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
With elevated inventory levels, you have excellent negotiating leverage. Request HOA financial records, push for seller credits toward closing costs, and don't hesitate to negotiate on price. Multiple units may be available in the same building, giving you options.
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
Condos often have a counter-cyclical market. While families focus on single-family homes during spring and summer, condo inventory can peak in fall and winter. This means less competition and more negotiating power for condo buyers during traditionally "slow" seasons.
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 condo. During this month, prices average around $1.03M, which is 26.9% lower than peak prices in June. Condos often have a counter-cyclical market. While families focus on single-family homes during spring and summer, condo inventory can peak in fall and winter. This means less competition and more negotiating power for condo buyers during traditionally "slow" seasons.
The current median home price in Wailea is $1.23M. Condo prices vary based on location, size, and condition. Year-over-year, prices have changed N/A. Condos typically appreciate more slowly than single-family homes but offer lower entry costs and maintenance. Location within the building matters - higher floors and better views command premiums.
Yes, Wailea is currently a buyer's market with 12.6 months of inventory. With elevated inventory levels, you have excellent negotiating leverage. Request HOA financial records, push for seller credits toward closing costs, and don't hesitate to negotiate on price. Multiple units may be available in the same building, giving you options.
Key considerations for buying a condo in Wailea include: Review at least 3 years of HOA meeting minutes for hidden issues; Check the reserve fund percentage (ideally 70%+ funded); Verify what insurance the HOA covers vs. what you need. Also watch for red flags like HOA with less than 50% reserves and Multiple units for sale in same building (could indicate problems).
Homes in Wailea currently spend an average of 96 days on market. This suggests a slower market where you have more time to negotiate.
Some condos may not be FHA or VA approved - check early Non-warrantable condos require conventional financing with higher down payments 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 condos 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 condo 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.
Condos typically appreciate more slowly than single-family homes but offer lower entry costs and maintenance. Location within the building matters - higher floors and better views command premiums.
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 condos.