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Ohana
* Second home allowed on either a residential or an agricultural zoned property.
Surf
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Round Top Dr street homes for sale Honolulu | Oahu

Living in Round Top Dr

$850k  $75,000
Tantalus
3953 Round Top Drive, Honolulu
Land
0.751 acres
$850,000  $75,000
0.751
acres
Enjoy cool mountain breezes, Hawaiian songbirds, and ocean views in both directions. A tranquil, canopy-covered scenic road leads to this rare Tantalus Mountain top lot with stunning views of Diamond Head and Honolulu. First time on the market in over 100 years—this land has been in the same family for generations. A truly unique opportunity to build a private forest retreat just minutes from downtown Honolulu. Daily rain keeps the air fresh, offering a peaceful escape with natural beauty all around. The lot is cleared and ready for your dream home, featuring panoramic views of the South Shore, city lights, and unforgettable sunsets. Located in a historic neighborhood with award-winning architectural homes. Rainbows are a regular part of life here. This listing includes two parcels (TMKs ending in 022 and 008), totaling 32,697 sq. ft., and is being offered below the assessed tax value. Experience space, peace, and views—come build your mountain paradise today. Please do not enter the property, appointment only.
$2.69m  $210,000
Makiki Heights
2325/2327 Round Top Drive unit 2325/2327, Honolulu
Multi-Family Home
$2,690,000  $210,000
Opportunity knocks for a new owner to transform this multi-dwelling property into a grand estate! This large CPR'd lot with 2 single family homes and in-ground pool is located just along the stunning slopes of Round Top Drive. The main 5 bed, 3 bath dwelling was thoughtfully upgraded in 2025 and features a massive living room that acts as the beating heart of the home, taking your breath away with its impressive lofted ceilings, floor-to-ceiling windows, and views of Honolulu, extending all the way out to the sapphire blues of the Pacific. The finished basement is a unique and flexible feature that can be used in a variety of different ways, from an office, to a home gym, to an entertainment room. The rear dwelling is a 2-story 3 bed, 2 bath, built in 1982 with a large wood deck and 2-car carport. These homes have been loved for many years, and with just a little more TLC, both properties can be brought back to their original shine and glory. Perfect for multi-generational living and just a few minutes drive from Punahou School, MidPac, Ala Moana, and the beautiful Tantalus Lookout, this is truly a unique, one-of-a-kind property! Must see to fully appreciate all it has to offer.
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$1.7m  $105,000
Makiki Heights
2325 Round Top Drive, Honolulu
Home
5 bd
2,278 sqft
$1,695,000  $105,000
5
bd
2,278
sqft
A true place of grandeur awaits along the stunning slopes of Round Top Drive! One of two single family homes situated on a large CPR'd lot, this 5 bed, 3 bath dwelling was thoughtfully upgraded in 2025 and features a massive living room that acts as the beating heart of the home, taking your breath away with its impressive lofted ceilings, floor-to-ceiling windows, & views of Honolulu, extending all the way out to the sapphire blues of the Pacific. The open layout kitchen includea stainless steel appliances, island seating, and ample storage space, making cooking, hosting, and entertaining a breeze! The bedrooms all feature peek-a-boo views of the ocean and surrounding trees, and the lower level living area is a unique and flexible feature that can be used in a variety of different ways, from an office, to a home gym, to an entertainment/pool room. Loved by one Ohana for years, this is the perfect place for multi-generational living, or for flourishing families to create their own memories with a dip in the pool, and a bask in the sun. Just a few minutes drive from Punahou School, Ala Moana, & the beautiful Tantalus Lookout, this is a one-of-a-kind property!
$995k  $105,000
Makiki Heights
2327 Round Top Drive, Honolulu
Home
3 bd
1,792 sqft
$995,000  $105,000
3
bd
1,792
sqft
Opportunity knocks for a creative enthusiast eager to transform a home into a space uniquely their own. One of two properties (BACK house only) situated on a large CPR'd lot, this house is perched along the stunning slopes of Round Top Drive. Built in 1982 and cherished by one family for many years, this 3-bed, 3-bath home has all the makings of a truly stellar property: high, lofted beam ceilings, a cozy wood-paneled deck, a generously sized kitchen (with room for a designated dining area), and bedrooms with ample closet space. The pièce de résistance? Sweeping views of the famous Honolulu city lights and the Pacific Ocean beyond, visible from the window-lined walls of the second story. This is the perfect investment or starter home for the right buyer to add a little TLC and restore it to its original glory. Located just a short drive from Punahou School, Mid-Pacific Institute, Ala Moana Shopping Center, and the beautiful Tantalus Lookout—a must-see to fully appreciate all its potential, and what it has to offer.
$7m  $1,000,000
Tantalus
3711 Round Top Drive, Honolulu
Home
6 bd
4,843 sqft
$7,000,000  $1,000,000
6
bd
4,843
sqft
Welcome to the former home of Richard Chamberlain, a lush sanctuary perched on the iconic Mount Tantalus. Spanning 1.80 acres, this unique estate allows for private island living all while being a short drive away from a metropolitan city. Enjoy astonishing Diamond Head, Ocean, and City views. Three distinct residences - the Main House, Guest House, and Studio - offer a combination of relaxation & entertainment. A great lawn, tennis court, & infinity edge pool offer resort like amenities from the comfort of your own home. This legacy estate provides a plethora of opportunities.
$1.67m  $25,000
Makiki Heights
2023 Round Top Drive, Honolulu
Home
6 bd
2,323 sqft
$1,665,000  $25,000
6
bd
2,323
sqft
You'll enjoy the in-town convenience of Makiki Heights/Tantalus neighborhood, with excellent schools, hospitals, shopping and freeway access. Breezy country feel with green rainforest views from a 1940's Art Deco period home. Spacious open living/dining area with 2 new split system A/C, and electrical panel. Opens out back to a covered patio, great for BBQ and entertaining and a flat yard area perfect for herb garden or children's swing set. The flexible floor plan has 6 bedrooms and 4 baths that are separate for privacy and room for all in an extended family and/or for rental arrangement and income. Room for pool and to park 4 or more cars in front of home. Don't miss out on this chance to avoid long commutes and spend quality time with family.
$1.65m  $30,000
Makiki Heights
2168 Round Top Drive, Honolulu
Home
5 bd
2,351 sqft
$1,645,000  $30,000
5
bd
2,351
sqft
Sought after location on lower Tantalus! This 4 bedroom, 2 bath, 1,951 Sq. Ft. home offers a beautiful island setting with covered lanai and useable yard area. A large chef's kitchen is the heart of the home and perfect for entertaining. The spacious primary bedroom opens to the covered lanai and includes a flex space for office or other use. PLUS a separate 400 Sq. Ft. studio with bath above the garage is perfect for income, house guests or home office/gym. Avocado trees and fenced backyard. Convenient to Punahou, Manoa, downtown and more! Don't miss this opportunity!
$2.35m  $50,000
Tantalus
4005 Round Top Drive, Honolulu
Land
0.740 acres
$2,350,000  $50,000
0.740
acres
Historic Tantalus Mountain Retreat. Endless opportunities for restoration and renovation. Step back in time and discover this enchanting, historic gem nestled atop Tantalus Mountain on Oahu. Built in 1929, this charming residence presents a unique opportunity to restore a piece of island history and create your dream retreat and escape to serenity. As you ascend to this mountaintop haven, a sense of tranquility envelops you, transporting you to a world of unparalleled beauty and serenity. Living on Tantalus offers a peaceful retreat from the urban hustle, with Honolulu's amenities and attractions just 10 minutes away. Explore, unwind and discover nearby trails, indulge in outdoor activities, or simply unwind and embrace the serenity that surrounds you. Don't miss this chance to own a piece of island history. Contact us today to schedule a viewing!
1 – 8 of 8 homes for sale
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Lifestyle & outdoors In Round Top Dr

3 surf spots in this area

Baby Haleiwa's
Type: surfing
Big Rights
Type: surfing
Point Panic
Type: body-surfing
Kaka'ako, Honolulu 1-5 Dangerous rocks and reef bottom

8 parks in this area

Puu Ualakaa State Wayside

Makiki Tantalus State Park

Manoa Valley District Park

Archie Baker Mini Park

Makiki Street Mini Park

Kamanele Square

Punahou Square

Makiki District Park

2 beaches in this area

Duke Paoa Kahanamoku Beach Park

Ala Moana Beach

1 golf course in this area

Ala Wai Golf Course

Essentials in Round Top Dr

Farmers market is about 24 min walk
Hospital is about 26 min walk
Supermarket is about 27 min walk
Airport is about 16 min drive
Costco is about 19 min drive
* distance is calculated by average per house. Some homes maybe closer to the essentials

Walkability in Round Top Dr

6 / 20
Car dependent
18-20
15-18
10-15
1-10
Walkability according to the National Walkability Index

Living in Round Top Dr Round Top Dr is a street

Supermarkets are about 27 min walk, the nearest Hospital is about 26 min walk and the airport is about 16 min drive.

Round Top Dr is car dependent.

There are 8 parks in this area, and 2 public beaches. Nearby lifestyles include surfing, body surfing and golf.

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