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

78 communities near Winsted

Sort by:

Relevance

3.6 rating (7 reviews)

Heritage Village

$200ks - $500ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 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 - $900ks

Heritage Hills, Somers, NY

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

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

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

Questions? Call us: (860) 909-8066

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

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

Questions? Call us: (860) 909-8066

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 Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

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

Questions? Call us: (860) 909-8066

North Woods of Colchester

$300ks - $400ks

North Woods of Colchester, Colchester, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

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

O'Meara Farm

$400ks

O'Meara Farm, Farmington, CT

Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

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

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

Questions? Call us: (860) 909-8066

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

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

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

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

Want to learn more about 55+ rental 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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

Villas at Seminary Hill

$200ks - $300ks

Villas at Seminary Hill, Carmel, NY

New Construction | 55+ age-restricted | Built 2018 - present | 50 homes

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

Questions? Call us: (860) 909-8066

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

Hopmeadow Place

$200ks - $300ks

Hopmeadow Place, Simsbury, CT

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

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

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

The Woods at Dunham Pond

$200ks - $400ks

The Woods at Dunham Pond, New Fairfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes

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

Questions? Call us: (860) 909-8066

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

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

Bidwell Village

$300ks - $400ks

Bidwell Village, Coventry, CT

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

1...2

New The Village at Oxford Greens

114 COUNTRY CLUB DR 114, OXFORD, CT, 064..., Oxford, CT 06478

$575,000

2 beds

2 baths

1,590 sq ft

114 COUNTRY CLUB DR 114, OXFORD, CT, 064...

Community: The Village at Oxford Greens

New Newtown Woods

1211 BROOKSIDE CT 1211, NEWTOWN, CT, 064..., Newtown, CT 06470

$485,000

2 beds

2 baths

1,483 sq ft

Condo

1211 BROOKSIDE CT 1211, NEWTOWN, CT, 064...

Community: Newtown Woods

New Heritage Village

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

$489,900

2 beds

2 baths

1,398 sq ft

Condo

930 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Liberty at Newtown

66 SUZIE DR 66, NEWTOWN, CT, 06470, Newtown, CT 06470

$636,000

2 beds

3 baths

2,407 sq ft

Condo

66 SUZIE DR 66, NEWTOWN, CT, 06470

Community: Liberty at Newtown

New Glassbury Court at Cold Spring

19 REVOLUTION RD, PHILIPSTOWN, NY, 10516, Philipstown, NY 10516

$567,358

2 beds

3 baths

1,806 sq ft

Condo

19 REVOLUTION RD, PHILIPSTOWN, NY, 10516

Community: Glassbury Court at Cold Spring

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

Questions? Call us: (860) 909-8066

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

Questions? Call us: (860) 909-8066

New Jefferson Village

173 LONG HILL DR I, YORKTOWN, NY, 10598, Yorktown, NY 10598

$330,000

1 beds

1 baths

850 sq ft

Condo

173 LONG HILL DR I, YORKTOWN, NY, 10598

Community: Jefferson Village

New Heritage Hills

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

$649,000

2 beds

2 baths

1,483 sq ft

Condo

612 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Meadow Brook Estates

194 EASTWOOD DR 194, SEYMOUR, CT, 06483, Seymour, CT 06483

$599,000

2 beds

3 baths

2,295 sq ft

Condo

194 EASTWOOD DR 194, SEYMOUR, CT, 06483

Community: Meadow Brook Estates

New The Powder Forest Homes

47 ASHTON CIR 47, SIMSBURY, CT, 06070, Simsbury, CT 06070

$695,000

2 beds

3 baths

1,843 sq ft

47 ASHTON CIR 47, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

New Heritage Village

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

$229,900

2 beds

2 baths

1,044 sq ft

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

New Spring Lake Village

214 WATERS EDGE DR 214, SOUTHINGTON, CT,..., Southington, CT 06489

$317,000

2 beds

3 baths

1,564 sq ft

Condo

214 WATERS EDGE DR 214, SOUTHINGTON, CT,...

Community: Spring Lake Village

New Heritage Village

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

$358,000

2 beds

2 baths

1,398 sq ft

Condo

889 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New North Woods of Colchester

24 CENTER CT 24, COLCHESTER, CT, 06415, Colchester, CT 06415

$515,000

2 beds

2 baths

1,357 sq ft

Condo

24 CENTER CT 24, COLCHESTER, CT, 06415

Community: North Woods of Colchester

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

Questions? Call us: (860) 909-8066

New Oronoque Village

402 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$515,000

2 beds

3 baths

1,118 sq ft

Condo

402 MONTAUK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New 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

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

Questions? Call us: (860) 909-8066

New Heritage Village

36 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$525,000

3 beds

2 baths

1,716 sq ft

Condo

36 HERITAGE CIR B, SOUTHBURY, CT, 06488

Community: Heritage Village

New South Pond Village

78 SILO WAY 78, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$289,900

3 beds

3 baths

1,639 sq ft

Condo

78 SILO WAY 78, BLOOMFIELD, CT, 06002

Community: South Pond Village

New The Powder Forest Homes

3 RONAN WAY 3, SIMSBURY, CT, 06070, Simsbury, CT 06070

$629,900

2 beds

3 baths

1,284 sq ft

Condo

3 RONAN WAY 3, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

Heritage Hills

272 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$569,900

2 beds

2 baths

1,500 sq ft

Condo

272 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

The Village at Oxford Greens

575 INVERNESS CT 575, OXFORD, CT, 06478, Oxford, CT 06478

$699,900

3 beds

3 baths

2,008 sq ft

575 INVERNESS CT 575, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Oak Meadow Estates

65 OAK MEADOW LN 65, TORRINGTON, CT, 067..., Torrington, CT 06790

$485,000

2 beds

4 baths

2,164 sq ft

Condo

65 OAK MEADOW LN 65, TORRINGTON, CT, 067...

Community: Oak Meadow Estates

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

Questions? Call us: (860) 909-8066

Jefferson Village

119 VILLAGE RD H, YORKTOWN, NY, 10598, Yorktown, NY 10598

$439,000

2 beds

2 baths

1,100 sq ft

Condo

119 VILLAGE RD H, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Hills

725 HERITAGE HLS, SOMERS, NY, 10589, Somers, NY 10589

$774,900

2 beds

2 baths

1,526 sq ft

Condo

725 HERITAGE HLS, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

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

$249,000

1 beds

1 baths

928 sq ft

Condo

4 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Jefferson Village

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

$469,999

2 beds

2 baths

1,100 sq ft

Condo

129 COLUMBIA CT D, YORKTOWN, NY, 10598

Community: Jefferson Village

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

Questions? Call us: (860) 909-8066

Fairview at Oxford Greens

1077 AUGUSTA DR 1077, OXFORD, CT, 06478, Oxford, CT 06478

$684,900

3 beds

3 baths

2,256 sq ft

Condo

1077 AUGUSTA DR 1077, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$684,900

3 beds

3 baths

2,256 sq ft

Condo

1077 AUGUSTA DR 1077, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Overlook

2079 SUMMIT LOOP 103, CARMEL, NY, 10512, Carmel, NY 10512

$899,000

2 beds

2 baths

1,948 sq ft

Condo

2079 SUMMIT LOOP 103, CARMEL, NY, 10512

Community: Overlook

Heritage Village

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

$189,000

2 beds

2 baths

1,044 sq ft

Condo

331 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Hills

29 HERITAGE HLS 29D, SOMERS, NY, 10589, Somers, NY 10589

$495,000

2 beds

3 baths

1,340 sq ft

Condo

29 HERITAGE HLS 29D, SOMERS, NY, 10589

Community: Heritage Hills

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

Questions? Call us: (860) 909-8066

Oronoque Village

99 SEMINOLE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$485,000

1 beds

3 baths

1,426 sq ft

Condo

99 SEMINOLE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$279,000

2 beds

2 baths

1,432 sq ft

Condo

53 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

196 APACHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$365,000

1 beds

2 baths

1,175 sq ft

Condo

196 APACHE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Jefferson Village

10 REGENTS PL D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$240,000

1 baths

550 sq ft

Condo

10 REGENTS PL D, YORKTOWN, NY, 10598

Community: Jefferson Village

O'Meara Farm

1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032, Farmington, CT 06032

$480,000

2 beds

2 baths

1,416 sq ft

Condo

1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032

Community: O'Meara Farm

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

Questions? Call us: (860) 909-8066

Heritage Village

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

$360,000

2 beds

2 baths

1,432 sq ft

Condo

640 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Regency at Fishkill

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

$549,999

2 beds

2 baths

1,803 sq ft

Condo

145 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

Oronoque Village

47 HURON LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$409,000

2 beds

2 baths

1,360 sq ft

Condo

47 HURON LN A, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (860) 909-8066

Regency at Prospect

104 CHERRY CIR 104, PROSPECT, CT, 06712, Prospect, CT 06712

$328,417

3 beds

2 baths

1,500 sq ft

Condo

104 CHERRY CIR 104, PROSPECT, CT, 06712

Community: Regency at Prospect

Rivington

131 WINDING RIDGE WAY 131, DANBURY, CT, ..., Danbury, CT 06810

$770,000

3 beds

3 baths

1,592 sq ft

Condo

131 WINDING RIDGE WAY 131, DANBURY, CT, ...

Community: Rivington

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?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

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

78 communities

Remove Boundaries ×

Map Satellite

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.
© 2026 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: Apr 13, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

78 communities near Winsted

158 homes near Winsted

2 beds

2 baths

1,590 sq ft

2 beds

2 baths

1,483 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

3 baths

2,407 sq ft

Condo

2 beds

3 baths

1,806 sq ft

Condo

1 beds

1 baths

850 sq ft

Condo

2 beds

2 baths

1,483 sq ft

Condo

2 beds

3 baths

2,295 sq ft

Condo

2 beds

3 baths

1,843 sq ft

2 beds

2 baths

1,044 sq ft

Condo

2 beds

3 baths

1,564 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,357 sq ft

Condo

2 beds

3 baths

1,118 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

3 beds

3 baths

1,639 sq ft

Condo

2 beds

3 baths

1,284 sq ft

Condo

2 beds

2 baths

1,500 sq ft

Condo

3 beds

3 baths

2,008 sq ft