Vintage homes for sale & real estate in Waialae-Kahala, HI

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ABOUT THIS HOME
Vintage Home for sale in Waialae-Kahala, HI:
"The Crest, " an architecturally significant landmark oceanfront home in Diamond Head, offers unparalleled views and timeless design. Originally designed by Earl Nisbet, Frank Lloyd Wright's apprentice, 4131 Black Point Place has been dubbed "The Fallingwater of Honolulu. " Re-imagined and modernized in 2016, this one-of-a-kind residence fuses island luxury living with Hawaii's natural majesty on a unique scale. Wright's coined Organic Architecture flows in Nisbet's spectacular steel-frame creation, where terraced cliffside architecture maximizes Pacific Ocean views from every room. Offering a highly-flexible 3-bedroom, 3-story floor plan, execute your creative vision wi

$5,999,900

3 beds4 baths2,997 sq ft

4131 Black Point Pl, Honolulu, HI 96816

Oceanfront home • Private gated entry • Unparalleled views

ABOUT THIS HOME
Vintage Home for sale in Waialae-Kahala, HI:
Newly renovated! Spacious, single-level, indoor-outdoor Hawaiian-style home featuring manicured garden, Japanese tile roof and interior walls of teak and koa wood. This Papu Circle home offers 4 bedrooms and 3 baths. There is a luxurious open chef's kitchen, generous living room with magnificent Koolau Mountain and Diamond Head views from a large living room picture window, dining room, family room with enclosed lanai. Recent upgrades of $300K+ include new windows, new kitchen, new bathrooms, 5 new split A/C units, fresh interior paint, new ceiling fans, new kitchen, bathroom and enclosed lanai flooring, and new vinyl fence. Ideally located near the world-famous Shangri La estate and minute

$3,499,000

4 beds3 baths2,300 sq ft

4316 Papu Cir, Honolulu, HI 96816

Manicured garden • Japanese tile roof • Open chef's kitchen

ABOUT THIS HOME
Vintage Home for sale in Waialae-Kahala, HI:
Nestled in the heart of Kahala, this four-bedroom, two-bath residence, featuring a separate one-bedroom, one-bath guest suite, sits on an elevated 12,049 sq. ft. lot that offers views over Kahala and is cooled by the refreshing tradewinds. The main home opens to a spacious backyard with room for a pool, highlighted by mature mango and avocado trees, creating a serene retreat ideal for outdoor living and gatherings. Awaiting its new owner, this well-loved home presents an excellent opportunity to renovate and transform it into a dream residence. Located just moments away from beaches, parks, shopping, and dining, it combines comfort with the potential for personalization in a vibrant communi

$2,950,000

5 beds3 baths1,664 sq ft

1129 Koloa St, Honolulu, HI 96816

Spacious backyard • Views over kahala • Mature avocado trees

ABOUT THIS HOME
Vintage Home for sale in Waialae-Kahala, HI:
Seize the opportunity to own a coveted residence in the prestigious Diamond Head neighborhood, steps from Kaikoo's sparkling waters. This stunning home boast Ocean & Sunset views from the grand living/dining room and primary bedroom even captures views of Diamond Head. Elegant hardwood floors grace the living and dining areas, with stylish vinyl plank in bedrooms. Relax in the solar-heated pool/jacuzzi, covered by an awning to protect you from the elements. Spacious kitchen offers ocean views while washing the dishes and connects to the pool and the large two car garage, also in the back of kitchen is a convenient laundry room. A new gate ensures security, w/ parking for 5 cars or mo

$3,490,000

4 beds3 baths2,305 sq ft

4305 Kaikoo Pl, Honolulu, HI 96816

Separate entrance • Tesla battery backup • Solar heated pool

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Waialae-Kahala, HI:
Private Kahala Retreat - Versatile 2-Home Property on a Flag Lot. Rare opportunity in prestigious Kahala! This private flag lot at the end of a quiet cul-de-sac offers exceptional flexibility and charm. The property features two connected homes: a classic 2-bed, 1-bath single-wall home (1951, slab on grade, approx. 974 SqFt) and a spacious 2-bed, 2-bath double-wall addition (1985, post and pier, 9' ceilings, approx. 1,304 SqFt). Use as one large 4-bed home or live in one and rent the other or add an ADU. The large, level lot feels peaceful and secure - perfect for pets, kids, or simply enjoying quiet island living. Owned by the original family since 1951, with updated 200-amp underground e

$2,200,000

4 beds3 baths2,176 sq ft

4570 Ahuli Pl, Honolulu, HI 96816

Private flag lot • Quiet cul-de-sac • Large level lot

Property at 4470 Wahinekoa Pl, Honolulu, HI 96821, 4 beds, 6 baths

$2,190,000

4 beds6 baths2,349 sq ft

4470 Wahinekoa Pl, Honolulu, HI 96821

Property at 1358 Makaikoa St, Honolulu, HI 96821, 3 beds, 2 baths

$1,900,000

3 beds2 baths1,236 sq ft

1358 Makaikoa St, Honolulu, HI 96821

Property at 4219 Kaikoo Pl, Honolulu, HI 96816, 6 beds, 7.5 baths

$4,775,000

6 beds7.5 baths4,109 sq ft

4219 Kaikoo Pl, Honolulu, HI 96816

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ABOUT THIS HOME
Vintage Home for sale in Waialae-Kahala, HI:
An amazing investment opportunity you do not want to miss: a Single Family home with an unbeatable, highly sought-after location! A block in on a private lane, gated on one side and off of Kapahulu Ave, behind First Hawaiian Bank. Upstairs offers a tastefully upgraded and well cared for 2bd/1bath with a kitchen and a covered patio with Diamond Head and City views. Downstairs is a renovated studio with durable, easy to maintain upgrades. Enjoy generous 2-car carport and completely fenced in, leveled, easy to maintain yard. Just the studio is currently rented for $2,900 a month. Live in one and rent the other, or rent both. The studio features new cabinets, countertops, newer appliances

$1,280,000

2 beds2 baths1,522 sq ft

411 Kapahulu Ave Unit D, Honolulu, HI 96815

Private lane • City views • Covered patio

ABOUT THIS HOME
Vintage Home for sale in Waialae-Kahala, HI:
Discover an exceptional opportunity on highly sought-after Wilhelmina Rise. Perched on a rim lot with unobstructed Diamond Head and coastline views, this expansive 12,000+ sq. ft. parcel offers endless potential for investors, builders, or homeowners looking to create something truly special. The property features a nearly completed CPR—already well underway and offering the ability to split and develop. In addition, plans are currently in review with the Department of Planning & Permitting to construct an additional single-family dwelling, giving you a head start on future development. Its prime location places you just minutes from Kahala Mall, Kaimuki’s restaurants, bou

$1,424,000

3 beds2 baths1,344 sq ft

1729 Iwi Way, Honolulu, HI 96816

12 • Nearly completed cpr • 000 parcel

ABOUT THIS HOME
Vintage Home for sale in Waialae-Kahala, HI:
Located in a private lane, this spacious 5 bedroom, 2.5 bath two story home with 27 owned PV Panels offers comfort, convenience and Island charm. Enjoy sweeping views of Diamond Head and Waikiki from multiple vantage points throughout the home. Just a short walk to Kapiolani Community College and Diamond Head Theatre and only minutes away from Waikiki, Ala Moana, Kaimuki and Kahala, this home provides easy access to shopping, dining, beaches and entertainment, an Ideal blend of Island Living and Urban Accessibility.

$1,450,000

5 beds2.5 baths2,348 sq ft

3455A Wela St, Honolulu, HI 96815

Private lane • Easy access • Sweeping views

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Waialae-Kahala, HI:
Come and experience breathtaking ocean views from this rare beachfront 2 bedroom, located directly on a sandy beach at the base of Diamond Head. Situated on the private, tranquil end of Oahu’s prestigious Gold Coast, Kainalu is one of the most desirable boutique buildings in the area. This spacious Co-op unit welcomes your personal touches and offers an open layout with generous living and dining areas. Enjoy the soothing sound of waves and cool tradewinds drifting through your windows, creating the ultimate island retreat. Step outside to your own private sandy beach—swim, surf at Tonggs, or unwind in the oceanfront lounge area. The unit includes a covered parking stall and in-

$1,150,000

2 beds1 bath1,072 sq ft

2801 Coconut Ave Unit 3E, Honolulu, HI 96815

Minutes from waikiki • Easy walk-up access • Quiet environment

ABOUT THIS HOME
Vintage Home for sale in Waialae-Kahala, HI:
Don’t miss this charming contractor’s special tucked away in the peaceful back of Palolo Valley. This unique property sits on an attractive corner lot featuring a massive, mature mango tree and plenty of outdoor space to shape into your own island retreat. The home offers flexible layout possibilities—perfect for buyers looking to renovate, reconfigure, or create multi-generational living. Conveniently located near shopping, beaches, schools, and all that town has to offer, this property presents a rare opportunity to add value in a desirable Honolulu neighborhood. Offers are due by 5pm Tuesday, November 25th. Seller reserves the right to accept an offer prior to the revie

$863,600

4 beds2 baths1,851 sq ft

2442 10th Ave Unit C, Honolulu, HI 96816

Mature mango tree • Flexible layout • Outdoor space

ABOUT THIS HOME
Vintage Home for sale in Waialae-Kahala, HI:
Don't miss this ultra charming 2/1/2 single family home in Kaimuki! Located right next to KCC and Diamond Head. This home has been fully upgraded to meet all insurance standards, approximately $50k in upgrades: new roof, electrical, plumbing waste lines plus a brand new coat of paint! Preserve and enjoy the old school charm and quaint cottage-like characteristics this home has to offer. High ceilings, crown moldings, glass paneled doorways and expertly crafted beautiful built-ins. Enjoy a sweet picnic or late night dinner under the start in the back courtyard. Short walk away from multiple Kaimuki eateries. Close-by to freeways entrances. Skip the maintenance fees and own a piece of char

$990,000

2 beds1 bath672 sq ft

713 Ocean View Dr, Honolulu, HI 96816

New coat of paint • Brand new roof • New electrical

Property at 3602 Alani Dr, Honolulu, HI 96822, 4 beds, 2 baths

$1,598,000

4 beds2 baths1,534 sq ft

3602 Alani Dr, Honolulu, HI 96822

Property at 2801 Coconut Ave Unit 2G, Honolulu, HI 96815, 1 bath

$579,000

0 beds1 bath585 sq ft

2801 Coconut Ave Unit 2G, Honolulu, HI 96815

Property at 3316 Hinano St, Honolulu, HI 96815, 5 beds, 3 baths

$2,150,000

5 beds3 baths2,290 sq ft

3316 Hinano St, Honolulu, HI 96815

Property at 3031 Libert St, Honolulu, HI 96816, 6 beds, 3 baths

$998,000

6 beds3 baths2,520 sq ft

3031 Libert St, Honolulu, HI 96816

Property at 3025 Diamond Head Rd, Honolulu, HI 96815, 2 beds, 2 baths

$3,300,000

2 beds2 baths1,378 sq ft

3025 Diamond Head Rd, Honolulu, HI 96815

Property at 1541 Palolo Ave Unit A, Honolulu, HI 96816, 4 beds, 2 baths

$1,300,000

4 beds2 baths1,595 sq ft

1541 Palolo Ave Unit A, Honolulu, HI 96816

Property at 2955 Makalei Pl, Honolulu, HI 96815, 4 beds, 6.5 baths

$34,000,000

4 beds6.5 baths5,226 sq ft

2955 Makalei Pl, Honolulu, HI 96815

Property at 3741 Harding Ave, Honolulu, HI 96816, 7 beds, 5 baths

$1,950,000

7 beds5 baths2,799 sq ft

3741 Harding Ave, Honolulu, HI 96816

Property at 1944 10th Ave Unit A, Honolulu, HI 96816, 4 beds, 3 baths

$3,888,888

4 beds3 baths2,904 sq ft

1944 10th Ave Unit A, Honolulu, HI 96816

Property at 1935 9th Ave, Honolulu, HI 96816, 4 beds, 3 baths

$3,888,888

4 beds3 baths2,904 sq ft

1935 9th Ave, Honolulu, HI 96816

Property at 1944 10th Ave, Honolulu, HI 96816, 4 beds, 3 baths

$3,888,888

4 beds3 baths2,904 sq ft

1944 10th Ave, Honolulu, HI 96816

Property at 3422 Woodlawn Dr, Honolulu, HI 96822, 3 beds, 2 baths

$1,800,000

3 beds2 baths1,589 sq ft

3422 Woodlawn Dr, Honolulu, HI 96822

Property at 3045 Pualei Cir Unit B211, Honolulu, HI 96815, 1 bed, 1 bath

$628,000

1 bed1 bath590 sq ft

3045 Pualei Cir Unit B211, Honolulu, HI 96815

Property at 1148 2nd Ave, Honolulu, HI 96816

$1,900,000

— beds— baths— sq ft

1148 2nd Ave, Honolulu, HI 96816

Vintage Homes for Sale in Waialae-Kahala

There are currently 8 vintage homes for sale in Waialae-Kahala at a median listing price of $2.19M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Waialae-Kahala stay on the market for 91 days and receive 1 offers. Popular neighborhoods include Oahu Island, Manoa, Kaimuki, Hawaii Kai, and Waikiki. This map is refreshed with the newest listings in Waialae-Kahala every 15 minutes.

In the past month, 14 homes have been sold in Waialae-Kahala. In addition to houses in Waialae-Kahala, there were also 26 condos, 1 townhouse, and 0 multi-family units for sale in Waialae-Kahala last month. Waialae-Kahala is a minimally walkable neighborhood in Honolulu County with a Walk Score of 34. Waialae-Kahala is home to approximately 9,834 people and 4,506 jobs. Find your dream home in Waialae-Kahala using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Waialae-Kahala are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Waialae-Kahala. If you're looking to sell your home in the Waialae-Kahala area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Waialae-Kahala with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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