Set across 16 fully fenced and gated acres in Ha'iku, this expansive Maui estate offers privacy, substantial infrastructure, multiple structures, and considerable flexibility. The property is served by a County of Maui 5/8-inch water meter and a high-capacity well nearing completion, and is potentially subdividable subject to applicable County approvals. More than 20 varieties of mature exotic fruit trees and flowering plants are established throughout the grounds, with walking paths connecting the residences and amenities. At the center of the property is a 5,000+ square-foot main residence with five bedrooms, three bathrooms (two are large/bathhouse style), and a spacious commercial-type kitchen. The primary suite is surrounded by walls of glass overlooking the tropical landscape. The living room features a fireplace and concealed projection screen, while a large screened lanai provides additional space for dining and entertaining. A landscaped courtyard with a cascading waterfall and koi pond leads to trails winding throughout the property. A separate commercial-grade kitchen, adjoining screened gathering area, and dedicated men's and women's bathhouses reflect the property's history as a retreat destination and provide additional flexibility for larger gatherings. Additional structures include a two-room cottage currently used as an office, an upper guest cottage with a private outdoor shower house, and a separate two-story building tucked toward the rear of the acreage. These spaces provide options for guests, offices, studios, workshops, storage, or other uses. Outdoor amenities include a resort-style swimming pool with a waterfall and slide, pool house, massage pavilion, and extensive landscaped grounds. The estate is offered fully furnished, including more than $150,000 in furnishings, artwork, and antiques, with appraisals available. With 16 acres, multiple structures, established infrastructure, extensive landscaping, and potential subdivision opportunities, this Ha'iku property offers a range of possibilities as a private estate, multigenerational compound, creative retreat, or long-term Maui investment.
Ulumalu Ahupua`a, located between Haiku Road and the slopes of Haleakalā, is a rural and agricultural Haiku-Pauwela neighborhood with wide pasture views and a trade-wind, upcountry feel. The area reads as a patchwork of small farms, gulches, and long driveways, with homes ranging from plantation-era cottages to newer hillside builds. The neighborhood’s character concentrates around the Haiku Road and Kokomo Road junction, where a low-key cluster of local storefronts and coffee counters sets the daily rhythm. Colleen’s at the Cannery, Haiku Marketplace, and the Haiku Community Center act as familiar gathering points for meals, errands, and events. Life here tracks the landscape—green after rain, sunlit by late afternoon, and framed by distant ocean glimpses. Roadside fruit stands and garden gates reinforce a working-country atmosphere rather than a resort one.
Provided by Walk Score and Local Logic
Offer insights
1055 Kaupakalua Rd · $2,995,000
$2.93M and above
75% chance or better to win
Why $2.93M+ is a strong offer
DAYS ON MARKET
205 days
The average home goes pending in 83 days.
SALE-TO-LIST
96.9%
Most homes are selling 3% below list price.
About offer insights
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Interior features
Ceiling fans
Furnished
Kitchenware provided
Sauna
Fireplace
Bedrooms
Master bedroom on ground level
Bathrooms
3 total bathrooms
Kitchen
Dishwasher
Microwave
Range
Refrigerator
Laundry & utility
Dryer
Solar hot water
Flooring
Wood floors
Tile floors
Heating & cooling
Fireplace heating
Solar water heating
Exterior features
In-ground pool
Wall/fence
Mountain and ocean views
Public water
Home design
Single family residence
One story
Residential property
Built in 1975
Parking
No garage
Construction
Living area approximately 4,550
Driveway easement
Utilities
Public water
Financial info
Fee simple ownership
Electricity and solar
View estimated energy costs and solar savings for this home
This is the secret Haiku retreat that delighted visitors for 30 years. Revitalized, upgraded and downright enchanting, this is a must for your wellness clients to see as it has everything they will want: seclusion, privacy, spacious and luxurious movement rooms, a commercial kitchen with screened reception area, pool with water slide, hot tub, massage pavilion, private cabins and hiking trails. The main pavilion is a tropical ‘mountain lodge’ with two spacious bedrooms. The screened lanai converts from reception/game room to a dining room in short order and the 1000+ sq. ft. multi-purpose room (with sprung floor) works for dance, yoga, meditation and movie shows. The fireplace lounge is ideal for reading and relaxing. This building has a new roof, drywall, pine ceiling, electric wiring and lighting. Movie buffs will appreciate the overhead movie projector with dropdown screen and Bose surround-sound system. There is a courtyard with a waterfall/koi pond and next to that is a six-stall bathhouse. The swimming pool with water slide is very private as are the changing rooms, hot tub and along massage gazebo. A two-story art building has a potting studio and kiln downstairs and office above. The 16+ acres of land bordered by 30 acres of (optional)lease land. NOTE: Maui has no zoning that allows for retreats, nor is there a special use permit for retreats in agriculturally zoned areas. All of the smaller units are unpermitted and some may be non-conforming. Property to be sold in "AS IS" condition.
RAM MLS #321540
Jul 11, 2007
Listing Removed
—
Dec 11, 2006
Listed
$2,950,000
$648/sq ft
Public Records
Jul 29, 2003
Sold
$2,075,000
$456/sq ft
RAM MLS #222953
Oct 22, 2002
Listed
$2,400,000
$527/sq ft
RAM MLS #215725
Oct 27, 2002
Listing Removed
—
Mar 20, 2001
Listed
$2,400,000
$527/sq ft
Year
Property tax
Land + Additions
Assessment*
2026
$36,531 (+621.0%)
$1,899,900 + $1,587,200
$3,487,100
2025
$5,067 (+1.0%)
$1,899,900 + $1,587,200
$3,487,100
2024
$5,018 (+10.5%)
$1,899,900 + $1,323,400
$3,223,300
2023
$4,540 (+6.0%)
$1,646,600 + $1,262,600
$2,909,200
2022
$4,284 (−11.1%)
$1,355,300 + $1,264,800
$2,620,100
2021
$4,819 (+4.0%)
$1,139,900 + $1,147,500
$2,287,400
2020
$4,633 (−49.3%)
$1,051,800 + $1,066,600
$2,118,400
2019
$9,134 (−2.3%)
$1,183,200 + $835,800
$2,019,000
2018
$9,349 (+26.2%)
$1,314,700 + $223,000
$1,537,700
2017
$7,410
$979,600 + $253,400
$1,233,000
Public record
Public record
Zoning
Permits
Beds
8
Baths
1
Stories
1
Lot width
—
Lot depth
—
Lot size
16.03 Acres
Year renovated
2000
Finished Sq. Ft.
4,550
Unfinished Sq. Ft.
—
Total Sq. Ft.
4,550
Year built
1920
Style
Single Family Residential
County
Maui County
APN
270130500000
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 14, 2026.
AG
Agricultural District
The purpose of the agricultural district is to: Implement chapter 205, Hawai'i Revised Statutes, and the goals and policies of the Maui County general plan and community plans; Promote agricultural development; Preserve and protect agricultural resources; and Support the agricultural character and components of the County's economy and lifestyle; It is the intent of this chapter to: Reduce the land use conflicts arising from encroachment of nonagricultural uses into agricultural areas; Mitigate rising property values of farm lands to make agricultural use more economically feasible; Discourage developing or subdividing lands within the agricultural district for residential uses, thereby preserving agricultural lands and allowing proper planning of land use and infrastructure development; Discourage establishment of nonagricultural subdivisions; Ensure that the rezoning of land from the agricultural district shall be open for public debate and in the overall public interest, as evidenced by conformance with the Maui County general plan and community plan land use designations and policies, State land use law, this chapter and good planning practices; and Notify the public that lands within the agricultural district are used for agricultural purposes. Owners, residents, and other users of such property or neighboring properties may be subjected to inconvenience, discomfort, and the possibility of injury to property and health arising from normal and accepted agricultural practices and operations. Such normal and accepted agricultural practices and operations include but are not limited to noise, odors, dust, smoke, the operation of machinery of any kind, including aircraft, and the storage and disposal of manure. Owners, occupants, and users of such property or neighboring properties shall be prepared to accept such inconveniences, discomfort, and possibility of injury from normal agricultural operations.
Permitted uses
Include but are not limited to:
Agriculture
Livestock production
Infrastructure-Other
Park & open space
Nov 18, 2025 • Final
Electrical permit - residential
Install an entry and exit gate for a residence.
Electrical
Oct 30, 2024 • Final
Building permit - new/addition/alteration
Construct a pool equipment building.
Pool and hot tub
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
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
Haiku, HI • 96708
Average low and high temperatures (°F)
73
60
72
59
72
62
74
62
74
63
76
65
77
66
79
66
79
66
77
65
75
63
74
62
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
95/ 100
Exceptional sunlight
Sunscore
There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9 hrs
6.7 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 1055 Kaupakalua Rd
$2,941,761
$53K under list price of $3.00M
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $1.8M to $3.3M.