Status: Active
MLS Number: 202609794
List Price: $1,785,000Price changed from $1,899,000
Units: 5
0/1/2/3 Bed: 0/0/3/2
Fee:
Region: Kailua
Neighborhood: Waimanalo
List Date: 05-19-2026
Land: 48,568
Year Built: 1939
Listing courtesy of REMAX Hawaii
Description: A rare opportunity for multi-generational living in the heart of Waimanalo! This 1.1-acre property sits beneath the majestic Mount Olomana and features five single-family homes, each with its own cesspool, in varying conditions. With plenty of space and privacy, it’s perfect for extended families looking to create a shared retreat or for those wanting to renovate and make it their own. Enjoy the peaceful surroundings and the potential to build lasting memories in a truly special place. Just minutes from world-famous Waimanalo Beach and a short drive to Kailua Town, you’ll find the ideal mix of island seclusion and everyday convenience. Don’t miss this rare chance to own a legacy property in one of Oahu’s most scenic communities. Note - Flood Zones XS + AEF
Status: Active
MLS Number: 202615925
List Price: $1,989,000Price changed from $2,199,000
Open House Public: Sun Oct 18, 2:00PM-5:00PM
Units: 3
0/1/2/3 Bed: 1/0/0/2
Fee:
Region: Kailua
Neighborhood: Maunawili
List Date: 08-19-2026
Land: 7,961
Year Built: 1964
Listing courtesy of Hawaii Modern Realty
Description: Discover this rare multi-generational Kailua gem at 1031 Lunaai Place, now priced at $1,989,000! As the best-priced multi-family home on the Windward Side with a private pool, this move-in ready Maunawili property is exceptionally well-located. Enjoy a seamless commute with fast access to the Pali, H3, UH, and local military bases. Lovingly maintained by its original owners, the incredibly spacious floor plan features 7 bedrooms and 4.5 bathrooms, providing flexible living spaces tailored for extended families or guests. The main level boasts 4 bedrooms, 2 bathrooms, a large living room, family room, dining area, and a generous kitchen. Connected by an interior staircase, the upstairs adds 3 bedrooms, 1.5 bathrooms, and a massive family/rec room. Both levels include dedicated, separate laundry areas for complete convenience. Outside, the property shines with a wonderful swimming pool ready for new memories, plus a permitted fourth bathroom and bonus area with a separate entrance past the carport. Do not miss this versatile, high-value opportunity in a premier Kailua neighborhood.
Status: Active
MLS Number: 202605301
List Price: $2,188,000Price changed from $2,400,000
Units: 2
0/1/2/3 Bed: 0/0/1/1
Fee:
Region: Kailua
Neighborhood: Enchanted Lake
List Date: 03-16-2026
Land: 10,716
Year Built: 1972
Listing courtesy of Corcoran Pacific Properties
Description: 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 or a savvy investment. The front home features luxury vinyl plank and tile flooring, with split AC units in the living room and primary bedroom. The back home is accessible via a private walkway and includes a usable lanai and a window AC. Both residences enjoy their own separate fenced yards and share a large swimming pool equipped with a removable Guardian Pool Fence, creating an ideal environment for entertaining. Designed for convenience and privacy, the homes feature separately metered electricity, and the water system is ready for sub-metering. Parking is plentiful, with a two-car garage, additional off-street parking for four cars, and ample street parking available. Located in a prime Kailua neighborhood, the property is just minutes from schools, parks, the Enchanted Lake Shopping Center, and downtown Kailua, with the beach only a short distance away.
Status: Active
MLS Number: 202407147
List Price: $2,695,000Price changed from $2,985,000
Units: 2
0/1/2/3 Bed: 0/0/1/1
Fee:
Region: Kailua
Neighborhood: Enchanted Lake
List Date: 03-26-2024
Land: 7,772
Year Built: 1963
Listing courtesy of RE/MAX ALOHA HOMES
Description: No expense was spared in this, Fully Remodeled Multi Generational Home with automatic lighting, auto closing skylights, integral blinds, gas stove & dryer, 13 ft deep pool w/ diving board, over 40 PV panels, 4 tesla batteries and much more. There is a 4 bedroom 3 bath main house with 2 car garage, 2 connecting Ohana suites with private lanais, and a 2 bed 1 bath ADU over the new 1 car garage. This property has so much potential for so many buyers! Large extended families, Owner Occupants who want rental capabilities or an Investor who wants to buy a turn key property. DO NOT DISTURB TENANTS.
Status: Active
MLS Number: 202608942
List Price: $2,790,000Units: 2
0/1/2/3 Bed: 0/0/0/2
Fee:
Region: Kailua
Neighborhood: Waimanalo
List Date: 05-05-2026
Land: 11,250
Year Built: 2015
Listing courtesy of eXp Realty
Description: Rare opportunity with great potentials, for either own family living or rental investment, easy to afford mortgage! Located only a few houses away from world-famous Waimanalo white sand beach! Ideal for own living to enjoy lots of space in highly desirable beach neighborhood. 5704sf living space, 6 private entrances on 11,250sf lot. This 2-story house, 3811sf was newly built in 2015. Plus 1-story Ohana unit, 1893sf. This gated & spacious property offers 11 bedrooms, 8 full bathrooms, idyllic office space. Stunning, unobstructed Ko’olaumountain views. Total of 2 kitchens, 2 wet bars and plus. Huge sizes for all living rooms, kitchens, bedrooms, etc. 11ft tall ceiling for main living room; 9ft tall for other areas. Tons of upgrades: lanai, auto metal gate, natural stones, metal roof, solid wood cabinets & double-door entries, hardwood floor, granite & quartz countertops, Quartz staircase, etc. If for rental, since so close to beach, high rental demands paying good price to generate good incomes.
Status: Active
MLS Number: 202616607
List Price: $4,250,000Units: 3
0/1/2/3 Bed: 0/0/1/2
Fee:
Region: Kailua
Neighborhood: Govt/Ag
List Date: 08-29-2026
Land: 47,694
Year Built: 1965
Listing courtesy of Compass
Description: 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 COMPREHENSIVE RENOVATON and appraised at over 5 million dollars, this estate offers quite a lifestyle right here in Kailua. Just a few miles from one of the world's most beautiful beaches, minutes to Le Jardin Academy and 20 minutes to Honolulu, our location is ideal. The main part of this home is stunning, featuring an open floor plan with a well planned kitchen right in the heart of the home. Floor-to-ceiling windows, large rooms, and tall ceilings frame the mountain views. The lower floor is separate from the main home but could be connected if desired. It features 3 bedrooms and two full baths, plus a large entertainment area that is ideal for MULTIGENRATIONAL living, teenagers in their own space or a rental. VERSATILITY is key here, offering many options with this AG Land. The unpermitted Yellow cottage has an additional 3 bedrooms, 2 baths and kitchen. Enjoy a refreshing swim in the pool, with a big bowl of home grown fruits. Lots of parking for cars, toys, and entertaining. Come see us today!
Status: Active
MLS Number: 202616097
List Price: $4,900,000Units: 5
0/1/2/3 Bed: 0/1/2/2
Fee:
Region: Kailua
Neighborhood: Koolaupoko
List Date: 09-16-2026
Land: 27,725
Year Built: 1953
Listing courtesy of Coldwell Banker Realty
Description: This rare 27,725 sq. ft. estate property has fabulous mountain views over the wide canal, in a prime Kailua location one street from the beach. Enjoy over 295 ft of direct waterfront canal living! Kayak, SUP right from your yard. The layout gives you incredible flexibility, featuring multiple suites within a spacious compound. The original single-level 3-bedroom/2-bath home opens to a green yard along the waterfront, flanked by two 2-bedroom/1-bath wings with private entrances and ample parking. A breezeway carport connects to another living area with 3 bedrooms/2.5-baths upstairs opening to a gorgeous view lanai. On the ground level is a two-car enclosed garage and workshop plus a 1-bd/1-bath wing. The property has been well-kept and maintained over the years by one family. Everything Kailua has to offer is convenient to this estate including the canal, beach, restaurants and businesses, shopping centers, the Pali and H-3. 117 owned PV panels and EV Charger too! Don’t miss this one-of-a-kind opportunity!
Status: Active
MLS Number: 202510044
List Price: $5,388,000Price changed from $5,890,000
Units: 12
0/1/2/3 Bed: 0/10/0/0
Fee:
Region: Kailua
Neighborhood: Kalama/Cnut Grov
List Date: 04-15-2025
Land: 5,610
Year Built: 1965
Listing courtesy of Standard Management LLC
Description: 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 building was majorly renovated inside and outside including replacement of all utilities, new silicone waterproof roof and commercial grade gutter systems, all new stainless steel appliances, flooring, interiors, fencing and painting. All apartment units have dual-pane glass vinyl windows and balcony sliding doors, LED lighting, split AC units in bedrooms and living rooms, and individual full-size stacked LG washer-dryers located on the balconies.
The 2 retail spaces benefit from a high visibility location in this upscale retail corridor. In addition to abundant street parking in the immediate area, there are 7 covered parking stalls. Located just moments from Whole Foods Market and Kailua Beach. This is a trophy, renovated asset in an incredibly desirable submarket where investment properties are rarely available for sale and could be “turnkey” for a buyer.
The apartments and retails units have been split into separate TMKs (1-4-3-31-27-1 & -2) for lower property tax rates.
Status: Active
MLS Number: 202619101
List Price: $5,400,000Units: 2
0/1/2/3 Bed: 0/1/0/0
Fee:
Region: Kailua
Neighborhood: Waimanalo
List Date: 10-14-2026
Land: 353,925
Year Built: 1984
Listing courtesy of Coldwell Banker Realty
Description: A Rare Waimanalo Opportunity: Where Country Living Meets Exceptional Possibilities. Perfect for equestrian enthusiasts, ranchers, farmers, and those seeking a truly unique piece of paradise. Set against the dramatic beauty of the Ko'olau mountains, this private, fully fenced property offers a remarkable combination of natural beauty, usable space and convenient access to town. Enjoy the peaceful, open atmosphere of Waimanalo while remaining close to its beautiful white-sand beaches. Featuring two cottages, over 26,000 square feet of warehouse, office space, and other roofed area. Surrounded by O'ahu’s lush windward landscape and magnificent mountain views, it’s more than just a property; it’s an opportunity to create a distinctive lifestyle, agricultural operation, or private retreat in Waimanalo’s scenic setting. Private. Fully fenced. Expansive. Versatile. Enjoy the beauty and tranquility of country living while staying connected to the conveniences of O'ahu. Priced under the appraised value!
Status: Active
MLS Number: 202618731
List Price: $7,850,000Units: 9
0/1/2/3 Bed: 2/4/2/1
Fee:
Region: Kailua
Neighborhood: Waimanalo
List Date: 10-05-2026
Land: 17,646
Year Built: 1944
Listing courtesy of Chaney Brooks Residential LLC
Description: Amazing opportunity to own a very special non-conforming multi-family compound owned and operated by a Kama'aina family since 1956 right off of one of the worlds best beaches (#35 world/#4 US).
Waimanalo Beach Cottages offers the best in authentic local hospitality and in location. Steps to the world class Waimanalo Beach.
!DO NOT ENTER PROPERTY W/OUT AUTHORIZATION AND DO NOT DISTURB GUESTS!
2 Studio units, 4 One Bed units, 2 Two Beds units and 1 Three Bedroom unit.
See the 3D Virtual Tour herein.
Status: Contract
MLS Number: 202610580
List Price: $1,725,000Price changed from $1,875,000
Units: 2
0/1/2/3 Bed: 1/0/0/1
Fee:
Region: Kailua
Neighborhood: Kalaheo Hillside
List Date: 05-29-2026
Land: 10,017
Year Built: 1958
Listing courtesy of Homes of Hawai'i Real Estate
Description: Nestled within one of Kailua’s favorite neighborhoods, Kalaheo Hillside, 315 Iliaina Street is filled with potential and island charm. The property includes two separate structures --- a cute, detached cottage studio with a full bath and kitchenette, plus a classic home offering 3 bedrooms, 2 full baths, a great open floor plan, and a separate dining area with large windows looking out to the backyard. Much of the home remains in its original condition, including beautiful koa kitchen cabinet doors that could shine again with restoration. The spacious yard features a large in-ground pool and plenty of room to reimagine the outdoor spaces! Split ACs in each room. Owned PV panels with net metering. Just minutes from Aikahi Shopping Center, Aikahi Elementary School, Kailua’s beaches, shopping, dining opportunities, markets, and so much more! Also close to MCBH Kaneohe, H-3, and Likelike Highway access, this property combines location, flexibility, and opportunity in one of Kailua’s most convenient neighborhoods. (Also listed as MLS#202609716)
