Loading page
Homes for Sale in Windham, NY
Mountaintop ski and rental country
Windham is one of the two mountaintop markets in Greene County, and it sells on a completely different basis from the river side of the county. Buyers here are usually weighing rental income against personal use, and the right answer depends on details that do not show up in listing photos.
On the Ground
Buying and Selling in Windham
Slope proximity drives price, but so does how the property is actually set up for winter: heat that holds when the house sits empty, water lines that do not freeze, a driveway someone plows, and a road the town maintains in February. We walk those before the numbers, because they decide whether the rental math works at all.
If there is an HOA, its rules on rentals and its reserve position matter as much as the dues figure. Short term rental rules on the mountaintop are set locally and they change, so income projections need to be built on what is permitted now, not on what a listing sheet claims a property grossed two seasons ago.
What comes up most in Windham
- Ski access property and slope proximity comparables
- Short term rental setup and realistic income expectations
- HOA rules, reserves, and rental restrictions
- Winterization, road maintenance, and seasonal access
27 Active Now
Available in Windham
See all 27 in Windham
Start Looking
Search Windham
Market Snapshot · September 2026
Greene County by the Numbers
Median Sales Price
$184,500
-38.4%
Median Price / SqFt
$203
+26.3%
Closed Sales
2
-85.7%
New Listings
8
-74.2%
Active Inventory
83
+10.7%
Median Days on Market
60 days
-37.5%
These are single family sales across all of Greene County for September 2026, not Windham alone. A village market can move very differently from its county, which is why the figures sit below the local read rather than above it. Percentages compare the same period a year earlier. Figures come from the regional MLS feed and are refreshed monthly.
Also in the Area