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Newest Kailua Estates Homes For Sale

333 Aoloa Street Unit 318, Kailua image
333 Aoloa Street Unit 318, Kailua — Gardenia Manor $855,000

Both welcoming and thoughtfully designed this generously sized, two-story condo offers incredible indoor / outdoor living spaces, a vaulted ceiling fills the room with na...

  • 3 Beds
  • 3 Baths
  • 202613359 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Gardenia Manor Bldg.
  • 6 DOM
1030 Aoloa Place Unit 5105B, Kailua image
1030 Aoloa Place Unit 5105B, Kailua — Windward Harbour $825,000

Experience the best of island living at Windward Harbour in the heart of Kailua. Perfectly located within walking distance from shopping, restaurants, farmers markets, a...

  • 3 Beds
  • 2 Baths
  • 202616227 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Windward Harbour Bldg.
  • 7 DOM
1030 Aoloa Place Unit 212B, Kailua image
1030 Aoloa Place Unit 212B, Kailua — Windward Harbour $755,000

Welcome to Windward Harbour, a gated tropical oasis in the heart of beautiful Kailua! This spacious 3-bedroom, 2-bath condo offers the perfect opportunity to create your ...

  • 3 Beds
  • 2 Baths
  • 202616240 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Windward Harbour Bldg.
  • 10 DOM
119 Kahako Street Unit B, Kailua image
119 Kahako Street Unit B, Kailua — Kaopa Park Place $875,000

Kaopa Park Place is a quaint, established townhome community in Kailua, offering more of a charming neighborhood feel than a typical condominium complex. Surrounded by lu...

  • 3 Beds
  • 2 Baths
  • 202616392 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Kaopa Park Place Bldg.
  • 15 DOM
119 Kahako Street Unit B, Kailua image
119 Kahako Street Unit B, Kailua — Kaopa Park Place $875,000

Kaopa Park Place is a quaint, established townhome community in Kailua, offering more of a charming neighborhood feel than a typical condominium complex. Surrounded by lu...

  • 3 Beds
  • 2 Baths
  • 202616409 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Kaopa Park Place Bldg.
  • 15 DOM
1030 Aoloa Place Unit 412A, Kailua image
1030 Aoloa Place Unit 412A, Kailua — Windward Harbour $729,000

Live above the treeline in the heart of Kailua. This top-floor corner residence at Windward Harbour pairs sweeping Ko?olau Mountain views with an exceptional indoor-outdo...

  • 1 Beds
  • 1 Baths
  • 202616213 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • Windward Harbour Bldg.
  • 15 DOM
322 Aoloa Street Unit 611, Kailua image
322 Aoloa Street Unit 611, Kailua — Windward Passage $859,000

Completely renovated from top to bottom! Freshly painted throughout! No popcorn ceilings! New vinyl flooring throughout. New tile on the lanai. New kitchen cabinets, appl...

  • 3 Beds
  • 2 Baths
  • 202614735 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Windward Passage Bldg.
  • 20 DOM
1020 Aoloa Place Unit 404A, Kailua image
1020 Aoloa Place Unit 404A, Kailua — Windward Cove $895,000

Welcome to this beautifully renovated 3 bedroom/2 bath residence at Windward Cove, a gated community in the heart of Kailua that’s surrounded by koi ponds, lush landscapi...

  • 3 Beds
  • 2 Baths
  • 202615666 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • Windward Cove Bldg.
  • 24 DOM
350 Aoloa Street Unit C224, Kailua image
350 Aoloa Street Unit C224, Kailua — Koolau Vista $570,000

Welcome home to this adorable 2-bedroom, 1.5-bath condo offering the perfect blend of comfort and convenience in desirable Kailua. The thoughtfully designed first floor f...

  • 2 Beds
  • 2 Baths
  • 202612915 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Koolau Vista Bldg.
  • 28 DOM
1015 Aoloa Place Unit 437, Kailua image
1015 Aoloa Place Unit 437, Kailua — Poinciana Manor $550,000

Best value in Poinciana Manor! Bright and breezy top-floor end unit featuring peaceful garden views, cathedral ceiling, and two private lanais. This unit includes two cov...

  • 2 Beds
  • 2 Baths
  • 202615437 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Poinciana Manor Bldg.
  • 31 DOM
1622 Paukiki Street, Kailua image
1622 Paukiki Street, Kailua $1,729,000

Beautifully appointed 4-bedroom, 3.5-bath home offering spacious living, stunning mountain views, and an ideal indoor-outdoor Hawaii lifestyle. The thoughtfully designed ...

  • 4 Beds
  • 4 Baths
  • 202615230 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 31 DOM
1015 Aoloa Place Unit 247, Kailua image
1015 Aoloa Place Unit 247, Kailua — Poinciana Manor $690,000

Experience the best of Kailua living! This beautifully updated 959 sq ft unit offers a modern kitchen with updated cabinets & countertops, updated bathroom vanities, and ...

  • 2 Beds
  • 2 Baths
  • 202614286 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Poinciana Manor Bldg.
  • 45 DOM
322 Aoloa Street Unit PH8, Kailua image
322 Aoloa Street Unit PH8, Kailua — Windward Passage $645,000

Rarely available prestigious penthouse unit at the top of Windward Passage! Floor to ceiling windows open to a panoramic view out over Enchanted Lake & down the majestic...

  • 1 Beds
  • 1 Baths
  • 202614387 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Windward Passage Bldg.
  • 45 DOM
1015 Aoloa Place Unit 340, Kailua image
1015 Aoloa Place Unit 340, Kailua — Poinciana Manor $689,999 ▼

Welcome home to easy Kailua living at Poinciana Manor. This inviting 2-bedroom, 2-bath condo features LVP and tile flooring, an in-unit washer and dryer, additional stora...

  • 2 Beds
  • 2 Baths
  • 202613910 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Poinciana Manor Bldg.
  • 49 DOM
1015 Aoloa Place Unit 451, Kailua image
1015 Aoloa Place Unit 451, Kailua — Poinciana Manor $699,999 ▼

Finally, a top floor unit at Poinciana Manor with a fully renovated, open concept kitchen and living room. No neighbor above, and a ceiling that clears 20 feet at the pea...

  • 2 Beds
  • 2 Baths
  • 202611451 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Poinciana Manor Bldg.
  • 52 DOM
445 Kailua Road Unit 5304, Kailua image
445 Kailua Road Unit 5304, Kailua — Ka Malanai At Kailua $759,000

Tucked away in one of the most peaceful locations within Ka Malanai, this desirable one-bedroom residence enjoys a quiet back corner, top floor setting surrounded by lush...

  • 1 Beds
  • 1 Baths
  • 202613740 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • Ka Malanai At Kailua Bldg.
  • 52 DOM
322 Aoloa Street Unit 810, Kailua image
322 Aoloa Street Unit 810, Kailua — Windward Passage $660,000

Welcome to Windward Passage unit #810. This one-bedroom, one bathroom, and one assigned parking stall unit was just renovated with no expense spared. Every small detail w...

  • 1 Beds
  • 1 Baths
  • 202613708 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Windward Passage Bldg.
  • 57 DOM
1030 Aoloa Place Unit 2/302B, Kailua image
1030 Aoloa Place Unit 2/302B, Kailua — Windward Harbour $925,000

Wake up to breathtaking mountain views and end your day on your own private rooftop lanai. This rare, 3-bedroom 2-bathroom gem at Windward Harbor blends modern Kailua ele...

  • 3 Beds
  • 2 Baths
  • 202608120 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • Windward Harbour Bldg.
  • 102 DOM
361 Kailua Road Unit 8108, Kailua image
361 Kailua Road Unit 8108, Kailua — Ka Malanai At Kailua $1,150,000

Experience the best of Kailua living at "Ka Malanai in Kailua", one of the Windward side's newest condo communities. This 2-bedroom, 2-bath residence puts you in the hear...

  • 2 Beds
  • 2 Baths
  • 202611496 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Ka Malanai At Kailua Bldg.
  • 70 DOM
1020 Aoloa Place Unit 311B, Kailua image
1020 Aoloa Place Unit 311B, Kailua — Windward Cove $800,000

Welcome to Windward Cove—a gated community in the heart of Kailua, surrounded by 3 acres of lush tropical landscaping, koi ponds, and peaceful water features. This privat...

  • 3 Beds
  • 2 Baths
  • 202612305 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Windward Cove Bldg.
  • 77 DOM
409 Wanaao Road, Kailua image
409 Wanaao Road, Kailua $2,325,000 ▼

Back on the market and now offered at $174,000 below original list price — your opportunity to own in Kailua just got better! Our seller has made new improvements to make...

  • 4 Beds
  • 4 Baths
  • 202612015 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 82 DOM
1015 Aoloa Place Unit 335, Kailua image
1015 Aoloa Place Unit 335, Kailua — Poinciana Manor $674,000 ▼

New Price & Now Available with a 3.125% VA Assumable Interest Rate! – Enjoy the opportunity to make this 2-bedroom, 2-bath condo in Poinciana Manor your own! The perfect ...

  • 2 Beds
  • 2 Baths
  • 202611825 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Poinciana Manor Bldg.
  • 83 DOM
322 Aoloa Street Unit 1708, Kailua image
322 Aoloa Street Unit 1708, Kailua — Windward Passage $640,000 ▲

Rare high-floor one-bedroom unit with breathtaking views of Enchanted Lake, the Ko'olau Mountains and Kailua Town. Remodeled in 2025 with vinyl luxury flooring throughou...

  • 1 Beds
  • 1 Baths
  • 202611276 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Windward Passage Bldg.
  • 84 DOM
322 Aoloa Street Unit 306, Kailua image
322 Aoloa Street Unit 306, Kailua — Windward Passage $374,000 ▼

Welcome to Windward Passage, one of Kailua’s most established and desirable condominium residences, ideally positioned in the heart of Kailua Town. This exceptional addre...

  • 1 Beds
  • 1 Baths
  • 202611325 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Windward Passage Bldg.
  • 92 DOM
294 Awakea Road, Kailua image
294 Awakea Road, Kailua $2,650,000

Escape to the tranquility of your private sanctuary, conveniently located within a ten-minute walk from the renowned Kailua Beach. This exquisite residence was meticulous...

  • 3 Beds
  • 3 Baths
  • 202609988 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 107 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
355 Aoloa Street Unit G205, Kailua image
355 Aoloa Street Unit G205, Kailua — Hokulani In Kailua $700,000

Wonderful 2 Bedroom 2 Bath at Hokulani in Kailua! Covered Parking Space and ample guest parking! High, vaulted ceilings, laminate floors, and a bright kitchen with Cor...

  • 2 Beds
  • 2 Baths
  • 202609173 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • Hokulani In Kailua Bldg.
  • 124 DOM
350 Aoloa Street Unit C214, Kailua image
350 Aoloa Street Unit C214, Kailua — Koolau Vista $569,000 ▼

Koolau Vista - Move In Ready! Priced to sell! Great for First Time Buyer or Investor! Live in the Heart of Kailua Town! Minutes to Shopping, Dining, Beaches. Two Bedro...

  • 2 Beds
  • 2 Baths
  • 202608729 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Koolau Vista Bldg.
  • 133 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
1479 Kanapuu Drive, Kailua image
1479 Kanapuu Drive, Kailua $1,430,000 ▼

Welcome home to this wonderful two story home that features 3 bedrooms and 2 1/2 bathrooms located in the highly desirable Kailua Bluffs neighborhood. Home features an op...

  • 3 Beds
  • 3 Baths
  • 202607772 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 141 DOM
437 Kailua Road Unit 6102, Kailua image
437 Kailua Road Unit 6102, Kailua — Ka Malanai At Kailua $1,029,000 ▼

MAJOR PRICE IMPROVEMENT! Here's your opportunity to secure a below-market VA loan at 2.25%! And the best part? It's open to both VA & non-VA buyers*!!! Approximate loan b...

  • 2 Beds
  • 2 Baths
  • 202606264 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Ka Malanai At Kailua Bldg.
  • 143 DOM
409 Kailua Road Unit 7106, Kailua image
409 Kailua Road Unit 7106, Kailua — Ka Malanai At Kailua $1,075,000

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,...

  • 2 Beds
  • 2 Baths
  • 202600852 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Ka Malanai At Kailua Bldg.
  • 190 DOM
1015 Aoloa Place Unit 217, Kailua image
1015 Aoloa Place Unit 217, Kailua — Poinciana Manor $695,000 ▼

Discover island living in this beautifully maintained 2 bdrm/2 bath condo at desirable Poinciana Manor in Kailua. Offering 959 sq ft of interior living space, this reside...

  • 2 Beds
  • 2 Baths
  • 202600370 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Poinciana Manor Bldg.
  • 244 DOM
322 Aoloa Street Unit 709, Kailua image
322 Aoloa Street Unit 709, Kailua — Windward Passage $699,000

On the makai side of the bldg with a coastline view. Unit fire sprinklers & bldg plumbing update has been completed. Both baths have walk-in showers. Updated kitchen ap...

  • 2 Beds
  • 2 Baths
  • 202528439 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Windward Passage Bldg.
  • 255 DOM
1459 Akamai Street, Kailua image
1459 Akamai Street, Kailua $1,488,000

Tucked away in one of Kailua's most sought-after neighborhoods, this spacious 4-bedroom, 3-bathroom home presents a wonderful opportunity to create your dream home. This...

  • 4 Beds
  • 3 Baths
  • 202525520 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 297 DOM
322 Aoloa Street Unit 208, Kailua image
322 Aoloa Street Unit 208, Kailua — Windward Passage $469,999 ▼

Short sale lender has already done their Broker Price Opinion. Just need your offer. Welcome to Windward Passage in the heart of Kailua! This spacious 1-bedroom, 1-bath...

  • 1 Beds
  • 1 Baths
  • 202513528 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Windward Passage Bldg.
  • 463 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 Estates is home to gorgeous, vintage houses from the 1940s and 1950s, still standing in pristine condition on generous plots of land. What started as a small beachside town is now home to some of the finest, private real estate in Oahu.

The homes for sale in Kailua include a mix of plantation-style homes, vintage beach cottages, and large luxury homes, all surrounded by gently swaying palm trees, minutes from the Kailua Beach. All the residents in Kailua Estates are within walking distance from the beautiful white sand beaches and turquoise waters of Kailua Bay.

These grand estates sit on spacious lots, most of them are between 10,000-12,000 square feet with a few over 20,000 square feet. The large lots make for perfectly private living quarters, giving residents a real sense of country living while being able to take in the sites and sounds of the nearby beach.

Real estate in Kailua Estates typically costs between $1.5 million and $3 million. The homes for sale feature large, open floor plans, grand balconies and terraces, separate guest housing, and many more incredible features that allow the residents to live in the lap of luxury.

View All Homes For Sale in Kailua, HI >>>

Living In Kailua Estates, Honolulu

With many of the homes for sale in Kailua Estates being conveniently located within walking distance to the Kailua Beach, it’s easy to see why these homes get snatched up quickly. Kailua Beach is 2.5 miles of gorgeous white sand. The bottom of the ocean gently slopes down off of the coastline with little to no coral heads to get in the way, making this beach a fantastic swimming destination. The light to medium waves are ideal for aspiring surfers and Kailua Beach is known to be the top windsurfing and kitesurfing destination on the island.

Locals can explore the exciting Kailua Farmers Market. This fabulous market is filled to the brim with local produce and goods, crafting booths, and, best of all, delicious food stalls featuring barbecue, authentic Hawaiian and Japanese cuisine, homemade pizzas, pastries, and more. The Kailua Farmers Market also features live, local music, setting the ambience for the perusers and those who stay for a bite to eat.

For the adventurous sort, the Lanikai Pillbox Hike, also known as Ka’iwa Ridge Trai,l is located just a few minutes to the southeast of the Kailua neighborhood. This trail has consistently been dubbed the best hike in Oahu. The trail starts out with a steep climb and is ranked as an intermediate-level hike, but eventually the slope falls to a more gradual climb. The views alone are enough to make this one of the best trails on the island. The more you climb, the more spectacular the sites out over the surrounding beaches, bays, mountains, and endless stretch of ocean water. At the top of the ridge are two concrete bunkers (pillboxes) that were used during WWI and WWII as part of Oahu’s coastal defense system.

View All Homes For Sale in Honolulu, HI >>>

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Kailua Home Types

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Kailua Homes For Sale By Price

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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
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  • 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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