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Browse All Kailua HI Historical Properties for Sale

743 Akumu Street, Kailua $1,799,000 ▼

New price! Motivated seller! Great location! Don't miss this incredible opportunity to own a charming newly Completely renovated 3-bedroom, 2.5-bathroom home plus an work...

3 Beds
3 Baths
202614109 MLS
FS - Fee Simple Tenure
93 DOM
ACTIVE Status

970 Apokula Place, Kailua $1,550,000 ▼

Unbelievable value: $400K below March 2024 appraisal! Rare opportunity to own a massive 31,000+ square foot oasis in one of Kailua's most desirable neighborhoods, Keolu H...

5 Beds
3 Baths
202610133 MLS
FS - Fee Simple Tenure
97 DOM
ACTIVE Status

75 Kihapai Street Unit 5, Kailua — 75 Kihapai $399,500

Welcome home! Conveniently located one bedroom, one bath condo walking distance to Kailua town's shops and restaurants, and a few minutes bike ride or drive to beautiful ...

1 Beds
1 Baths
202614348 MLS
FS - Fee Simple Tenure
75 Kihapai Bldg.
100 DOM
ACTIVE Status

621 Palawiki Street, Kailua $1,460,000 ▼

Rare Opportunity! $100,000 price improvement creates outstanding value for buyers in Kailua! Enjoy effortless island living in desirable Enchanted Lake. This refreshed s...

3 Beds
2 Baths
202614243 MLS
FS - Fee Simple Tenure
99 DOM
ACTIVE UNDER CONTRACT Status

1225 Mokapu Boulevard, Kailua $1,580,000 ▼

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 o...

4 Beds
3 Baths
202614340 MLS
FS - Fee Simple Tenure
102 DOM
ACTIVE Status

650 Oneawa Street Unit A, Kailua $1,359,500 ▼

Experience refined island living in this beautifully remodeled 3-bedroom, 2-bath residence, ideally located in the heart of Kailua. Just moments from Kailua Beach, Kailua...

3 Beds
2 Baths
202614171 MLS
FS - Fee Simple Tenure
103 DOM
ACTIVE Status

725 Kihapai Place Unit B1, Kailua — 725 Kihapai Pl $459,000 ▼

Seller relisted with HUGE Price Reduction! Don't miss this rare opportunity to own a charming 2-bedroom, 1-bath ground floor corner unit in Kailua's highly desirable Coco...

2 Beds
1 Baths
202614153 MLS
FS - Fee Simple Tenure
725 Kihapai Pl Bldg.
104 DOM
ACTIVE Status

433 Kaimake Loop Unit A, Kailua $1,295,000 ▼

Priced Below Tax Assessed Value! Lowest-Priced Home in Ko'olaupoko under 1.3Mil! SELLER SAYS, "SELL!" Don't miss this incredible opportunity to own a home on a quiet, pri...

4 Beds
3 Baths
202613595 MLS
FS - Fee Simple Tenure
110 DOM
ACTIVE Status

1127 Lauloa Street, Kailua $2,050,000

Gorgeous, rare and turnkey single-level home in the desirable Enchanted Lake neighborhood of Kailua. The open-concept floor plan is complemented by split A/C throughout, ...

4 Beds
2 Baths
202613001 MLS
FS - Fee Simple Tenure
110 DOM
ACTIVE Status

319 Kihapai Street Unit C, Kailua $1,350,000

Wake up to stunning, unobstructed views of the majestic Olomana mountain range from this property brimming with potential. This home presents a rare opportunity to renova...

4 Beds
2 Baths
202609502 MLS
FS - Fee Simple Tenure
118 DOM
ACTIVE UNDER CONTRACT Status

1237 Hele Street, Kailua $1,695,000 ▼

Discover your own private tropical oasis in the highly desirable Keolu Hills neighborhood. This beautifully updated 6-bedroom, 2-bath home offers exceptional versatility,...

6 Beds
2 Baths
202612433 MLS
FS - Fee Simple Tenure
121 DOM
ACTIVE Status

344 Lama Place, Kailua $6,650,000

Experience breathtaking Mokulua Islands views from every corner of this Lanikai hillside home. The home offers head-on, unobstructed views of the Mokes, with the sea & co...

4 Beds
4 Baths
202612902 MLS
FS - Fee Simple Tenure
124 DOM
ACTIVE Status

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
FS - Fee Simple Tenure
126 DOM
ACTIVE UNDER CONTRACT Status

633 Keolu Drive, Kailua $1,495,000 ▼

Enjoy the best of Kailua living in this beautifully updated 4-bedroom, 2-bath home, conveniently located just minutes from the heart of town. Renovated in 2021, the kitch...

4 Beds
2 Baths
202612259 MLS
FS - Fee Simple Tenure
132 DOM
ACTIVE Status

1414 Mokulua Drive, Kailua $7,495,000 ▼

Set on the oceanfront along the coveted Mokulua Drive in Lanikai, this timeless island retreat captures the charm and spirit of old Hawai‘i. Nestled at the peaceful end o...

4 Beds
4 Baths
202611655 MLS
FS - Fee Simple Tenure
134 DOM
ACTIVE UNDER CONTRACT Status

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
FS - Fee Simple Tenure
135 DOM
ACTIVE Status

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
FS - Fee Simple Tenure
137 DOM
ACTIVE Status

45 Hoolai Street, Kailua $2,800,000

Rare opportunity to be the owner of a fee-simple, business zoned property in desirable Kailua. Centrally located in the heart of Kailua Town, with lots of foot traffic an...

202610761 MLS
FS - Fee Simple Tenure
154 DOM
ACTIVE Status

140C N Kalaheo Avenue, Kailua — Kamaaina Beach $5,280,000 ▲

KAILUA BEACH is Absolutely one of the most BREATHTAKING beachfront neighborhoods on Oahu and this property doesn't disappoint! Nestled among the palm trees with direct b...

3 Beds
2 Baths
202610235 MLS
FS - Fee Simple Tenure
Kamaaina Beach Bldg.
161 DOM
ACTIVE Status

1031 Lunaai Place, Kailua $1,989,000 ▼

Now adjusted to a remarkable $1,989,000, this is officially the lowest-priced single-family home on the Windward Side with a private pool—an extraordinary value in Kailua...

7 Beds
5 Baths
202610167 MLS
FS - Fee Simple Tenure
162 DOM
ACTIVE UNDER CONTRACT Status

244 Awakea Road, Kailua $3,045,000 ▼

MAJOR PRICE REDUCTION! Exceptional opportunity in a desirable location within Kailua Estates! 244 Awakea Road is a beautifully remodeled plantation style property situat...

6 Beds
3 Baths
202608800 MLS
FS - Fee Simple Tenure
177 DOM
ACTIVE UNDER CONTRACT Status

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
FS - Fee Simple Tenure
180 DOM
ACTIVE UNDER CONTRACT Status

75 Kihapai Street Unit 3, Kailua — 75 Kihapai $412,500 ▼

Recently renovated, this one-bedroom single level unit on the ground floor features a covered lanai that is gated for privacy and includes one designated parking spot. In...

1 Beds
1 Baths
202606606 MLS
FS - Fee Simple Tenure
75 Kihapai Bldg.
217 DOM
ACTIVE Status

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
FS - Fee Simple Tenure
245 DOM
PENDING Status

223 Lanipo Drive, Kailua $4,150,000 ▼

Don't miss the best value in Lanikai! Experience elevated island living in this fully renovated Lanikai retreat where luxury, privacy, and the natural beauty of Hawaii co...

4 Beds
4 Baths
202525307 MLS
FS - Fee Simple Tenure
358 DOM
ACTIVE Status

54 Maluniu Avenue, Kailua $5,388,000 ▼

PRICE REDUCTION! 5.5% cap rate on current income! This exceptional property offers 10 apartment units and 2 ground floor retail units in prestigious Kailua. The buildin...

202510044 MLS
FS - Fee Simple Tenure
568 DOM
ACTIVE Status

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.

Kailua Historical Real Estate

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