Call us at (860) 909-8066 to learn more about active adult communities in Winsted

Winsted, CT 55+ active adult communities & homes for sale

156 homes near Winsted

Sort by:

Relevance

Relevance

No reviews yet Clockmaker's Hill
$100Ks - $100Ks
Clockmaker's Hill, Winsted, CT
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 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 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
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
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 Spring Lake Village
$200Ks - $300Ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 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
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 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
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 The Powder Forest Homes
$600Ks - $700Ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
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 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
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 Fieldstone Village
$500Ks - $800Ks
Fieldstone Village, Orange, CT
Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 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 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 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
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
No reviews yet O'Meara Farm
$400Ks - $500Ks
O'Meara Farm, Farmington, CT
Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes
No reviews yet Liberty at Newtown
$300Ks - $400Ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
No reviews yet Pond Spring Village
$300Ks - $300Ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
No reviews yet Founders Village
$500Ks - $500Ks
Founders Village, Southold, NY
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes
No reviews yet Glassbury Court at Cold S...
$700Ks - $700Ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 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.
5 rating (1 reviews) Paris Square
$400Ks - $700Ks
Paris Square, Northvale, NJ
New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes
No reviews yet Castle Heights of Cheshir...
$500Ks - $600Ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes
No reviews yet Bartlett Hill
$500Ks - $500Ks
Bartlett Hill, Portland, CT
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes
No reviews yet Baldwin Station
$400Ks - $400Ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
5 rating (2 reviews) Benson Woods
$400Ks - $600Ks
Benson Woods, Middlebury, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
No reviews yet Shaker Heights
$400Ks - $500Ks
Shaker Heights, Enfield, CT
New Construction | 55+ age-restricted | Built 2018 - present | 77 homes
5 rating (3 reviews) Founders Ridge
$500Ks - $600Ks
Founders Ridge, Middletown, CT
New Construction | 55+ age-restricted | Built 2017 - present | 75 homes
No reviews yet Long Hill Village
$300Ks - $400Ks
Long Hill Village, Trumbull, CT
Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes
No reviews yet Regency at Woodbridge
$500Ks - $700Ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 homes
No reviews yet The Village at Hunt Glen
$300Ks - $300Ks
The Village at Hunt Glen, Granby, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 homes
Heritage Village 170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$404,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Sonoma Woods 46 SONOMA LN # 46, MIDDLETOWN, CT, 06457, Middletown, CT 06457
$689,900

2 beds

|

3 baths

|

2,515 sq ft

46 SONOMA LN # 46, MIDDLETOWN, CT, 06457
Community: Sonoma Woods
Heritage Village 1005 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$299,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

1005 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
Heritage Village 881 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$409,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

881 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 28 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$394,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

28 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
New Heritage Village 93 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$250,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

93 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
New South Pond Village 6 WILD ROSE CT # 6, BLOOMFIELD, CT, 0600..., Bloomfield, CT 06002
$199,700

2 beds

|

2 baths

|

1,210 sq ft

|

Condo

6 WILD ROSE CT # 6, BLOOMFIELD, CT, 0600...
Community: South Pond Village
Heritage Village 12 HERITAGE CRST E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$485,000

2 beds

|

2 baths

|

1,447 sq ft

|

Condo

12 HERITAGE CRST E, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 760 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$429,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

760 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Founders Ridge UNIT 2-45 WEBSTER LN, MIDDLETOWN, CT, 06..., Middletown, CT 06457
$669,995

2 beds

|

2 baths

|

1,555 sq ft

UNIT 2-45 WEBSTER LN, MIDDLETOWN, CT, 06...
Community: Founders Ridge
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.
The Powder Forest Homes 30 CARSON WAY # 30, SIMSBURY, CT, 06070, Simsbury, CT 06070
$674,900

3 beds

|

4 baths

|

1,862 sq ft

30 CARSON WAY # 30, SIMSBURY, CT, 06070
Heritage Village 21 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$290,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

21 HERITAGE CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
Bartlett Hollow 39 BARTLETT HOLW # 39, MIDDLETOWN, CT, 0..., Middletown, CT 06457
$579,900

3 beds

|

3 baths

|

3,147 sq ft

39 BARTLETT HOLW # 39, MIDDLETOWN, CT, 0...
Community: Bartlett Hollow
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
New Oronoque Village 227 SHOSHONI LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$365,000

1 beds

|

2 baths

|

1,625 sq ft

|

Condo

227 SHOSHONI LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Billingsgate 15 BILLINGSGATE DR # 15, SIMSBURY, CT, 0..., Simsbury, CT 06070
$675,000

2 beds

|

4 baths

|

2,729 sq ft

|

Condo

15 BILLINGSGATE DR # 15, SIMSBURY, CT, 0...
Community: Billingsgate
Heritage Village 1 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$384,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 920 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$389,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

920 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$419,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
O'Meara Farm 1 PRIMROSE LN # 1, FARMINGTON, CT, 06032, Farmington, CT 06032
$530,000

3 beds

|

3 baths

|

2,062 sq ft

|

Condo

1 PRIMROSE LN # 1, FARMINGTON, CT, 06032
Community: O'Meara Farm
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.
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
Oronoque Village 92 SEMINOLE LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$639,000

3 beds

|

3 baths

|

1,438 sq ft

|

Condo

92 SEMINOLE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
O'Meara Farm 7 SUNFLOWER TER # 7, FARMINGTON, CT, 060..., Farmington, CT 06032
$539,900

4 beds

|

4 baths

|

1,934 sq ft

|

Condo

7 SUNFLOWER TER # 7, FARMINGTON, CT, 060...
Community: O'Meara Farm
Heritage Village 894 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$359,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

894 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Spring Lake Village 443 LAKEVIEW DR # 443, SOUTHINGTON, CT, ..., Southington, CT 06489
$275,000

2 beds

|

2 baths

|

1,188 sq ft

|

Condo

443 LAKEVIEW DR # 443, SOUTHINGTON, CT, ...
Community: Spring Lake Village
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Heritage Village 98 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$347,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

98 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 740 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$430,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

740 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 79 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$205,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

79 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 922 TILLINGHAST DR # 922, OXFORD, CT, 06..., Oxford, CT 06478
$599,900

2 beds

|

2 baths

|

1,688 sq ft

|

Condo

922 TILLINGHAST DR # 922, OXFORD, CT, 06...
Fairview at Oxford Greens 922 TILLINGHAST DR # 922, OXFORD, CT, 06..., Oxford, CT 06478
$599,900

2 beds

|

2 baths

|

1,688 sq ft

|

Condo

922 TILLINGHAST DR # 922, OXFORD, CT, 06...
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.
The Village at Oxford Greens 633 CHAMPIONSHIP DR # 633, OXFORD, CT, 0..., Oxford, CT 06478
$619,900

2 beds

|

3 baths

|

2,002 sq ft

|

Condo

633 CHAMPIONSHIP DR # 633, OXFORD, CT, 0...
Heritage Village 740 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$345,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

740 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 164 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$320,000

1 beds

|

2 baths

|

1,175 sq ft

|

Condo

164 BISON LN A, STRATFORD, CT, 06614
Community: Oronoque 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
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
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Heritage Village 948 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$259,900

2 beds

|

2 baths

|

1,071 sq ft

|

Condo

948 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Spring Lake Village 543 S FARMS TER # 543, SOUTHINGTON, CT, ..., Southington, CT 06489
$250,000

2 beds

|

3 baths

|

1,782 sq ft

|

Condo

543 S FARMS TER # 543, SOUTHINGTON, CT, ...
Community: Spring Lake Village
Regency at Woodbridge 11 HERITAGE LN # 65, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$659,000

3 beds

|

3 baths

|

2,028 sq ft

|

Condo

11 HERITAGE LN # 65, WOODBRIDGE, CT, 065...
Regency at Woodbridge 15 HERITAGE LN # 63, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$729,000

3 beds

|

3 baths

|

2,486 sq ft

|

Condo

15 HERITAGE LN # 63, WOODBRIDGE, CT, 065...
Regency at Woodbridge 29 HERITAGE LN # 56, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$719,000

3 beds

|

3 baths

|

2,239 sq ft

|

Condo

29 HERITAGE LN # 56, WOODBRIDGE, CT, 065...

Frequently Asked Questions


Want more information about active adult communities around Winsted?

Global - Lead Form - Buyer or Renter

*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

156 homes near Winsted
Remove Boundaries ×
Map Satellite

Want to learn more about 55+ communities in Winsted?

Call us: (860) 909-8066

Call Us Call Us
Scroll to Top