in Windermere, FL • 2026 Buying Guide
Best Month
October
$734K
Avoid
September
$967K
Potential Savings
$234K
24.1% difference
Market Type
Buyer's
30.0 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
$544K
N/A YoY
Days on Market
6
median days
Inventory
30
active listings
Sale-to-List Ratio
97.3%
room to negotiate
Jan
$808K
Feb
$768K
Mar
$783K
Apr
$809K
May
$822K
Jun
$896K
Jul
$796K
Aug
$849K
Sep
$967K
PeakOct
$734K
BestNov
$854K
Dec
$761K
Based on historical sales data in Windermere
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.
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Pro Tip: With Windermere's median price at $544K, a 20% down payment would be approximately $109K. Get pre-approved early to know exactly what you can afford.
Based on our analysis of Windermere's housing market, October is typically the best time to buy a condo. During this month, prices average around $734K, which is 24.1% lower than peak prices in September. 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 Windermere is $544K. 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, Windermere is currently a buyer's market with 30.0 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 Windermere 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 Windermere currently spend an average of 6 days on market. This indicates a fast-moving market where you need to be prepared to act quickly.
Some condos may not be FHA or VA approved - check early Non-warrantable condos require conventional financing with higher down payments With Windermere's median price of $544K, you'll want to get pre-approved early to understand your budget.
Looking for the best time to buy a condo in Windermere? Our analysis shows that October typically offers the best prices, with homes averaging around $734K. Buying during this time could save you up to $234K compared to peak months like September.
With a median price of $544K and homes spending an average of 6 days on market, Windermere is currently a buyer's market. There's currently 30.0 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.
There are 9 real estate agents active in Windermere who can help you find the perfect condo. A local expert understands neighborhood nuances, pricing trends, and can help you navigate Windermere's specific market conditions.
Connect with local agents who specialize in condos.