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Western Connecticut 55+ Active Adult Retirement Communities in CT | 55places You are using an outdated browser. Please upgrade your browser to improve your experience. <![endif]--> Discover what’s next. ™ Home Blog About Us Search by state, city, or community Search Our Site Advanced Search Western Connecticut 55+ Active Adult Retirement Communities Home Connecticut Western Connecticut Go back to Connecticut Communities About Western Connecticut 28 Communities in Western Connecticut Per Page: 25 Communities 50 Communities 100 Communities Sort By: # Homes (High-Low) # Homes (Low-High) # Homes Sold (High-Low) # Homes Sold (Low-High) Name (A-Z) Name (Z-A) Price (Low-High) Price (High-Low) City (A-Z) City (Z-A) Page: First 1 2 Next Page Last Heritage Village Southbury , CT Below $100k - High $300s 2,580 Homes 55+ Age Restriction Resale Homes Only Save Community View Community Rivington Danbury , CT High $200s - Mid $600s 1,050 Homes New And Resale Homes Save Community View Community The Village at Oxford Greens Oxford , CT Low $300s - High $400s 835 Homes 55+ Age Restriction New And Resale Homes Save Community View Community Regency at Prospect Prospect , CT High $200s - High $300s 379 Homes 55+ Age Restriction New And Resale Homes Save Community View Community Meadow Brook Estates Oxford , CT Low $300s - Mid $400s 250 Homes 55+ Age Restriction New And Resale Homes Save Community View Community The Summit at Bethel Bethel , CT High $400s - Mid $500s 232 Homes 55+ Age Restriction New And Resale Homes Save Community View Community Chatfield Farms Beacon Falls , CT Mid $300s - High $300s 231 Homes 55+ Age Restriction New Homes Only Save Community View Community Palmer Hill Stamford , CT Mid $500s - Mid $1Ms 195 Homes Resale Homes Only Save Community View Community Newtown Woods Newtown , CT High $300s - High $400s 178 Homes 55+ Age Restriction New And Resale Homes Save Community View Community West Lyon Farm Greenwich , CT Low $1Ms - High $1Ms 155 Homes Resale Homes Only Save Community View Community Fieldstone Village Orange , CT High $300s - High $600s 142 Homes 55+ Age Restriction Resale Homes Only Save Community View Community Fairview at Oxford Greens Oxford , CT High $200s - Low $300s 125 Homes 55+ Age Restriction New Homes Only Save Community View Community Newbury Village Brookfield , CT High $400s - Low $500s 120 Homes 55+ Age Restriction New And Resale Homes Save Community View Community Liberty at Newtown Newtown , CT Mid $400s - Mid $500s 96 Homes 55+ Age Restriction Resale Homes Only Save Community View Community Pond Spring Village Beacon Falls , CT Low $200s - Low $300s 92 Homes 55+ Age Restriction New And Resale Homes Save Community View Community Benson Woods Middlebury , CT High $200s - High $400s 79 Homes 55+ Age Restriction New And Resale Homes Save Community View Community The Kingswood Stamford , CT Low $100s - Mid $400s 71 Homes Resale Homes Only Save Community View Community Whitney Glen Westport , CT Low $300s - Mid $400s 62 Homes 55+ Age Restriction Resale Homes Only Save Community View Community Doral Farm Stamford , CT Mid $700s - Low $1Ms 58 Homes Resale Homes Only Save Community View Community 77 Sunset Lane Ridgefield , CT Mid $400s - High $700s 54 Homes 55+ Age Restriction New And Resale Homes Save Community View Community The Meadows Fairfield , CT Low $700s - High $700s 48 Homes Resale Homes Only Save Community View Community Clockmaker's Hill Winsted , CT Low $100s - Mid $100s 38 Homes 55+ Age Restriction Resale Homes Only Save Community View Community Boulder Brook Prospect , CT High $100s - Mid $200s 35 Homes 55+ Age Restriction Resale Homes Only Save Community View Community The Woods at Dunham Pond New Fairfield , CT Mid $200s - Mid $300s 33 Homes 55+ Age Restriction Resale Homes Only Save Community View Community Oak Meadow Estates Torrington , CT Mid $200s - Low $300s 31 Homes 55+ Age Restriction New And Resale Homes Save Community View Community Page: First 1 2 Next Page Last 28 communities match filters Overview Western Connecticut has plenty of age-restricted communities that have scenic views of lush landscapes, flowing rivers, farms, and golf courses that attract many active adults and retirees to these 55+ communities. Active adult communities within Western Connecticut also enjoy great healthcare facilities, outdoor recreational activities as well as close to big-city attractions in New York City. Climate & Geography Active adults and retirees will enjoy the four-season climate in Western Connecticut. The relatively mild climate has an average temperature in the high 80s during the summer months and an average temperature in the low 30s during the winter months. Residents living in age-restricted communities in Western Connecticut can experience all four seasons and enjoy crisp days in autumn, beautiful sunrises in June, and even witness a winter wonderland in December. Western Connecticut is made up of three counties: Fairfield County, Litchfield County, and New Haven County. Active adult communities are found around the cities and towns of Bridgeport, Cannondale, Darien, Danbury, Stamford, Greenwich, Saugatuck, Westport, Riverside, and Monroe, just to name a few. The state of New York, which can appeal to active adults and retirees who like having access to the city for quick day trips or weekend getaways also border Western Connecticut. The Berkshire Mountains also provide scenic views in Western Connecticut. Recreation, Culture & Entertainment There are plenty of things for active adults and retirees to do near 55+ communities in Western Connecticut. The great outdoors offer activities such as canoeing and kayaking along the Long Island Sound or Saugatuck River, hiking and picnicking in Bear Mountain Reservation, bird watching and gardening displays around Fairfield County and in Tarrywile Mansion, as well as fishing, swimming, and ice skating at Squantz Pond State Park and Danbury Candlewood Park. There are also many museums in Western Connecticut, such as Aldrich Museum of Contemporary Art, Military Museum of Southern New England, Bruce Museum, Bush-Holley House, and Easton Historical Society. Active adults and retirees can also visit the farmers markets and vineyards that are sprinkled throughout Western Connecticut for fresh locally grown organic produce and wine sampling. Cost of Living & Taxes The cost of living is 33.7% higher than the national average in Western Connecticut. Stamford, Danbury, Darien, and Bethel have higher than average median home prices in Western Connecticut. Western Connecticut is known for having multi-million dollar homes, top-rated universities and education systems, natural landscapes, and proximity to New York City, which make it an interesting location for retirees and active adults. Healthcare 55+ communities in Western Connecticut have many great healthcare facilities and major hospitals. Some of the hospitals include Danbury Hospital, New Milford Hospital, Bridgeport Hospital, and Saint Mary s Hospital. 55places.com Blog The 10 Best New Communities of 2019 The 10 Best New Communities of 2019 The Ultimate Guide to Snowbirds The Ultimate Guide to Snowbirds The Most Affordable Places to Retire in the US in 2019 The Most Affordable Places to Retire in the US in 2019 The 25 Best Value Active Adult Communities of 2019 The 25 Best Value Active Adult Communities of 2019 Visit our Blog Communities in Western Connecticut Western Connecticut (28) Waterbury Area (11) Oxford (4) Orange (1) Southbury (1) Beacon Falls (2) Middlebury (1) Prospect (2) Danbury Area (9) Danbury (1) Newtown (2) Ridgefield (2) New Milford (1) Bethel (1) Brookfield (1) New Fairfield (1) Winchester Area (2) Torrington (1) Winsted (1) Stamford Area (6) Stamford (3) Greenwich (1) Westport (1) Fairfield (1) + Show More Refine Search Home Type Single-Family Attached Condos Price Range Price Low Min Price $100k $125k $150k $175k $200k $225k $250k $275k $300k $350k $400k $450k $500k $550k $600k...