Kailua, HI Homes for Sale under $2,000,000

Single-level 4-bedroom, 2-bath home in Olomana, Kailua, located on a quiet cul-de-sac street with minimal through traffic. Features 1,848 sq. ft. of living space on a 10,944 sq. ft. lot. Easy access to the Pali Highway and H-3 provides a quick commute to town, with Castle Medical Center and Maunawili Elementary nearby. The open, light-filled floor plan features a skylight, Saltillo tile, and

Corinda Wong Hawaii Modern Realty

Location, Location, Location in the heart of Kailua bordering Kawainui Marsh. This CPR is only attached at the carport and VA approved. Numerous upgrades include a second story primary bedroom ensuite with a View of the wetland completed in 2014! Freshly painted w/ updated kitchen, bathrooms, hardwood flooring, windows, two split a/c, aluminum roof & one car carport. Front property is also for

Kitty Cano Residential Resource, Inc.

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.

Michael DeMello Redfin Corporation

A peaceful Kailua retreat where privacy, comfort, and the natural beauty of Hawai'i come together. Wake up to the beauty of Kailua and unwind in this serene, lovingly maintained single-level home, tucked beside a tranquil wetland and bird sanctuary with breathtaking Olomana views. A timeless tile roof and distinctive rock wall add character and lasting appeal. Designed for true island living, the

Veronica Munez Redfin Corporation

Nestled in the established Kailua neighborhood of Olomana, this spacious, 5-bedroom, 3-bath home, is perfectly set up for multigenerational living and can generate rental income. It is ideally located on a quiet cul-de-sac. One of the larger homes, with 2,729 square feet of living space, is on a generous 9,875 square foot lot. It offers a versatile floor plan, with separate entrances that are

Beth Yoshimura Coldwell Banker Realty

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

Solana Grover SC Realty, LLC

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

Sean Lopez Corcoran Pacific Properties

Great value, located in one of Kailua's most desirable neighborhoods! No through traffic, and surrounded by Golf Course & Canal front homes. Spacious layout, with lots of potential to bring your creative touch to take it to the next level. This home features 4 bedrooms and 3 full bathes (one bedroom has separate entrance), enclosed garage, and lots of storage space. 25 owned PV panels with net

Leon Mosher Coldwell Banker Realty

With stunning upgrades in the last year,, this five bedroom home located in Kailua Bluffs has unobstructed views of the Olomana peaks, a private greenbelt backdrop, and no rear neighbors — just mountain, sky, and quiet.Inside, the home has been updated with care: fully renovated kitchen with new cabinets, countertops, appliances, and flooring. Updated bathrooms. New paint, baseboards, and

Jeffrey Samuels Jeffrey Samuels Realty

621 Palawiki Street offers 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 with minimal through traffic. This property enjoys cooling Tradewinds, and a peaceful private retreat feeling. Inside, high beam ceilings, updated LED lighting, fresh interior paint, luxury

Michele Mihalko Coldwell Banker Realty

Back on the market! Excellent location on a quiet cul-de-sac in one of Kailua's most sought after neighborhoods. This Large level and very private lot is 8,470 sq ft of usable land. Plenty of room for your vehicles or even a boat or pool. This 4 bedroom 2 bath Single Level home is 1,598 sqft and has been tastefully upgraded throughout, new shaker cabinets, quartz countertops, luxury vinyl plank

Clinton Criado NextHome All Islands

Hands down the best value in all of Kailua at under $580/sqft for a custom built, move in ready home!!! For buyers' peace of mind, the pre-listing home inspection was completed in 2025 with minimal findings. This home presents an incredible opportunity...don't miss out!! The 3/2 main level features a deck, lg living room transitioning into chefs kitchen w/ island & walk-in pantry + family room w/

Michael Marks Real Broker

Step into your own private tropical retreat in desirable Keolu Hills. This beautifully updated 6-bedroom, 2-bath home offers exceptional flexibility with 3 bedrooms and 1 bath upstairs and 3 bedrooms and 1 bath downstairs, each with its own entrance—ideal for multigenerational living, extended family, guests, or a variety of living arrangements.Modern upgrades blend seamlessly with the home's

Nicole Mosk Coldwell Banker Realty

Price reduction of $200,000! Very motivated sellers. 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

David Li Aloha Properties, Inc.

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

Ellie Zeng HomeSmart Island Homes

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

Tahiti Reed REMAX Hawaii

Step into your own slice of island paradise & prepare to fall in love. This exceptional property on1.21 acres captures ocean views & the essence of tropical living. Wander the lush grounds and enjoy your own orchard filled with banana, mango, papaya, avocado, orange, lemon, lime, papaya, lychee, starfruit, jaboticaba, cacao, loquat, guava, breadfruit, many coffee trees and many floral

LesLee Delaney Better Homes and Gardens Real Estate Island Lifestyle

OPEN HOUSE 1-4PM Sunday 8/30!! E komo mai to this charming home in one of Kailua's most sought after neighborhoods. 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

Chris Shomo eXp Realty

Welcome to 609 Olomana Street, a newer-built residence in the highly desirable Coconut Grove neighborhood of Kailua. Constructed in 2022 this expansive property offers 8 bedrooms, 6 full bathrooms, and 2 half bathrooms, including a permitted Accessory Dwelling Unit (ADU) —providing exceptional flexibility for multigenerational living, guest accommodations, or potential rental income.The home

Carlin Yamashita Island Life Homes

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

Laura Awana Lewis Homes of Hawai'i Real Estate

Spacious two story Kailua Home built in 2006 as a multi-generational home. The exterior walls are concrete and the roof is covered in concrete tile. This home sits in the perfect location between Kailua Beach, Kailua Town Center, Enchanted Lake Elementary, & Enchanted Lake Center. There are three bedrooms, two bathrooms, a living room, kitchen and laundry connection downstairs. Both downstairs

Aaron Jones Blue Ribbon Realty Inc

This estate features two separate residences thoughtfully configured to offer up to four individual rental opportunities, or the flexibility to live in one and rent the other three—an ideal setup for multigenerational living, long-term rentals, guest accommodations, or investment income.Whether you're searching for a private family compound, an income-producing investment, or a

Angie Metriyakool eXp Realty