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

209 homes 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
$400Ks - $700Ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1975 - 2003 | 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
$400Ks - $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
$300Ks - $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 - $200Ks
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 - $800Ks
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...
$300Ks - $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
New and Resale | 55+ age-restricted | Built 2014 - present | 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 - $400Ks
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 - $500Ks
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 - $400Ks
O'Meara Farm, Farmington, CT
Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes
Heritage Village 701 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$400,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

701 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 151 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$245,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

151 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Liberty at Newtown 5 FRANKLIN CT # 5, NEWTOWN, CT, 06470, Newtown, CT 06470
$599,000

2 beds

|

3 baths

|

2,407 sq ft

|

Condo

5 FRANKLIN CT # 5, NEWTOWN, CT, 06470
Community: Liberty at Newtown
Oronoque Village 635 NORTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$659,900

2 beds

|

3 baths

|

1,642 sq ft

|

Condo

635 NORTH TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
The Village at Oxford Greens 644 CHAMPIONSHIP DR # 644, OXFORD, CT, 0..., Oxford, CT 06478
$659,000

2 beds

|

3 baths

|

2,296 sq ft

|

Condo

644 CHAMPIONSHIP DR # 644, OXFORD, CT, 0...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Rivington 802 CENTER MEADOW LN # 802, DANBURY, CT,..., Danbury, CT 06810
$500,000

2 beds

|

2 baths

|

1,312 sq ft

802 CENTER MEADOW LN # 802, DANBURY, CT,...
Community: Rivington
Oronoque Village 588 ARAPAHO LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$419,999

1 beds

|

2 baths

|

1,438 sq ft

|

Condo

588 ARAPAHO LN B, STRATFORD, CT, 06614
Community: Oronoque Village
The Powder Forest Homes 3 PROSPECT RDG, SIMSBURY, CT, 06070, Simsbury, CT 06070
$799,900

4 beds

|

4 baths

|

2,557 sq ft

3 PROSPECT RDG, SIMSBURY, CT, 06070
Heritage Village 57 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$235,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

57 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 38 WINDING RIDGE WAY, DANBURY, CT, 06810, Danbury, CT 06810
$799,900

3 beds

|

3 baths

|

1,767 sq ft

|

Condo

38 WINDING RIDGE WAY, DANBURY, CT, 06810
Community: Rivington
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.
Regency at Woodbridge 7 HERITAGE LN # 67, WOODBRIDGE, CT, 0652..., Woodbridge, CT 06525
$764,995

3 beds

|

3 baths

|

2,486 sq ft

|

Condo

7 HERITAGE LN # 67, WOODBRIDGE, CT, 0652...
Heritage Village 331 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$315,000

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

331 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
Regency at Woodbridge 5 HERITAGE LN # 68, WOODBRIDGE, CT, 0652..., Woodbridge, CT 06525
$599,995

3 beds

|

3 baths

|

2,006 sq ft

|

Condo

5 HERITAGE LN # 68, WOODBRIDGE, CT, 0652...
Heritage Village 1000 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$435,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

1000 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
The Summit at Bethel 63 GREAT HILL DR # 63, BETHEL, CT, 06801, Bethel, CT 06801
$725,000

3 beds

|

3 baths

|

2,743 sq ft

|

Condo

63 GREAT HILL DR # 63, BETHEL, CT, 06801
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Billingsgate 2 PENNINGTON DR # 2, SIMSBURY, CT, 06070, Simsbury, CT 06070
$690,000

2 beds

|

3 baths

|

2,867 sq ft

|

Condo

2 PENNINGTON DR # 2, SIMSBURY, CT, 06070
Community: Billingsgate
Heritage Village 122 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

122 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Benson Woods 112 PERIWINKLE DR # 112, MIDDLEBURY, CT,..., Middlebury, CT 06762
$569,900

2 beds

|

3 baths

|

2,593 sq ft

|

Condo

112 PERIWINKLE DR # 112, MIDDLEBURY, CT,...
Community: Benson Woods
Heritage Village 740 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$435,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

740 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 21 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$180,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

21 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage 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.
South Pond Village 175 THISTLE POND DR # 175, BLOOMFIELD, C..., Bloomfield, CT 06002
$399,000

2 beds

|

2 baths

|

1,535 sq ft

|

Condo

175 THISTLE POND DR # 175, BLOOMFIELD, C...
Community: South Pond Village
The Village at Oxford Greens 403 MULLIGAN DR # 403, OXFORD, CT, 06478, Oxford, CT 06478
$679,000

2 beds

|

2 baths

|

2,080 sq ft

|

Condo

403 MULLIGAN DR # 403, OXFORD, CT, 06478
Heritage Village 669 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$300,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

669 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
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
Newtown Woods 231 BROOKSIDE CT 231, NEWTOWN, CT, 06470, Newtown, CT 06470
$529,999

2 beds

|

2 baths

|

1,483 sq ft

|

Condo

231 BROOKSIDE CT 231, NEWTOWN, CT, 06470
Community: Newtown Woods
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Heritage Village 607 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$279,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

607 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$424,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 11 HERITAGE CRST B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$549,900

3 beds

|

2 baths

|

1,847 sq ft

|

Condo

11 HERITAGE CRST B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 8 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$269,900

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

8 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 143 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$389,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

143 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage 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.
Heritage Village 999 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$350,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

999 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Bidwell Village 94 STONEHOUSE RD UNIT 16, COVENTRY, CT, ..., Coventry, CT 06238
$499,000

3 beds

|

3 baths

|

1,570 sq ft

|

Condo

94 STONEHOUSE RD UNIT 16, COVENTRY, CT, ...
Community: Bidwell Village
South Pond Village 179 THISTLE POND DR # 179, BLOOMFIELD, C..., Bloomfield, CT 06002
$369,000

2 beds

|

2 baths

|

1,341 sq ft

|

Condo

179 THISTLE POND DR # 179, BLOOMFIELD, C...
Community: South Pond Village
Newtown Woods 18 BROOKSIDE CT # 18, NEWTOWN, CT, 06470, Newtown, CT 06470
$599,900

2 beds

|

3 baths

|

2,001 sq ft

|

Condo

18 BROOKSIDE CT # 18, NEWTOWN, CT, 06470
Community: Newtown Woods
Meadow Brook Estates 306 SPRUCE HILL DR, OXFORD, CT, 06478, Oxford, CT 06478
$539,900

2 beds

|

3 baths

|

1,691 sq ft

|

Condo

306 SPRUCE HILL DR, OXFORD, CT, 06478
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Bramble Ridge 56 BOYSENBERRY CT # 56, SUFFIELD, CT, 06..., Suffield, CT 06078
$499,900

2 beds

|

2 baths

|

2,001 sq ft

|

Condo

56 BOYSENBERRY CT # 56, SUFFIELD, CT, 06...
Community: Bramble Ridge
Spring Lake Village 6 LAKEVIEW DR # 6, SOUTHINGTON, CT, 0648..., Southington, CT 06489
$289,900

3 beds

|

3 baths

|

1,471 sq ft

|

Condo

6 LAKEVIEW DR # 6, SOUTHINGTON, CT, 0648...
Community: Spring Lake Village
Bartlett Hill 107 CHESTNUT HILL RD # 107, PORTLAND, CT..., Portland, CT 06480
$529,900

2 beds

|

3 baths

|

1,985 sq ft

107 CHESTNUT HILL RD # 107, PORTLAND, CT...
Community: Bartlett Hill
Regency at Prospect 127 SYCAMORE DR # 127, PROSPECT, CT, 067..., Prospect, CT 06712
$424,900

2 beds

|

2 baths

|

1,503 sq ft

|

Condo

127 SYCAMORE DR # 127, PROSPECT, CT, 067...
Community: Regency at Prospect
The Woods at Dunham Pond 48 HERON VIEW RD # 48, NEW FAIRFIELD, CT..., New Fairfield, CT 06812
$449,900

1 beds

|

3 baths

|

1,550 sq ft

|

Condo

48 HERON VIEW RD # 48, NEW FAIRFIELD, CT...



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