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

196 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 - $600Ks
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 - $500Ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes
No reviews yet Oronoque Village
$500Ks - $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 - $300Ks
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 - $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 - $400Ks
O'Meara Farm, Farmington, CT
Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes
Spring Lake Village 6 LAKEVIEW DR # 6, SOUTHINGTON, CT, 0648..., Southington, CT 06489
$284,900

3 beds

|

3 baths

|

1,471 sq ft

|

Condo

6 LAKEVIEW DR # 6, SOUTHINGTON, CT, 0648...
Community: Spring Lake Village
New Newtown Woods 231 BROOKSIDE CT 231, NEWTOWN, CT, 06470, Newtown, CT 06470
$499,999

2 beds

|

2 baths

|

1,483 sq ft

|

Condo

231 BROOKSIDE CT 231, NEWTOWN, CT, 06470
Community: Newtown Woods
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
Heritage Village 134 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$419,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

134 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 106 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$429,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

106 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
New Heritage Village 29 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$300,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

29 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 740 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$360,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

740 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
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
Heritage Village 760 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$434,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

760 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 685 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$379,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

685 HERITAGE VLG A, 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 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
Heritage Village 79 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$214,900

1 beds

|

1 baths

|

928 sq ft

|

Condo

79 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New The Village at Oxford Greens 89 LINKS WAY # 89, OXFORD, CT, 06478, Oxford, CT 06478
$675,000

2 beds

|

2 baths

|

2,008 sq ft

|

Condo

89 LINKS WAY # 89, OXFORD, CT, 06478
New Heritage Village 12 HERITAGE CRST E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$499,000

2 beds

|

2 baths

|

1,447 sq ft

|

Condo

12 HERITAGE CRST E, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 128 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,999

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

128 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Heritage Village 419 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$289,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

419 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Bartlett Hollow 39 BARTLETT HOLW # 39, MIDDLETOWN, CT, 0..., Middletown, CT 06457
$619,000

2 beds

|

3 baths

|

3,147 sq ft

|

Condo

39 BARTLETT HOLW # 39, MIDDLETOWN, CT, 0...
Community: Bartlett Hollow
Heritage Village 644 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$328,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

644 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Meadow Brook Estates 326 SPRUCE HILL DR # 326, OXFORD, CT, 06..., Oxford, CT 06478
$555,000

2 beds

|

3 baths

|

1,683 sq ft

|

Condo

326 SPRUCE HILL DR # 326, OXFORD, CT, 06...
Rivington 19 MILL RD # 19, DANBURY, CT, 06810, Danbury, CT 06810
$749,000

3 beds

|

3 baths

|

2,076 sq ft

|

Condo

19 MILL RD # 19, 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.
New Heritage Village 926 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$338,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

926 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 881 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$459,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

881 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 1022 COUNTRY VIEW RD # 1022, DANBURY, CT..., Danbury, CT 06810
$489,900

2 beds

|

2 baths

|

1,330 sq ft

|

Condo

1022 COUNTRY VIEW RD # 1022, DANBURY, CT...
Community: Rivington
Heritage Village 894 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$379,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

894 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 1036 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$499,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

1036 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Heritage Village 953 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$279,900

1 beds

|

1 baths

|

928 sq ft

|

Condo

953 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Founders Ridge 20 WEBSTER LN # 20, MIDDLETOWN, CT, 0645..., Middletown, CT 06457
$550,000

2 beds

|

2 baths

|

1,548 sq ft

|

Condo

20 WEBSTER LN # 20, MIDDLETOWN, CT, 0645...
Community: Founders Ridge
Heritage Village 1042 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$325,000

2 beds

|

2 baths

|

1,071 sq ft

|

Condo

1042 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
O'Meara Farm 8 MULBERRY LN # 8, FARMINGTON, CT, 06032, Farmington, CT 06032
$515,000

3 beds

|

3 baths

|

1,896 sq ft

8 MULBERRY LN # 8, FARMINGTON, CT, 06032
Community: O'Meara Farm
Park Glen 15 HARMONY TRL # 15, NEW MILFORD, CT, 06..., New Milford, CT 06776
$699,900

2 beds

|

4 baths

|

2,720 sq ft

|

Condo

15 HARMONY TRL # 15, NEW MILFORD, CT, 06...
Community: Park Glen
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 976 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$325,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

976 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Oronoque Village 646 ONONDAGA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$550,000

2 beds

|

3 baths

|

1,434 sq ft

|

Condo

646 ONONDAGA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
The Summit at Bethel 81 GREAT HILL DR # 81, BETHEL, CT, 06801, Bethel, CT 06801
$750,000

3 beds

|

3 baths

|

2,447 sq ft

|

Condo

81 GREAT HILL DR # 81, BETHEL, CT, 06801
Heritage Village 345 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$439,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

345 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Spring Lake Village 472 CARRIAGE DR # 472, SOUTHINGTON, CT, ..., Southington, CT 06489
$299,000

2 beds

|

2 baths

|

1,188 sq ft

|

Condo

472 CARRIAGE DR # 472, SOUTHINGTON, CT, ...
Community: Spring Lake Village
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Spring Lake Village 42 VILLAGE RD # 42, SOUTHINGTON, CT, 064..., Southington, CT 06489
$230,000

1 beds

|

1 baths

|

860 sq ft

|

Condo

42 VILLAGE RD # 42, SOUTHINGTON, CT, 064...
Community: Spring Lake Village
New Oronoque Village 513 OPA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$535,000

2 beds

|

3 baths

|

1,454 sq ft

|

Condo

513 OPA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Regency at Woodbridge 3 HERITAGE LN # 69, WOODBRIDGE, CT, 0652..., Woodbridge, CT 06525
$659,000

3 beds

|

3 baths

|

Condo

3 HERITAGE LN # 69, WOODBRIDGE, CT, 0652...
Regency at Woodbridge 13 HERITAGE LN # 64, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$699,000

3 beds

|

3 baths

|

2,239 sq ft

|

Condo

13 HERITAGE LN # 64, WOODBRIDGE, CT, 065...
Regency at Woodbridge 15 HERITAGE LN # 63, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$767,000

3 beds

|

3 baths

|

2,486 sq ft

|

Condo

15 HERITAGE LN # 63, WOODBRIDGE, CT, 065...



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196 homes near Winchester Area
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