in Wailea, HI • 2026 Buying Guide
Best Month
September
$1.03M
Avoid
June
$1.40M
Potential Savings
$378K
26.9% difference
Market Type
Buyer's
12.6 mo. supply
Buyer's markets are ideal for building your portfolio. Negotiate aggressively, look for distressed or estate sales, and consider properties that need work. Multi-unit properties offer better cash flow and economies of scale.
Median Sale Price
$1.23M
N/A YoY
Days on Market
96
median days
Inventory
226
active listings
Sale-to-List Ratio
94.6%
room to negotiate
Jan
$1.35M
Feb
$1.06M
Mar
$1.17M
Apr
$1.16M
May
$1.13M
Jun
$1.40M
PeakJul
$1.21M
Aug
$1.20M
Sep
$1.03M
BestOct
$1.22M
Nov
$1.13M
Dec
$1.16M
Based on historical sales data in Wailea
Investment property timing is about numbers, not emotions. Off-season purchases (fall/winter) often yield better cap rates because you're competing against fewer primary residence buyers. However, also consider tenant move-in timing - summer moves are easier for families.
Pro Tip: With Wailea's median price at $1.23M, a 20% down payment would be approximately $246K. Get pre-approved early to know exactly what you can afford.
Based on our analysis of Wailea's housing market, September is typically the best time to buy a investment property. During this month, prices average around $1.03M, which is 26.9% lower than peak prices in June. Investment property timing is about numbers, not emotions. Off-season purchases (fall/winter) often yield better cap rates because you're competing against fewer primary residence buyers. However, also consider tenant move-in timing - summer moves are easier for families.
The current median home price in Wailea is $1.23M. Investment Property prices vary based on location, size, and condition. Year-over-year, prices have changed N/A. Investment property returns come from both cash flow and appreciation. In high-growth markets, prioritize appreciation; in stable markets, focus on cash flow. The best investments often offer both.
Yes, Wailea is currently a buyer's market with 12.6 months of inventory. Buyer's markets are ideal for building your portfolio. Negotiate aggressively, look for distressed or estate sales, and consider properties that need work. Multi-unit properties offer better cash flow and economies of scale.
Key considerations for buying a investment property in Wailea include: Calculate cap rate, cash-on-cash return, and cash flow; Factor in realistic vacancy rates (typically 5-8%); Budget for property management (10% of rent) even if self-managing. Also watch for red flags like Seller won't provide actual expense records and Deferred maintenance that will need immediate attention.
Homes in Wailea currently spend an average of 96 days on market. This suggests a slower market where you have more time to negotiate.
Investment properties require 15-25% down typically Interest rates are 0.5-1% higher than primary residence With Wailea's median price of $1.23M, you'll want to get pre-approved early to understand your budget.
September is the current seasonal value signal for investment properties in Wailea, but the least competitive month can shift with mortgage rates, new listings, and local inventory. Track days on market and price cuts before making an offer.
A lower offer may make sense when the property has been listed longer than the local average of 96 days, has visible repair needs, or recently had a price reduction. In faster markets, strengthen the offer with clean terms rather than relying only on price.
Looking for the best time to buy a investment property in Wailea? Our analysis shows that September typically offers the best prices, with homes averaging around $1.03M. Buying during this time could save you up to $378K compared to peak months like June.
With a median price of $1.23M and homes spending an average of 96 days on market, Wailea is currently a buyer's market. There's currently 12.6 months of inventory available.
Investment property returns come from both cash flow and appreciation. In high-growth markets, prioritize appreciation; in stable markets, focus on cash flow. The best investments often offer both.
Working with a local real estate agent who knows Wailea can help you understand neighborhood dynamics, identify the best opportunities, and negotiate effectively in this market.
Connect with local agents who specialize in investment properties.