Where Conroy-Windermere Road enters Windermere town limits, it reduces to one lane in each direction. Traffic is currently warned about the closure of Main Street.
As of the censusGR2 of 2000, there were 1,897 people, 704 households, and 561 families residing in the town. The population density was 654.0/km² (1,688.2/mi²). There were 723 housing units at an average density of 249.2/km² (643.4/mi²).
This sign welcomes drivers on Conroy-Windermere Road to Windermere.
There were 704 households out of which 36.9% had children under the age of 18 living with them, 70.3% were married couples living together, 6.5% had a female householder with no husband present, and 20.2% were non-families. 17.3% of all households were made up of individuals and 6.7% had someone living alone who was 65 years of age or older. The average household size was 2.69 and the average family size was 3.05.
In the town the population was spread out with 27.5% under the age of 18, 5.1% from 18 to 24, 25.8% from 25 to 44, 30.5% from 45 to 64, and 11.1% who were 65 years of age or older. The median age was 41 years. For every 100 females there were 104.2 males. For every 100 females age 18 and over, there were 96.3 males.
The median income for a household in the town was $88,809, and the median income for a family was $105,737. Males had a median income of $80,693 versus $37,321 for females. The per capita income for the town was $51,370. About 2.4% of families and 3.1% of the population were below the poverty line, including 3.0% of those under age 18 and 9.1% of those age 65 or over.