UNDER CONTRACT

Contingent

$2,125,000

Est. $12,143/mo —

•

2,772

sq ft

4186 Upa Rd, Koloa, HI 96756

About this home

Located in the desirable Omao neighborhood on Kauai's South Shore, this five-bedroom, four-bath residence offers a rare combination of privacy, flexibility, and island living less than ten minutes from Poipu's beaches, dining, golf, and shopping. Set on nearly half an acre of beautifully landscaped grounds, the property offers a private setting while remaining close to the area's most sought-after amenities. Centered around a sparkling swimming pool, covered lanai, and expansive outdoor living spaces, the home embraces Kauai's year-round indoor-outdoor lifestyle. Vaulted ceilings, hardwood floors, and abundant natural light create a warm and inviting atmosphere throughout the main residence. The updated kitchen features granite countertops, stainless steel appliances, and generous cabinetry, while the adjoining living and dining spaces are designed for both everyday living and entertaining. A spacious primary suite offers comfort and privacy, while the flexible floor plan provides room for guests, family, or changing lifestyle needs. Adding to the home's versatility, a separate two-bedroom wing connected by a breezeway offers exceptional flexibility as guest accommodations, a home office, creative studio, or multigenerational living space. Additional features include a 30-panel solar system, fully fenced grounds, mature fruit trees, exterior workshop and storage space, potting area, outdoor fitness space, and a two-car garage. Opportunities to own a private retreat with usable land, flexible living spaces, and resort-style amenities mere minutes from Poipu are exceedingly rare. This property offers the space, privacy, and lifestyle that make island living so special. If you would like to tour this property there are two videos for you, copy and paste this links into a new browser window: Property Overview https://bit.ly/4186UpaRoad Virtual Walk Through https://bit.ly/4186-tour

Single-familyProperty Type

1986Year Built

0.5 acresLot Size

$767Price/Sq.Ft.

2 car garageParking

Listed by Lynda Gill • Hawaii Life

Contact: 8083460056

Listing updated: Aug 5, 2026 at 05:11pm

Redfin checked: 2 minutes ago

•Source:HI Information Service #730824

Payment calculator

$12,143 per month

Principal and interest$11,168

Property taxes

$409

HOA dues

Home insurance

$567

Utilities

Add

5 minutes to get started. No credit impact.

Affordability tools

Open houses

No upcoming open houses.

Nearby open houses (6)

OPEN SUN, 10AM TO 3PM
$1,875,000
3 beds4 baths3,499 sq ft
3352 Hailima Rd, Koloa, HI 96756
OPEN SUN, 11AM TO 3PM
$859,000
1 bed1.5 baths956 sq ft
1565 Pee Rd #418, Koloa, HI 96756
OPEN AUG 31, 2PM TO 7PM3D WALKTHROUGH
$6,100,000
4 beds3 baths2,471 sq ft
2211-A Pane Rd, Koloa, HI 96756
OPEN SEP 7, 10AM TO 12PM
$650,000
2 beds1.5 baths872 sq ft
3934-E Lawehana St Unit A, Lihue, HI 96766
OPEN SEP 7, 10AM TO 1PM
$2,588,000
3 beds3 baths2,325 sq ft
4272 Iliohu Pl, Lihue, HI 96766
OPEN SEP 17, 3PM TO 6PM
$569,000
1 bed1 bath640 sq ft
2253 Poipu Rd #123, Koloa, HI 96756

Around this home

Schools

K - 12
Preschool & daycare

Koloa Elementary School

Public PreK-5 • Assigned • 2.1mi

4/10

Chiefess Kamakahelei Middle School

Public 6-8 • Assigned • 7.0mi

6/10

Kauai High School

Public 9-12 • Assigned • 8.5mi

7/10

Provided by GreatSchools

About Omao

Homesteads

Omao Homesteads, located between Koloa and Poipu, is a rural and residential Omao neighborhood with a mauka hillside setting and broad garden lots. The neighborhood’s character concentrates along Omao Road near the Omao Post Office, where mailboxes, small farm stands, and morning traffic set a practical, local rhythm. Homes read as plantation-influenced and island-ranch, with carports, lanais, and mature fruit trees shaping the streetscape. Daily errands often orbit Old Koloa Town’s independent storefronts and cafes rather than big-box corridors. For a cultural anchor, Kauai Coffee Company and the Shops at Kukuiula add tastings, galleries, and low-key events within a short drive. Outdoor time tends to follow the South Shore’s beaches and the greenbelt feel of nearby open land.

Provided by Walk Score and Local Logic

Market insights

4186 Upa Rd · $2,125,000

DAYS ON MARKET

The average home goes pending in 97 days.

SALE-TO-LIST

Most homes are selling 2% below list price.

LIST PRICE

Median sale price in this area is $1,176,874. (45% lower than this home)

PRICE DROP

20% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Hardwood and laminate flooring

Bathrooms
Four full bathrooms

Kitchen
Range
Microwave hood
Dishwasher
Disposal
Refrigerator

Laundry & utility
Washer
Dryer
Stacked washer/dryer

Flooring
Hardwood
Laminate

Heating & cooling
Wall/window unit(s) for cooling

Sale and tax history for 4186 Upa Rd

Sale History
Tax History

Date

Event

Price

HI Information Service #730824

Aug 5, 2026

Contingent

—

Aug 5, 2026

Relisted

—

Jul 18, 2026

Contingent

—

Jun 9, 2026

Listed

$2,125,000

$767/sq ft

HI Information Service #644999

Jan 28, 2021

Sold

$1,149,000

$415/sq ft

Dec 9, 2020

Listed

—

Dec 9, 2020

Listed

$1,149,000

$415/sq ft

+25

SPACIOUS OMAO HOME, MOSTLY SINGLE LEVEL, WITH SWIMMING POOL AND PHOTOVOLTAIC SITUATED ON A HALF ACRE LOT!This special property is sure to check a lot of the boxes on your wish list starting with the half acre lot (21,780 sq ft) that provides lots of privacy! The floorpan of this home is all single level with the exception of one bedroom located on the second floor. The configuration is ideal for extended family or guests. The living area has high vaulted ceilings, hardwood flooring, and a large built in bookcase/shelving unit. The sliding glass doors and windows provide lots of natural light and nice views of the beautiful backyard and swimming pool. The updated kitchen has granite countertops, stainless steel appliances, and an abundance of cabinetry for storage and pantry items. Some of the many features include: * 5BR/4BA * 21,780sf Lot * Swimming Pool * Photovoltaic (30 Panels) * Gas Hot Water Heater, Dryer, and Range * Oversized Primary Bedroom Suite * Walk-in Closet * Lots of Storage Space * Window A/C Units (In 3 Bedrooms) * Skylights * Ceiling Fans * Backyard Storage Shed/Workshop * Outdoor Sink/Potting Bench * Backyard Pergolas * Fruit Trees (Lemon, Orange, Tangerine, Mango) * Fully Fenced * Lots of Privacy * Two Car GarageView the 3D Matterport Tour by copying and pasting this link: https://my. matterport.com/show/ ?m=ggmSbBrebin & brand=0 & mls=1 &

HI Information Service #279321

Aug 20, 2015

Sold

$730,000

$263/sq ft

Jul 2, 2015

Contingent

—

Jun 24, 2015

Relisted

—

Jun 24, 2015

Listing Removed

—

May 13, 2015

Listed

$825,000

$298/sq ft

+15

Enchanting home with resort style back yard. . . . . custom pool, lanai and tropical landscaping. This is a 4br/3.5ba home on nearly 1/2 an acre offers lots of room and privacy. A fully upgraded kitchen includes granite counter tops, oak cabinets with custom lighting and SS appliances. Floors in kitchen and living area are oak & rosewood, SOLID HARDWOOD not veneer! Living area is huge with vaulted and exposed beam ceiling that overlooks the pool and tropical landscaping. ~~~~ SOLAR VOLTAIC SYSTEM ~~~~~ 15 panels 3.5KW The creative floor plan offers many choices on how to enjoy this large home and maximize the square footage. So many great features and a must see home!

HI Information Service #274537

Jun 18, 2014

Listed

$995,900

$359/sq ft

HI Information Service #143475

Mar 30, 2005

Sold

$995,000

$359/sq ft

Oct 1, 2004

Listed

$995,000

$359/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$5,083 (+3.6%)

2025

$4,908 (+3.6%)

2024

$4,738 (−2.8%)

2023

$4,876 (+3.4%)

2022

$4,715 (+1.2%)

2021

$4,661 (+3.3%)

2020

$4,510 (+0.2%)

2019

$4,502 (+3.4%)

$388,400 + $607,700

$996,100

2018

$4,355 (+3.4%)

$379,100 + $615,300

$994,400

2017

$4,213 (+3.1%)

$374,900 + $590,500

$965,400

2016

$4,086 (−29.5%)

$388,400 + $548,900

$937,300

2014

$5,797 (+18.4%)

2013

$4,895 (+77.1%)

2012

$2,764

$284,800 + $489,900

$774,700

Public record

Public record
Zoning

Beds

Baths

2.5

Stories

1.5

Lot width

—

Lot depth

—

Lot size

0.5 Acres

Year renovated

1990

Finished Sq. Ft.

2,132

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,132

Year built

1986

Style

Single Family Residential

County

Kauai County

APN

4 270080470000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 7, 2026.

R-2

Residential District - 2 DU per Acre

The Residential District regulates the number of people living in a given area by specifying the maximum allowable number of dwelling units that may be developed on any given parcel of land. In order not to differentiate between economic groups or life-styles, a reasonable flexibility in the type of dwelling units and their placement on the land has been provided; to establish standards governing the development, construction and use of housing and dwelling facilities; to provide opportunity for all groups of persons to obtain adequate housing within each area of the County suitable for residential use in relation to other land uses and consistent with the preservation of natural, scenic, and historic resources; to establish the level of minimum services necessary to assure the adequacy of housing; to encourage a variety of housing types, sizes and densities necessary to meet the needs of all economic groups and to avoid environmental monotony detrimental to the quality of life; and to maintain the character and integrity of communities within residential districts and support residents in continuing to live and raise their families in these neighborhoods.

Permitted uses

Include but are not limited to:

Housing-Single unit
Housing-Multiple units
Housing-Senior
Park & open space

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

Koloa, HI • 96756

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

97/ 100

Exceptional sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8 hrs

6.9 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 4186 Upa Rd

$2,084,850

$40K under list price of $2.13M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $1.2M to $2.9M.

SOLD JUN 22, 2026
$1,850,000 Last sold price
4 beds3 baths2,714 sq ft
4179 Puu Pinao Way, Koloa, HI 96756
$85/sq ft
1 year newer
SOLD NOV 21, 2025
$1,285,000 Last sold price
3 beds3.5 baths1,822 sq ft
3470 Lawailoa Ln, Koloa, HI 96756
$62/sq ft
smaller lot
6 years older
SOLD MAY 21, 2026
$1,880,000 Last sold price
3 beds2 baths2,196 sq ft
5025 Kikala Rd, Kalaheo, HI 96741
$89/sq ft
larger lot
16 years newer
SOLD MAR 11, 2026
$2,900,000 Last sold price
3 beds3 baths2,763 sq ft
5387 Milo Hae Pl, Koloa, HI 96756
$283/sq ft
smaller lot
3 years newer
SOLD JUL 17, 2026
$2,224,000 Last sold price
3 beds3.5 baths3,074 sq ft
1161 Nohea St, Kalaheo, HI 96741
$44/sq ft
smaller lot
19 years newer
SOLD AUG 11, 2026
$1,240,000 Last sold price
2 beds3 baths1,536 sq ft
3695 Waha Rd, Kalaheo, HI 96741
$40/sq ft
smaller lot
3 years newer

Rental earnings

Est. $4,986 per month, based on comparable rentals

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3D WALKTHROUGH

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3559 Hanapepe Rd #3, Hanapepe, HI 96716

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VIDEO TOUR

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New listings for sale in 96756

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VIDEO TOUR

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2253 Poipu Rd #216, Koloa, HI 96756

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5061 Lawai Rd #337, Koloa, HI 96756

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2721 Poipu Rd #423, Koloa, HI 96756

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5015 Lau Nahele St, Koloa, HI 96756

OPEN SUN, 10AM TO 3PM

$1,875,000

3 beds4 baths3,499 sq ft

3352 Hailima Rd, Koloa, HI 96756

$2,000,000

3 beds3 baths2,014 sq ft

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Details provided by HI Information Service 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 (6)

Around this home

Schools

Market insights

Property details

Sale and tax history for 4186 Upa Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 4186 Upa Rd

This home may not be allowing tours right now

Nearby similar homes

New listings for sale in 96756

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