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Winchester Area, CT 55+ active adult communities & homes for sale
92 communities near Winchester Area
246 homes near Winchester Area
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2 beds
|1 baths
|1,000 sq ft
|Condo
3 beds
|2 baths
|1,905 sq ft
|Condo
2 beds
|2 baths
|1,468 sq ft
|Condo
2 beds
|1 baths
|1,278 sq ft
|Condo
2 beds
|2 baths
|1,587 sq ft
|Condo
2 beds
|2 baths
|1,499 sq ft
|Condo
2 beds
|1 baths
|840 sq ft
|Mobile Home
2 beds
|2 baths
|1,180 sq ft
|Condo
2 beds
|1 baths
|875 sq ft
|Condo
2 beds
|2 baths
|1,555 sq ft
|Condo
2 beds
|2 baths
|970 sq ft
|House
2 beds
|3 baths
|1,350 sq ft
|Condo
2 beds
|1 baths
|874 sq ft
|Condo
2 beds
|3 baths
|1,972 sq ft
|Condo
1 beds
|1 baths
|684 sq ft
|Condo
2 beds
|2 baths
|1,803 sq ft
|Condo
1 beds
|1 baths
|850 sq ft
|Condo
2 beds
|1 baths
|1,048 sq ft
|Condo
2 beds
|1 baths
|1,100 sq ft
|Condo
2 beds
|1 baths
|816 sq ft
|Mobile Home
1 beds
|1 baths
|684 sq ft
|Condo
2 beds
|2 baths
|1,500 sq ft
|Manufactured Home
1 beds
|1 baths
|782 sq ft
|Condo
2 beds
|2 baths
|1,820 sq ft
|Townhouse
2 beds
|2 baths
|1,820 sq ft
|Condo
3 beds
|2 baths
|1,716 sq ft
|Condo
2 beds
|2 baths
|1,447 sq ft
|Condo
3 beds
|4 baths
|2,644 sq ft
|Condo
3 beds
|3 baths
|Condo
3 beds
|3 baths
|Condo
3 beds
|3 baths
|Condo
2 beds
|2 baths
|1,432 sq ft
|Condo
Frequently Asked Questions
In the Winchester Area, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.
The smallest 55+ communities in the Winchester Area has 31 homes, the largest has 38 homes, and the average communities consists of 34 homes.
Yes, there is new 55+ home available in the Winchester Area. The most recent communities started in the Winchester Area include Oak Meadow Estates, Clockmaker's Hill. There is also 1 communities in the Winchester Area that offers new construction homes, including Oak Meadow Estates.
No, there are no gated 55+ communities in the Winchester Area.
On average, listings in 55+ communities in the Winchester Area stay on the market for around 788 days. The average price of homes for sale in these communities is approximately $389,900, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Oak Meadow Estates average around $389,900.

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REIN updates its listings on a daily basis. Data last updated: Oct 29, 2025.
This application does not include information on all of the properties available for sale at this time.