Apartments for Rent in Winchester, CT

Prices and availability in Winchester, CT were last updated on 27 May 2026.

The best apartments in Winchester, CT are: 279 N Main St, Unit 5 and 17 Union Street, Unit Second Floor.

The average rent in Winchester, CT is $1,359.

In Winchester, 34% of the residents are renting compared to 66% owning a home, according to data from the U.S. Census Bureau. Large-scale apartment buildings with more than 50 units represent 8% of Winchester's rentals, 88% are small-scale complexes with under 50 units, and 4% are single-family rentals.

The age and size of multifamily buildings are among the most visible characteristics of the rental market in a city. In this case, the apartment buildings in Winchester are about 52 years old, on average. Of these, none have been built since 2000, representing the newer options on the market and typically offering more amenities. Rental buildings in the city have an average height of 3 stories. About all of the rental communities here are low-rise, garden-style communities, none are mid-rises, and none are high-rise buildings. These are true especially for large-scale multifamily buildings with over 50 apartments.

Rental apartments in Winchester come in a range of sizes and floorplans. Studio apartments represent 0% of units for rent, ideal for singles, renters on a budget and people who value central locations more than space. Rentals with 1-bedroom floorplans make up 12% of the total apartments in the city, while 2-bedroom floorplans represent around 76% of all rentals in Winchester. The rest are larger floorplans with 3 bedrooms or more, typically preferred by families, larger households or roommates sharing space.