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Simsbury, CT 55+ active adult communities & homes for sale - Page 3

193 homes near Simsbury

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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
3 rating (2 reviews) Heritage Hills
$400ks - $800ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
5 rating (2 reviews) Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 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
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Questions? Call us: (860) 784-7675
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
Harmony Place
$400ks - $500ks
Harmony Place, Rutland, MA
New Construction | 55+ age-restricted | Built 2023 - present | 142 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 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.
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
Setauket Meadows
$500ks - $600ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Windcrest East
$400ks - $500ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
5 rating (1 reviews) The Villages at Mount Sin...
$600ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 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.
Regency at Woodbridge
$500ks - $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
Village Vistas
$800ks - $1Ms
Village Vistas, Port Jefferson, NY
Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes
Pond Spring Village
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
Founders Village
$400ks - $500ks
Founders Village, Southold, NY
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes
Meadow Brook Estates
$300ks - $400ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
1 rating (1 reviews) Plymouth Estates at Mount...
$400ks - $500ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes
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Questions? Call us: (860) 784-7675
The Retreat at Carmel
$300ks - $800ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 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 Cottages at Wire Mill
$1Ms
The Cottages at Wire Mill, Stamford, CT
New Construction | 55+ age-restricted | Built 2026 - present | 9 homes
The Gardens of Wilbraham
$200ks - $400ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes
The Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Regency Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
Hopmeadow Place
$200ks - $300ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes
Shaker Heights
$400ks - $500ks
Shaker Heights, Enfield, CT
New Construction | 55+ age-restricted | Built 2018 - present | 77 homes
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
The Vineyards at Miller P...
$500ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 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.
12...3
The Village at Oxford Greens 1129 ST ANDREWS DR 49, OXFORD, CT, 06478, Oxford, CT 06478
$709,555

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478
Fairview at Oxford Greens 1129 ST ANDREWS DR 49, OXFORD, CT, 06478, Oxford, CT 06478
$709,555

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478
Fairview at Oxford Greens 1111 ST ANDREWS DR 16, OXFORD, CT, 06478, Oxford, CT 06478
$778,585

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478
The Village at Oxford Greens 1111 ST ANDREWS DR 16, OXFORD, CT, 06478, Oxford, CT 06478
$778,585

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478
The Village at Oxford Greens 1138 ST ANDREWS DR 90, OXFORD, CT, 06478, Oxford, CT 06478
$754,150

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1138 ST ANDREWS DR 90, OXFORD, CT, 06478
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Fairview at Oxford Greens 1138 ST ANDREWS DR 90, OXFORD, CT, 06478, Oxford, CT 06478
$754,150

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1138 ST ANDREWS DR 90, OXFORD, CT, 06478
Oronoque Village 372 PIUTE LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$384,900

1 beds

|

2 baths

|

1,375 sq ft

|

Condo

372 PIUTE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Hills 371 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$699,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

371 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Hills 241 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$499,900

2 beds

|

2 baths

|

1,138 sq ft

|

Condo

241 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
Newtown Woods 1227 BROOKSIDE CT 1227, NEWTOWN, CT, 064..., Newtown, CT 06470
$500,000

2 beds

|

2 baths

|

1,483 sq ft

|

Condo

1227 BROOKSIDE CT 1227, NEWTOWN, CT, 064...
Community: Newtown Woods
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.
Newtown Woods 23 WOODS LN 23, NEWTOWN, CT, 06470, Newtown, CT 06470
$600,000

2 beds

|

3 baths

|

2,073 sq ft

|

Condo

23 WOODS LN 23, NEWTOWN, CT, 06470
Community: Newtown Woods
Heritage Village 581 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$342,500

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

581 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Windcrest East 5 GREEN ASH ST, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$775,000

3 beds

|

3 baths

|

2,449 sq ft

|

House

5 GREEN ASH ST, RIVERHEAD, NY, 11933
Community: Windcrest East
Oronoque Village 383 SEQUOIA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$485,000

1 beds

|

3 baths

|

1,360 sq ft

|

Condo

383 SEQUOIA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 895 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$349,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

895 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Stoneleigh Woods at Riverhead 159 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$674,999

2 beds

|

3 baths

|

2,172 sq ft

|

Condo

159 STONELEIGH DR, RIVERHEAD, NY, 11901
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Heritage Village 16 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$389,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

16 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Spring Lake Village 626 OVERLOOK PATH 626, SOUTHINGTON, CT, ..., Southington, CT 06489
$350,000

2 beds

|

2 baths

|

1,230 sq ft

|

Condo

626 OVERLOOK PATH 626, SOUTHINGTON, CT, ...
Community: Spring Lake Village
Heritage Village 38 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

38 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 407 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$439,000

1 beds

|

2 baths

|

1,360 sq ft

|

Condo

407 MONTAUK LN B, 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.
Leisure Village 368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$394,990

2 beds

|

1 baths

|

Condo

368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119...
Community: Leisure Village
Baldwin Station 15 JASMINE CIR 15, MILFORD, CT, 06461, Milford, CT 06461
$599,000

2 beds

|

3 baths

|

2,331 sq ft

|

Condo

15 JASMINE CIR 15, MILFORD, CT, 06461
Community: Baldwin Station
Fairview at Oxford Greens 941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478
$699,900

2 beds

|

2 baths

|

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478
The Village at Oxford Greens 941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478
$699,900

2 beds

|

2 baths

|

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478
Rivington 64 WARRINGTON ROUND 64, DANBURY, CT, 068..., Danbury, CT 06810
$615,000

3 beds

|

3 baths

|

1,600 sq ft

|

Condo

64 WARRINGTON ROUND 64, DANBURY, CT, 068...
Community: Rivington
Glenwood Village 1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,..., Riverhead, NY 11901
$469,000

2 beds

|

2 baths

|

1,500 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,...
Community: Glenwood Village
Heritage Village 1008 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$518,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

1008 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Leisure Village 66 ENFIELD CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$359,900

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

66 ENFIELD CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
Setauket Meadows 66 BRIANNA DR, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733
$739,999

2 beds

|

3 baths

|

1,878 sq ft

|

Condo

66 BRIANNA DR, BROOKHAVEN, NY, 11733
Community: Setauket Meadows
Heritage Village 773 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$245,000

2 beds

|

2 baths

|

1,071 sq ft

|

Condo

773 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 Hills 358 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$620,000

2 beds

|

3 baths

|

1,550 sq ft

|

Condo

358 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
Newtown Woods 232 BROOKSIDE CT 232, NEWTOWN, CT, 06470, Newtown, CT 06470
$595,000

2 beds

|

2 baths

|

1,747 sq ft

|

Condo

232 BROOKSIDE CT 232, NEWTOWN, CT, 06470
Community: Newtown Woods
Glenwood Village 1661 OLD COUNTRY RD 233, RIVERHEAD, NY, ..., Riverhead, NY 11901
$239,999

2 beds

|

2 baths

|

980 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 233, RIVERHEAD, NY, ...
Community: Glenwood Village
Pond Spring Village 111 PONDVIEW CIR, BEACON FALLS, CT, 0640..., Beacon Falls, CT 06403
$438,000

2 beds

|

2 baths

|

1,328 sq ft

|

Condo

111 PONDVIEW CIR, BEACON FALLS, CT, 0640...
Community: Pond Spring Village
Heritage Village 233 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$310,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

233 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 349 NIBLICK LN 349, OXFORD, CT, 06478, Oxford, CT 06478
$658,000

3 beds

|

2 baths

|

2,008 sq ft

|

Condo

349 NIBLICK LN 349, OXFORD, CT, 06478
Heritage Hills 600 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$575,000

2 beds

|

2 baths

|

1,265 sq ft

|

Condo

600 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Village 972 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$360,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

972 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
The Village at Oxford Greens 349 NIBLICK LN, OXFORD, CT, 06478, Oxford, CT 06478
$658,000

3 beds

|

2 baths

|

2,152 sq ft

349 NIBLICK LN, OXFORD, CT, 06478
Heritage Village 176 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$284,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

176 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.
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