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1253 Nanawale Way, Kailua
$1,750,000
6 Beds ⋅ 4 Baths ⋅ 202619307 MLS ⋅ FS - Fee Simple Tenure ⋅ 12 DOM
$50,000 SELLER CREDIT! Legacy Pool Property in Kailua with 2 Separate Entry Rentals & Tons of Living Space! Located in the desirable Enchanted Lake area, 1253 Nanawale Way offers a flexible layout with rare versatility to have rental income offset your mortgage! Main home a spacious 4 bedroom with massive primary bedroom and 2 living rooms. A private-entry studio can optionally connect to the main house floor plan if desired. Separate-entry 2-bedroom 1 bathroom studio upstairs, has ocean views. Situated near Enchanted Lake Shopping Center, Safeway, Starbucks, restaurants, coffee shops, neighborhood conveniences, and schools, this location makes everyday living easy. Enjoy quick access to Kailua Town, Kailua Beach Park, Lanikai, Ka?elepulu/Enchanted Lake, Pali Highway, H-3, Adventist Health Castle, and Marine Corps Base Hawaii. Don't miss out on this property that has the potential to BUILD YOUR LEGACY!

1253 Nanawale Way, Kailua
1310 Kupau Street, Kailua
$1,730,000
3 Beds ⋅ 2 Baths ⋅ 202618141 MLS ⋅ FS - Fee Simple Tenure ⋅ 11 DOM
Escape to paradise in the heart of the Kailua Beach community. This charming single-level, 3-bedroom, 2-bath home features an airy, open layout with vaulted ceilings & slate flooring throughout. The spacious living area flows into a well-appointed kitchen with an eat-in bar. The dining room offers a flexible space for a home office or media room, if desired. A large primary suite is a relaxing retreat with French doors to the backyard, a walk-in closet, & an ensuite featuring a custom rock shower floor. A bright & light coastal inspired 2nd full bathroom w/ pretty tiled shower & 2 more bedrooms at the opposite end of house offer privacy. The island lifestyle extends outdoors through 2 different sets of French doors to a level, fully fenced 7,500 sq ft lot complete with a tiled saltwater pool & hot tub & cascading waterfall, flagstone lanais, lava-rock walls, & lush greenery. Additional features include split ACs throughout, inside laundry room, a 2-car garage, a 46-panel fully paid for PV system w/ net metering, & solar hot water. Set on a peaceful side street close to all Kailua has to offer, this home captures the essence of Hawaii living. Open House Sunday 2-5 or by appointment.

1310 Kupau Street, Kailua
1312 Aupapaohe Street, Kailua
$1,699,000
3 Beds ⋅ 3 Baths ⋅ 202614621 MLS ⋅ FS - Fee Simple Tenure ⋅ 86 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
1458 Uluhala Place, Kailua
$1,695,000
5 Beds ⋅ 3 Baths ⋅ 202618644 MLS ⋅ FS - Fee Simple Tenure ⋅ 24 DOM
This spacious, 5-bedroom, 3-bath home, is perfectly set up for multigenerational living and also has the potential of generating additional income. One of the larger homes, with 2,729 square feet of living space, is on a level 9,875 square foot lot, ideally located on a quiet cul-de-sac, in the established Kailua neighborhood of Olomana. Majority of the home is single-level, with one bedroom and living space upstairs. It offers a versatile floor plan, with separate entrances that are perfect for guests, investment opportunities, or a dedicated home office. The fully fenced yard and large covered lanai space provide exceptional indoor-outdoor living, with plenty of room to relax, play with pets, or entertain friends. Mature fruit trees and lush landscaping create a private, tropical setting for you to enjoy. Large carport and driveway area, along with lots of storage, and a workshop, provide lots of room for 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
701 Kihapai Street, Kailua
$1,695,000
3 Beds ⋅ 2 Baths ⋅ 202611826 MLS ⋅ FS - Fee Simple Tenure ⋅ 75 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.

701 Kihapai Street, Kailua
1237 Hele Street, Kailua
$1,695,000
6 Beds ⋅ 2 Baths ⋅ 202612433 MLS ⋅ FS - Fee Simple Tenure ⋅ 112 DOM
Discover your own private tropical oasis in the highly desirable Keolu Hills neighborhood. This beautifully updated 6-bedroom, 2-bath home offers exceptional versatility, featuring 3 bedrooms and 1 bath on each level, each with its own private entrance—ideal for multigenerational living, extended family, or guests. Thoughtful upgrades blend modern comfort with classic island charm and include 21 owned PV panels, solar water heating, a solar attic fan, split AC systems, stainless steel appliances, and laminate and tile flooring. The fully fenced property is surrounded by lush, mature tropical landscaping and fruit trees, creating a peaceful and private retreat. The backyard is truly something special, featuring a beautiful cascading waterfall, relaxing jacuzzi, and majestic mango tree known for its delicious fruit. An expansive covered lanai of approximately 1,000 square feet provides an incredible space for entertaining, outdoor dining, or simply enjoying the tropical surroundings. Conveniently located just minutes from Kailua's world-famous beaches, shopping, dining, hiking, and more. Experience the best of Windward O?ahu living!

1237 Hele Street, Kailua
1247 Ulupalakua Street, Kailua
$1,680,000
6 Beds ⋅ 5 Baths ⋅ 202614426 MLS ⋅ FS - Fee Simple Tenure ⋅ 75 DOM
Discover the possibilities of this spacious, single-level home in Kailua’s Pohakupu neighborhood! Offering 6 bedrooms and 5 bathrooms, this property features a versatile floor plan with generous living spaces and flexibility to accommodate a variety of needs. The expansive living room flows into an open dining and kitchen area featuring a large island ideal for meal preparation, casual dining, and entertaining. A separate den provides additional options for a home office, media room, or creative space. Enjoy the convenience of single-level living with no interior steps, along with accessibility features throughout. Additional highlights include 14 ceiling fans, 8 split AC units, and 21 photovoltaic panels. Ample parking includes a carport, driveway, and additional side parking. Outdoor features include a covered laundry area, a patio off the primary bedroom, backyard space, and a storage shed. Conveniently situated near shopping, dining, schools, and Kailua’s recreational amenities, this property presents an opportunity to personalize a spacious home to suit your vision. Explore the space, flexibility, and potential this Kailua property has to offer!

1247 Ulupalakua Street, Kailua
970 Apokula Place, Kailua
$1,680,000
5 Beds ⋅ 3 Baths ⋅ 202610133 MLS ⋅ FS - Fee Simple Tenure ⋅ 88 DOM
Rare opportunity to own a massive 31,000+ square foot oasis in one of Kailua's most desirable neighborhoods, Keolu Hills. Tucked away on a quiet cul-de-sac with no rear neighbors and a beautiful hillside backdrop, this 5-bedroom, 3-bath home has remained in the same family for nearly six decades. With endless potential, it offers an ideal opportunity for multi-generational living or update a well-built home in an exceptional location. The expansive covered lanai opens to the lush backyard creating the perfect space for effortless island-style living, whether you’re relaxing in privacy or entertaining family and friends. Positioned at a higher elevation, the home naturally captures cooling trade winds and Koolau mountain sunsets. Located in one of Oahu’s most sought-after communities, this unique property must be seen to fully appreciate its scale, privacy, and setting. Tax record has 4 bedrooms. Buyer to do their own due diligence. House has alarm system. Appraisal valued at $1,950,000 (March 2024). Closing contingent upon acceptance of petition by Land Court to note the successor trustee(s). Open house on Sunday, October 25 from 2 to 4 P.M.

970 Apokula Place, Kailua
237 Kihapai Street Unit A, Kailua
$1,650,000
4 Beds ⋅ 2 Baths ⋅ 202618352 MLS ⋅ FS - Fee Simple Tenure ⋅ 17 DOM
This home is all about the views. Framed by the beautiful mountains and the marsh, the spacious deck offers the perfect setting to enjoy your morning coffee or unwind at the end of the day. Just off the deck is the primary suite that features a beautifully renovated bathroom done in 2022. Down the hall are 3 additional bedrooms, a full guest bathroom, and 2 storage closets. The open and inviting living area seamlessly connects the updated kitchen with the dining and living space, creating an ideal setting for both everyday living and entertaining. All while keeping those beautiful views front and center. Updates completed in 2026 include new flooring throughout, fresh exterior paint, & fresh deck paint. Other notable features include double wall construction, a kitchen renovation completed in 2022, and split AC in both the primary suite and living room. Despite its peaceful, quiet setting, you’re just a few blocks from some of Kailua’s best coffee shops, boutiques, grocery stores, and other local conveniences. While the home is incredible as is. Plans are with DPP for an addition & renovations & can potentially be transferred to the buyer if desired. Inquire for details.

237 Kihapai Street Unit A, Kailua
563 Alihi Place, Kailua
$1,645,000
3 Beds ⋅ 2 Baths ⋅ 202618852 MLS ⋅ FS - Fee Simple Tenure ⋅ 20 DOM
Meet your favorite morning spot: a sun-filled living room framed by distinctive trapezoid windows, where natural light pours in and beautiful mountain views set the tone for the day. Tucked at the end of a double-ended cul-de-sac, this gracious single-level home offers comfort, privacy, and easy living. The spacious lanai is perfect for morning coffee, weekend BBQs, entertaining, or unwinding with majestic Olomana as your backdrop. Pride of ownership shines throughout, with beautifully renovated bathrooms, new appliances, tasteful lighting, and thoughtful improvements that make this home truly move-in ready. Additional features include soft-close hardware added to existing kitchen cabinetry, new vinyl gates, new interior doors, an updated electrical panel, fresh interior paint (2023), and preventative ground termite treatment (2025). Enjoy indoor-outdoor living with beaches, parks, dining, and shopping just minutes away in Kailua Town. $10,000 Seller credit toward Buyer’s closing costs.

563 Alihi Place, Kailua
558 Ulumu Street, Kailua
$1,625,000
4 Beds ⋅ 2 Baths ⋅ 202615259 MLS ⋅ FS - Fee Simple Tenure ⋅ 68 DOM
Beautifully renovated single level home tucked away from the main roads, offering privacy and serenity. A spacious entry welcomes you into the bright living room featuring beautiful porcelain tile flooring. The gorgeous eat in kitchen boasts Quartz countertops, a tile backsplash, pendant lighting, and new stainless steel appliances. Stay comfortable year round with split A/C in every room. Numerous windows, replaced in 2016, provide abundant natural light, cool breezes, and lovely views of the fully fenced backyard with room to expand. Enjoy the shade and fruit of the mature mango tree and the irrigation system for the Palms. The large covered lanai is perfect for entertaining family and friends. Additional features include an extra-large storage unit. Conveniently located near world famous Kailua beaches, parks, shopping, and restaurants, with easy access to H3 and the Pali Highway without having to fight Kailua town traffic. Put this home on your must see list! One or more photos have been enhanced.

558 Ulumu Street, Kailua
650 Oneawa Street, Kailua
$1,600,000
6 Beds ⋅ 3 Baths ⋅ 202617501 MLS ⋅ FS - Fee Simple Tenure ⋅ 40 DOM
More Aloha, A Lot More Possibility! Short Sale and potential 5.75% VA Assumable for any buyer! Welcome to this thoughtfully renovated 6+bedroom, 3-bath home offering approximately 2,100 SF of versatile living space. Currently arranged as a 3-bedroom main home plus bonus room, an attached 1-bedroom living space with bonus room, and a separate attached studio, this unique layout offers flexibility for multigenerational living, extended family, and guests. The additional living spaces may also be incorporated into the main home to create an even more expansive living arrangement. Buyer to conduct their own due diligence regarding permitted uses. Enjoy updated kitchens & baths, ceramic tile flooring, a 120 gallon water heater, 8 split ACs, and 40 solar panels plus batteries! The semi-enclosed carport lanai extends the living experience outdoors, offering a versatile space for entertaining, relaxing, storage, or additional parking. An electric gated yard provides privacy & room to garden, or simply enjoy. Near world-famous Kailua Beach and the heart of Kailua town, this move-in-ready home offers comfort, flexibility, and the relaxed island lifestyle Kailua is known for.

650 Oneawa Street, Kailua
443 Maluniu Avenue, Kailua
$1,598,000
5 Beds ⋅ 3 Baths ⋅ 202613151 MLS ⋅ FS - Fee Simple Tenure ⋅ 81 DOM
Back on the market and better than before, including repairs and a $25k credit toward closing costs! This Coconut Grove Kailua home offers the rare combination of space, flexibility, and location. Less than a half-mile to Kalama Beach Park, this 5-bedroom, 3-bathroom property should jump out for its multi-generational living potential. The main house features 4 bedrooms and 2 baths, has been freshly repainted throughout, and includes an updated main kitchen, a handy kitchenette, and no carpet. On the far side of the property where the carport is located, a newly carpeted two-story suite offers built-in privacy: an en suite primary bedroom upstairs with its own private balcony, plus a cozy sitting room and kitchenette downstairs. The primary suite also has separate access via the carport, which is perfect for extended family, guests, or rental potential. Enjoy easy access to everything Kailua Town has to offer, from local eateries to boutique shopping, plus quick highway access for commuting across the island. Come see it for yourself!

443 Maluniu Avenue, Kailua
1278 Ulupalakua Street, Kailua
$1,595,000
4 Beds ⋅ 2 Baths ⋅ 202618213 MLS ⋅ FS - Fee Simple Tenure ⋅ 10 DOM
Priced almost 100k below recent appraisal, this charming Kailua home offers a rare opportunity to own a space filled with warmth, character, and island style. Far from a cookie-cutter, this home is surrounded by lush tropical landscaping that creates a sense of privacy and tranquility, complemented by peaceful mountain views and lush outdoor spaces. Enjoy indoor/outdoor living with a covered gazebo, a cozy fire pit for evening conversations, tree swings for the young at heart, and a thriving vegetable garden. This backyard oasis invites you to slow down and enjoy the beauty of everyday life. Inside, the flexible floor plan offers plenty of room for entertaining, remote work, or hobbies. Conveniently located with quick access to Castle medical center and the H-3 and Pali Highway, commuting is a breeze. Just minutes from the world-renowned beaches of Kailua and Waimanalo as well as the shops, restaurants, markets, and vibrant energy of Kailua Town. The home has a newer roof, photovoltaic with net metering (lease is pre-paid until Feb 2033) and newer solar hot water. This welcoming Kailua home offers value, space, privacy, and the authentic charm that makes Kailua living so special.

1278 Ulupalakua Street, Kailua
839 Oneawa Street, Kailua
$1,590,000
6 Beds ⋅ 3 Baths ⋅ 202617350 MLS ⋅ FS - Fee Simple Tenure ⋅ 36 DOM
“I Love Kailua” - Experience the ultimate Hawaii lifestyle in a town famous for world-renowned beaches, vibrant open markets, abundant eateries, and boutique shopping, all wrapped in a charming heritage town vibe. This newly built, move-in-ready home offers an exceptional dual-living or multi-generational layout: •Top Floor: Features 3 bedrooms and 2 bathrooms, a spacious living area, and a beautiful outdoor deck perfect for hosting gatherings with family and friends. •Ground Floor: Includes 3 bedrooms and 1 bathroom, centered around a large, open entertaining space complete with a wet bar.

839 Oneawa Street, Kailua
1320C Kamahele Street Unit 2302, Kailua
$1,586,800
3 Beds ⋅ 3 Baths ⋅ 202617647 MLS ⋅ FS - Fee Simple Tenure ⋅ 40 DOM ⋅ Bluestone BLDG.
Welcome to Bluestone – 53 beautiful acres of gated hillside overlooking Kailua! Picture yourself sipping your morning coffee or dining in the evening on your lanai while looking across acres of green to sunsets dipping behind the Ko'olau Mountain Range. Or waking up to the sound of birds sing and perhaps a rainbow over the golf course. Maybe join a friend for a meal or round of golf at nearby Mid-Pacific Country Club. Enjoy a walk through the complex or the resort-like amenities that Bluestone has to offer such as tennis courts, pickle ball, salt-water pool, hot tub, sauna. Venture out to one-of-many other activities available to you nearby. It’s the Kailua lifestyle, beautiful Lanikai Beach, the open spaces and the scenic beauty that makes Bluestone a truly fabulous place to live. Add to that list a lovely townhome in a gated community with stunning views and cooling breezes. Spacious, scenic, and serene, Bluestone is a very special place to call home.

1320C Kamahele Street Unit 2302, Kailua
1225 Mokapu Boulevard, Kailua
$1,580,000
4 Beds ⋅ 3 Baths ⋅ 202614340 MLS ⋅ FS - Fee Simple Tenure ⋅ 93 DOM
Experience elevated island living in this fully remodeled, single-level home in the heart of Kailua. Renovated from top to bottom, this property feels virtually new and offers the perfect blend of modern design and everyday comfort. The home features a 3-bedroom, 2-bath main residence plus a connected 1-bedroom, 1-bath suite with a kitchenette, providing exceptional flexibility for extended family, guests, a home office, or potential rental income. Inside, a bright open-concept floor plan seamlessly connects the kitchen, living, and dining areas, creating an inviting space for both entertaining and daily living. The bedrooms feature premium DuChâteau hardwood flooring, adding warmth and an elegant finish throughout. A thoughtfully designed hidden laundry room enhances functionality while maintaining clean lines and a spacious feel. Outside, enjoy a fully fenced, oversized backyard—perfect for entertaining, pets, or relaxing in your own private retreat—along with a generous front yard that enhances the home's curb appeal. Turnkey and move-in ready, this exceptional property offers modern island living in one of Oahu's most desirable beach communities.

1225 Mokapu Boulevard, Kailua
453 Iliaina Street, Kailua
$1,539,500
3 Beds ⋅ 2 Baths ⋅ 202616142 MLS ⋅ FS - Fee Simple Tenure ⋅ 59 DOM
MAJOR PRICE REDUCTION & EXTRAORDINARY VALUE!! E komo mai to this charming pool 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. Seller will consider Seller Credit towards Buyer's Closing Costs and/or Interest Rate Reduction! Home Sweet Home Hawaii. Love where you live!

453 Iliaina Street, Kailua
526 Ulumawao Street, Kailua
$1,525,000
4 Beds ⋅ 2 Baths ⋅ 202617085 MLS ⋅ FS - Fee Simple Tenure ⋅ 50 DOM
$100,000 Price Improvement. Incredible Value and Best Buy on the Market. This highly desirable, single story, 4 bedroom, 2 bath home is located in the beautiful neighborhood of Pohakapu. Amazing new Kitchen including cabinets, countertop and appliances. The bathrooms have been designed in a luxurious manner that provides warmth and comfort. New Eurpoean style ceiling. Split level air conditioning systems and ceiling fans have been added to ther luxurious nature of this home. The property's exterior has been adorned with a bright inviting color scheme. The intrerior design and color palette provides a unique opportunity to utilize your personal touch to make this house your home. Easy to see and Easy to own.

526 Ulumawao Street, Kailua
1375 Kupau Street, Kailua
$1,498,000
3 Beds ⋅ 2 Baths ⋅ 202616698 MLS ⋅ FS - Fee Simple Tenure ⋅ 52 DOM
Beautifully remodeled with panoramic Koolau views. Stylishly renovated with modern finishes, this home features a bright, open-concept design with vaulted ceilings, exposed beams, warm wood accents, and a new kitchen that flows seamlessly into the living and dining areas. Large windows and doors bring in natural light while capturing the stunning, unobstructed mountain views. The living area opens to a spacious lanai, creating an ideal setting for indoor-outdoor living and entertaining, with ample land to expand if desired. A prime location on desirable Kupau Street.

1375 Kupau Street, Kailua
633 Keolu Drive, Kailua
$1,495,000
4 Beds ⋅ 2 Baths ⋅ 202612259 MLS ⋅ FS - Fee Simple Tenure ⋅ 123 DOM
Enjoy the best of Kailua living in this beautifully updated 4-bedroom, 2-bath home, conveniently located just minutes from the heart of town. Renovated in 2021, the kitchen and bathrooms offer modern finishes, and a brand-new split AC system was recently installed for added comfort. The home's thoughtful layout features two bedrooms and one full bath on each side, providing flexibility for a variety of living arrangements. Three bedrooms feature sliding glass doors that create a seamless connection to the outdoor spaces and bring in abundant natural light. The open-concept kitchen, living, and dining areas serve as the heart of the home and flow directly to the backyard, where you'll find a sparkling pool that was replastered in recent years. Enjoy easy access to Kailua Beach, Marine Corps Base Hawaii (Kaneohe Bay), Whole Foods, Target, local boutiques, restaurants, and the many shopping, dining, and recreational opportunities that make Kailua such a sought-after destination.

633 Keolu Drive, Kailua
1459 Akamai Street, Kailua
$1,488,000
4 Beds ⋅ 3 Baths ⋅ 202525520 MLS ⋅ FS - Fee Simple Tenure ⋅ 343 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
621 Palawiki Street, Kailua
$1,460,000
3 Beds ⋅ 2 Baths ⋅ 202614243 MLS ⋅ FS - Fee Simple Tenure ⋅ 90 DOM
Rare Opportunity! $100,000 price improvement creates outstanding value for buyers in Kailua! Enjoy effortless island living in desirable Enchanted Lake. This refreshed single-level 3-bedroom, 2-bath home is nestled on a generous 7,500 square foot lot along a quiet street with 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. Don't miss out!

621 Palawiki Street, Kailua
1536 Kina Street, Kailua
$1,449,000
5 Beds ⋅ 2 Baths ⋅ 202617232 MLS ⋅ FS - Fee Simple Tenure ⋅ 40 DOM
Welcome to 1536 Kina Street — a rare opportunity to own a generously sized 5-bedroom, 2-bath single-family home in the heart of Kailua. Nestled in a great neighborhood, this property offers the perfect blend of island living and modern comfort. With an expansive layout ideal for multigenerational living or growing families, this home features flexible living spaces, a functional kitchen. The yard provides ample room for outdoor entertaining, gardening, or workshop. Conveniently located just minutes from world-renowned Kailua Beach, shopping, dining, schools, and parks — enjoy the best of Windward O‘ahu living in this desirable location. Don’t miss your chance to own a piece of paradise — schedule your private showing today! First Open House 9/20 from 2-5PM!

1536 Kina Street, Kailua
1254 Ulupii Street, Kailua
$1,445,000
3 Beds ⋅ 2 Baths ⋅ 202619271 MLS ⋅ FS - Fee Simple Tenure ⋅ 13 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
1233 Keolu Drive, Kailua
$1,430,000
5 Beds ⋅ 3 Baths ⋅ 202519336 MLS ⋅ FS - Fee Simple Tenure ⋅ 418 DOM
Amazing opportunity to own in Kailua! This flexible floor plan offers endless possibilities with a well-maintained 4-bedroom, 2-bath main home (currently configured as a 3/1 plus a spacious studio). An additional remodeled studio (5th bedroom), separated by the saltwater pool, enjoys treetop and mountain views of Enchanted Lake, along with cool breezes and privacy. Ideal for multigenerational living, a home office, or rental income potential. The property is fully fenced and landscaped with a sprinkler system—perfect for your fur babies! Conveniently located near world-famous Kailua beaches, parks, shops, and restaurants, with easy access to the H-3 and Pali Highway—without having to fight traffic in Kailua town. Put this home on your must-see list! Number of bedrooms differs from tax records. One or more photos have been enhanced.

1233 Keolu Drive, Kailua
433 Kaimake Loop Unit A, Kailua
$1,395,000
4 Beds ⋅ 3 Baths ⋅ 202613595 MLS ⋅ FS - Fee Simple Tenure ⋅ 101 DOM
Lowest-Priced Home in Ko'olaupoko! SELLER SAYS, "SELL!" Don't miss this incredible opportunity to own a home on a quiet, private loop in the heart of Kailua! This single-level 3-bedroom, 2-bath home offers comfortable island living with a flexible layout and plenty of potential. Previous owners added a wet bar and a separate entrance to the primary suite, creating an opportunity to live in one area and rent out the other, or use the space to accommodate extended family or guests. Minimal yard work means more time to enjoy everything Kailua has to offer, including Kailua Town and the world-famous Kailua Beach. Additional features include owned solar panels to help reduce electricity costs and split A/C units throughout to keep you cool and comfortable year-round. Motivated Seller - let's make a deal! Schedule your private showing today and come see all this exceptional Kailua home has to offer!

433 Kaimake Loop Unit A, Kailua
322 Aoloa Street Unit 1601, Kailua
$1,385,000
3 Beds ⋅ 2 Baths ⋅ 202617370 MLS ⋅ FS - Fee Simple Tenure ⋅ 40 DOM ⋅ Windward Passage BLDG.
Rarely available 16th floor 01 stack at Windward Passage, just two floors from the top offering spectacular ocean, mountain and sunrise views from nearly every room! Originally a 3 bedroom 2 bath residence, the third bedroom has been thoughtfully opened to create an inviting sitting room and bar area, giving the home a spacious, open feel. The beautifully remodeled kitchen is complemented by extensive built-ins and storage surrounding the dining area. Located on the quieter side of the building, enjoy refreshing breezes and peaceful island living while being just a stroll from Kailua Town’s Whole Foods, boutiques, restaurants and shops_and the famous 3 mile stretch of white sandy Kailua Beach. Unmatched windward-side amenities include a heated saltwater pool, spa, tennis, pickleball and squash courts, fitness center, dog park, recently remodeled clubhouse, and storage for bikes, surfboards and kayaks. Pets and parking. VA approved. An exceptional Kailua lifestyle with a view!! This has FIVE parking stalls!! Rent three out to subsidize your HOA fee! It’s like lowering your interest rate!!

322 Aoloa Street Unit 1601, Kailua
650 Oneawa Street Unit A, Kailua
$1,359,500
3 Beds ⋅ 2 Baths ⋅ 202614171 MLS ⋅ FS - Fee Simple Tenure ⋅ 94 DOM
Experience refined island living in this beautifully remodeled 3-bedroom, 2-bath residence, ideally located in the heart of Kailua. Just moments from Kailua Beach, Kailua Town, Kailua Racquet Club, and convenient freeway access, this move-in-ready home offers the perfect blend of comfort, style, and location. Thoughtful updates include split A/C units, luxury vinyl flooring, fresh interior/exterior paint, and nice finishes throughout—an exceptional opportunity in one of Kailua’s most sought-after communities. Easy to See.

650 Oneawa Street Unit A, Kailua
427 Kawainui Street Unit B, Kailua
$1,350,000
2 Beds ⋅ 1 Baths ⋅ 202615974 MLS ⋅ FS - Fee Simple Tenure ⋅ 18 DOM
Come and see!! Coconut Grove charm, completely reimagined. Fully remodeled in 2021, this thoughtfully designed home blends modern comfort with the warmth and character of island living. The kitchen features an oversized island with seating, extensive cabinetry, warm wood countertops, farmhouse sink, stainless-steel appliances, gas cooking with double ovens, statement range hood, tile backsplash and under-cabinet lighting—perfect for quiet mornings or entertaining friends. The remodeled bath features striking herringbone tile, rainfall shower, matte-black fixtures, vessel sink and warm wood cabinetry. The primary bedroom offers a beautiful natural wood accent wall, multiple windows, recessed lighting and A/C. Step outside to one of the home’s best surprises: a private tropical retreat with generous lawn, mature palms, custom wood privacy features and outdoor gathering areas. As the sun goes down, string lighting beneath the palms gives the backyard an entirely different personality.

427 Kawainui Street Unit B, 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.

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