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

160 homes near Winsted

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3.6 rating (7 reviews)

Heritage Village

$200ks - $500ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes

3 rating (2 reviews)

Heritage Hills

$400ks - $800ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

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Questions? Call us: (860) 909-8066

The Village at Oxford Gre...

$400ks - $500ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 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.

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes

Rivington

$300ks - $900ks

Rivington, Danbury, CT

New and Resale | Age-targeted | Built 2006 - present | 1,050 homes

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes

4.9 rating (14 reviews)

Chatfield Farms

$400ks - $700ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes

Newbury Village

$400ks - $500ks

Newbury Village, Brookfield, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes

Hopmeadow Place

$200ks - $300ks

Hopmeadow Place, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes

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

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

New Construction | 55+ age-restricted | Built 2023 - present | 70 homes

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes

The Village at Whispering...

$400ks

The Village at Whispering...Rotterdam, NY

New Construction | 55+ age-restricted | Built 2025 - present | 85 homes

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes

Billingsgate

$400ks - $600ks

Billingsgate, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes

Boulder Brook

$200ks

Boulder Brook, Prospect, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes

Gloria Commons

$200ks - $300ks

Gloria Commons, Milford, CT

Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes

The Bridges at Oxford Gre...

$600ks

The Bridges at Oxford Gre..., Oxford, CT

New Construction | 55+ age-restricted | Built 2025 - present | 99 homes

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes

Park Glen

$300ks - $500ks

Park Glen, New Milford, CT

Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

RiverBend Estates

$400ks

RiverBend Estates, Oxford, CT

New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes

Summer Wind Estates

$300ks - $400ks

Summer Wind Estates, North Haven, CT

New Construction | 55+ age-restricted | Built 2015 - present | 18 homes

1...2

New Heritage Village

132 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$439,000

2 beds

2 baths

1,432 sq ft

Condo

132 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Jefferson Village

113 VILLAGE RD C, YORKTOWN, NY, 10598, Yorktown, NY 10598

$420,000

2 beds

2 baths

1,200 sq ft

Condo

113 VILLAGE RD C, YORKTOWN, NY, 10598

Community: Jefferson Village

New Founders Village

2555 YOUNGS AVE 1D, SOUTHOLD, NY, 11971, Southold, NY 11971

$560,000

2 beds

2 baths

1,100 sq ft

House

2555 YOUNGS AVE 1D, SOUTHOLD, NY, 11971

Community: Founders Village

New Oronoque Village

13 ALGONQUIN LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$396,000

1 beds

2 baths

1,480 sq ft

Condo

13 ALGONQUIN LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New Meadow Brook Estates

806 SAGE HILL DR 806, OXFORD, CT, 06478, Oxford, CT 06478

$599,000

2 beds

3 baths

1,850 sq ft

Condo

806 SAGE HILL DR 806, OXFORD, CT, 06478

Community: Meadow Brook Estates

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

New Heritage Village

877 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$289,000

2 beds

2 baths

1,365 sq ft

Condo

877 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New The Summit at Bethel

6 LOCKWOOD CIR 6, BETHEL, CT, 06801, Bethel, CT 06801

$619,000

3 beds

3 baths

1,771 sq ft

Condo

6 LOCKWOOD CIR 6, BETHEL, CT, 06801

Community: The Summit at Bethel

New Pond Spring Village

37 SEPTEMBER LN 37, BEACON FALLS, CT, 06..., Beacon Falls, CT 06403

$450,000

2 beds

3 baths

1,328 sq ft

Condo

37 SEPTEMBER LN 37, BEACON FALLS, CT, 06...

Community: Pond Spring Village

New Heritage Village

657 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$525,000

3 beds

3 baths

1,716 sq ft

Condo

657 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Heritage Village

343 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$215,000

2 beds

2 baths

1,044 sq ft

Condo

343 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

New Rivington

925 OLD PASTURE DR 925, DANBURY, CT, 068..., Danbury, CT 06810

$510,000

2 beds

2 baths

1,258 sq ft

Condo

925 OLD PASTURE DR 925, DANBURY, CT, 068...

Community: Rivington

New Chatfield Farms

24 BAYBERRY CT 24, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403

$725,000

3 beds

3 baths

1,981 sq ft

Condo

24 BAYBERRY CT 24, BEACON FALLS, CT, 064...

Community: Chatfield Farms

New Regency at Fishkill

541 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$529,000

2 beds

2 baths

1,499 sq ft

Condo

541 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

Jefferson Village

131 COLUMBIA CT D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$399,000

2 beds

2 baths

1,141 sq ft

Condo

131 COLUMBIA CT D, YORKTOWN, NY, 10598

Community: Jefferson Village

The Retreat at Carmel

2 BLAIR HEIGHTS 3323, CARMEL, NY, 10512, Carmel, NY 10512

$455,000

2 beds

2 baths

1,323 sq ft

Condo

2 BLAIR HEIGHTS 3323, CARMEL, NY, 10512

Community: The Retreat at Carmel

Regency at Wappinger

2 AVONDALE LN, WAPPINGER, NY, 12590, Wappinger, NY 12590

$799,000

2 beds

4 baths

2,941 sq ft

Condo

2 AVONDALE LN, WAPPINGER, NY, 12590

Community: Regency at Wappinger

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Heritage Hills

386 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$679,999

2 beds

2 baths

1,416 sq ft

Condo

386 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Jefferson Village

23 DORSET CT C, YORKTOWN, NY, 10598, Yorktown, NY 10598

$339,000

1 beds

1 baths

700 sq ft

Condo

23 DORSET CT C, YORKTOWN, NY, 10598

Community: Jefferson Village

Meadow Brook Estates

223 MEADOW BROOK RD 223, OXFORD, CT, 064..., Oxford, CT 06478

$589,900

2 beds

2 baths

1,480 sq ft

Condo

223 MEADOW BROOK RD 223, OXFORD, CT, 064...

Community: Meadow Brook Estates

Oronoque Village

261 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614

$550,000

2 beds

3 baths

1,620 sq ft

Condo

261 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

899 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$479,000

2 beds

2 baths

1,432 sq ft

Condo

899 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

209 ACORN LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$599,000

1 beds

3 baths

1,438 sq ft

Condo

209 ACORN LN B, STRATFORD, CT, 06614

Community: Oronoque Village

The Powder Forest Homes

9 ASHTON CIR, SIMSBURY, CT, 06070, Simsbury, CT 06070

$700,000

2 beds

2 baths

1,809 sq ft

Condo

9 ASHTON CIR, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

Applegate Estates

90 APPLE GATE 190, SOUTHINGTON, CT, 0648..., Southington, CT 06489

$450,000

2 beds

2 baths

1,350 sq ft

Condo

90 APPLE GATE 190, SOUTHINGTON, CT, 0648...

Community: Applegate Estates

The Village at Oxford Greens

71 LINKS WAY 71, OXFORD, CT, 06478, Oxford, CT 06478

$598,000

2 beds

2 baths

1,590 sq ft

Condo

71 LINKS WAY 71, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Heritage Village

397 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$264,999

2 beds

2 baths

1,432 sq ft

Condo

397 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Regency at Fishkill

145 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$539,999

2 beds

2 baths

1,803 sq ft

Condo

145 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Heritage Hills

$500,000

1 beds

1 baths

955 sq ft

Condo

37 HERITAGE HILLS DR A, SOMERS, NY, 1058...

Community: Heritage Hills

Regency Meadows

108 IMPERIAL CT 108, TRUMBULL, CT, 06611, Trumbull, CT 06611

$739,000

2 beds

3 baths

2,891 sq ft

Condo

108 IMPERIAL CT 108, TRUMBULL, CT, 06611

Community: Regency Meadows

Heritage Village

139 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$409,000

2 beds

2 baths

1,432 sq ft

Condo

139 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Regency at Fishkill

246 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$499,999

1 beds

2 baths

1,543 sq ft

Condo

246 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

Heritage Village

738 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$365,000

2 beds

2 baths

1,398 sq ft

Condo

738 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

69 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$289,900

2 beds

2 baths

1,044 sq ft

Condo

69 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

122 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$354,000

2 beds

2 baths

1,432 sq ft

Condo

122 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

47 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$324,900

2 beds

2 baths

1,398 sq ft

Condo

47 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Jefferson Village

23 DORSET CT F, YORKTOWN, NY, 10598, Yorktown, NY 10598

$315,000

2 beds

1 baths

925 sq ft

Condo

23 DORSET CT F, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Village

69 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$270,000

2 beds

2 baths

1,044 sq ft

Condo

69 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$349,900

2 beds

2 baths

1,432 sq ft

Condo

170 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

Regency at Fishkill

326 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$519,000

1 beds

2 baths

1,543 sq ft

Condo

326 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

Oronoque Village

488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$575,000

2 beds

3 baths

1,438 sq ft

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

1 2 3…4

Frequently Asked Questions

What size 55+ communities are there in Winsted?

In Winsted, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Winsted?

The smallest 55+ community in Winsted has 38 homes, the largest has 38 homes, and the average community consists of 38 homes.

Are there gated 55+ communities in Winsted?

No, there are no gated 55+ communities in Winsted.

Want more information about active adult communities around Winsted?

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160 homes

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

78 communities near Winsted

160 homes near Winsted

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Condo

2 beds

2 baths

1,100 sq ft

House

1 beds

2 baths

1,480 sq ft

Condo

2 beds

3 baths

1,850 sq ft

Condo

2 beds

2 baths

1,365 sq ft

Condo

3 beds

3 baths

1,771 sq ft

Condo

2 beds

3 baths

1,328 sq ft

Condo

3 beds

3 baths

1,716 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

3 beds

3 baths

1,981 sq ft

Condo

2 beds

2 baths

1,499 sq ft

Condo

2 beds

2 baths

1,141 sq ft

Condo

2 beds

2 baths

1,323 sq ft

Condo

2 beds

4 baths

2,941 sq ft

Condo

2 beds

2 baths

1,416 sq ft

Condo

1 beds

1 baths

700 sq ft

Condo

2 beds

2 baths

1,480 sq ft

Condo

2 beds