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Search Kailua 5 Bedroom Homes

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Newest Kailua, HI 5 Bedroom Homes For Sale

151 Alala Road, Kailua image
151 Alala Road, Kailua $2,625,000

Welcome to this single-level, classic Hawaii-style home, steps from the best stretch of sandy beach for miles, nestled between Kailua and Lanikai. See the ocean from the ...

  • 5 Beds
  • 3 Baths
  • 202616563 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 7 DOM
248 Pauahilani Place, Kailua image
248 Pauahilani Place, Kailua $3,085,000 ▼

Opportunities to own in Country Club Knolls don’t come around often, and this stunning 5-bedroom, 4-bathroom residence shows exactly why this neighborhood is so highly co...

  • 5 Beds
  • 4 Baths
  • 202615511 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 23 DOM
1247 Ulupalakua Street, Kailua image
1247 Ulupalakua Street, Kailua $1,700,000 ▼

Seriously spacious rare single-story multigenerational home in Kailua’s Pohakupu community offering 6 bedrooms, 5 bathrooms, and a flexible floor plan with plenty of room...

  • 6 Beds
  • 5 Baths
  • 202614426 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 29 DOM
1225 Ulupii Street, Kailua image
1225 Ulupii Street, Kailua $1,600,000

Rarely available, massive Kailua opportunity! This highly versatile property boasts an impressive 9 bedrooms and 4 bathrooms, featuring 2,823 sq ft of interior living spa...

  • 9 Beds
  • 4 Baths
  • 202615061 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 36 DOM
1458 Uluhala Place, Kailua image
1458 Uluhala Place, Kailua $1,795,000

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...

  • 5 Beds
  • 3 Baths
  • 202614738 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 38 DOM
970 Apokula Place, Kailua image
970 Apokula Place, Kailua $1,680,000 ▼

Total Price reduction of $300,000! Rare opportunity to own a massive 31,000+ square foot oasis in one of Kailua's most desirable neighborhoods, Keolu Hills. Tucked away o...

  • 5 Beds
  • 3 Baths
  • 202610133 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 42 DOM
314 Lapa Place, Kailua image
314 Lapa Place, Kailua $4,250,000

Nestled on a hillside cul-de-sac in the quiet end of Lanikai, this move-in ready, architect-designed, custom-built home offers a perfect blend of luxury & tranquility. A ...

  • 5 Beds
  • 6 Baths
  • 202614376 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 45 DOM
646 Wanaao Road, Kailua image
646 Wanaao Road, Kailua $1,990,000 ▼

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

  • 7 Beds
  • 5 Baths
  • 202614077 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 48 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
  • 54 DOM
846 Mokulua Drive, Kailua image
846 Mokulua Drive, Kailua $7,855,000 ▼

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
  • 65 DOM
821 Kainui Drive, Kailua image
821 Kainui Drive, Kailua $2,500,000 ▼

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
  • 65 DOM
1237 Hele Street, Kailua image
1237 Hele Street, Kailua $1,775,000 ▼

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
  • 66 DOM
802 Pahumele Place, Kailua image
802 Pahumele Place, Kailua $3,550,000 ▼

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
  • 71 DOM
969 Auloa Road, Kailua image
969 Auloa Road, Kailua $4,250,000

MAUNAWILI AT ITS FINEST! One Acre+ lot in the heart of the Valley. Overlooking your very own Kailua estate and the horses of Maunawili Farms. Having just undergone a COM...

  • 8 Beds
  • 8 Baths
  • 202608906 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 80 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
  • 99 DOM
6 N Kalaheo Avenue, Kailua image
6 N Kalaheo Avenue, Kailua $4,349,000

Experience multi generational luxury living,just moments from famous white sand Kailua Beach with shopping and dining close by.Situated on a landscaped 11,005 sq. ft. lev...

  • 6 Beds
  • 5 Baths
  • 202610270 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 100 DOM
1031 Lunaai Place, Kailua image
1031 Lunaai Place, Kailua $2,199,000 ▼

$50k PRICE REDUCTION! Now listed at $2,199,000! Move-in ready and ideal for multi-generational living, Maunawili’s 1031 Lunaai Place is a rare Kailua gem! Lovingly maint...

  • 7 Beds
  • 5 Baths
  • 202610167 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 107 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
  • 111 DOM
244 Awakea Road, Kailua image
244 Awakea Road, Kailua $3,045,000 ▼

MAJOR PRICE REDUCTION! Exceptional opportunity in a preferred location within Kailua Estates. 244 Awakea Rd is a beautifully remodeled plantation-style property on a spac...

  • 6 Beds
  • 3 Baths
  • 202608800 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 122 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
  • 125 DOM
1614 Paukiki Street, Kailua image
1614 Paukiki Street, Kailua $1,728,000 ▼

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
  • 139 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
  • 152 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
  • 178 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
  • 181 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
  • 190 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
  • 239 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
  • 363 DOM
1233 Keolu Drive, Kailua image
1233 Keolu Drive, Kailua $1,440,000 ▼

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
  • 372 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
  • 1000 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 Home Types

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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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