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Winchester Area, CT 55+ active adult communities & homes for sale

89 communities near Winchester Area

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No reviews yet Clockmaker's Hill
$100Ks - $100Ks
Clockmaker's Hill, Winsted, CT
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes
No reviews yet Oak Meadow Estates
$200Ks - $400Ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
3 rating (2 reviews) Heritage Hills
$300Ks - $900Ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
3.6 rating (7 reviews) Heritage Village
$100Ks - $400Ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes
No reviews yet Leisure Village
$200Ks - $400Ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
No reviews yet Rivington
$400Ks - $1Ms
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
4 rating (1 reviews) Jefferson Village
$300Ks - $600Ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes
No reviews yet Oronoque Village
$300Ks - $600Ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
No reviews yet The Village at Oxford Gre...
$500Ks - $600Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes
No reviews yet Leisure Knoll
$400Ks - $500Ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
No reviews yet Leisure Glen
$400Ks - $500Ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
No reviews yet Spring Lake Village
$200Ks - $300Ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
4 rating (8 reviews) Glenwood Village
$100Ks - $400Ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
No reviews yet Regency at Prospect
$400Ks - $400Ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
No reviews yet The Retreat at Carmel
$300Ks - $600Ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
3.5 rating (2 reviews) Foxwood Village
$300Ks - $400Ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
1 rating (1 reviews) Plymouth Estates at Mount...
$500Ks - $500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes
No reviews yet Meadow Brook Estates
$500Ks - $500Ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
No reviews yet The Summit at Bethel
$700Ks - $700Ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
4.9 rating (14 reviews) Chatfield Farms
$500Ks - $500Ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
No reviews yet Woodridge Strathmore Terr...
$400Ks - $400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
No reviews yet Regency at Wappinger
$700Ks - $800Ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes
No reviews yet Saddle Lakes
$400Ks - $400Ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
5 rating (1 reviews) Sunken Pond Estates
$400Ks - $500Ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
5 rating (1 reviews) The Villages at Mount Sin...
$700Ks - $800Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
No reviews yet The Powder Forest Homes
$600Ks - $700Ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
5 rating (1 reviews) Newtown Woods
$400Ks - $400Ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
No reviews yet Stoneleigh Woods at River...
$400Ks - $600Ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
No reviews yet Beckley Farms
$300Ks - $400Ks
Beckley Farms, Berlin, CT
New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes
No reviews yet Regency at Fishkill
$500Ks - $500Ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
No reviews yet South Pond Village
$200Ks - $400Ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
No reviews yet Setauket Meadows
$600Ks - $700Ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes
No reviews yet Fieldstone Village
$500Ks - $800Ks
Fieldstone Village, Orange, CT
Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes
No reviews yet North Woods of Colchester
$300Ks - $400Ks
North Woods of Colchester, Colchester, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes
No reviews yet Windcrest East
$600Ks - $600Ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
No reviews yet Fairview at Oxford Greens
$500Ks - $600Ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
3.5 rating (2 reviews) Harvest Pointe
$800Ks - $3Ms
Harvest Pointe, Cutchogue, NY
New Construction | 55+ age-restricted | Built 2017 - present | 124 homes
No reviews yet Newbury Village
$400Ks - $500Ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes
No reviews yet The Gardens of Wilbraham
$300Ks - $400Ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes
No reviews yet O'Meara Farm
$400Ks - $500Ks
O'Meara Farm, Farmington, CT
Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes
O'Meara Farm 8 MULBERRY LN # 8, FARMINGTON, CT, 06032, Farmington, CT 06032
$499,999

3 beds

|

3 baths

|

1,896 sq ft

8 MULBERRY LN # 8, FARMINGTON, CT, 06032
Community: O'Meara Farm
Heritage Village 231 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$265,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

231 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Paris Square 152 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647
$775,000

3 beds

|

3 baths

|

Townhouse

152 RIO VISTA LN, NORTHVALE, NJ, 07647
Community: Paris Square
Paris Square 2301 RIO VISTA LN # 2301, NORTHVALE, NJ,..., Northvale, NJ 07647
$699,999

3 beds

|

2 baths

|

Condo

2301 RIO VISTA LN # 2301, NORTHVALE, NJ,...
Community: Paris Square
Heritage Hills 133 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$700,000

3 beds

|

2 baths

|

1,780 sq ft

|

Condo

133 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
New Glenwood Village 1661 OLD COUNTRY RD UNIT 586, RIVERHEAD,..., Riverhead, NY 11901
$489,000

3 beds

|

2 baths

|

1,680 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD UNIT 586, RIVERHEAD,...
Community: Glenwood Village
New Jefferson Village 73 INDEPENDENCE CT D, YORKTOWN, NY, 1059..., Yorktown, NY 10598
$385,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

73 INDEPENDENCE CT D, YORKTOWN, NY, 1059...
Community: Jefferson Village
Jefferson Village 84 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598
$375,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

84 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,...
Community: Jefferson Village
New Foxwood Village 1407 MIDDLE RD UNIT 4 UNIT 4, CALVERTON,..., Calverton, NY 11933
$425,000

2 beds

|

2 baths

|

1,400 sq ft

|

Manufactured Home

1407 MIDDLE RD UNIT 4 UNIT 4, CALVERTON,...
Community: Foxwood Village
New Foxwood Village 1407 MIDDLE RD UNIT 144 UNIT 4, CALVERTO..., Calverton, NY 11933
$425,000

2 beds

|

2 baths

|

1,300 sq ft

|

Manufactured Home

1407 MIDDLE RD UNIT 144 UNIT 4, CALVERTO...
Community: Foxwood Village
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Glenwood Village 425 CIRCLEWOOD, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$329,000

2 beds

|

2 baths

|

1,086 sq ft

|

Manufactured Home

425 CIRCLEWOOD, RIVERHEAD, NY, 11901
Community: Glenwood Village
Leisure Knoll 525 CRANSTON LN, RIDGE, NY, 11961, Ridge, NY 11961
$499,999

2 beds

|

2 baths

|

1,334 sq ft

|

Condo

525 CRANSTON LN, RIDGE, NY, 11961
Community: Leisure Knoll
Glenwood Village 1661 OLD COUNTRY RD 360, RIVERHEAD, NY, ..., Riverhead, NY 11901
$210,000

2 beds

|

2 baths

|

1,776 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 360, RIVERHEAD, NY, ...
Community: Glenwood Village
Glenwood Village 1661 OLD COUNTRY RD 301, RIVERHEAD, NY, ..., Riverhead, NY 11901
$259,900

2 beds

|

2 baths

|

1,088 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 301, RIVERHEAD, NY, ...
Community: Glenwood Village
The Villages at Mount Sinai Park 15 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766
$825,000

3 beds

|

4 baths

|

3,048 sq ft

|

Condo

15 LOUDEN LOOP, MOUNT SINAI, NY, 11766
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Glenwood Village 1661 OLD COUNTRY RD UNIT 290, RIVERHEAD,..., Riverhead, NY 11901
$245,000

2 beds

|

2 baths

|

1,152 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD UNIT 290, RIVERHEAD,...
Community: Glenwood Village
Glenwood Village 1661 OLD COUNTRY RD UNIT 521, RIVERHEAD,..., Riverhead, NY 11901
$359,000

2 beds

|

2 baths

|

Condo

1661 OLD COUNTRY RD UNIT 521, RIVERHEAD,...
Community: Glenwood Village
Jefferson Village 4 DEVON CT B, YORKTOWN HEIGHTS, NY, 1059..., Yorktown Heights, NY 10598
$450,000

2 beds

|

1 baths

|

975 sq ft

|

Condo

4 DEVON CT B, YORKTOWN HEIGHTS, NY, 1059...
Community: Jefferson Village
Sunken Pond Estates 1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$469,000

2 beds

|

3 baths

|

1,350 sq ft

|

Condo

1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
Jefferson Village 101 VILLAGE RD A, YORKTOWN HEIGHTS, NY, ..., Yorktown Heights, NY 10598
$650,000

2 beds

|

2 baths

|

1,555 sq ft

|

Condo

101 VILLAGE RD A, YORKTOWN HEIGHTS, NY, ...
Community: Jefferson Village
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Glenwood Village 1661 OLD COUNTRY RD 540, RIVERHEAD, NY, ..., Riverhead, NY 11901
$425,000

2 beds

|

2 baths

|

1,700 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 540, RIVERHEAD, NY, ...
Community: Glenwood Village
Plymouth Estates at Mount Sinai 211 POND CIR, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766
$574,888

2 beds

|

2 baths

|

1,662 sq ft

|

Condo

211 POND CIR, MOUNT SINAI, NY, 11766
New Leisure Village 406 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961
$235,500

1 beds

|

1 baths

|

679 sq ft

|

Condo

406 WOODBRIDGE DR A, RIDGE, NY, 11961
Community: Leisure Village
New Leisure Village 369B WOODBRIDGE DR 55+, BROOKHAVEN, NY, ..., Brookhaven, NY 11961
$349,000

2 beds

|

1 baths

|

975 sq ft

|

Condo

369B WOODBRIDGE DR 55+, BROOKHAVEN, NY, ...
Community: Leisure Village
New Leisure Village 423 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961
$259,000

1 beds

|

1 baths

|

782 sq ft

|

Condo

423 WOODBRIDGE DR A, RIDGE, NY, 11961
Community: Leisure Village
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Glenwood Village 1661 OLD COUNTRY RD 179, RIVERHEAD, NY, ..., Riverhead, NY 11901
$215,000

2 beds

|

2 baths

|

1,036 sq ft

|

Mobile Home

1661 OLD COUNTRY RD 179, RIVERHEAD, NY, ...
Community: Glenwood Village
The Retreat at Carmel 31 LANGDON GROVE, CARMEL, NY, 10512, Carmel, NY 10512
$675,000

2 beds

|

2 baths

|

1,979 sq ft

|

House

31 LANGDON GROVE, CARMEL, NY, 10512
Heritage Hills 957 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$659,000

2 beds

|

3 baths

|

1,559 sq ft

|

Condo

957 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
Jefferson Village 32 CAMBRIDGE CT A, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598
$399,000

2 beds

|

1 baths

|

951 sq ft

|

Condo

32 CAMBRIDGE CT A, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
Heritage Hills 631 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$465,000

1 beds

|

2 baths

|

967 sq ft

|

Condo

631 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Woodridge Strathmore Terrace 78 HEARTHSIDE DR # 78, MOUNT SINAI, NY, ..., Mount Sinai, NY 11766
$449,000

2 beds

|

2 baths

|

1,501 sq ft

|

Condo

78 HEARTHSIDE DR # 78, MOUNT SINAI, NY, ...
Glenwood Village 1661 OLD COUNTRY RD UNIT 200, RIVERHEAD,..., Riverhead, NY 11901
$249,900

2 beds

|

1 baths

|

753 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD UNIT 200, RIVERHEAD,...
Community: Glenwood Village
Heritage Hills 480 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$649,000

2 beds

|

2 baths

|

1,468 sq ft

|

Condo

480 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Leisure Village 137 EASTBOURNE CT A, RIDGE, NY, 11961, Ridge, NY 11961
$299,999

2 beds

|

1 baths

|

836 sq ft

|

Condo

137 EASTBOURNE CT A, RIDGE, NY, 11961
Community: Leisure Village
Heritage Hills 331 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$395,000

1 beds

|

1 baths

|

955 sq ft

|

Condo

331 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Sunken Pond Estates 3804 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$519,000

2 beds

|

3 baths

|

1,674 sq ft

|

Condo

3804 AMEN COR, RIVERHEAD, NY, 11901
Community: Sunken Pond Estates
Glenwood Village 1661 OLD COUNTRY RD UNIT 423, RIVERHEAD,..., Riverhead, NY 11901
$199,900

2 beds

|

2 baths

|

960 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD UNIT 423, RIVERHEAD,...
Community: Glenwood Village
Jefferson Village 143 FLINTLOCK WAY D, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598
$449,900

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

143 FLINTLOCK WAY D, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
Jefferson Village 18 HASTINGS CT E, YORKTOWN, NY, 10598, Yorktown, NY 10598
$325,000

1 beds

|

1 baths

|

725 sq ft

|

Condo

18 HASTINGS CT E, YORKTOWN, NY, 10598
Community: Jefferson Village
Leisure Village 269 BERWICK CT B, RIDGE, NY, 11961, Ridge, NY 11961
$374,999

2 beds

|

1 baths

|

1,048 sq ft

|

Condo

269 BERWICK CT B, RIDGE, NY, 11961
Community: Leisure Village



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