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Wailea Market Trends: What Matters to Buyers

December 4, 2025

Are you tracking Wailea listings and wondering what the numbers really mean? In a small, resort-driven market like Wailea and Wailea–Mākena, a single sale can move the charts and headlines. You deserve a simple way to read the data so you can act with confidence, whether you are buying a vacation condo or a luxury home. This guide explains the key metrics, the local forces behind them, and the buyer steps that matter most. Let’s dive in.

Read Wailea market reports

Months of inventory explained

Months of inventory (MoI) estimates how long it would take to sell all active listings at the current pace. Formula: MoI = Active listings divided by average monthly sales. As a rule of thumb, about 6 months is considered balanced, under 4 months tends to favor sellers, and over 7 to 8 months leans toward buyers.

In Wailea, treat those thresholds as directional. Small sample sizes and high-dollar sales can swing MoI quickly. Use 3 to 12 month rolling windows to smooth noise and watch the trend instead of a single month.

Absorption rate at a glance

Absorption rate shows the share of active inventory that sells each month. Formula: Monthly sales divided by active listings. It is also the inverse of MoI.

Absorption is a quick way to sense pace. Pair it with MoI for a fuller picture of supply and demand.

DOM vs Days to Contract

Days on Market (DOM) counts the days from list date to closing or removal, depending on the MLS. Days to Contract (DTC) counts from list date to accepted offer. DTC is usually a better signal of market heat because it is less affected by escrow length or relisting.

Shorter DTC hints at competition. Longer DTC suggests slower demand. In Wailea, median DOM can jump because of seasonality and small sample counts, so look at both the median and the range and note the number of sales.

PPSF the right way

Price per square foot (PPSF) is sold price divided by living area. PPSF is most useful when you compare like to like, such as condos in the same building or homes on similar lots. Always state the property type, time window, sample size, and whether the square footage source is MLS or tax records.

PPSF can mislead if you mix property types or unusual lots. For single-family homes, a large share of value may be land, location, or view. For condos, PPSF is usually more comparable because the land is shared. Luxury outliers and oceanfront sales can skew averages, so rely on medians or trimmed means that remove the very top and bottom values.

Use medians and rolling windows

Medians reduce the impact of outliers and are recommended for Wailea reporting. Trimmed means can help in very small samples. Use 3 to 12 month rolling windows for price and PPSF to smooth seasonal swings and visitor-driven bursts of activity.

Whenever you review a chart or table, confirm the time period and the sample size. A “big jump” with only a few sales can be noise, not a trend.

Local forces shaping trends

Resort and second-home influence

Wailea is a resort-oriented market with many second-home and vacation buyers. Sales cadence follows visitor seasons and discretionary timelines. This changes how quickly listings go under contract and how pricing responds to demand.

Short-term rentals and regulations

Short-term rental eligibility and compliance are major pricing factors for many condos and select homes. Permit status, HOA rules, and county regulations affect buyer demand and can support premiums for units with legal, documented rental histories. Rules can change, so verify status, occupancy, and gross revenue during due diligence.

Limited new supply and land constraints

Maui’s geography, zoning, conservation areas, and community plans limit new development along the Wailea–Mākena coast. Large new projects are rare. Land scarcity supports long-term price resilience, yet short-term liquidity can be low, especially in narrow price bands.

Seasonality and tourism demand

Visitor arrivals and flight capacity influence buyer activity. Seasonal peaks can compress DTC and lift PPSF for a few months. Compare year-over-year by the same season rather than only month-to-month snapshots.

Insurance, hazards, and compliance

Coastal exposure brings insurance considerations such as wind, flood, and coastal erosion coverage. Environmental rules and wastewater requirements can add time and cost to escrow. Expect longer due diligence timelines and factor these into offer terms.

Small samples and luxury outliers

Wailea’s total sales count is low compared to most mainland markets. A single oceanfront or off-market sale can move medians notably. Look for multi-month patterns and segment by property type and price band before drawing conclusions.

What matters to Wailea buyers

  • Segment the data. Review condos and single-family homes separately. For condos, compare by building, stack, and view corridor. For homes, compare by lot features, distance to the ocean, and view quality.
  • Track MoI with sales volume. A change in MoI is more meaningful when sales volume confirms demand rather than just a shift in listing mix.
  • Prefer DTC over DOM. DTC better captures competition. Watch both the median and the range.
  • Use medians and rolling windows. Avoid reacting to a single month. Seek 3 to 12 month rolling medians with sample sizes noted.
  • Compare season to season. Line up this winter vs last winter to account for tourism-driven timing.
  • Note PPSF context. For condos, use building-level comps. For homes, pair PPSF with lot size, orientation, and improvements.

Practical buyer checklist

Before viewing properties

  • Confirm short-term rental eligibility and permit status for each unit. Review HOA rules and any rental caps.
  • Pull recent MLS sales in the same building or block with similar features and views.
  • Compare PPSF only within true peers such as the same stack, floor, or plan.

During due diligence

  • Request HOA budgets, reserve studies, insurance policies, special assessment history, and rental occupancy data if relevant.
  • Verify wastewater compliance and any required upgrades or septic work.
  • For oceanfront or near-shore lots, confirm shoreline certification, setbacks, and any coastal erosion studies.
  • Order local inspections for structure, pests, roof, and systems. Build in time since island scheduling can run longer.

Mortgage and closing logistics

  • Ask lenders about appraisal turn times and local appraiser availability. Remote appraisals can add uncertainty.
  • Obtain insurance quotes early. Coastal properties may need specialized wind, flood, or earthquake riders.

Wailea vs mainland

  • Inventory size and volatility. Wailea has fewer listings, so medians can swing. Multi-month averages are more reliable.
  • Buyer mix. A higher share of discretionary and visitor-driven buyers means demand is tied to travel patterns as much as local employment.
  • Price composition. Location, view, and rental potential carry more weight. Separate condos from single-family homes and beachfront from inland when comparing.
  • Timelines and costs. Expect potentially longer scheduling for inspectors and contractors and consider specialized insurance needs.

Red flags to watch

  • Big jumps in median price or PPSF without a rise in sales volume. This may signal outliers rather than broad demand.
  • A high share of active listings that are rental-eligible but unpermitted. This can signal regulatory risk.
  • Falling sales volume while active listings shrink. This can reflect a pricing mismatch or buyer pullback.
  • Rising DOM with flat or falling prices. This points to waning demand or unrealistic pricing.

How Stacy helps

You want more than numbers. You want clarity, timing, and a plan that fits your lifestyle and goals. With 34 plus years on island and the reach of Coldwell Banker Global Luxury, Stacy pairs building-by-building insight with concierge coordination for local and off-island buyers.

Here is how that helps you:

  • Clean, segmented comps by property type, building, and view so you can price and negotiate with confidence.
  • Smart contract strategy that considers MoI, DTC, and seasonality to set terms that win.
  • On-island coordination of inspections, insurance quotes, vendors, and escrow so you stay on track from offer to closing.
  • Clear guidance on short-term rental rules, HOA documents, and coastal due diligence so you avoid surprises.

If you are ready to buy smart in Wailea or Wailea–Mākena, connect with Stacy Levin for tailored guidance and next steps.

FAQs

What is a good months of inventory for Wailea condos?

  • Around 6 months is commonly viewed as balanced, under 4 months tends to favor sellers, and over 7 to 8 months can favor buyers, but in Wailea treat these as directional since small samples can swing MoI.

How should I use price per square foot in Wailea?

  • Compare condos within the same building, stack, and view, and compare homes with similar lots and orientation, while stating the time window, sample size, and whether the square footage source is MLS or tax records.

Do short-term rental rules affect condo values in Wailea?

  • Yes, permit status and documented rental history can support premiums, so verify eligibility, occupancy, and gross revenue during due diligence and stay aware of county rule changes.

Why do Wailea market numbers jump month to month?

  • Wailea has few sales and many luxury outliers, so a single transaction can move medians; use medians, rolling 3 to 12 month windows, and note sample sizes.

How long does closing take for a Wailea purchase?

  • Timelines vary with inspections, appraisals, insurance, and off-island parties, so plan for longer coordination and build in time for coastal and HOA document reviews.

Work With Stacy

Whether you're looking for a luxurious residence or a small getaway, Stacy is here to make your dreams a reality with expertise and personalized care, Work with her today!

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