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

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

77 communities 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 - $500Ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes
No reviews yet Rivington
$400Ks - $500Ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
4 rating (1 reviews) Jefferson Village
$200Ks - $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 - $700Ks
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 - $200Ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
No reviews yet Regency at Prospect
$300Ks - $500Ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
No reviews yet The Retreat at Carmel
$400Ks - $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 Overlook
$600Ks - $900Ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 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
$600Ks - $600Ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
4.9 rating (14 reviews) Chatfield Farms
$500Ks - $600Ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 homes
No reviews yet Regency at Wappinger
$600Ks - $700Ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
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 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
$400Ks - $500Ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
No reviews yet South Pond Village
$100Ks - $200Ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 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 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
$500Ks - $500Ks
North Woods of Colchester, Colchester, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes
No reviews yet Fairview at Oxford Greens
$600Ks - $700Ks
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
$600Ks - $700Ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
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
No reviews yet The Bridges at Oxford Gre...
$600Ks - $600Ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction | 55+ age-restricted | Built 2025 - present | 99 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 Applegate Estates
$500Ks - $400Ks
Applegate Estates, Southington, CT
New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 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 Founders Village
$500Ks - $600Ks
Founders Village, Southold, NY
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 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 Glassbury Court at Cold S...
$500Ks - $700Ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 homes
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
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
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
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
1...2
Heritage Village 862 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$499,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

862 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 7 HERITAGE CRST B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$449,900

2 beds

|

2 baths

|

1,447 sq ft

|

Condo

7 HERITAGE CRST B, SOUTHBURY, CT, 06488
Community: Heritage Village
Newbury Village 21 GREAT HERON LN # 21, BROOKFIELD, CT, ..., Brookfield, CT 06804
$720,000

3 beds

|

4 baths

|

2,644 sq ft

|

Condo

21 GREAT HERON LN # 21, BROOKFIELD, CT, ...
Community: Newbury Village
New Regency at Woodbridge 21 HERITAGE LN # 60, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$729,000

3 beds

|

3 baths

|

Condo

21 HERITAGE LN # 60, WOODBRIDGE, CT, 065...
New Regency at Woodbridge 6 WHISPER RIDGE WAY # 42, WOODBRIDGE, CT..., Woodbridge, CT 06525
$619,000

3 beds

|

3 baths

|

Condo

6 WHISPER RIDGE WAY # 42, WOODBRIDGE, CT...
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
New Regency at Woodbridge 12 WHISPER RIDGE WAY # 45, WOODBRIDGE, C..., Woodbridge, CT 06525
$679,000

3 beds

|

3 baths

|

Condo

12 WHISPER RIDGE WAY # 45, WOODBRIDGE, C...
New Heritage Village 1008 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$399,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

1008 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
Heritage Village 890 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$325,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

890 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 133 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$300,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

133 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 73 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$259,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

73 HERITAGE VLG D, 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 568A HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488
$429,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

568A HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
New Rivington 94 WARRINGTON ROUND # 94, DANBURY, CT, 0..., Danbury, CT 06810
$585,000

2 beds

|

3 baths

|

1,600 sq ft

|

Condo

94 WARRINGTON ROUND # 94, DANBURY, CT, 0...
Community: Rivington
Heritage Village 919 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

919 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 916 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$415,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

916 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Oronoque Village 619B ERIE LN # 619B, STRATFORD, CT, 0661..., Stratford, CT 06614
$410,000

2 beds

|

3 baths

|

2,420 sq ft

|

Condo

619B ERIE LN # 619B, STRATFORD, CT, 0661...
Community: Oronoque Village
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
New The Village at Oxford Greens 709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0..., Oxford, CT 06478
$615,000

2 beds

|

2 baths

|

1,532 sq ft

|

Condo

709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0...
New Fairview at Oxford Greens 709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0..., Oxford, CT 06478
$615,000

2 beds

|

2 baths

|

1,532 sq ft

|

Condo

709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0...
Regency at Woodbridge 13 HERITAGE LN # 64, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$599,000

3 beds

|

3 baths

|

2,239 sq ft

|

Condo

13 HERITAGE LN # 64, WOODBRIDGE, CT, 065...
Oronoque Village 617 CHEROKEE LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$544,999

3 beds

|

3 baths

|

1,438 sq ft

|

Condo

617 CHEROKEE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 740 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$415,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

740 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.
New The Woods at Dunham Pond 12 HERON VIEW RD # 12, NEW FAIRFIELD, CT..., New Fairfield, CT 06812
$419,900

1 beds

|

2 baths

|

1,550 sq ft

12 HERON VIEW RD # 12, NEW FAIRFIELD, CT...
The Village at Oxford Greens 1130 ST ANDREWS DR 94, OXFORD, CT, 06478, Oxford, CT 06478
$729,900

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1130 ST ANDREWS DR 94, OXFORD, CT, 06478
The Village at Oxford Greens 1097 SAINT ANDREWS DR LOT 9, OXFORD, CT,..., Oxford, CT 06478
$773,625

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1097 SAINT ANDREWS DR LOT 9, OXFORD, CT,...
Fairview at Oxford Greens 1097 SAINT ANDREWS DR LOT 9, OXFORD, CT,..., Oxford, CT 06478
$773,625

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1097 SAINT ANDREWS DR LOT 9, OXFORD, CT,...
The Village at Oxford Greens 1132 ST ANDREWS DR 93, OXFORD, CT, 06478, Oxford, CT 06478
$719,900

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1132 ST ANDREWS DR 93, OXFORD, CT, 06478
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Fairview at Oxford Greens 1132 ST ANDREWS DR 93, OXFORD, CT, 06478, Oxford, CT 06478
$719,900

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1132 ST ANDREWS DR 93, OXFORD, CT, 06478
Fairview at Oxford Greens 1130 ST ANDREWS DR 94, OXFORD, CT, 06478, Oxford, CT 06478
$729,900

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1130 ST ANDREWS DR 94, OXFORD, CT, 06478
The Village at Oxford Greens 1111 ST ANDREWS DR 16, OXFORD, CT, 06478, Oxford, CT 06478
$699,900

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478
Fairview at Oxford Greens 1111 ST ANDREWS DR 16, OXFORD, CT, 06478, Oxford, CT 06478
$699,900

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478
Heritage Village 825 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$289,900

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

825 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.
New Heritage Village 44 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488
$239,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

44 HERITAGE VLG F, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 578 PUTTING GREEN LN # 578, OXFORD, CT, ..., Oxford, CT 06478
$715,000

2 beds

|

3 baths

|

2,008 sq ft

|

Condo

578 PUTTING GREEN LN # 578, OXFORD, CT, ...
Newtown Woods 603 BROOKSIDE CT # 603, NEWTOWN, CT, 064..., Newtown, CT 06470
$489,000

2 beds

|

2 baths

|

1,504 sq ft

|

Condo

603 BROOKSIDE CT # 603, NEWTOWN, CT, 064...
Community: Newtown Woods
Heritage Village 123 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

123 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Long Hill Village 17 RAINBOW DR, TRUMBULL, CT, 06611, Trumbull, CT 06611
$484,900

2 beds

|

2 baths

|

1,370 sq ft

|

Condo

17 RAINBOW DR, TRUMBULL, CT, 06611
Community: Long Hill Village
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
New Oronoque Village 375 PIUTE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$620,000

2 beds

|

3 baths

|

1,550 sq ft

|

Condo

375 PIUTE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Chatfield Farms 18 FIELDSTONE LN # 18, BEACON FALLS, CT,..., Beacon Falls, CT 06403
$599,000

2 beds

|

3 baths

|

2,719 sq ft

18 FIELDSTONE LN # 18, BEACON FALLS, CT,...
Community: Chatfield Farms
Oronoque Village 87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$447,000

1 beds

|

2 baths

|

1,454 sq ft

|

Condo

87 CREEK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Oronoque Village 50 CEDAR BARK LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$375,000

1 beds

|

2 baths

|

1,118 sq ft

|

Condo

50 CEDAR BARK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 623 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$535,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

623 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
1234…5

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.

Want to learn more about 55+ communities in Winsted?

Call us: (860) 909-8066
77 communities near Winsted
Remove Boundaries ×
Map Satellite

Reinmlsx

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2025 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Oct 29, 2025.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top