Call us at (860) 238-3620 to learn more about active adult communities near Winchester Area

Winchester Area, CT 55+ active adult communities & homes for sale - Page 2

89 communities near Winchester Area

Sort by:

Relevance

Relevance

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 The Vineyards at Mount Si...
$800Ks - $1Ms
The Vineyards at Mount Si..., Mount Sinai, NY
New Construction | 55+ age-restricted | Built 2020 - present | 91 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
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
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
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 The Vineyards at Miller P...
$600Ks - $600Ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes
No reviews yet Baldwin Station
$400Ks - $400Ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
No reviews yet Bartlett Hill
$500Ks - $500Ks
Bartlett Hill, Portland, CT
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 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 (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
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
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
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
No reviews yet Stoneleigh Woods at Carme...
$400Ks - $400Ks
Stoneleigh Woods at Carme..., Carmel, NY
Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes
No reviews yet Sonoma Woods
$300Ks - $300Ks
Sonoma Woods, Middletown, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes
No reviews yet Hopmeadow Place
$200Ks - $300Ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes
No reviews yet Glassbury Court at Hunter...
$500Ks - $700Ks
Glassbury Court at Hunter..., Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 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 Whitney Glen
$500Ks - $600Ks
Whitney Glen, Westport, CT
Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes
No reviews yet RiverWalk
$500Ks - $600Ks
RiverWalk, Branford, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes
No reviews yet Woodcrest at Jacobs Hill
$300Ks - $300Ks
Woodcrest at Jacobs Hill, Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 homes
No reviews yet The Village at Buckingham
$500Ks - $600Ks
The Village at Buckingham, Avon, CT
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes
No reviews yet The Atrium of Portland
<$100k - $100Ks
The Atrium of Portland, Portland, CT
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
No reviews yet Autumn Fields
$200Ks - $300Ks
Autumn Fields, Enfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 homes
No reviews yet 77 Sunset Lane
$400Ks - $700Ks
77 Sunset Lane, Ridgefield, CT
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes
No reviews yet Evergreen
$400Ks - $500Ks
Evergreen, Cromwell, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes
No reviews yet Regency Meadows
$500Ks - $500Ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
No reviews yet Villas at Seminary Hill
$400Ks - $400Ks
Villas at Seminary Hill, Carmel, NY
New Construction | 55+ age-restricted | Built 2018 - present | 50 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 Gloria Commons
$400Ks - $400Ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes
No reviews yet The Residences at Butterf...
$500Ks - $600Ks
The Residences at Butterf..., Cold Spring, NY
Resale Only | 55+ age-restricted | Built 2018 - 2023 | 49 homes
No reviews yet Bramble Ridge
$400Ks - $500Ks
Bramble Ridge, Suffield, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 homes
No reviews yet Chimney Hill
$500Ks - $700Ks
Chimney Hill, Farmington, CT
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes
No reviews yet Village Vistas
$800Ks - $1Ms
Village Vistas, Port Jefferson, NY
Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
No reviews yet Forest Mews
$300Ks - $400Ks
Forest Mews, Avon, CT
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 homes
No reviews yet Bidwell Village
$300Ks - $400Ks
Bidwell Village, Coventry, CT
New Construction | 55+ age-restricted | Built 2020 - present | 37 homes
No reviews yet Billingsgate
$400Ks - $600Ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
No reviews yet Boulder Brook
$200Ks - $200Ks
Boulder Brook, Prospect, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes
No reviews yet The Woods at Dunham Pond
$400Ks - $500Ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes
Oronoque Village 288 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614
$389,000

1 beds

|

2 baths

|

1,175 sq ft

|

Condo

288 AGAWAM DR B, STRATFORD, CT, 06614
Community: Oronoque Village
The Village at Oxford Greens 1097 SAINT ANDREWS DR, OXFORD, CT, 06478, Oxford, CT 06478
$773,625

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

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

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1097 SAINT ANDREWS DR, OXFORD, CT, 06478
Fairview at Oxford Greens 1099 SAINT ANDREWS DR, OXFORD, CT, 06478, Oxford, CT 06478
$747,075

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1099 SAINT ANDREWS DR, OXFORD, CT, 06478
The Village at Oxford Greens 1099 SAINT ANDREWS DR, OXFORD, CT, 06478, Oxford, CT 06478
$747,075

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1099 SAINT ANDREWS DR, OXFORD, CT, 06478
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Fairview at Oxford Greens 1105 ST ANDREWS DR, OXFORD, CT, 06478, Oxford, CT 06478
$709,900

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1105 ST ANDREWS DR, OXFORD, CT, 06478
The Village at Oxford Greens 1105 ST ANDREWS DR, OXFORD, CT, 06478, Oxford, CT 06478
$709,900

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1105 ST ANDREWS DR, OXFORD, CT, 06478
Fairview at Oxford Greens 1101 ST ANDREWS DR, OXFORD, CT, 06478, Oxford, CT 06478
$709,900

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1101 ST ANDREWS DR, OXFORD, CT, 06478
The Village at Oxford Greens 1101 ST ANDREWS DR, OXFORD, CT, 06478, Oxford, CT 06478
$709,900

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1101 ST ANDREWS DR, OXFORD, CT, 06478
The Village at Oxford Greens 1109 ST ANDREWS DR, OXFORD, CT, 06478, Oxford, CT 06478
$699,900

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1109 ST ANDREWS DR, OXFORD, CT, 06478
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.
Fairview at Oxford Greens 1109 ST ANDREWS DR, OXFORD, CT, 06478, Oxford, CT 06478
$699,900

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1109 ST ANDREWS DR, OXFORD, CT, 06478
The Village at Oxford Greens 1107 ST ANDREWS DR, OXFORD, CT, 06478, Oxford, CT 06478
$699,900

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1107 ST ANDREWS DR, OXFORD, CT, 06478
Fairview at Oxford Greens 1107 ST ANDREWS DR, OXFORD, CT, 06478, Oxford, CT 06478
$699,900

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1107 ST ANDREWS DR, OXFORD, CT, 06478
Fairview at Oxford Greens 1103 ST ANDREWS DR, OXFORD, CT, 06478, Oxford, CT 06478
$659,900

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1103 ST ANDREWS DR, OXFORD, CT, 06478
The Village at Oxford Greens 1103 ST ANDREWS DR, OXFORD, CT, 06478, Oxford, CT 06478
$659,900

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1103 ST ANDREWS DR, OXFORD, CT, 06478
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Heritage Village 192 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$283,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

192 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
New Oronoque Village 248 SOUTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614
$475,000

2 beds

|

3 baths

|

1,175 sq ft

|

Condo

248 SOUTH TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
New The Summit at Bethel 81 GREAT HILL DR # 81, BETHEL, CT, 06801, Bethel, CT 06801
$699,000

3 beds

|

3 baths

|

2,447 sq ft

|

Condo

81 GREAT HILL DR # 81, BETHEL, CT, 06801
Heritage Village 741 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$229,900

1 beds

|

1 baths

|

928 sq ft

|

Condo

741 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 633 CHAMPIONSHIP DR # 633, OXFORD, CT, 0..., Oxford, CT 06478
$599,900

2 beds

|

3 baths

|

1,983 sq ft

|

Condo

633 CHAMPIONSHIP DR # 633, OXFORD, CT, 0...
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 1 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$359,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
The Summit at Bethel 63 GREAT HILL DR # 63, BETHEL, CT, 06801, Bethel, CT 06801
$695,000

3 beds

|

3 baths

|

2,743 sq ft

|

Condo

63 GREAT HILL DR # 63, BETHEL, CT, 06801
New Oronoque Village 535 NARRAGANSET LN B, STRATFORD, CT, 066..., Stratford, CT 06614
$409,900

2 beds

|

2 baths

|

1,434 sq ft

|

Condo

535 NARRAGANSET LN B, STRATFORD, CT, 066...
Community: Oronoque Village
Oronoque Village 87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$449,900

1 beds

|

2 baths

|

1,454 sq ft

|

Condo

87 CREEK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Founders Ridge 22 WEBSTER LN # 22, MIDDLETOWN, CT, 0645..., Middletown, CT 06457
$575,000

2 beds

|

2 baths

|

1,412 sq ft

|

Condo

22 WEBSTER LN # 22, MIDDLETOWN, CT, 0645...
Community: Founders Ridge
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
New Baldwin Station 26 JASMINE CIR # 26, MILFORD, CT, 06461, Milford, CT 06461
$649,900

2 beds

|

3 baths

|

2,331 sq ft

|

Condo

26 JASMINE CIR # 26, MILFORD, CT, 06461
Community: Baldwin Station
Oronoque Village 383 SEQUOIA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$490,000

1 beds

|

2 baths

|

1,360 sq ft

|

Condo

383 SEQUOIA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 143 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$369,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

143 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 32 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$214,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

32 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 194 BAYFIELD LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$660,000

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

194 BAYFIELD LN A, STRATFORD, CT, 06614
Community: Oronoque 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 Spring Lake Village 434 LAKEVIEW DR # 434, SOUTHINGTON, CT, ..., Southington, CT 06489
$319,900

2 beds

|

2 baths

|

1,199 sq ft

|

Condo

434 LAKEVIEW DR # 434, SOUTHINGTON, CT, ...
Community: Spring Lake Village
Rivington 5 BRINSCALL CT # 5, DANBURY, CT, 06810, Danbury, CT 06810
$540,000

2 beds

|

3 baths

|

1,467 sq ft

|

Condo

5 BRINSCALL CT # 5, DANBURY, CT, 06810
Community: Rivington
New Gloria Commons 10 LUCIUS CT # 10, MILFORD, CT, 06461, Milford, CT 06461
$489,900

2 beds

|

3 baths

|

2,061 sq ft

|

Condo

10 LUCIUS CT # 10, MILFORD, CT, 06461
Community: Gloria Commons
The Village at Oxford Greens 217 CHIP SHOT LN # 217, OXFORD, CT, 0647..., Oxford, CT 06478
$729,900

2 beds

|

2 baths

|

2,080 sq ft

|

Condo

217 CHIP SHOT LN # 217, OXFORD, CT, 0647...
Heritage Village 231 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

231 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Spring Lake Village 9 VILLAGE RD # 9, SOUTHINGTON, CT, 06489, Southington, CT 06489
$254,900

2 beds

|

2 baths

|

1,264 sq ft

|

Condo

9 VILLAGE RD # 9, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Heritage Village 264 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$300,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

264 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 280 HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488
$199,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

280 HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
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
The Village at Oxford Greens 185 COUNTRY CLUB DR # 185, OXFORD, CT, 0..., Oxford, CT 06478
$690,000

3 beds

|

3 baths

|

2,595 sq ft

|

Condo

185 COUNTRY CLUB DR # 185, OXFORD, CT, 0...



Frequently Asked Questions


Connect with an agent
Want to learn more about 55+ communities in the Winchester Area?
  • Insights and market stats
  • Instant new home alerts
  • Answers from local 55+ experts

Call us now: (860) 238-3620

Want to learn more about 55+ communities in Winchester Area?

Call us: (860) 238-3620
89 communities near Winchester Area
Remove Boundaries ×
Map Satellite

Call Us Call Us
Scroll to Top