Browse Condo Guides on the map
Kaanapali Hillside • Kaanapali
Gated • Luxury • Owner-Oriented Community
18 active listings • Median ~$1.4M • Avg DOM ~144
Masters at Kaanapali is better understood as a residential West Maui condo community than a generic vacation-rental play. Buyers here are usually weighing everyday livability, owner-occupant feel, HOA structure, parking, pet rules, and how the building compares with other residential options in Kaanapali.
Explore current listings, recent sales, and ownership insights for Masters at Kaanapali in Kaanapali, Maui.
See active listings at Masters at KaanapaliWest Maui Condo GuideMarket intelligenceCompare Condo CommunitiesCompare Masters at Kaanapali to nearby picks
Building-level facts for Masters at Kaanapali—ownership, rental posture, HOA context, and scale. Unit-specific tenure, fees, and rental status can differ; confirm on the listing and in AOAO documents.
Verify before relying on this for purchase or rental decisions. Confirm material facts with AOAO documents, MLS listing packages, and Maui County records before you offer or model rental income.
We can help you request AOAO packages, interpret rental posture, and line up recent sales against the unit you are considering—before you write an offer.
Masters at Kaanapali is a gated, luxury, and residential-feel condo community in Kaanapali. It is well suited to buyers who want a more residential West Maui setting, everyday livability, and fee simple ownership. Built in 1991 with about 200 units.
Masters at Kaanapali is primarily a residential Kaanapali community. If rental income matters, confirm what is actually permitted for the unit—many buyers here prioritize owner-use and long-term hold over nightly turnover.
Highly regarded gated hillside community with strong owner-occupant and second-home appeal.
Ownership for Masters at Kaanapali is summarized as Fee Simple. Leasehold and fee-simple carry different financing and long-term cost profiles—confirm the interest conveyed on the unit you are buying.
Pricing is hovering near $1,395,000 across this MLS slice—model HOA, taxes, and financing before banking on rent.
Gated • Pool • Tennis courts • Panoramic views
Day-to-day life at Masters at Kaanapali is shaped by Kaanapali: a comparatively residential day-to-day cadence within West Maui. Expect a profile that often reads as gated • luxury • owner-oriented community—helpful orientation, not a substitute for a showing.
Walkability, parking, and resort traffic ebb and flow with season—visit at different times of day if Masters at Kaanapali is a serious contender.
Buyers who want Kaanapali Hillside positioning with clear community character often shortlist Masters at Kaanapali—especially when town-adjacent convenience and neighborhood texture matches their goals.
Fee-simple ownership appeals to many primary and second-home buyers who prefer a traditional fee-simple interest.
Buyers who want a calmer owner profile should confirm rental rules and policies against how long they plan to hold.
Investors typically weigh Masters at Kaanapali on documented STR posture (No), guest demand in Kaanapali, and how reserves and assessments fit the model.
Zoning is listed as Residential—use it as context, then confirm how it interacts with association rules and county requirements for your intended use.
Underwriting should stay unit-specific: two stacks in the same building can perform very differently.
Derived from West Maui MLS matches for Masters at Kaanapali; figures shift as inventory turns.
Median (MLS blend)
$1,395,000
$ / sqft (range)
$661–1,437/sqft
Avg. days on market
~144
Active listings
18
Closed sales (12 mo)
11
Pricing in the current MLS window clusters near a $1,395,000 midpoint when blending active and recent closed activity. Several active options give buyers room to compare floor plans and views before deciding.
Expect a wide $661/sqft–$1,437/sqft /sqft band as views and floor plans diverge.
Expect closer to 144 days on market in this slice—buyers have runway to compare, negotiate, and line up financing.
There is evidence of negotiation in this window—worth comparing each comp’s starting ask vs closed figure with your advisor.
Masters at Kaanapali’s MLS footprint includes 1-bedroom, 2-bedroom, and 3-bedroom residences, with marketing language often referencing ocean-oriented, resort-view, golf angles. Views and floor plans vary by stack—confirm on each listing.
In current and recent marketing copy, generous lanai space, ocean views, interior updates, beach proximity, and furnished interiors surface repeatedly—useful signal, but confirm on the unit you pursue.
Want help evaluating this?
Based on current listings, pricing trends, and overall value within this building.
$1,295,000
2 bd · 2 ba · 1,269 sq ft
Strong rental-ready context
Masters at Kaanapali 1707
$1,999,000
2 bd · 3 ba · 1,850 sq ft
Standout views & premium positioning
Masters at Kaanapali 3404
$998,888
2 bd · 2 ba · 1,512 sq ft
Best value in the building right now
Masters at Kaanapali 1803
$1,300,000
2 bd · 2 ba · 1,728 sq ft
Best value in the building right now
Masters at Kaanapali 2206
$750,000
1 bd · 1 ba · 901 sq ft
Standout views & premium positioning
Masters at Kaanapali 4203
Want help deciding if this is worth it?
Book a Quick BreakdownClosed sales at Masters at Kaanapali from the MLS (rolling 12-month window — same basis as the market snapshot above).
11 closed sales at Masters at Kaanapali in the last 12 months.
Recent sales at Masters at Kaanapali set the anchor—but view, floor, renovation, and rental status still move the number. We will compare your unit to active and pending competition before you list.
Masters at Kaanapali is located in Kaanapali Hillside, within Lahaina. Kaanapali ties into West Maui beaches, dining, and resort corridors; drive times shift with traffic and season. Use the map for orientation, then validate commute and access on your own visits.
Kaanapali pairs a long beach walk with golf-adjacent resort pockets and Whalers Village–style shopping—useful context when comparing foot traffic and owner-use versus guest nights.
Kaanapali • Kaanapali Hillside
50 Puu Anoano St
See where Masters at Kaanapali sits relative to nearby resorts, beaches, and West Maui condo communities.
Masters at Kaanapali in Kaanapali deserves the same diligence as any Maui condo: understand construction era (year built near 1991), community scale (~200 units), 2 floors, and how those factors influence maintenance, insurance, and long-term upkeep.
Zoning (Residential) frames common use patterns in the area; buyers should still reconcile zoning with HOA rules and county requirements for any intended use.
Insurance, windstorm exposure, and building-wide projects can move assessments. Review the latest association financials, reserve study, and meeting minutes where available—Masters at Kaanapali is no exception.
Facts on this Masters at Kaanapali guide are drawn from the Aina building dataset, West Maui MLS activity shown on this page, and editorial review. Material items—zoning, transient rental eligibility, HOA fees, special assessments, and insurance—must be confirmed with AOAO documents, listing packages, and Maui County records before you rely on them for a purchase, sale, or rental decision.
Last guide review: 2026-07-05. Market metrics refresh as MLS inventory changes.
Related market guides
This page is market education from a licensed Hawaii real estate brokerage—not legal, tax, or investment advice. Equal Housing Opportunity.
Masters at Kaanapali short-term rental status: Residential / likely no STR.
Masters at Kaanapali ownership type is listed as Fee Simple.
Suitability depends on timeline, financing, and tolerance for HOA costs and rental regulation. Highly regarded gated hillside community with strong owner-occupant and second-home appeal. Review association documents, rental rules, and recent sales with a licensed professional—avoid treating any building as a generic “yes” or “no.”
We do not flag Masters at Kaanapali as oceanfront; many units may still capture ocean or partial views. Confirm on the unit you are considering.
Short-term rental posture is summarized as: No. Confirm current association and county requirements before marketing a rental.
Ownership type is listed as Fee Simple. Confirm the interest conveyed on your purchase contract and title report.
Masters at Kaanapali includes amenities such as: Gated • Pool • Tennis courts • Panoramic views
Masters at Kaanapali is in Kaanapali (Kaanapali Hillside). Buyers often weigh beach access, walkability, and drive time to Lahaina, Kaanapali, and Kapalua depending on lifestyle.
Year built is listed near 1991. Phasing and renovations may span multiple years—confirm for your building section.
Within Kaanapali, in the Kaanapali Golf Resort area, buyers trade beachfront intensity for fairway tranquility, larger low-rise floor plans, and walkable access to beaches via resort paths or short drives. Maui Eldorado, Kaanapali Royal, and Kaanapali Plantation each sit in a different lane—leasehold rental value, golf-course residential scale, and low-density hillside views.
Comparison here is often about tenure and lifestyle rhythm: leasehold economics versus fee simple, cart-friendly residential pace versus beach-tower guest volume, and how much sand proximity you need daily versus a few times a week. Nearby communities such as The Vintage at Kaanapali, Honua Kai, International Colony Club are common cross-shops when pricing overlaps.
Golf Resort buyers usually compare two or three communities on tenure, views, and beach access before they pick a stack.
We can help you review listings, compare listings side by side, and understand how Masters at Kaanapali fits your goals.
