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

87 communities 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
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
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
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Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 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
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
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 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
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
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
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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
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 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
Hopmeadow Place
$200ks - $300ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 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 (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 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
Park Glen
$300ks - $500ks
Park Glen, New Milford, CT
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes
Regency at Woodbridge
$500ks - $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 homes
Newbury Village
$400ks - $500ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes
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
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Questions? Call us: (860) 784-7675
Granite Woods
$600ks - $700ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 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 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.
Founders Village
$400ks - $500ks
Founders Village, Southold, NY
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Setauket Meadows
$500ks - $600ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes
Village Vistas
$800ks - $1Ms
Village Vistas, Port Jefferson, NY
Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 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
The Retreat at Carmel
$300ks - $800ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
Regency Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 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
Glenwood Village 1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901
$419,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
New 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
New 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
New 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...
New Sunken Pond Estates 403 WINGED FOOT WAY, RIVERHEAD, NY, 1190..., Riverhead, NY 11901
$520,000

2 beds

|

2 baths

|

1,350 sq ft

|

Condo

403 WINGED FOOT WAY, RIVERHEAD, NY, 1190...
Community: Sunken Pond Estates
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
New Saddle Lakes 157 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$595,000

2 beds

|

2 baths

|

1,386 sq ft

|

Condo

157 SCENIC LAKE DR, RIVERHEAD, NY, 11901
Community: Saddle Lakes
New 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
New Heritage Village 49 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$135,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

49 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Leisure Glen 279 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$569,999

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

279 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New 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
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 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
New 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
New 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
New 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
New 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
New Heritage Village 23 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$269,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

23 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
New Heritage Village 4 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$465,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

4 HERITAGE CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 569 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$315,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

569 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Meadow Brook Estates 188 EASTWOOD DR 188, SEYMOUR, CT, 06483, Seymour, CT 06483
$624,500

2 beds

|

3 baths

|

2,358 sq ft

|

Condo

188 EASTWOOD DR 188, SEYMOUR, CT, 06483
New Heritage Hills 481A HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$799,000

2 beds

|

2 baths

|

1,353 sq ft

|

Condo

481A HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
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 Oronoque Village 315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$475,000

2 beds

|

3 baths

|

1,434 sq ft

|

Condo

315 NAVAJO LN A, STRATFORD, CT, 06614
Community: Oronoque Village
New Overlook 2050 SUMMIT LOOP 61, CARMEL, NY, 10512, Carmel, NY 10512
$929,000

2 beds

|

2 baths

|

2,102 sq ft

|

Condo

2050 SUMMIT LOOP 61, CARMEL, NY, 10512
Community: Overlook
New Oronoque Village 138 BISON LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$480,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

138 BISON LN B, STRATFORD, CT, 06614
Community: Oronoque Village
New Heritage Village 774 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$325,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

774 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Woodridge Strathmore Terrace 8 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$549,000

2 beds

|

2 baths

|

1,240 sq ft

|

Condo

8 CHIPPENDALE DR, BROOKHAVEN, NY, 11766
Spring Lake Village 20 VILLAGE RD 20, SOUTHINGTON, CT, 06489, Southington, CT 06489
$219,000

2 beds

|

2 baths

|

1,224 sq ft

|

Condo

20 VILLAGE RD 20, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Heritage Village 28 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$232,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

28 HERITAGE CIR 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
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
$210,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

214 HERITAGE VLG B, 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.
Leisure Village 238 BLACKPOOL CT A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$369,000

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

238 BLACKPOOL CT A, BROOKHAVEN, NY, 1196...
Community: Leisure Village
Leisure Glen 15 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$569,900

2 beds

|

2 baths

|

1,476 sq ft

|

Condo

15 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Leisure Knoll 232 BELFAST LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$499,999

2 beds

|

2 baths

|

1,172 sq ft

|

Condo

232 BELFAST LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
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
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
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Hopmeadow Place 1 W ST 315, SIMSBURY, CT, 06070, Simsbury, CT 06070
$385,000

2 beds

|

2 baths

|

1,477 sq ft

|

Condo

1 W ST 315, SIMSBURY, CT, 06070
Community: Hopmeadow Place
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
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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