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Under contract
$2,125,000
5beds
2,772sqft

4186 Upa Rd, Koloa, HI 96756

5beds
2,772sqft
Single family residence
Built in 1986
0.50 Acres
2 Garage spaces
$767 price/sqft

What's special

Sparkling swimming poolCovered lanaiTwo-car garageFully fenced groundsPotting areaVaulted ceilingsAbundant natural light

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

97 days
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108
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0
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Source: Hawaii Information Service,MLS#: 730824MLS Logo
Travel times

Living Room

Kitchen

Primary Bedroom

Zillow last checked:

Listing updated:

Listed by:

Lynda Gill 8083460056,

Hawaii Life

Source: Hawaii Information Service,MLS#: 730824MLS Logo

Facts & features

Interior

Bedrooms & bathrooms
  • Bedrooms: 5
  • Bathrooms: 4
  • Full bathrooms: 4
Cooling
  • Wall/Window Unit(s)
Appliances
  • Included: Dishwasher, Disposal, Dryer, Microwave Hood, Range, Refrigerator, Washer, Washer/Dryer Stacked
Features
  • Flooring: Hardwood, Laminate
  • Has fireplace: No
Interior area
  • Total structure area: 2,772
  • Total interior livable area: 2,772 sqft
Video & virtual tour

Property

Parking
  • Total spaces: 2
  • Parking features: Attached, Unassigned
  • Garage spaces: 2
Features
  • Pool features: In Ground
  • Fencing: Full,Wood
  • Has view: Yes
  • View description: Garden
Lot
  • Size: 0.5 Acres
Details
  • Parcel number: 4270080470000
  • Zoning: R-2
  • Special conditions: Fee Simple,Standard

Construction

Type & style
  • Home type: SingleFamily
  • Property subtype: Single Family Residence
Condition
  • Year built: 1986

Utilities & green energy

  • Sewer: Cesspool
  • Utilities for property: Cable Available, Electricity Available, Phone Available

Community & HOA

Community
  • Subdivision: PUU PINAO SUBDIVISION
Location
  • Region: Koloa

Financial & listing details

  • Price per square foot: $767/sqft
  • Tax assessed value: $1,189,600
  • Annual tax amount: $4,908
  • Date on market: 6/10/2026
  • Listing terms: 1031 Exchange,Cash,Conventional
  • Ownership: Full
  • Electric utility on property: Yes
  • Road surface type: Paved

Price history

DateEventPrice
8/6/2026Contingent$2,125,000$767/sqft
Source: Hawaii Information Service #730824 Report a problem
8/5/2026Listed for sale$2,125,000$767/sqft
Source: Hawaii Information Service #730824 Report a problem
7/19/2026Contingent$2,125,000$767/sqft
Source: Hawaii Information Service #730824 Report a problem
6/10/2026Listed for sale$2,125,000+84.9%$767/sqft
Source: Hawaii Information Service #730824 Report a problem
1/28/2021Sold$1,149,000$415/sqft
Source: Hawaii Information Service #644999 Report a problem
1/5/2021Contingent$1,149,000$415/sqft
Source: Hawaii Information Service #644999 Report a problem
12/9/2020Pending sale$1,149,000$415/sqft
Source: RE/MAX Kauai Living - Poipu #644999 Report a problem
12/9/2020Listed for sale$1,149,000+57.4%$415/sqft
Source: RE/MAX Kauai Living - Poipu #644999 Report a problem
8/20/2015Sold$730,000-11.5%$263/sqft
Source: Hawaii Information Service #279321 Report a problem
7/2/2015Pending sale$825,000$298/sqft
Source: Century 21 All Islands - Princeville #279321 Report a problem
5/8/2015Price change$825,000-5.7%$298/sqft
Source: Century 21 All Islands - Princeville #279321 Report a problem
3/25/2015Price change$875,000-10.3%$316/sqft
Source: Century 21 All Islands #279321 Report a problem
3/19/2015Price change$975,000+8.3%$352/sqft
Source: CENTURY 21 All Islands #279321 Report a problem
1/10/2015Price change$899,950-7.7%$325/sqft
Source: Century 21 All Islands #279321 Report a problem
12/3/2014Price change$975,000-2.1%$352/sqft
Source: Century 21 All Islands #279321 Report a problem
10/25/2014Price change$995,900-13.3%$359/sqft
Source: Sleeping Giant Sotheby's International Realty #274537 Report a problem
9/19/2014Price change$1,149,000-2.7%$415/sqft
Source: Debra H. Blachowiak #274537 Report a problem
6/19/2014Listed for sale$1,181,000+18.7%$426/sqft
Source: Debra H. Blachowiak #274537 Report a problem
3/30/2005Sold$995,000$359/sqft
Source: Public Record Report a problem

Public tax history

YearProperty taxesTax assessment
2025$4,908 +3.6%$1,154,900 +3%
2024$4,738 -2.8%$1,121,200 +3%
2023$4,876 +3.4%$1,088,500 +3%
2022$4,715 +7.8%$1,056,700 +3%
2021$4,373 -3%$1,026,000 +3%
2020$4,510 $996,100 +0.2%
2019-- $994,400 +3%
2018$4,355 +3.4%$965,400 +24.2%
2017$4,213 +125.9%$777,300 +3.4%
2016$1,865 $752,100 -16.3%
2015$1,865 -30.1%$898,800 +10.3%
2014$2,670 $815,100 +12.2%
2013-- $726,700 +6.8%
2012-- $680,200 +11.8%
2011-- $608,200 -1.9%
2010-- $620,000 -16.9%
2009-- $746,500 -6.4%
2008-- $797,200 -7.5%
2007-- $861,900 +2.6%
2006-- $840,100 +118.1%
2004-- $385,200 +15.2%
2003-- $334,500 +2.8%
2002$1,288 $325,400 -21.3%
2000-- $413,300 +3.5%
1999-- $399,200

Find assessor info on the county website

Monthly payment

Est. payment
$11,365/mo
Principal & interest
$10958
Property taxes
$407
More affordability toolsChevron Right

Estimated market value

$2,039,000

$1.94M - $2.14M

$7,355/mo

Climate risks

Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.

Neighborhood: 96756

Nearby schools

Koloa Elementary School
Grades PK-52.1 miles
4/10
GreatSchools® Rating
Test Score Rating
6/10
Student Progress Rating
2/10
Chiefess Kamakahelei Middle School
Grades 6-87 miles
6/10
GreatSchools® Rating
Test Score Rating
7/10
Student Progress Rating
4/10
Kauai High School
Grades 9-128.5 miles
7/10
GreatSchools® Rating
Test Score Rating
5/10
College Readiness Rating
8/10