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Newest Kailua Estates Homes For Sale

350 Aoloa Street Unit A112, Kailua image
350 Aoloa Street Unit A112, Kailua — Koolau Vista $475,000

Embrace laid-back beach town living right in the heart of Kailua Town! This rare, affordable one-bedroom, one-bathroom condo offers incredible value in one of O‘ahu’s mos...

  • 1 Beds
  • 1 Baths
  • 202619614 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Koolau Vista Bldg.
  • 3 DOM
409 Kailua Road Unit 7101, Kailua image
409 Kailua Road Unit 7101, Kailua — Ka Malanai At Kailua $995,000

PRICED BELOW TAX ASSESSED VALUE! An incredible opportunity to own in Ka Malanai, where the convenience of Kailua living meets the comfort of a beautifully maintained home...

  • 2 Beds
  • 2 Baths
  • 202619687 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Ka Malanai At Kailua Bldg.
  • 4 DOM
455 Kailua Road Unit 4204, Kailua image
455 Kailua Road Unit 4204, Kailua — Ka Malanai At Kailua $738,888

Experience the ultimate in Kailua living! Nestled in a highly desirable, vibrant neighborhood, this pet-friendly complex places you moments away from world-class beaches,...

  • 1 Beds
  • 1 Baths
  • 202619088 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Ka Malanai At Kailua Bldg.
  • 7 DOM
322 Aoloa Street Unit 309, Kailua image
322 Aoloa Street Unit 309, Kailua — Windward Passage $619,000

Enjoy island living in this beautifully situated 2-bedroom, 2-bath condo in the heart of Kailua. Offering 956 sq ft of interior space plus a generous 92 sq ft lanai, this...

  • 2 Beds
  • 2 Baths
  • 202619380 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Windward Passage Bldg.
  • 7 DOM
225 Awakea Road, Kailua image
225 Awakea Road, Kailua $2,295,000

Classic Kailua charm meets modern comfort in this beautifully updated 4-bedroom, 2.5-bath home offering 2,520 square feet of living space, just a short stroll from Kailua...

  • 4 Beds
  • 3 Baths
  • 202619050 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 17 DOM
471 Kailua Road Unit 3202, Kailua image
471 Kailua Road Unit 3202, Kailua — Ka Malanai At Kailua $1,150,000

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 Kail...

  • 3 Beds
  • 2 Baths
  • 202618877 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • Ka Malanai At Kailua Bldg.
  • 19 DOM
322 Aoloa Street Unit 1706, Kailua image
322 Aoloa Street Unit 1706, Kailua — Windward Passage $595,000

Stunning views and the best of Kailua living await at Windward Passage! This inviting one-bedroom condo on the 17th floor features floor-to-ceiling windows spanning the m...

  • 1 Beds
  • 1 Baths
  • 202617742 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Windward Passage Bldg.
  • 35 DOM
322 Aoloa Street Unit 1601, Kailua image
322 Aoloa Street Unit 1601, Kailua — Windward Passage $1,385,000

Rarely available 16th floor 01 stack at Windward Passage, just two floors from the top offering spectacular ocean, mountain and sunrise views from nearly every room! Ori...

  • 3 Beds
  • 2 Baths
  • 202617370 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Windward Passage Bldg.
  • 40 DOM
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 UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • Gardenia Manor Bldg.
  • 52 DOM
1030 Aoloa Place Unit 5105B, Kailua image
1030 Aoloa Place Unit 5105B, Kailua — Windward Harbour $825,000

SELLER OFFERING A $15,000 BUYER CREDIT! PUBLIC OPEN HOUSE SUNDAY 10-25 2PM-5PM Experience the best of island living at Windward Harbour in the heart of Kailua. Perfect...

  • 3 Beds
  • 2 Baths
  • 202616227 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Windward Harbour Bldg.
  • 53 DOM
1030 Aoloa Place Unit 212B, Kailua image
1030 Aoloa Place Unit 212B, Kailua — Windward Harbour $730,000 ▼

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.
  • 56 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.
  • 61 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.
  • 61 DOM
322 Aoloa Street Unit 611, Kailua image
322 Aoloa Street Unit 611, Kailua — Windward Passage $835,000 ▼

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.
  • 66 DOM
350 Aoloa Street Unit C224, Kailua image
350 Aoloa Street Unit C224, Kailua — Koolau Vista $550,000 ▼

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 UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • Koolau Vista Bldg.
  • 74 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.
  • 77 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.
  • 91 DOM
1015 Aoloa Place Unit 340, Kailua image
1015 Aoloa Place Unit 340, Kailua — Poinciana Manor $660,000 ▼

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.
  • 95 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.
  • 103 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.
  • 123 DOM
409 Wanaao Road, Kailua image
409 Wanaao Road, Kailua $2,295,000 ▼

Now offered below tax assessed value — your opportunity to own in Kailua just got better! Our seller has made new improvements to make this home shine! Experience the bes...

  • 4 Beds
  • 4 Baths
  • 202612015 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 128 DOM
1015 Aoloa Place Unit 335, Kailua image
1015 Aoloa Place Unit 335, Kailua — Poinciana Manor $659,000 ▼

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.
  • 129 DOM
322 Aoloa Street Unit 1708, Kailua image
322 Aoloa Street Unit 1708, Kailua — Windward Passage $629,000 ▼

$10,000 CREDIT OFFERED TO BUYER TOWARDS CLOSING COSTS! Spectacular high-floor one-bedroom with breathtaking views of Enchanted Lake, the Ko'olau Mountains & Kailua Town. ...

  • 1 Beds
  • 1 Baths
  • 202611276 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Windward Passage Bldg.
  • 130 DOM
322 Aoloa Street Unit 306, Kailua image
322 Aoloa Street Unit 306, Kailua — Windward Passage $349,700 ▼

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.
  • 138 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 UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 168 DOM
409 Kailua Road Unit 7106, Kailua image
409 Kailua Road Unit 7106, Kailua — Ka Malanai At Kailua $1,100,000 ▲

**10/24 & 10/25 OPEN HOUSES CANCELLED** Experience the convenience and charm of life in the heart of Kailua with a rare feature that sets this home apart: THREE assigned ...

  • 2 Beds
  • 2 Baths
  • 202600852 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Ka Malanai At Kailua Bldg.
  • 236 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 UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • Poinciana Manor Bldg.
  • 290 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.
  • 301 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
  • 343 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.
  • 509 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 Neighborhoods

  • Aikahi Park
  • Kalama Tract
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  • Kailua Estates
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  • Kailua Town
  • Enchanted Lake
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  • Bluestone
  • Beachside Kailua
  • Kawailoa Kailua
  • Keolu Hills
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  • 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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