Haiku

1055 Kaupakalua Rd, Haiku, HI

Listing Price: $2,995,000

5

Beds

3

Baths

4,550

Square feet

16.03

Acres

About 1055 Kaupakalua Rd

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.

View Similar Properties For Sale

Haiku Real Estate

1055 Kaupakalua Rd

This property for sale at 1055 Kaupakalua Rd is listed for $2,995,000.00 and has been on the market for 212 day(s). It is a Fee Simple property located in Haiku on Maui. It features 5 bedroom(s) and 3.00 bathroom(s) with 4550 square feet of living space. To ask a question or to schedule a showing of this property or any other property on Maui, please contact Evan Harlow with Coldwell Banker Island Properties at 808-214-4799 or email Evan directly at evan@mauieliteproperty.com.

Facts & Features

MLS® # 408773
Price $2,995,000
Bedrooms 5
Bathrooms 3.00
Square Footage 4,550
Land Tenure Fee Simple
Acres 16.03
Year Built 1975
Type Residential
Sub-Type SF w/Det Ohana or Cottage
Status Active
Property Tax View Records
Short-Term Rental Allowed No

Price History For 1055 Kaupakalua Rd

Date Details Change
Date: 07/08/2026 Details: Price decreased from $3,950,000 to $3,495,000 Change: ↓ $455,000
Date: 09/01/2026 Details: Price decreased from $3,495,000 to $2,995,000 Change: ↓ $500,000

Community Information

Address 1055 Kaupakalua Rd
Area Haiku
City Haiku
State HI
Zip Code 96708

Amenities

Parking No Garage
View Mountain/Ocean
Is Waterfront No
Waterfront None
Has Pool Yes
Pool In Ground

Interior

Interior Features Ceiling Fan(s), Furnished, Kitchen Ware, Sauna
Appliances Dishwasher, Dryer, Microwave, Range, Refrigerator, Solar Hot Water
Fireplace Yes
Stories One

Additional Information

Date Listed February 16th, 2026
Days on Market 212
Short Sale No
RE / Bank Owned No
Tax Map Key 2270130500000

Listing Details

OfficeHawaii Life (W)
Office ContactCell: 808-283-2222

Listing Map

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