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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
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
554-A Auwai Street, Kailua
$1,125,000
3 Beds ⋅ 2 Baths ⋅ 202618584 MLS ⋅ FS - Fee Simple Tenure ⋅ 18 DOM
KAILUA COCONUT GROVE Opportunity awaits in this fee-simple 3-bedroom, 2-bath home on a 5,000 sq. ft. flag lot. Enjoy added privacy, a carport, yard space, and desirable single-level living. This home is ready for updating and offers excellent potential for renovation. Conveniently located near Kailua Town's shopping, dining, farmers markets, parks, and beautiful beaches. A great opportunity to create your dream home in one of Kailua's most sought-after neighborhoods.

554-A Auwai Street, Kailua
413 Kihapai Street Unit A, Kailua
$1,200,000
2 Beds ⋅ 1 Baths ⋅ 202618788 MLS ⋅ FS - Fee Simple Tenure ⋅ 20 DOM
You've dreamt about living in Kailua - in a Single Family Home with no maintenance fees and your own yard. Now is your chance to live the beach town lifestyle! Seller is offering a $10,000 credit toward Buyer's Closing Costs. This adorable Kailua cottage has a quiet location on a private lane off of Kihapai St. It sits on a 5,000 sf lot with a Meyer lemon tree, an avocado tree, coconut & plumeria trees. There's room in the carport to pull foward enough to allow two tandem parking stalls. A washer/dryer is also located in the carport. Inside the home has wood floors, a nice kitchen, a living room with a sliding glass door leading out to a spacious yard, a full bathroom with a tiled shower and two bedrooms.

413 Kihapai Street Unit A, Kailua
1322 Ulupuni Street, Kailua
$1,249,000
3 Beds ⋅ 2 Baths ⋅ 202617723 MLS ⋅ FS - Fee Simple Tenure ⋅ 38 DOM
PRICE IMPROVEMENT!!! Have you been searching for your forever home to raise a young family and build lasting memories? Or maybe looking for a home to age-in-place? Look no further! Welcome to 1322 Ulupuni Street. Tucked away in a quiet neighborhood, this single-level 3 bed, 2 bath gem offers the space, flexibility, and opportunity to create the home you’ve been dreaming of or simply move-in and start living life! The vaulted ceilings in the living room create a generous, open feel, while warm wood finishes bring natural texture and island charm. Moreover, experience indoor-outdoor living with a large covered lanai, perfect for grilling or unwinding after a long day of work. Not only that, but the expansive flat yard is great for hosting and entertaining events with your favorite people. Truly making the home feel like your own personal oasis. Featuring 32 Tesla photovoltaic panels to help reduce electricity costs, blends everyday practicality with future possibilities. Being centrally located, your just moments away from Kailua, Town, and everything Oahu has to offer. Don’t miss out on this rare opportunity! TMK DOES NOT MATCH ACTUAL BATHROOMS.

1322 Ulupuni 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
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
320 Oneawa Street, Kailua
$1,250,000
3 Beds ⋅ 1 Baths ⋅ 202616190 MLS ⋅ FS - Fee Simple Tenure ⋅ 40 DOM
VA ASSUMABLE LOAN OPPORTUNITY AT 5.625% INTEREST! Ask about available financing details. This well-maintained 3-bedroom, 1-bath single-family home sits on a very spacious lot, move-in ready, NO HOA, and a wonderful blend of comfort, thoughtful updates, and future potential. Inside, enjoy a refreshed kitchen featuring shaker-style cabinetry, stone countertops, and beach-friendly vinyl plank flooring that flows throughout the living spaces. The home also features a beautiful bathroom vanity and new split A/C systems, providing efficient comfort throughout the home. Step outside to a generous yard with plenty of room for hosting, expansion, and more. The property has been thoughtfully cared for and recently enhanced with newly planted avocado, lemon, and lime trees, along with additional native flowers that add to the lush outdoor setting. The large carport can easily fit 2-3 vehicles comfortably. Located in the heart of Kailua, just minutes from world-famous Kailua Beach, local shops, restaurants, schools, and everything this vibrant beach community has to offer.

320 Oneawa 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
1410 Akamai Street, Kailua
$1,289,000
3 Beds ⋅ 2 Baths ⋅ 202615500 MLS ⋅ FS - Fee Simple Tenure ⋅ 60 DOM
NEW PRICE + $15,000 SELLER CREDIT! Freshly renovated and move-in ready, 1410 Akamai St. is a beautifully refreshed 3-bedroom, 1.5-bath single-family home offering an easy blend of modern updates and classic Kailua living. The bright, open interior features new LVP flooring throughout, an updated kitchen with new cabinetry, countertops and appliances, refreshed bathrooms, new lighting, and split-system air conditioning. A bonus room attached to the carport provides additional flexible space. Outside, enjoy a spacious yard with refreshed landscaping, updated fencing, a mature mango tree and plenty of room to relax, entertain or enjoy the outdoors. The property also offers city, mountain, ocean and sunrise views. Now offered at $1,289,000, with Seller offering up to a $15,000 credit toward Buyer’s eligible closing costs and/or interest-rate buydown with an acceptable offer, subject to lender approval. An opportunity to not only purchase a refreshed Kailua home at a new price, but potentially use the Seller credit to help reduce upfront costs or improve monthly affordability. Schedule your private showing or visit our upcoming open house!

1410 Akamai Street, Kailua
1503 Kupau Street, Kailua
$1,268,000
3 Beds ⋅ 2 Baths ⋅ 202615339 MLS ⋅ FS - Fee Simple Tenure ⋅ 75 DOM
Enjoy the cool trade wind breezes on the top of Keolu Hills. Single level home with 3 bedrooms, 2 baths and a den or additional office space. A fenced yard with a water sprinkler system and an open covered lanai just off an enlarged kitchen. Convenient to shopping at Enchanted Lake Center - Safeway, McDonalds, L&L Barbecue & Much MORE!!! Number of bedrooms differ from tax records. Open House on Sunday, October 11, 2-5 pm

1503 Kupau Street, Kailua
491 Kihapai Street, Kailua
$1,250,000
2 Beds ⋅ 1 Baths ⋅ 202615245 MLS ⋅ FS - Fee Simple Tenure ⋅ 80 DOM
Charming 2-bedroom, 1bath Kailua home offering 828 sq ft of comfortable living space surrounded by a beautiful Tropical Garden. Move-in ready with complete updates including Plumbing redone and total Electrical rewiring. Freshly painted inside and out in September 2025 using Top-tier Sherwin Williams paint. Set on a fully fenced 5,000 sq ft landscaped, fenced yard with a Gated Entry and Banana Trees bearing Fruit. A Pergola including Funiture to enjoy the Outdoors. Enjpy the ultimate Kailua Lifestyle just a short walk or bike riide to world famous Kailua Beach and vibrant Town with Shops and Restaurants. Well loved and cared for by Owner.

491 Kihapai 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
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
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
319 Kihapai Street Unit C, Kailua
$1,350,000
4 Beds ⋅ 2 Baths ⋅ 202609502 MLS ⋅ FS - Fee Simple Tenure ⋅ 109 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
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
319 Kaelepulu Drive Unit 202, Kailua
$1,350,000
3 Beds ⋅ 3 Baths ⋅ 202607472 MLS ⋅ FS - Fee Simple Tenure ⋅ 194 DOM ⋅ Bluestone BLDG.
$30,000 RENOVATION CREDIT TO BUYER!! Ideally located by the main gate, tennis court, Lowest price in Bluestone, Kailua Living! Enjoy sweeping, unobstructed views of the golf course, majestic mountains, and a hint of ocean from the highly desirable Lanikai side of Bluestone. This well-maintained residence offers a kitchen with granite countertops, a stylish bathroom, and thoughtfully designed vinyl windows that bring in natural light and enhance overall comfort. A skylight further elevates the interior, filling the space with brightness and creating a warm, open atmosphere. Ideally situated near beautiful beaches, shopping, and dining, this home delivers both convenience and the best of island living. A strong investment opportunity with excellent rental appeal in a highly sought-after community.

319 Kaelepulu Drive Unit 202, Kailua
409 Kailua Road Unit 7106, Kailua
$1,100,000
2 Beds ⋅ 2 Baths ⋅ 202600852 MLS ⋅ FS - Fee Simple Tenure ⋅ 236 DOM ⋅ Ka Malanai At Kailua BLDG.
**10/24 & 10/25 OPEN HOUSES CANCELLED** Experience the convenience and charm of life in the heart of Kailua with a rare feature that sets this home apart: THREE assigned parking stalls. A true rarity in Kailua, the additional stall offers flexibility for multiple vehicles, visiting guests, or even potential rental income by leasing the extra stall to another resident. Moments from world-famous beaches, popular dining, shopping, cafes, and everyday essentials, this beautifully maintained 2-bed/2-bath condo offers an exceptional opportunity to enjoy one of Oahu's most desirable communities. Built in 2017, this modern residence combines comfort and style with central AC, stainless steel appliances, and a bright open-concept layout that extends seamlessly to a spacious covered lanai. The generous primary suite serves as a private retreat, featuring a walk-in closet & a spa-inspired bath with a separate soaking tub. Ka Malanai offers beautifully landscaped courtyards, BBQ areas, gathering spaces, and secure bike, surfboard, & kayak storage. Conveniently located near Kailua Beach Park, Target, & the many shops, restaurants, & services that make Kailua such a special place to call home.

409 Kailua Road Unit 7106, 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

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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