UNDER CONTRACT

Contingent

$3,045,000

Est. $17,838/mo —

•

3,150

sq ft

244 Awakea Rd, Kailua, HI 96734

About this home

MAJOR PRICE REDUCTION! Exceptional opportunity in a desirable location within Kailua Estates! 244 Awakea Road is a beautifully remodeled plantation style property situated on a spacious 10,000 sqft lot, just a short stroll to Kailua Beach and minutes from Kailua Town. Thoughtfully renovated in 2019, this versatile property offers separate living spaces with a combined 6 bedrooms, 3 bathrooms, and approximately 3,150 sqft, ideal for multigenerational living, extended family, or rental income potential. The main residence features 4 bedrooms, 2 bathrooms plus a den, vaulted ceilings, hardwood flooring, PV, and solar hot water. The separate 2 bedroom, 1 bathroom ADU has its own electrical meter and solar hot water. A dedicated storage/yoga room provides additional flexibility. Now offered at $3,045,000, or approximately $966/sqft, below the recent Kailua Estates average of $1,046/sqft. Enjoy convenient access to Kailua and Lanikai beaches, Kalapawai Market, Buzz's, Whole Foods, boutique shops, dining, and everything Kailua has to offer. A rare opportunity to own a beautifully updated property with flexible living options in one of Kailua's most sought after neighborhoods!

Single-familyProperty Type

1947Year Built

10,000 sq ftLot Size

$967Price/Sq.Ft.

5 spacesParking

Listed by Jason Carey • Compass

Contact: (808) 825-4277

Listing updated: Oct 30, 2026 at 12:09pm

Redfin checked: a minute ago

•Source:HiCentral MLS #202608800

Payment calculator

$17,838 per month

Principal and interest$16,618

Property taxes

$560

HOA dues

Home insurance

$660

Utilities

Add

5 minutes to get started. No credit impact.

Affordability tools

Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN SUN, 11:30AM TO 2:30PM3D WALKTHROUGH
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1004 Hanohano Way, Honolulu, HI 96825
0.35 acre lot • Garage • Pool
REDFIN OPEN SUN, 2PM TO 5PM3D WALKTHROUGH
$370,000
1 bed1 bath542 sq ft
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$1,081 HOA • Parking • Community pool
REDFIN OPEN SUN, 2PM TO 5PM3D & VIDEO TOUR
$1,875,000
4 beds2 baths2,079 sq ft
1188 Akuila Pl, Kailua, HI 96734
6,087 sq ft lot • 2 garage spots • Built 1972
REDFIN OPEN SUN, 2PM TO 5PM
$332,000
2 beds1 bath711 sq ft
1519 Nuuanu Ave #1440, Honolulu, HI 96817
$1,322 HOA • Parking • Community pool
OPEN SUN, 2PM TO 5PM
$1,200,000
4 beds3 baths1,914 sq ft
6204 Keokea Pl Unit A102, Honolulu, HI 96825
$1,025 HOA • 2 parking spots • Community pool
OPEN SUN, 2PM TO 5PM
$190,000
Studio1 bath318 sq ft
750 Amana St #911, Honolulu, HI 96814
$630 HOA • Community pool • Built 1967
OPEN SUN, 2PM TO 5PM
$369,000
2 beds1 bath700 sq ft
1415 Liholiho St #901, Honolulu, HI 96822
$844 HOA • Parking • Built 1979
OPEN SUN, 2PM TO 5PM
$1,590,000
5 beds3 baths2,056 sq ft
1942 St Louis Dr, Honolulu, HI 96816
6,900 sq ft lot • 2 garage spots • Built 1946
OPEN SUN, 2PM TO 5PMVIDEO TOUR
$1,575,000
4 beds2 baths1,860 sq ft
513 Iliaina St, Kailua, HI 96734
9,520 sq ft lot • 2 garage spots • Built 1960
OPEN SUN, 3:30PM TO 6:30PM
$79,900
1 bed1 bath588 sq ft
1720 Ala Moana Blvd Unit 304A, Honolulu, HI 96815
$792 HOA • Community pool • Built 1961

Around this home

Schools

K - 12
Preschool & daycare

Kailua Elementary School

Public PreK-6 • Assigned • 0.5mi

4/10

Kailua Intermediate School

Public 7-8 • Assigned • 0.2mi

7/10

Kalaheo High School

Public 9-12 • Assigned • 1.8mi

8/10

Provided by GreatSchools

About

Ko'olaupoko

Ko'olaupoko, located between the Koʻolau Range and Kāneʻohe Bay, is a coastal and mountain Kailua neighborhood with windward ridgelines and broad ocean views. The character concentrates around Kamehameha Highway at Kāneʻohe Bay Drive, where plate-lunch counters, local markets, and small service storefronts meet steady commuter energy. Hoʻomaluhia Botanical Garden and the Hawaiʻi Theatre Center at Windward Community College act as cultural anchors, with Hoʻokipa Hale nearby for community gatherings. Homes range from mid-century hillside streets to newer townhome clusters, shaped by trade winds and rain-fed greenery. Daily life orbits shoreline parks, paddling routes, and trailheads that rise fast into the pali. The geography keeps the pace outdoors-forward, with town conveniences threaded along the highway corridor.

Provided by Walk Score and Local Logic

Market insights

244 Awakea Rd · $3,045,000

DAYS ON MARKET

The average home goes pending in 66 days.

SALE-TO-LIST

Most homes are selling 1% below list price.

LIST PRICE

Median sale price in this area is $1,097,730. (64% lower than this home)

PRICE DROP

12% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Bedrooms
Bedroom on the main level

Bathrooms
3 full bathrooms
Full bathroom on the main level

Flooring
Ceramic tile, hardwood, and vinyl flooring

Sale and tax history for 244 Awakea Rd

Sale History
Tax History

Date

Event

Price

HiCentral MLS #202608800

Oct 23, 2026

Contingent

—

Oct 2, 2026

Relisted

—

Sep 17, 2026

Contingent

—

Sep 17, 2026

Pending

—

Sep 2, 2026

Price Changed

$3,045,000

$967/sq ft

Jul 9, 2026

Price Changed

$3,150,000

$1,000/sq ft

May 10, 2026

Listed

$3,295,000

$1,046/sq ft

HiCentral MLS #201611040

Jul 29, 2016

Sold

$1,250,000

$397/sq ft

May 26, 2016

Price Changed

$1,250,000

$397/sq ft

Apr 29, 2016

Listed

$1,300,000

$413/sq ft

HiCentral MLS #201604682

Apr 21, 2016

Listing Removed

—

Mar 7, 2016

Listed

$1,300,000

$413/sq ft

HiCentral MLS #201419645

Jan 8, 2015

Listing Removed

—

Oct 19, 2014

Listed

$1,300,000

$413/sq ft

HiCentral MLS #201325025

Jun 12, 2013

Listing Removed

—

May 28, 2013

Listed

$1,200,000

$381/sq ft

HiCentral MLS #2506209

May 31, 2005

Sold

$1,095,000

$348/sq ft

Apr 25, 2005

Listed

$1,095,000

$348/sq ft

Public Records

Feb 10, 2003

Sold

$585,000

$186/sq ft

Year

Property tax

Land + Additions

Assessment*

2022

$5,669 (+33.2%)

$1,400,000 + $319,700

$1,719,700

2021

$4,255 (+3.1%)

$1,400,000 + $319,700

$1,719,700

2020

$4,127 (−39.1%)

$1,120,000 + $195,600

$1,315,600

2019

$6,773 (−1.3%)

$1,120,000 + $159,000

$1,279,000

2018

$6,863 (+35.2%)

$1,120,000 + $96,500

$1,216,500

2017

$5,075 (+52.8%)

$1,080,000 + $182,600

$1,262,600

2016

$3,322 (+2.3%)

$950,000 + $113,900

$1,063,900

2014

$3,247 (+9.1%)

$760,000 + $122,600

$882,600

2013

$2,975 (+5.2%)

$760,000 + $167,900

$927,900

2012

$2,829

$700,000 + $150,000

$850,000

Public record

Public record
Zoning
Permits

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

10,000 Sq. Ft.

Year renovated

1957

Finished Sq. Ft.

2,440

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,440

Year built

1947

Style

Single Family Residential

County

Honolulu County

APN

1 4 2 020 082 0000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on May 2, 2026.

R-10

Residential District 10

The purpose of the Residential District is to allow for a range of residential densities. The primary use shall be detached residences. Other types of dwellings may also be allowed, including zero lot line, cluster and common wall housing arrangements. Nondwelling uses that support and complement residential neighborhood activities shall also be permitted. The intent of the R-10 districts is to provide areas for large lot developments. These areas would be located typically at the outskirts of urban development and may be applied as a transitional district between preservation, agricultural or country districts and urban districts. They would also be applied to lands where residential use is desirable but some development constraints are present.

Permitted uses

Include but are not limited to:

Housing-Single unit
Housing-Multiple units
Infrastructure-Other
Public service

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

Fire Factor

We're working on getting current and accurate fire risk information for this home.

Heat Factor

We're working on getting current and accurate heat risk information for this home.

Wind Factor

We're working on getting current and accurate wind risk information for this home.

1/10 Air Factor

Minimal risk of unhealthy air over next 30 years

Provided by First Street

Historical weather

Kailua, HI • 96734

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

95/ 100

Exceptional sunlight

Sunscore

This home ranks in the top 6% for direct sun exposure in Kailua. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.4 hrs

6.9 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 244 Awakea Rd

$2,921,568

$123K under list price of $3.05M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $1.9M to $3.9M.

SOLD OCT 13, 2026
$2,150,000 Last sold price
4 beds4 baths2,282 sq ft
415 Iana St, Kailua, HI 96734
$25/sq ft
13 years newer
SOLD OCT 7, 2026
$2,500,000 Last sold price
3 beds2.5 baths2,545 sq ft
294 Awakea Rd, Kailua, HI 96734
$15/sq ft
5 years newer
SOLD AUG 10, 2026
$3,775,000 Last sold price
5 beds3.5 baths3,512 sq ft
485 Wanaao Rd, Kailua, HI 96734
$108/sq ft
larger lot
7 years newer
SOLD SEP 21, 2026
$1,999,999 Last sold price
7 beds5 baths3,264 sq ft
646 Wanaao Rd, Kailua, HI 96734
$354/sq ft
smaller lot
59 years newer
SOLD SEP 14, 2026
$1,900,000 Last sold price
4 beds3 baths2,024 sq ft
176 Kuulei Rd, Kailua, HI 96734
$28/sq ft
larger lot
3 years newer
SOLD SEP 17, 2026
$3,910,000 Last sold price
4 beds3.5 baths2,919 sq ft
851 Aalapapa Dr, Kailua, HI 96734
$372/sq ft
smaller lot
70 years newer

Rental earnings

Est. $5,671 per month, based on comparable rentals

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Details provided by HiCentral MLS and may not match the public record. Learn more.

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About this home

Payment calculator

Affordability tools

Open houses

Nearby open houses (10)

Around this home

Schools

Market insights

Property details

Sale and tax history for 244 Awakea Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 244 Awakea Rd

This home may not be allowing tours right now

Nearby similar homes

New listings for sale in 96734

More real estate resources