Kailua Homes under $2 million

Kailua Homes under $2 million

Welcome to Kailua, a hidden gem nestled on the stunning windward coast of Oahu, Hawaii. Known for its pristine beaches, lush landscapes, and a laid-back lifestyle, Kailua offers a unique blend of natural beauty and vibrant community spirit. With the majestic Ko'olau Mountains as a backdrop, this charming town is a paradise for outdoor enthusiasts, featuring activities like hiking, kayaking, and paddleboarding in the crystal-clear waters of Kailua Beach and Lanikai Beach.

Kailua boasts a rich cultural scene, with a variety of local shops, delightful eateries, and farmers’ markets that reflect the island’s diverse heritage. The town’s welcoming atmosphere is perfect for families, retirees, and anyone looking to escape the hustle and bustle of city life. Whether you’re enjoying a sunset picnic at Kailua Beach Park or exploring the enchanting Mokulua Islands, every day feels like a vacation in this idyllic locale.

For those considering making Kailua their home, you’ll be thrilled to discover a range of beautiful properties available for under $2 million. From charming single-family homes to modern condos with breathtaking ocean views, there’s something to suit every taste and budget. With its strong sense of community and proximity to Honolulu, Kailua is not just a place to live; it’s a lifestyle choice that offers the perfect balance of relaxation and adventure.

Come and experience the magic of Kailua, where your dream home awaits amidst the beauty of Hawaii’s enchanting landscape!

Newest Kailua Homes under $2 million

1278 Ulupalakua Street, Kailua
$1,595,000
4 Beds ⋅ 2 Baths ⋅ 202618213 MLS ⋅ FS - Fee Simple Tenure ⋅ 3 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 retreat 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 for gatherings, 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 both 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, leased photovoltaic with net metering 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
1310 Kupau Street, Kailua
$1,730,000
3 Beds ⋅ 2 Baths ⋅ 202618141 MLS ⋅ FS - Fee Simple Tenure ⋅ 4 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.Click link for video.

1310 Kupau Street, Kailua
1253 Nanawale Way, Kailua
$1,750,000
6 Beds ⋅ 4 Baths ⋅ 202619307 MLS ⋅ FS - Fee Simple Tenure ⋅ 5 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
675 Ulumalu Street, Kailua
$1,000,000
3 Beds ⋅ 2 Baths ⋅ 202619286 MLS ⋅ FS - Fee Simple Tenure ⋅ 5 DOM
Single-level home in Pohakupu on a 7,500 sq ft lot, offered at $1,000,000. This 3-bedroom, 2-bath home has 1,386 sq ft of interior living space, a 596 sq ft lanai, and an interior laundry area. This is a project home. The kitchen, bathrooms, and the rest of the interior are ready for a full remodel. A kitchen remodel was started several years ago and never completed. The kitchen also has 12-foot ceilings, which gives you a lot to work with in a redesign. The 888 sq ft garage is the standout. It fits three cars and has 12-foot ceilings. A garage door opens at the front, and at the back a heavy-duty Raynor overhead coiling roll-up door opens through to the other side, the type usually found in commercial buildings. Room for vehicles, a boat, a workshop, or serious storage. The lot offers space to garden, expand outdoor living, or explore future additions. Pohakupu is an established Kailua neighborhood, and this corner location puts everyday conveniences close by, with quick access to Kalanianaole Hwy, Kailua town, and the beaches. A single-level Kailua home with a garage and lot like this, at this price, is a rare opportunity for a buyer ready to take on a project.

675 Ulumalu Street, Kailua
1254 Ulupii Street, Kailua
$1,445,000
3 Beds ⋅ 2 Baths ⋅ 202619271 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 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
237 Kihapai Street Unit A, Kailua
$1,650,000
4 Beds ⋅ 2 Baths ⋅ 202618352 MLS ⋅ FS - Fee Simple Tenure ⋅ 10 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
398 Kaimake Loop, Kailua
$1,250,000
3 Beds ⋅ 1 Baths ⋅ 202618566 MLS ⋅ FS - Fee Simple Tenure ⋅ 10 DOM
A rare opportunity in a desirable Kailua location! Just minutes from Kailua Beach and a short stroll to Kalaheo Neighborhood Park, this property offers the chance to create something truly special. Situated on a generous 7,500 sq. ft. level lot, the property is being offered in tear-down condition, presenting an opportunity to start fresh and bring your vision to life. Bring your contractor, your ideas, and your vision. Your Kailua dream starts here! **Property to be sold strictly AS-IS. Seller will not make any repairs or provide credits ** Some photos have been digitally enhanced for illustrative purposes. The in-ground pool shown is a conceptual rendering to illustrate potential possibilities only. No pool currently exists on the property.

398 Kaimake Loop, Kailua
427 Kawainui Street Unit B, Kailua
$1,350,000
2 Beds ⋅ 1 Baths ⋅ 202615974 MLS ⋅ FS - Fee Simple Tenure ⋅ 11 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 ⋅ 11 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
471 Kailua Road Unit 3202, Kailua
$1,150,000
3 Beds ⋅ 2 Baths ⋅ 202618877 MLS ⋅ FS - Fee Simple Tenure ⋅ 12 DOM ⋅ Ka Malanai At Kailua BLDG.
Live-Work-Play! This is the heart of Kailua with so much to offer. The Urban lifestyle and the conveniences of daily living in a three bedroom that's just minutes to Kailua beach. Modern Architecture with an open breezy floorplan and lifestyle. This beautiful luxury condo features upgraded cabinets, custom Plantation windows treatments and upgraded tile floors. Enjoy cooking in your well-appointed kitchen offering stainless GE appliances, big farm sink and elegant dine-in countertops. One of the rare Kailua condos with central air conditioning to keep cool year round. A generous sized living/dining room filled with natural light plus a covered lanai taking in the majestic mountain views. The primary suite features walk-in closet, built-ins cabinet, ensuite bathroom with double vanities plus a separate bathtub and shower. Relax in the colorful landscaped gardens with BBQ areas and walking paths. Located directly across the street from Kailua district park, swimming pool & tennis courts. Enjoy a fabulous array of shopping, dining and recreational activities nearby. A perfect blend of island living at Ka Malanai@ Kailua.

471 Kailua Road Unit 3202, Kailua
636 Kaiemi Street Unit A, Kailua
$1,850,000
4 Beds ⋅ 3 Baths ⋅ 202618881 MLS ⋅ FS - Fee Simple Tenure ⋅ 12 DOM
Located in the Koolaupoku neighborhood, on a quiet street - 4 bedrooms, 3 bathrooms. Single Level open concept home with covered patio. Full street facing property with 2 car carport with views of Koolau Mountains. Fenced in yard with automatic gate. Original home built in 1955. Remodeled in 1987 with new Kitchen design, Added a true primary Bedroom with bathroom, Laundry Room inside home and an Office/Craft Room. 2 split AC systems. Three AC wall units. There are 22 Photovoltaic panels that helps offset Electricity Bill with possibility of new owner hooking up a critical load panel. Warranty is transferrable to new owner. Home comes with 2 split AC systems. Walkable to Kawainui Marsh Trail. Minutes to H-3, Kailua Town and Kailua & Lanikai Beach.

636 Kaiemi Street Unit A, Kailua
563 Alihi Place, Kailua
$1,645,000
3 Beds ⋅ 2 Baths ⋅ 202618852 MLS ⋅ FS - Fee Simple Tenure ⋅ 13 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
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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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