLS ⋅ FS - Fee Simple Tenure ⋅ 79 DOM
Experience tranquil beachfront living in one of the most pristine areas along Kailua Beach, featuring stunning ocean views from the modern kitchen, spacious living room, and primary bedroom with a private oceanfront deck. Recent renovations include stylish baths that enhance the contemporary vibe. The custom kitchen flows into a welcoming dining area, ideal for gatherings and entertaining. A cozy cottage offers guest privacy, while ample parking and a three-car garage provide convenience. A dedicated office with courtyard access creates a peaceful workspace. Enjoy the lagoon pool and waterfall spa, with the beach just steps away for swimming, paddleboarding, or relaxing. Minutes from Kailua Beach Park, Mid-Pac Country Club, and Kailua Town, this home combines luxury and convenience. Your dream island lifestyle awaits!

200 S Kalaheo Avenue, Kailua
$4,250,000
4 Beds ⋅ 4 Baths ⋅ 202527969 MLS ⋅ FS - Fee Simple Tenure ⋅ 228 DOM
This stunning home is ready for you to live the ultimate Hawaii paradise lifestyle in the gorgeous community of Lanikai. Do not miss the opportunity to reside in this impeccable custom-built 4 bedroom 3.5 bathroom beauty! Built brand new and finished in 2018, the upper level showcases a chef’s kitchen and an open-concept living space that seamlessly extends to a spacious lanai, offering breathtaking ocean views—ideal for hosting or simply unwinding. This home features not one, but two luxurious primary suites, each with spa-inspired bathrooms and soaring windows that flood the space with natural light. High-quality materials were used, including marble countertops and gorgeous Walnut hardwood and Travertine floors throughout. The best part is that you’re just a short five-minute stroll from the pristine sands of both Kailua Beach and Lanikai Beach!

851 Aalapapa Drive, Kailua
$2,125,000
4 Beds ⋅ 3 Baths ⋅ 202525463 MLS ⋅ FS - Fee Simple Tenure ⋅ 119 DOM
This beautiful home provides the perfect blend of Security, Privacy & TONS of space!! The 3/2 Main floor features a deck, large living room transitioning into chefs kitchen w/ island & walk-in pantry + a family room w/ wet bar & laundry room w/ extra storage. Main bedroom includes a tasteful en-suite bathroom & walk-in closet. Outside is a landscaped, fully fenced yard, & a covered patio w/ utility sink. Upstairs living area is substantial & unique. It includes a large office leading to the huge ~750 sqft. bedroom with its own entertainment area & oversized walk-in closet. The bathroom includes dual sinks, vanity, linen closet & open format shower. Sliding doors lead to the fully enclosed ~280 sq. ft. private deck. Truly a one of a kind space. There is a 2 car garage with workshop space & storage, and a total of 5 parking (1 for boat/jet skis). Original construction was done with post tension slabs to ensure structural stability. The home also includes an insulated attic, 4 split ac units, 40 owned PV panels, 3 Tesla batteries & Tesla power charger. Pre-listing Home inspection completed 8/28/2025 with no major findings.

1386 Nanialii Street, Kailua
$1,488,000
4 Beds ⋅ 3 Baths ⋅ 202525520 MLS ⋅ FS - Fee Simple Tenure ⋅ 254 DOM
Tucked away in one of Kailua's most sought-after neighborhoods, this spacious 4-bedroom, 3-bathroom home presents a wonderful opportunity to create your dream home. This property features two 8-foot storage containers, a 1,232 sq ft deck with ocean & mountain views, ample parking for up to five cars or a boat, and a unique steel-frame construction with solid Styrofoam walls that deliver insulation, structural stability, and built-in termite resistance. Situated on a generous 9,410-square-foot lot, the property offers plenty of room to relax, entertain, and embrace the Kailua lifestyle. The versatile floor plan lends itself beautifully to multi-generational living or a rental opportunity, providing flexibility to suit your needs. Ideally located just minutes from world-famous Kailua Beach, charming boutiques, and favorite, local restaurants, this property offers the perfect blend of location, potential, and lifestyle. Whether you choose to refresh the current design or reimagine the space entirely, this home invites you to bring your vision to life in one of Oahu's most exceptional communities.

1459 Akamai Street, Kailua
$4,300,000
4 Beds ⋅ 4 Baths ⋅ 202525307 MLS ⋅ FS - Fee Simple Tenure ⋅ 260 DOM
Experience elevated island living in this fully renovated Lanikai retreat where luxury, privacy, and the natural beauty of Hawaii come together. Just two blocks from a secluded beach cove and a short paddle to the Mokulua Islands, this thoughtfully designed property captures the laid-back yet refined Lanikai lifestyle. Enter through a landscaped courtyard into a 3-bed, 3-bath main home featuring two spacious primary suites, customizable closets, and open-air lanais that make indoor-outdoor living effortless. High ceilings, large sliding doors, hardwood floors, large-format tile, and custom cabinetry reflect quality at every turn. The kitchen features a generous island, sunlit dining nook, and designer finishes ideal for casual meals or entertaining. Surrounded by mature landscaping, the property offers room for a pool in either the front courtyard or level backyard. A detached 1-bed, 1-bath suite with wet bar, laundry, and large private lanai above the garage offers versatility for guests, multi-generational living, or rental income—while preserving privacy for the main residence. Furnishings and decor negotiable with purchase, creating a turn-key paradise ready for your enjoyment.

223 Lanipo 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.