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$3,050,000
3 Beds 3 Baths 202615416 MLS FS - Fee Simple Tenure 23 DOM
Kailua Beachside living at its finest, where an exceptional corner lot, incredible outdoor living, and one of Kailua’s most coveted neighborhoods come together to create the ultimate Hawaiian lifestyle. W/ deeded private beach access, this spacious residence invites you to start your mornings walking the white sands of Kailua Beach, enjoy an afternoon swim, & return home to your own private backyard oasis. Set on over 12,000 sqft of outdoor space, the fully fenced yard offers room to relax and entertain, w/ a private pool deck & outdoor sitting area. Inside, the generous floor plan provides plenty of space to live & gather, w/ new engineered hardwood floors throughout the main living area, updated bathroom w/ marble-top vanity, large laundry room, & a private office off one of the bedrooms. The home is ready for a fresh vision, offering the opportunity to renovate & create a residence uniquely your own while taking advantage of its exceptional size, layout, & location. W/ its corner lot, private pool, spacious floor plan, & unbeatable location in Kailua Beachside, this is a rare opportunity to create the beach home you’ve always dreamed of in one Oahu's most desirable communities.

138 Kailuana Place, Kailua

$2,800,000
3 Beds 1 Baths 202612038 MLS FS - Fee Simple Tenure 83 DOM
Located on Kalanianaole Highway in Waimanalo with high visibility and traffic from both locals and tourists, this expansive 19,569 square-foot property presents an incredible opportunity for investors and entrepreneurs alike. The property sports a three-bedroom residence, rented parking section leased by the post office and Business Zoned space for your imagination. With a vacant section on-site, this property invites various development possibilities. Situated just moments away from the popular Waimanalo Beach Park, this location attracts continuous pedestrian and vehicle traffic, ensuring a steady flow of potential customers. Whether you're looking to grow an established business, start a new venture, or take advantage of the property’s prime location, this versatile space has everything you need to make your vision a reality.

41-35 Wailea Street, Waimanalo

$2,650,000
3 Beds 3 Baths 202609988 MLS FS - Fee Simple Tenure 108 DOM
Escape to the tranquility of your private sanctuary, conveniently located within a ten-minute walk from the renowned Kailua Beach. This exquisite residence was meticulously designed for casual island entertaining and seamless indoor-outdoor living. A sparkling pool, a luxurious jacuzzi, & a verdant landscape of mature tropical vegetation create a serene and visually appealing ambiance. Nestled within the picturesque town of Kailua, this property offers unparalleled convenience, with all necessary amenities within a short bicycle ride. The tranquil neighborhood provides a peaceful retreat, while the presence of a thriving lime tree named Eileen adds a touch of local charm. Pau Hana or intimate gatherings with family and friends will create lasting memories. This is the home everyone wants to come to for every occasion! Boasting a spacious yard, expansive pool deck, and an open-floor plan that is aesthetically pleasing and easy to maintain. The apartment can be kept and collected for $2,500+ per month or used as a chic private primary suite…steps to the jacuzzi and pool for midnight swims. Masterful! Hurry over. Owned solar panels, split AC, Gas Cooking, Oversized Garage, Limes!

294 Awakea Road, Kailua

$2,199,000
3 Beds 3 Baths 202615714 MLS FS - Fee Simple Tenure 25 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

$1,925,000
3 Beds 2 Baths 202610224 MLS FS - Fee Simple Tenure 102 DOM
Tucked away on Oahu’s Windward Coast, this charming mid-century home captures the essence of Hawaiian beach living. A short walk from the powder-soft sands and turquoise waters of Waimanalo Beach—consistently ranked among the most beautiful shorelines in the world—this thoughtfully maintained 3-bedroom, 2-bath residence offers a rare opportunity to live the lifestyle so many dream about. Set on an expansive 14,518 sq. ft. level lot, the property provides exceptional outdoor space for entertaining, gardening, or simply unwinding in the tropical breeze. Mature fruit trees dot the grounds, offering both shade and a true taste of island abundance. The home’s mid-century character shines through with timeless lines and a welcoming, move-in ready feel. Every detail reflects pride of ownership, making this a turn-key opportunity for buyers seeking a seamless transition to coastal living. The 24 owned photovoltaic panels provide meaningful savings. Positioned between the conveniences of Honolulu and the charm of Kailua, yet nestled in the quiet, country feel of Waimanalo, this property strikes the balance of seclusion and accessibility. Beach living, mountain views and abundant space.

41-1025 Nenue Street, Waimanalo

$1,849,000
3 Beds 3 Baths 202614109 MLS FS - Fee Simple Tenure 39 DOM
Price reduction! 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.

743 Akumu Street, Kailua

$1,840,000
3 Beds 2 Baths 202609963 MLS FS - Fee Simple Tenure 113 DOM
Welcome to the country lifestyle of Waimanalo - where sunrises, sandy beaches, surfing, diving, hiking, and the natural beauty of Hawai'i is part of everyday life. This special property offers a rare opportunity to slow down, recharge, and embrace island living in one of Oahu's most treasured beach communities. The cozy three-bedroom home captures the simple charm and relaxed feeling of an old Hawai'i beach house, while the expansive 11,700 square foot level lot may offer the potential to accommodate an accessory dwelling unit. With the beach approximately 400 feet away, the property is framed by the dramatic Koolau mountains, creating a breathtaking backdrop where mountains meet the sea. Enjoy the convenience of being just minutes from Kailua, yet worlds away from the pace of town. Honolulu, Costco and the airport are all within a short drive. This beachfront neighborhood is ideally situated near Waimanalo Beach Park, the local post office, fuel station, and Kalapawai Market.

41-020 Puuone Street, Waimanalo

$1,825,000
3 Beds 2 Baths 202606901 MLS FS - Fee Simple Tenure 123 DOM
Live on ONE LEVEL with a very private backyard oasis complete with Pool, Jacuzzi and covered Patio! Enjoy high open-beamed ceilings throughout the home. A quality kitchen with real wood cabinets and granite countertops. Updates include a 30,000 BTU split A/C, Roof re-coating, Acasia flooring, windows, Pentair Pool Pump, new pool skimmer, a new ABS sewer line from street to house, new incoming copper water lines, ceiling fans, lighting, primary bathroom vanity, automated sprinkler system, and a large detached storage shed complete with electrical and double walled framing. Exceptional curb appeal with a six-foot lava rock wall bordering the street, landscaped front yard, stamped concrete driveway, two-car carport, and extra driveway parking. Situated on a quiet dead-end street with sidewalks, this is the ideal peaceful Kailua neighborhood if you like morning/evening walks. The shops, groceries, eateries, and a movie theaters of Enchanted Lakes shopping plaza are within walking distance. This home is a turnkey gem designed to make memories!

533 Iana Street, Kailua

$1,775,000
3 Beds 2 Baths 202611826 MLS FS - Fee Simple Tenure 30 DOM
Welcome to this extensively upgraded Kailua home, ideally located between world-famous Kailua Beach and the scenic Kawainui Marsh. Move-in ready, this property combines modern finishes, exceptional energy efficiency, and the best of Windward living. The modern kitchen features custom cabinetry, quartz countertops, farmhouse sink, gas range, and newer stainless steel appliances. Additional improvements include split AC throughout, engineered hardwood flooring, newer windows, French shutters, vinyl fencing, tankless water heater, and a freshly painted exterior. Enjoy significant energy savings with 25 owned Tesla solar panels paired with two Tesla Powerwall batteries for backup power and added peace of mind. Gas service powers the water heater, range, and dryer. The fully enclosed yard offers plenty of room for pets, relaxing, entertaining, or gardening. Conveniently located just minutes from Kailua's beaches, shopping, dining, MCBH, and Kawainui Marsh Opportunity for qualified buyers to assume the existing VA loan at an attractive 2.625% interest rate. Seller offering a $20,000 Seller Credit

701 Kihapai Street, Kailua

$1,725,000
3 Beds 3 Baths 202609716 MLS FS - Fee Simple Tenure 105 DOM
Nestled within one of Kailua’s favorite neighborhoods, Kalaheo Hillside, 315 Iliaina Street is filled with potential and island charm. The property includes two separate structures --- a cute, detached cottage studio with a full bath and kitchenette, plus a classic home offering 3 bedrooms, 2 full baths, a great open floor plan, and a separate dining area with large windows looking out to the backyard. Much of the home remains in its original condition, including beautiful koa kitchen cabinet doors that could shine again with restoration. The spacious yard features a large in-ground pool and plenty of room to reimagine the outdoor spaces! Just minutes from Aikahi Shopping Center, Aikahi Elementary School, Kailua’s beaches, shopping, dining opportunities, markets, and so much more! Also close to MCBH Kaneohe, H-3, and Likelike Highway access, this property combines location, flexibility, and opportunity in one of Kailua’s most convenient neighborhoods. Split ACs in each room. PV panels on net metering.

315 Iliaina Street, Kailua

$1,699,000
3 Beds 3 Baths 202614621 MLS FS - Fee Simple Tenure 41 DOM
2.75% assumable loan, open to anyone. Veteran or not. That rate doesn’t exist today. Completely remodeled — 3x5 granite kitchen island, luxury vinyl plank throughout, split AC, double wall construction, leased PV on tile roof. 2 car garage. Minutes to Kailua Beach. From this house in Hillcrest, the views arrive at your windows. 180 degrees of Kailua, windward O'ahu, Enchanted Lake unobstructed from nearly every room. Sunrise over water, sunsets behind the Ko'olaus. Enjoy fruit trees and puakenikeni.  Open the interior stairwell and it’s one home — 1,950 sq ft, 3 bed, 2.5 bath, primary on the main level overlooks the front garden, oversized closet, dedicated laundry. Leave it closed and the lower level stays a private one bed, one bath rental with its own entrance and lanai.  The floor plan can change. The expansive views never will.

1312 Aupapaohe Street, Kailua

$1,665,000
3 Beds 2 Baths 202609934 MLS FS - Fee Simple Tenure 107 DOM
Meet your favorite morning spot: a sun-filled living room framed by distinctive trapezoid windows that flood the home w/natural light & showcase beautiful mountain views. This gracious & single level layout home is tucked at the end of a double-ended cul-de-sac; offering comfort, convenience, and privacy. The spacious lanai is ideal for weekend BBQs, entertaining, or relaxing w/ Olomana as your backdrop. You'll notice the care & pride of ownership throughout , w/ beautifully renovated bathrooms, new appliances, tasteful lighting & thoughtful improvements. Truly move in ready. Additional features include hardwood kitchen cabinetry enhanced with new soft-close hardware, new vinyl gates, new solid wood interior doors, updated electrical panel, fresh interior paint (2023), and preventative ground termite treatment (2025). Enjoy indoor-outdoor living w/ easy access to beaches, parks, dining & shopping in Kailua Town. Photos reflect prior furnishings. $ 10,000 Seller credit toward buyer's closing costs.

563 Alihi Place, Kailua

$1,650,000
3 Beds 2 Baths 202616142 MLS FS - Fee Simple Tenure 14 DOM
OPEN HOUSE SUNDAY 9/13, 1-4PM!! E komo mai to this charming home in one of Kailua's most sought after neighborhoods with less than a mile walk to beautiful Castles Beach! Located on a quiet street in the award winning Aikahi school district. Recently repainted interior & new luxury vinyl flooring in all bedrooms. This lovely home is single level with open floor plan, light and bright and plenty of privacy. Indoor/outdoor living with huge lanai area and pool perfect for social gatherings and Ohana get-togethers. Move right in or have a blank canvas ready for the most discerning buyer's upgrades, with plenty of room for expansion. Enclosed, private and large rear yard with swimming pool that is regularly serviced and cleaned. There is also a separate fenced area ideal for the pups. Close to all that Kailua has to offer. Home Sweet Home Hawaii. Love where you live!

453 Iliaina Street, Kailua

$1,580,000
3 Beds 2 Baths 202612434 MLS FS - Fee Simple Tenure 36 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

$1,530,000
3 Beds 2 Baths 202614243 MLS FS - Fee Simple Tenure 45 DOM
New Price, Same Amazing Location! This price improvement creates an exceptional opportunity to own a home in Enchanted Lake Estate. 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 w/ minimal through traffic. Enjoy 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. Large permitted covered lanai, fully fenced and landscaped yard, and 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

$1,499,999
3 Beds 2 Baths 202615210 MLS FS - Fee Simple Tenure 33 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

$1,499,000
3 Beds 2 Baths 202611963 MLS FS - Fee Simple Tenure 72 DOM
Welcome to this a bright and airy 3BR/2BA home perfectly positioned at the end of a quiet cul-de-sac in the heart of Kailua. This home has been refreshed with new paint inside and out, making it feel crisp, clean, and ready for you to move right in. Nestled on a generous lot of over 9,200 sq. ft., the property is a true outdoor oasis. Whether you’re hosting weekend gatherings on the lanai or taking a dip in the saltwater pool, there’s plenty of room to soak up the island sun. The expansive yard offers endless possibilities for gardening or play, all while benefiting from the efficiency of leased solar panels. Inside, the nearly 1,500 sq. ft. layout flows seamlessly, offering a wonderful blend of classic charm and modern potential. With a two-car garage and a prime location near the iconic sands of Kailua Beach and the desirable Kaelepulu Elementary School, this residence is designed for an easygoing lifestyle. Come see why this gem wont last!

545 Ka Awakea Place, Kailua

$1,495,000
3 Beds 3 Baths 202614708 MLS FS - Fee Simple Tenure 42 DOM Bluestone BLDG.
Bluestone's Kamahele Townhome - under $1.5M! Welcome to Bluestone, one of Kailua’s most private and prestigious gated communities. Set on nearly 50 acres of lush grounds fronting Mid-Pacific Country Club and surrounded by preservation land, this 3-bedroom, 2.5-bath townhome offers rare privacy, sweeping golf course, Ko‘olau mountain, and sunset views, plus an attached full-size garage and driveway parking for two additional vehicles. Three covered lanais capture cooling trade winds and provide seamless indoor-outdoor living. Bluestone residents enjoy resort-style amenities including a pool, whirlpool, BBQ areas, recreation spaces, tennis/pickleball courts, sauna, and gated security with patrol. Ideally located in the hills of Kailua, just minutes from Lanikai Beach and the Pillbox hike, this is a rare opportunity to own a townhome style with attached garage in the prestigious community of Bluestone at $1,495,000 — one of the few under $1.5M. Come and see what the Bluestone community has to offer! Sold As-Is. Furniture is negotiable.

1150B Kamahele Street Unit #3002, Kailua

$1,495,000
3 Beds 2 Baths 202613582 MLS FS - Fee Simple Tenure 59 DOM
Need $$ to help pay the Mortg? This charming homes has a cottage in the back yard that has been rented for $2,300 a mo. House features lovely hardwood floors, updated kitchen, bath, & lighting. Main house has three bedrooms, one bath w/lots of closet space. Cottage features cathedral ceilings, upgraded wet bar and bath, spacious private deck, and a separate gated entry. Many leased PV panels keep energy costs low. Large private yard has plenty of room for potential expansion. Property is located in the friendly neighborhood of Pohakupu. Kailua town and beach are a short distance away. This is a very special property. This is the only one that I can find for this price with a separate cottage. (Some of the photos are digitally staged.)

1254 Ulupii Street, Kailua

$1,450,000
3 Beds 3 Baths 202607704 MLS FS - Fee Simple Tenure 106 DOM Windsurfer BLDG.
Experience the quintessential Kailua LIFESTYLE at The WINDSURFER, a boutique 10-unit townhome community situated directly across from Kailua Beach. LOCATION. This part of Kailua Beach has Oahu's BEST KITESURFING; it's heaven! The Windsurfers Unit #4 Is the Special Unit that sits right on the lily pond, a happy and serene spot to reflect the days activities.  This RARELY AVAILABLE residence features a freshly painted interior, loft, new washer and dryer, and updated kitchen and bathrooms from a 2018 renovation. The versatile layout can accommodate either three bedrooms, or two bedrooms with a flex space and a half bath. The large tiled private patio offers many opportunities, entertaining, dining, outdoor living room and is has a lighted walk in storage closet for bikes, tools, and equipment. 2 reserved and excellent parking spaces right outside your door and guest parking is available for your friends. Most importantly ... Yes, PET FRIENDLY! Located just steps from world-class windsurfing, Kalapawai Market, and BUZZ'S Steakhouse, this serene retreat offers a welcome escape from the bustle of Honolulu.  CALL today to learn all about the outstanding lifestyle at the Windsurfer!

445 Kawailoa Road Unit 4, Kailua

$1,379,000
3 Beds 2 Baths 202611762 MLS FS - Fee Simple Tenure 58 DOM
HIGHLY MOTIVATED SELLERS! Welcome to this beautifully upgraded single-level home in Kailua's desirable Coconut Grove. Built in 1990 with double-wall construction, this home blends modern upgrades, quality craftsmanship, and the relaxed island lifestyle Kailua is known for. The bright, open-concept floorplan is filled with natural light and features luxury vinyl flooring, a beautifully remodeled kitchen with quartz countertops, a waterfall-edge island, white shaker cabinetry, stainless steel appliances & custom floating wood shelves. Custom built-in closet systems throughout the home provide exceptional organization & storage. Extensive upgrades include split ACs throughout, high-efficiency double-pane windows, premium board-and-batten wood exterior siding, a vapor barrier, added insulation, roof kick-out flashing, fresh exterior paint, reinforced structural carport posts, carport closet with locking sliding doors & an outdoor shower. Just minutes from world-famous Kailua Beach, Kalama Beach Park, Kailua Town, boutique shopping, local cafés, restaurants, farmers markets, and endless outdoor recreation, this home is move-in-ready for you to experience the very best of island living.

447-A Manono Street, Kailua

$1,360,000
3 Beds 1 Baths 202616680 MLS FS - Fee Simple Tenure 10 DOM
Nestled at the end of a private lane, this cozy 3-bed 1-bath Kailua home offers a laidback beach lifestyle + modern charm. Located on the desirable beach-side of Coconut Grove and a nice walk to the beach, this home features a spacious, updated kitchen with sleek finishes, a 13-panel owned PV system, and ample storage. The oversized + fully enclosed yard with automatic gate is the standout and a true blank canvas, providing endless potential to expand the home, build a sparkling pool, create a lush outdoor oasis, or all of the above. Perfectly situated to enjoy the best of Kailua, with Kailua beach and the endless shopping + dining options of Kailua town just a short walk away. This home serves as the ultimate base for a relaxed, active lifestyle and is a rare opportunity to secure your own piece of paradise.

324 Olomana Street Unit D, 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.