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Search Kailua 5 Bedroom Homes

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Newest Kailua, HI 5 Bedroom Homes For Sale

646 Wanaao Road, Kailua image
646 Wanaao Road, Kailua $2,000,000

Spacious two story Kailua Home built in 2006 as a multi-generational home. The exterior walls are concrete and the roof is covered in tile. This home sits in the perfec...

  • 7 Beds
  • 5 Baths
  • 202614077 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 3 DOM
21 Kalaka Place, Kailua image
21 Kalaka Place, Kailua $11,980,000

Completed in 2022, this classic beachfront home was redesigned into a spacious, modern property. 21 Kalaka's unique elevation offers commanding views and privacy; feature...

  • 5 Beds
  • 5 Baths
  • 202613970 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 7 DOM
824 N Kalaheo Avenue Unit A, Kailua image
824 N Kalaheo Avenue Unit A, Kailua $2,750,000

Best Value in Beachside, Kailua priced under tax assessed value! Only seven homes away from the beach without the oceanfront premium. Set within the private 14-home Hale ...

  • 5 Beds
  • 5 Baths
  • 202613874 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 9 DOM
846 Mokulua Drive, Kailua image
846 Mokulua Drive, Kailua $7,880,000

Experience one-of-a-kind oceanfront living in the heart of Lanikai. Nestled along the shoreline in one of Hawai?i's most coveted neighborhoods, this private tropical retr...

  • 5 Beds
  • 4 Baths
  • 202613137 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 20 DOM
821 Kainui Drive, Kailua image
821 Kainui Drive, Kailua $2,625,000

Rare opportunity to own a canal front home on a nearly 10,000 sq. ft. R-5 zoned lot with a legal ‘ohana unit, each with its own utility meters, complete with pool & spa. ...

  • 5 Beds
  • 5 Baths
  • 202612304 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 20 DOM
664 Kihapai Street, Kailua image
664 Kihapai Street, Kailua $1,395,000

Spacious 6-bedroom, 3-bath home approximately 1968 sq. ft. of living area in a desirable Kailua neighborhood. This versatile home features a functional floor plan with 4 ...

  • 6 Beds
  • 3 Baths
  • 202604953 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 21 DOM
1237 Hele Street, Kailua image
1237 Hele Street, Kailua $1,805,000

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...

  • 6 Beds
  • 2 Baths
  • 202612433 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 21 DOM
802 Pahumele Place, Kailua image
802 Pahumele Place, Kailua $3,750,000

Set along the peaceful shoreline of a tranquil lake, this stunning five-bedroom, four-bathroom residence offers a lifestyle where every day starts and ends with views tha...

  • 5 Beds
  • 4 Baths
  • 202612388 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 26 DOM
528 Halela Street Unit A, Kailua image
528 Halela Street Unit A, Kailua $1,689,000

Experience the perfect blend of modern comfort and island living. Tucked away on a private flag lot, this five-bedroom, three-bathroom residence offers a rare combination...

  • 5 Beds
  • 3 Baths
  • 202612287 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 33 DOM
969 Auloa Road, Kailua image
969 Auloa Road, Kailua $4,250,000

Ideally positioned on a rare, level one-acre lot in the heart of Maunawili Valley, 969 Auloa honors a peaceful,Japanese-inspired roots. The estate has undergone a COMPREH...

  • 8 Beds
  • 8 Baths
  • 202608906 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 35 DOM
609 Olomana Street, Kailua image
609 Olomana Street, Kailua $1,880,000

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 ...

  • 8 Beds
  • 8 Baths
  • 202610511 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 54 DOM
1031 Lunaai Place, Kailua image
1031 Lunaai Place, Kailua $2,249,000 ▼

$200k PRICE REDUCTION! Now listed at $2,249,000! Move-in ready and ideal for multi-generational living, Maunawili’s 1031 Lunaai Place is a rare Kailua gem! Lovingly main...

  • 7 Beds
  • 5 Baths
  • 202610167 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 62 DOM
125 N Kalaheo Avenue, Kailua image
125 N Kalaheo Avenue, Kailua $4,925,000

The most extraordinary remodel transformation you’ll ever see! This stunning 7 bedroom, 6.5 bath residence spans over 6,000 square feet on a generous 14,125-square-foot l...

  • 7 Beds
  • 7 Baths
  • 202610108 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 66 DOM
244 Awakea Road, Kailua image
244 Awakea Road, Kailua $3,150,000 ▼

Rarely available in Kailua Estates, 244 Awakea Rd is a beautifully remodeled plantation-style property on a spacious 10,000 sq ft lot just a short stroll to Kailua Beach ...

  • 6 Beds
  • 4 Baths
  • 202608800 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 77 DOM
260 Kuukama Street, Kailua image
260 Kuukama Street, Kailua $2,599,000 ▼

One of Kailua's most sought-after neighborhoods. This lovely home comes with 5 bedrooms and 3 baths, a 3035 square foot home located on a cul-de-sac just a 10-minute, hal...

  • 5 Beds
  • 3 Baths
  • 202609140 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 80 DOM
1315 Kupau Street, Kailua image
1315 Kupau Street, Kailua $2,490,000 ▼

Motivated seller willing to review all offers!!! Welcome to Keolu Hills offering sweeping views of the Ko’olau Mountains! Meticulously maintained 6 bedrooms, 4 full baths...

  • 6 Beds
  • 4 Baths
  • 202608541 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 82 DOM
151 Alala Road, Kailua image
151 Alala Road, Kailua $2,700,000

Two blocks from turquoise water and best strip of sandy beach for miles, nestled between Kailua Beach and Lanikai, this classic Hawaiian style home offers the perfect bal...

  • 5 Beds
  • 3 Baths
  • 202606811 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 84 DOM
485 Wanaao Road, Kailua image
485 Wanaao Road, Kailua $4,098,000 ▼

Set along the coveted waterfront canal of Kailua, this iconic property 485 Wanaao, captures the essence of modern island living with rare versatility & timeless appeal. S...

  • 5 Beds
  • 4 Baths
  • 202608270 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 91 DOM
1614 Paukiki Street, Kailua image
1614 Paukiki Street, Kailua $1,798,000 ▼

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 n...

  • 5 Beds
  • 3 Baths
  • 202608144 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 94 DOM
1091 Alahaki Street, Kailua image
1091 Alahaki Street, Kailua $2,195,000 ▼

Recently reintroduced to the market, this spacious 5-bedroom, 3-bath single-family home sits on a large, level lot in the desirable Kailua neighborhood. Its thoughtful la...

  • 5 Beds
  • 3 Baths
  • 202607327 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 107 DOM
1439 Akuleana Place, Kailua image
1439 Akuleana Place, Kailua $2,188,000 ▼

This legal multi-family property spans 10,716 sq ft and features two spacious detached homes on a quiet cul-de-sac, offering a perfect setup for multi-generational living...

  • 6 Beds
  • 4 Baths
  • 202605300 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 133 DOM
451 Lanae Way, Kailua image
451 Lanae Way, Kailua $2,495,000

Elegant 5-year-old home offering exceptional investment potential and flexible multigenerational living. This spacious property features a two-level main home with an att...

  • 9 Beds
  • 4 Baths
  • 202605514 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 136 DOM
837 Oneawa Street, Kailua image
837 Oneawa Street, Kailua $1,649,000 ▼

Spacious 6-bedroom, 3-bath home located in the heart of Kailua. This versatile property offers a flexible layout that is ideal for extended family and multi-generational ...

  • 6 Beds
  • 3 Baths
  • 202605034 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 139 DOM
1251 Kainui Drive, Kailua image
1251 Kainui Drive, Kailua $4,350,000

Discover the perfect blend of lifestyle, comfort, and value at 1251 Kainui Drive—an exceptional canal-front retreat situated along an established, palm tree-lined street ...

  • 6 Beds
  • 4 Baths
  • 202525771 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 145 DOM
1240 Mokulua Drive, Kailua image
1240 Mokulua Drive, Kailua $31,000,000

The Mokulua Estate is a breathtaking oceanfront sanctuary set within the prestigious Lanikai neighborhood. This exceptional property offers unobstructed views of the Moku...

  • 9 Beds
  • 10 Baths
  • 202600075 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 194 DOM
676 Mokapu Road, Kailua image
676 Mokapu Road, Kailua $3,100,000 ▼

BEAUTIFUL FLEX HOME! Prestigious Kaimalino Neighborhood! This spacious 5 bedroom, 4 bathroom home offers versatile living options with possible seperate entrances, 3 bed...

  • 5 Beds
  • 4 Baths
  • 202522041 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 286 DOM
572C N Kalaheo Avenue, Kailua image
572C N Kalaheo Avenue, Kailua $18,880,000

Welcome to this exceptional Kailua beachfront estate. This gated resort-like retreat is situated on nearly an acre of land fronting one of the most beautiful beaches in ...

  • 12 Beds
  • 16 Baths
  • 202520168 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 318 DOM
1233 Keolu Drive, Kailua image
1233 Keolu Drive, Kailua $1,450,000 ▼

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 ...

  • 5 Beds
  • 3 Baths
  • 202519336 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 327 DOM
508 N Kalaheo Avenue, Kailua image
508 N Kalaheo Avenue, Kailua $50,000,000

Unparalleled, the Mele Komo Beachfront Estate located on the pristine shores of Kailua Beach, offers the most discerning connoisseur the ultimate in coastal living. With ...

  • 12 Beds
  • 15 Baths
  • 202327941 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 955 DOM

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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Kailua Neighborhoods

  • Aikahi Park
  • Kalama Tract
  • Kalaheo Hillside
  • Kaimalino
  • Kailua Estates
  • Kailua Bluffs
  • Kailua Town
  • Enchanted Lake
  • Coconut Grove
  • Bluestone
  • Beachside Kailua
  • Kawailoa Kailua
  • Keolu Hills
  • Koolaupoko
  • Kukilakila
  • Kuulei Tract
  • Lanikai
  • Maunawili
  • Olomana
  • Zip code: 96734

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Elizabeth La Riva is a real estate team affiliated with Compass. Compass is a licensed real estate broker with a principal office in Oahu, Hawaii, and abides by all applicable equal housing opportunity laws. All material presented herein is intended for informational purposes only. Information is compiled from sources deemed reliable but is subject to errors, omissions, changes in price, condition, sale, or withdrawal without notice. No statement is made as to accuracy of any description. All measurements and square footages are approximate. This is not intended to solicit property already listed. Nothing herein shall be construed as legal, accounting or other professional advice outside the realm of real estate brokerage.

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