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

80 communities 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

5 rating (2 reviews)

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

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

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

Questions? Call us: (860) 909-8066

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 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 Fishkill

$300ks - $400ks

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.

The Village at Whispering...

$400ks

The Village at Whispering...Rotterdam, NY

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

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

Questions? Call us: (860) 909-8066

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

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

The Cottages at Wire Mill

$1Ms

The Cottages at Wire Mill, Stamford, CT

New Construction | 55+ age-restricted | Built 2026 - present | 9 homes

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

New Construction | 55+ age-restricted | Built 2020 - present | 24 homes

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

Park Glen

$300ks - $500ks

Park Glen, New Milford, CT

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

Newbury Village

$400ks - $500ks

Newbury Village, Brookfield, CT

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

Autumn Fields

$200ks - $300ks

Autumn Fields, Enfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 homes

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Billingsgate

$400ks - $600ks

Billingsgate, Simsbury, CT

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

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

Questions? Call us: (860) 909-8066

5 rating (1 reviews)

Paris Square

$500ks - $700ks

Paris Square, Northvale, NJ

New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes

Hopmeadow Place

$200ks - $300ks

Hopmeadow Place, Simsbury, CT

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

Glassbury Court at Hunter...

$500ks - $700ks

Glassbury Court at Hunter..., Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes

Woodcrest at Jacobs Hill

$200ks - $300ks

Woodcrest at Jacobs Hill, Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 homes

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

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

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

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

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

RiverBend Estates

$400ks

RiverBend Estates, Oxford, CT

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

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

Questions? Call us: (860) 909-8066

Summer Wind Estates

$300ks - $400ks

Summer Wind Estates, North Haven, CT

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

Bidwell Village

$300ks - $400ks

Bidwell Village, Coventry, CT

New Construction | 55+ age-restricted | Built 2020 - present | 37 homes

1...2

New Regency at Wappinger

5 PALMERTON DR, WAPPINGER, NY, 12590, Wappinger, NY 12590

$829,900

2 beds

3 baths

3,156 sq ft

Condo

5 PALMERTON DR, WAPPINGER, NY, 12590

970 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

Rivington

44 WARRINGTON ROUND ST 44, DANBURY, CT, ..., Danbury, CT 06810

$628,000

3 beds

3 baths

1,600 sq ft

Condo

44 WARRINGTON ROUND ST 44, DANBURY, CT, ...

Community: Rivington

Heritage Village

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

$427,500

2 beds

2 baths

1,398 sq ft

Condo

411 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$319,000

2 beds

2 baths

1,432 sq ft

Condo

620 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

733 CHAMPIONSHIP DR 733, OXFORD, CT, 064..., Oxford, CT 06478

$624,900

2 beds

3 baths

1,673 sq ft

Condo

733 CHAMPIONSHIP DR 733, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Regency at Prospect

133 SYCAMORE DR, PROSPECT, CT, 06712, Prospect, CT 06712

$550,000

2 beds

3 baths

1,850 sq ft

Condo

133 SYCAMORE DR, PROSPECT, CT, 06712

Community: Regency at Prospect

Newtown Woods

623 BROOKSIDE CT 623, NEWTOWN, CT, 06470, Newtown, CT 06470

$498,900

2 beds

2 baths

1,504 sq ft

Condo

623 BROOKSIDE CT 623, NEWTOWN, CT, 06470

Community: Newtown Woods

Heritage Hills

675 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589

$825,000

2 beds

2 baths

1,663 sq ft

Condo

675 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

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

$225,000

1 beds

1 baths

928 sq ft

Condo

875 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Retreat at Carmel

88 BLAIR HEIGHTS, CARMEL, NY, 10512, Carmel, NY 10512

$699,000

3 beds

3 baths

2,695 sq ft

Condo

88 BLAIR HEIGHTS, CARMEL, NY, 10512

Community: The Retreat at Carmel

Heritage Hills

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

$679,000

2 beds

2 baths

1,470 sq ft

Condo

370 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

The Village at Buckingham

13 KENINGTON RD 13, AVON, CT, 06001, Avon, CT 06001

$639,900

3 beds

3 baths

2,024 sq ft

Condo

13 KENINGTON RD 13, AVON, CT, 06001

Condo

28 HERITAGE CIR 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

Jefferson Village

148 FLINTLOCK WAY G, YORKTOWN, NY, 10598, Yorktown, NY 10598

$599,900

2 beds

2 baths

1,302 sq ft

Condo

148 FLINTLOCK WAY G, YORKTOWN, NY, 10598

Community: Jefferson Village

Oronoque Village

443 N TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$499,000

1 beds

3 baths

1,175 sq ft

Condo

443 N TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

South Pond Village

8 S POND RD 8, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$499,900

3 beds

3 baths

1,912 sq ft

Condo

8 S POND RD 8, BLOOMFIELD, CT, 06002

Community: South Pond Village

Heritage Village

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

$200,000

2 beds

2 baths

1,076 sq ft

Condo

214 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

South Pond Village

37 REED CT 37, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$299,000

2 beds

3 baths

1,258 sq ft

Condo

37 REED CT 37, BLOOMFIELD, CT, 06002

Community: South Pond Village

Oronoque Village

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

$649,000

2 beds

2 baths

1,426 sq ft

Condo

237 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

Glassbury Court at Hunterbrook

2314 DEPEYSTER DR, YORKTOWN, NY, 10567, Yorktown, NY 10567

$952,900

2 beds

3 baths

2,265 sq ft

Condo

2314 DEPEYSTER DR, YORKTOWN, NY, 10567

Community: Glassbury Court at Hunterbrook

Heritage Village

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

$235,000

2 beds

2 baths

1,000 sq ft

Condo

732 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Park Glen

4 RAINBOW CT 4, NEW MILFORD, CT, 06776, New Milford, CT 06776

$649,000

2 beds

4 baths

2,600 sq ft

Condo

4 RAINBOW CT 4, NEW MILFORD, CT, 06776

Community: Park Glen

Heritage Village

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

$395,000

2 beds

2 baths

1,432 sq ft

Condo

783 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$329,900

2 beds

2 baths

1,398 sq ft

Condo

738 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

Granite Woods

35 NUTMEG RD B2, MIDDLEBURY, CT, 06762, Middlebury, CT 06762

$224,900

1 beds

1 baths

889 sq ft

Condo

35 NUTMEG RD B2, MIDDLEBURY, CT, 06762

Community: Granite Woods

Oronoque Village

393 OTTAWA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$350,000

1 beds

3 baths

1,118 sq ft

Condo

393 OTTAWA LN B, STRATFORD, CT, 06614

Community: Oronoque Village

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.

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80 communities

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

80 communities near Winsted

177 homes near Winsted

2 beds

3 baths

3,156 sq ft

Condo

3 beds

3 baths

2,008 sq ft

Condo

1 beds

2 baths

1,235 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

3 baths

1,600 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

3 baths

1,673 sq ft

Condo

2 beds

3 baths

1,850 sq ft

Condo

2 beds

2 baths

1,504 sq ft

Condo

2 beds

2 baths

1,663 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

3 beds

3 baths

2,695 sq ft

Condo

2 beds

2 baths

1,470 sq ft

Condo

3 beds

3 baths

2,024 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

2 beds