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1254 Ulupii Street, Kailua
$1,445,000
3 Beds ⋅ 2 Baths ⋅ 202619271 MLS ⋅ FS - Fee Simple Tenure ⋅ 14 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 ⋅ 19 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

413 Kihapai Street Unit A, Kailua
$1,200,000
2 Beds ⋅ 1 Baths ⋅ 202618788 MLS ⋅ FS - Fee Simple Tenure ⋅ 21 DOM
Your own Kailua cottage on a 5,000 sf lot, with no maintenance fees and a $10,000 seller credit toward buyer’s closing costs. Tucked down a quiet private lane in Coconut Grove, this single-family, detached 2-bedroom, 1-bath home is minutes from Kailua town and the beach. Inside are rich ipe hardwood floors. Ipe is one of the densest hardwoods in the world and naturally resists moisture, rot, and termites, making it ideal for island living. You’ll also find a well-laid-out kitchen, a tiled shower, and a living room whose sliding door opens to a big, level, fenced yard with Meyer lemon, avocado, coconut, and plumeria trees. The carport fits two cars tandem and holds the washer/dryer & water heater. Room to grow, with neighboring homes having expanded over the years. Fee simple, self-managed CPR with no monthly or annual fees. Easy to show. Check out the video tour!

413 Kihapai Street Unit A, Kailua

1322 Ulupuni Street, Kailua
$1,249,000
3 Beds ⋅ 2 Baths ⋅ 202617723 MLS ⋅ FS - Fee Simple Tenure ⋅ 39 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 ⋅ 41 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 ⋅ 41 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
$1,239,000
3 Beds ⋅ 1 Baths ⋅ 202616190 MLS ⋅ FS - Fee Simple Tenure ⋅ 41 DOM
PRICE IMPROVEMENT + $25,000 IN SELLERS CREDITS TO THE BUYER! Seller is offering $25,000 toward buyer's allowable closing costs and/or interest rate buydown, subject to lender approval and purchase contract terms. VA ASSUMABLE LOAN OPTION AT 5.625% INTEREST RATE available to qualified VA buyers, subject to loan servicer approval and applicable assumption requirements. Discover this charming 3-bedroom, 1-bath single-family home in Kailua's desirable Coconut Grove neighborhood! Situated on a spacious lot with NO HOA, this move-in-ready home offers comfort, thoughtful updates, and future potential. Inside, enjoy a refreshed kitchen featuring shaker cabinets, stone countertops, and stainless-steel appliances, along with vinyl plank flooring, an updated bathroom vanity, and newer split A/C units installed in 2024. Outside, enjoy a spacious yard with newly planted avocado, lemon, and lime trees, beautiful landscaping, and ample parking. Conveniently located near Kailua Town, shopping, dining, and world-famous beaches. Don't miss this opportunity to own a single-family home in Kailua with no HOA and valuable financing incentives!

320 Oneawa Street, Kailua

1410 Akamai Street, Kailua
$1,289,000
3 Beds ⋅ 2 Baths ⋅ 202615500 MLS ⋅ FS - Fee Simple Tenure ⋅ 61 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

433 Kaimake Loop Unit A, Kailua
$1,395,000
4 Beds ⋅ 3 Baths ⋅ 202613595 MLS ⋅ FS - Fee Simple Tenure ⋅ 102 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

633 Keolu Drive, Kailua
$1,495,000
4 Beds ⋅ 2 Baths ⋅ 202612259 MLS ⋅ FS - Fee Simple Tenure ⋅ 124 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 ⋅ 195 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 ⋅ 237 DOM ⋅ Ka Malanai At Kailua BLDG.
*READY FOR MOVE-IN 10/31!* 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 ⋅ 419 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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