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99 Kailua Homes for Sale

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New 1 hour ago
$1,995,000
275 Kainalu Dr
5 Beds | 5 Baths
2,787 sqft
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41-937 Laumilo St
4 Beds | 4.5 Baths
2,440 sqft
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1302 Akamai St
3 Beds | 2 Baths
1,612 sqft
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1422 Auauki St
6 Beds | 4 Baths
2,728 sqft
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1042 LOHO St
7 Beds | 4 Baths
3,336 sqft
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1159 Aukele St
5 Beds | 4 Baths
1,170 sqft
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1407 Lekeona St
3 Beds | 1 Bath
880 sqft
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1072 Koohoo Pl
3 Beds | 2 Baths
1,968 sqft
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1306 Aupapaohe St
4 Beds | 3 Baths
2,385 sqft
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21 Aalapapa Pl
4 Beds | 3 Baths
2,220 sqft
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1111 Manulani St
3 Beds | 2.5 Baths
1,405 sqft
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627 Pauku St
3 Beds | 2 Baths
1,707 sqft
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577 Kawailoa Rd
3 Beds | 2 Baths
1,461 sqft
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77 Kaiholu Pl
5 Beds | 3 Baths
2,714 sqft
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572 Kalaheo Ave
3 Beds | 2 Baths
2,031 sqft
The MLS properties are based on information from the Multiple Listing Service of Hicentral MLS, Ltd.
Total 99 Kailua Homes - 15 loaded

The MLS properties are based on information from the Multiple Listing Service of Hicentral MLS, Ltd.

Kailua - Real Estate & General Info

Kailua Videos
See our video flying above homes in Kailua and also our video of Kailua Beach Park

About Kailua
Kailua is one of Hawaii's classic beach communities. Slower moving, quiet - yet lively - and defiantly low-rise in the face of the development that's overtaken so many other parts of the Island of Oahu. You will never mistake Kailua Town (the main shopping area of Kailua) for the built-up real estate in Honolulu even with a Target and Whole Foods plus three supermarkets and small strip malls.

Homes
Kailua homes for sale range from about $700,000 for a small home that needs some serious work in the Coconut Grove area to about $20,000,000 for the most incredible homes in Kailua Beachside (example: Throughout his presidency, Kailua Beachside was the setting for President Obama’s holiday retreat – an incredible private enclave of three luxury homes.) Although Kailua real estate has a wide price range and the neighborhoods are noticeably different, one thing they all have in common is a laid-back lifestyle vibe.

Below are some quick-read reviews of the real estate in Kailua - specifically several Kailua single-family home neighborhoods. Just click on the name of the neighborhood for our blog that contains much more detail. If you want more information on condos or townhomes visit our Kailua condos for sale page.

Beachside: The name alone tells you this is where you’ll find beach estates. Even better, these luxury homes line some of the most magnificent sands in Hawaii - Kailua Beach and are some of the most expensive beachfront properties on Oahu.

Residents are a mix of longtime locals as well as some of the wealthy, and even famous, who love the singularity of this town, along with the absence of anything even resembling pretentiousness.
Numerous celebrities own, or have owned, homes here. It's not unusual to see a famous face enjoying time in Kailua Town, dressed in the local uniform of slippers, shorts and t-shirt. They can blend in and, even if they don't, people here give them their space. Star-chasing is not pursued in Kailua.

Lanikai: Kailua’s exclusive beachside community, just south of Kailua Beach, features homes made even more valuable because there are so few of them. The views of the Mokulua Islands from the beach and the ocean views from Lanikai’s hillsides are unforgettable. In keeping with its exclusivity, the streets are narrow, with just one, a circle of sorts that gets you in and out of the neighborhood.

Kailua Beach and Lanikai have both famously held the #1 spot on Dr. Beach’s list of the top stretches of sand in the United States. That 'best beaches' claim is a serious one, considering the stiff competition Oahu has on its shores. It's a legitimate one, though. Dr. Beach finally changed the rules because of Kailua Beach’s dominance year-after-year. He now retires those beaches that have reached the #1 position on his annual list. However, both Kailua and Lanikai beaches remain in first place in the minds of all Kailuans and of those who visit these shores.

Kailua Bluffs: The houses here are contemporary in style, with a more uniform look than other areas. Significantly, it has underground utilities, uncommon in Kailua, so there's a clean, uncluttered look overall. There are a few duplexes, found on the western end of Kahako St.

In keeping with the locals' low-rise preference, Kailua real estate is mainly houses, with just a few condos or townhomes in the mix. The lack of high-rise buildings and the obvious attractions of the town have raised the pricing on homes for sale in Kailua.

Enchanted Lake: A well-known neighborhood, it encircles a freshwater lake. The lakefront houses look out on the calming waters. Only residents can use the small lake that eventually makes its way to the sea. Usage is limited to boating only – no motors. Kayaks are perfect.

Kailua Estates: Most lots are in the 10,000 to 16,000 sq. ft. range, which is large for homes in Kailua. These generous proportions extend to the wider streets as well. Kakahiaka and Awina Streets are especially notable, because of the canal that runs by them, giving some homeowners a backyard vista of flowing waters.

Kawailoa: The selling point for this small collection of homes is that they're right next to Kailua Beach Park! Some are built against the hillside, high enough to have incredible views of the Pacific Ocean and that #1 beach. Lots generally are 4,500 to 6,000 sq. ft. in size. Don't confuse this neighborhood with the North Shore neighborhood that has the same name.

Hillcrest & Keolu Hills: These two areas are very close together, both being hillside communities found east of Keolu Dr, above Enchanted Lake. Up here the breezes are cool and plentiful. The views are good, too, looking towards the town side of Kailua as well as the ocean.

Kalama Tract: If you know the area, you know that Kalama Tract's location along N Kalaheo Avenue puts it just one block from Kailua Beach! That makes for perfect access and the kind of real estate that often pays back on its investment. As a place to live, you'll enjoy a quiet, serene neighborhood where you'll brake often for ducks crossing the road. Everybody goes to the beach here (except for the ducks). 

Kailua has successfully maintained its genteel small-town feel despite the overwhelming growth in development almost everywhere else on Oahu. While this has raised home prices, it has preserved a special character that evokes the Old Hawaii where life was taken in stride. There's an understanding that a faster pace doesn't necessarily improve the quality of the day.

Kaimalino: We travel to the far side of Kailua Bay, near Kaneohe MCBH, to find these large lots, typically starting at 10,000 sq. ft. The beaches are a little rockier, but that makes for a quieter ambience, and more privacy, with fewer outsiders coming to use the sands here. Some houses lie along the canal, while others sit directly on the oceanfront itself. This is where there is a secret place to quietly tiptoe across the rocks to see honu (green sea turtle) hatchlings.

Aikahi Park and Kalaheo Hillside: These two communities lie on the north side of the canal and Mokapu Blvd. In Aikahi Park, spacious homes have well-groomed lawns and the large lots are flat. Aikahi Park Shopping Center and Aikahi Park Elementary School, one of Oahu’s best, divide the two neighborhoods. Kalaheo Hillside is a bit more country, with homes that sit on lots that are mostly 10,000 square feet, many with ocean views. Most homes in both areas are an easy 10-minute walk to the beach.

Maunawili: Part of Kailua’s real estate, but the location makes it feels like it is sort of an area of its own, located between Kailua and Kaneohe. The dominant hue in Maunawili, unmistakably, is green. You live in the lushness of the mountains where life grows freely all around you. The cooler climes also bring more precipitation, which falls regularly, something locals love because it makes for crisp, fresh air and the rich, emerald green flora. There are some large country estates, which range from 10,000 sq. ft. on up to two acres and a golf course in the midst.

Although Kailua faces continued challenges ahead about its future, with so many developers eager to enter the city limits, if one had to place a bet, it would be that this town would be the one to stand firm. From a real estate perspective, this will raise home values, but, more importantly, it would prove that a special neighborhood like this one can be protected and preserved.


Kailua History
Kailua has been occupied almost from the first arrival of the Polynesian settlers. Archeologists believe that this was home to early Hawaiians at least 1,500 years ago. They lived primarily around Kawainui Marsh, subsisting mainly on fish and other seafood as the land could not be cultivated at the time. The community would remain small until the Ali'i (royalty) moved their Oahu center here from Waikiki in the 16th century. The numerous heiau (religious) sites that survived are a testament to the importance of the area.

Over the centuries, developments in land use and farming techniques occurred, revealing the area's agricultural potential. Sugar, taro and rice were staple crops, feeding a growing population. Starting in the 1800s, the focus would turn to raising cattle on the lands owned by businessman James Castle. His Kaneohe Ranch dominated the windward side of Oahu, covering a vast territory that was used as pastureland. In the 1940s, his son, Harold, would make a move that would change Kailua real estate forever.

In 1942, Harold Castle closed down Kaneohe Ranch, recognizing that changes were coming to Hawaii. This freed up thousands of acres of land where developers built the beginnings of Kailua Town. The Castles also donated large tracts of their land to schools, hospitals and churches to serve this side of Oahu, many of which still bear the Castle name.

Kailua homes, especially in the post-war years, sprung up quickly, creating a large community around the existing small town. Before the Pali Highway and its tunnels were finished in the 1950s, motorists had to take a slow, winding dirt road over the Koolau mountains to reach the Windward side. Finally, one could travel easily from downtown Honolulu to the Windward Side. Those working in the city moved to the country in large numbers as they were now able to commute – resulting in a thriving town that was soon to become a real city – albeit a laid-back beachy one – as more and more houses were being built.

Kailua is still going through growing pains today as residents try to preserve the small-town feeling in the face of development and tourism. Having two of the 'Best Beaches in America' doesn't help, either. Changes may come, but there will always be something uniquely Kailua: Life is just taken a little differently here than it is on the other side of the Koolau; and that makes all the difference.

Of course, there is a big difference between the Kailua of yesteryear and today’s Kailua when it comes to restaurants – once upon a time, there was one coffee shop in Kailua. Today, you can find all kinds of foods served at all times of day – everything from little sandwich shops to gourmet white-tablecloth fine-dining experiences. (Kailua Breakfast Restaurants, Best Places for Happy Hour in Kailua).

Decades ago it was just Liberty House (department store), the only place to buy men and women’s wear and beachwear. Now, Liberty House is gone and scattered throughout Kailua are many choices for the latest in high-fashion and beachwear for men, women and children. (Shops for Beach Wear in Kailua).

More Details

Recently Sold in Kailua
Sold5/14/'21
$1,386,000 (Sold Price)
1272 Kina St
4 Bd | 2 | 1,980 sqft
Sold5/13/'21
$1,725,000 (Sold Price)
576 Paokano Pl
4 Bd | 4 | 2,604 sqft
Sold5/13/'21
$910,000 (Sold Price)
321 Hualani St
4 Bd | 1 | 888 sqft
Sold5/13/'21
$1,600,000 (Sold Price)
263 Kahako St
3 Bd | 2.5Ba | 2,065 sqft
Sold5/13/'21
$3,500,000 (Sold Price)
142 Pauahilani Pl
6 Bd | 5 | 3,664 sqft
Sold5/12/'21
$2,894,000 (Sold Price)
42-125 Kooku Pl
4 Bd | 5 | 3,044 sqft
Sold5/11/'21
$1,890,000 (Sold Price)
451 Lanae Way
9 Bd | 4 | 3,120 sqft
Sold5/10/'21
$1,575,000 (Sold Price)
60 Kaneohe Bay Dr
4 Bd | 3 | 1,752 sqft
Sold5/7/'21
$1,350,000 (Sold Price)
1391 Kina St
5 Bd | 3 | 2,571 sqft
Sold5/7/'21
$2,110,000 (Sold Price)
1306 Aulepe St
4 Bd | 4 | 2,744 sqft
Sold5/6/'21
$1,275,000 (Sold Price)
522 Ulukou St
4 Bd | 2.5Ba | 2,214 sqft
Sold5/6/'21
$1,350,000 (Sold Price)
41-978L Waikupanaha St
3 Bd | 1 | 1,578 sqft
Sold5/6/'21
$1,249,000 (Sold Price)
1021 Akumu St
3 Bd | 3 | 2,266 sqft
Sold5/4/'21
$4,500,000 (Sold Price)
22 Palione Pl
6 Bd | 5.5Ba | 3,759 sqft
Sold5/4/'21
$1,425,000 (Sold Price)
701 Kihapai St
4 Bd | 3 | 2,435 sqft
Sold5/4/'21
$1,875,000 (Sold Price)
536 Paumakua Pl
5 Bd | 3 | 2,224 sqft
Sold5/3/'21
$1,500,000 (Sold Price)
523 Kihapai St
6 Bd | 4 | 2,278 sqft
Sold5/3/'21
$1,414,265.66 (Sold Price)
1308 Kuuna St
4 Bd | 3.5Ba | 2,063 sqft
Sold4/30/'21
$1,575,000 (Sold Price)
1617 Kanapuu Dr
4 Bd | 3 | 2,322 sqft
Sold4/30/'21
$1,240,000 (Sold Price)
1272 Kupau St
4 Bd | 2 | 1,937 sqft
Sold4/30/'21
$1,395,000 (Sold Price)
1797 Kanapuu Dr
3 Bd | 2.5Ba | 1,620 sqft
Sold4/30/'21
$995,000 (Sold Price)
419-C Kawainui St
3 Bd | 1.5Ba | 1,097 sqft
Sold4/29/'21
$784,000 (Sold Price)
431C Kalama St
2 Bd | 1 | 672 sqft
Sold4/28/'21
$3,500,000 (Sold Price)
127 Kailuana Pl
5 Bd | 3 | 2,626 sqft
Sold4/28/'21
$755,800 (Sold Price)
546A Ilimano St
4 Bd | 3 | 2,013 sqft
Sold4/27/'21
$3,999,000 (Sold Price)
47 Mahiloa Pl
4 Bd | 4 | 2,940 sqft
Sold4/27/'21
$2,100,000 (Sold Price)
126 Uilama St
5 Bd | 4 | 2,360 sqft
Sold4/23/'21
$1,400,000 (Sold Price)
1371 Hele St
4 Bd | 2.5Ba | 1,829 sqft
Sold4/22/'21
$865,000 (Sold Price)
661A Kihapai St
2 Bd | 1 | 548 sqft
Sold4/20/'21
$1,245,000 (Sold Price)
570 Ulukou St
4 Bd | 3 | 1,880 sqft
Sold4/16/'21
$1,350,000 (Sold Price)
1271 Ulunahele St
4 Bd | 3 | 1,662 sqft
Sold4/16/'21
$959,000 (Sold Price)
819 Oneawa St
2 Bd | 1 | 625 sqft
Sold4/15/'21
$1,655,000 (Sold Price)
425 Kawailoa Rd
4 Bd | 4 | 1,920 sqft
Sold4/15/'21
$1,500,000 (Sold Price)
1087 Keolu Dr
5 Bd | 3.5Ba | 1,839 sqft
Sold4/14/'21
$2,452,000 (Sold Price)
6 Kalaheo Ave
5 Bd | 4.5Ba | 3,827 sqft
Sold4/14/'21
$2,100,000 (Sold Price)
953 Mokulua Dr
4 Bd | 3.5Ba | 2,400 sqft
Sold4/13/'21
$1,075,000 (Sold Price)
1077 Mowai St
3 Bd | 2 | 1,682 sqft
Sold4/12/'21
$2,150,000 (Sold Price)
1053 Koohoo Pl
3 Bd | 3.5Ba | 2,389 sqft
Sold4/9/'21
$1,456,000 (Sold Price)
326 Kainalu Dr
3 Bd | 2.5Ba | 1,208 sqft
Sold4/9/'21
$6,250,000 (Sold Price)
20 Puukani Pl
6 Bd | 4 | 3,171 sqft
Sold4/9/'21
$1,600,000 (Sold Price)
183 Kuumele Pl
2 Bd | 3 | 2,118 sqft
Sold4/8/'21
$1,211,000 (Sold Price)
1335 Manu Aloha St
3 Bd | 3 | 1,636 sqft
Sold4/8/'21
$790,000 (Sold Price)
41-540 Inoaole St
4 Bd | 4 | 1,977 sqft
Sold4/8/'21
$1,400,000 (Sold Price)
1054 Mokapu Blvd
5 Bd | 3 | 3,493 sqft
Sold4/6/'21
$1,655,000 (Sold Price)
531 Kaiemi St
5 Bd | 3 | 2,143 sqft
Sold4/6/'21
$1,775,000 (Sold Price)
976 Kalawai Pl
6 Bd | 4 | 2,553 sqft
Sold4/5/'21
$1,200,000 (Sold Price)
1176 Uluopihi Lp
3 Bd | 2.5Ba | 1,289 sqft
Sold4/5/'21
$1,333,000 (Sold Price)
467 Lanae Way
4 Bd | 3 | 1,692 sqft
Sold4/1/'21
$1,550,000 (Sold Price)
658 Iana St
4 Bd | 3 | 1,889 sqft
Sold4/1/'21
$2,198,000 (Sold Price)
270 Kaha St
6 Bd | 4 | 3,104 sqft
Sold4/1/'21
$9,000,000 (Sold Price)
2 Palione Pl
5 Bd | 5 | 4,847 sqft
Sold3/31/'21
$985,000 (Sold Price)
623 Kaulani Way
3 Bd | 2.5Ba | 1,260 sqft
Sold3/30/'21
$1,460,000 (Sold Price)
142 Aikahi Lp
3 Bd | 2 | 1,580 sqft
Sold3/30/'21
$1,350,000 (Sold Price)
445 Keolu Dr
4 Bd | 3 | 1,634 sqft
Sold3/30/'21
$1,695,000 (Sold Price)
1226 A Aalapapa Dr
7 Bd | 5.5Ba | 3,144 sqft
Sold3/25/'21
$1,050,000 (Sold Price)
1066 Loho St
3 Bd | 3 | 1,820 sqft
Sold3/25/'21
$1,875,000 (Sold Price)
1370 Mokolea Dr
4 Bd | 3 | 3,100 sqft
Sold3/24/'21
$1,288,000 (Sold Price)
209 Aikane St
4 Bd | 2 | 1,315 sqft
Sold3/24/'21
$1,175,000 (Sold Price)
339C Kawainui St
3 Bd | 4 | 2,213 sqft
Sold3/22/'21
$3,000,000 (Sold Price)
120 Kalaheo Ave
5 Bd | 4.5Ba | 5,699 sqft
Sold3/19/'21
$1,276,000 (Sold Price)
950 Apokula St
3 Bd | 2 | 1,583 sqft
Sold3/17/'21
$1,200,000 (Sold Price)
41-038 Puuone St
4 Bd | 2 | 1,320 sqft
Sold3/16/'21
$789,000 (Sold Price)
41-523 Humuniki St
3 Bd | 2.5Ba | 912 sqft
Sold3/16/'21
$1,975,000 (Sold Price)
259 Kaelepulu Dr
4 Bd | 2 | 1,838 sqft
Sold3/12/'21
$830,000 (Sold Price)
1132 Uluopihi Lp
4 Bd | 3 | 1,870 sqft
Sold3/11/'21
$1,275,000 (Sold Price)
724 Nunu St
3 Bd | 2 | 1,626 sqft
Sold3/10/'21
$1,825,000 (Sold Price)
713 Nunu St
4 Bd | 2 | 1,961 sqft
Sold3/10/'21
$1,274,500 (Sold Price)
536 ILIAINA St
3 Bd | 2 | 1,560 sqft
Sold3/9/'21
$3,175,000 (Sold Price)
1543 Aalapapa Dr
6 Bd | 4.5Ba | 3,864 sqft
Sold3/5/'21
$2,118,000 (Sold Price)
161 Kaluamoo St
5 Bd | 3.5Ba | 3,314 sqft
Sold3/5/'21
$1,350,000 (Sold Price)
1231 Lola Pl
4 Bd | 2 | 2,030 sqft
Sold3/5/'21
$1,079,000 (Sold Price)
1015 Ilipilo St
3 Bd | 2 | 1,752 sqft
Sold3/5/'21
$1,250,000 (Sold Price)
602 Kawainui St
4 Bd | 3 | 1,582 sqft
Sold3/4/'21
$1,100,000 (Sold Price)
547 Auwai St
3 Bd | 2 | 1,926 sqft
Sold3/3/'21
$977,000 (Sold Price)
41-559 Hihimanu St
3 Bd | 3 | 2,049 sqft
Sold3/1/'21
$1,018,000 (Sold Price)
568-B Kawailoa Rd
4 Bd | 2 | 1,422 sqft
Sold3/1/'21
$937,500 (Sold Price)
1365 Humuula St
4 Bd | 2 | 2,049 sqft
Sold2/26/'21
$1,281,000 (Sold Price)
210 Kalama St
3 Bd | 2.5Ba | 924 sqft
Sold2/26/'21
$2,000,000 (Sold Price)
123 Ainoni St
3 Bd | 2.5Ba | 3,164 sqft
Sold2/22/'21
$1,410,000 (Sold Price)
1373 Kupau St
4 Bd | 4 | 2,304 sqft
Sold2/19/'21
$1,120,000 (Sold Price)
449 Ilimano St
5 Bd | 3 | 3,017 sqft
Sold2/19/'21
$2,700,000 (Sold Price)
228 Kainalu Dr
4 Bd | 3 | 2,797 sqft
Sold2/18/'21
$1,275,000 (Sold Price)
1023 Mokapu Blvd
4 Bd | 2 | 1,618 sqft
Sold2/16/'21
$2,800,000 (Sold Price)
1120 Maunawili Rd
4 Bd | 4.5Ba | 3,305 sqft
Sold2/12/'21
$2,863,500 (Sold Price)
381 Auwinala Rd
6 Bd | 4.5Ba | 3,538 sqft
Sold2/12/'21
$1,300,000 (Sold Price)
780 Iana St
3 Bd | 2 | 1,696 sqft
Sold2/10/'21
$875,000 (Sold Price)
2 Bd | 2 | 975 sqft
Sold2/10/'21
$1,780,000 (Sold Price)
1211 Kainui Dr
4 Bd | 3 | 2,278 sqft
Sold2/9/'21
$1,190,000 (Sold Price)
1532 Ulupii St
4 Bd | 2 | 2,223 sqft
Sold2/8/'21
$725,000 (Sold Price)
427 Kawainui St
3 Bd | 1 | 780 sqft
Sold2/8/'21
$957,500 (Sold Price)
413 Kihapai St
3 Bd | 2 | 1,220 sqft
Sold2/5/'21
$825,000 (Sold Price)
240 Kihapai St
3 Bd | 1 | 1,080 sqft
Sold2/4/'21
$1,560,000 (Sold Price)
1196 Punua Pl
4 Bd | 3 | 2,136 sqft
Sold2/4/'21
$1,200,000 (Sold Price)
620 Kaulani Way
4 Bd | 3.5Ba | 1,658 sqft
Sold2/4/'21
$1,050,000 (Sold Price)
939 Kaipii St
3 Bd | 2 | 1,815 sqft
Sold2/4/'21
$2,800,000 (Sold Price)
103 Kailuana Lp
4 Bd | 2.5Ba | 3,057 sqft
Sold2/4/'21
$1,402,000 (Sold Price)
423 Ilimano St
3 Bd | 2 | 1,501 sqft
Sold2/1/'21
$1,140,000 (Sold Price)
1286 ONIONI St
3 Bd | 2 | 1,494 sqft
Sold2/1/'21
$1,140,000 (Sold Price)
280 Kainalu Dr
3 Bd | 2 | 1,220 sqft
Sold2/1/'21
$1,400,000 (Sold Price)
1119 Akipola St
3 Bd | 2 | 1,938 sqft