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

85 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
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
3 rating (2 reviews) Heritage Hills
- $800ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 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
Harmony Place
$400ks - $500ks
Harmony Place, Rutland, MA
New Construction | 55+ age-restricted | Built 2023 - present | 142 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 Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 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.
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 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
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 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
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Setauket Meadows
$500ks - $600ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes
The Gardens of Wilbraham
$200ks - $400ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 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.
Newbury Village
$400ks - $500ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Village Vistas
$800ks - $1Ms
Village Vistas, Port Jefferson, NY
Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 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
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
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 Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
Evergreen
$400ks - $500ks
Evergreen, Cromwell, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 52 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.
Whitney Glen
$500ks - $600ks
Whitney Glen, Westport, CT
Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
Bartlett Hill
$300ks - $400ks
Bartlett Hill, Portland, CT
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
The Retreat at Carmel
$300ks - $800ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
Hopmeadow Place
$200ks - $300ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes
Beckley Farms
$300ks - $400ks
Beckley Farms, Berlin, CT
New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes
5 rating (2 reviews) Benson Woods
$400ks - $600ks
Benson Woods, Middlebury, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
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
Castle Heights of Cheshir...
$500ks - $600ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 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
New Heritage Village 69 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$270,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

69 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 176 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$199,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

176 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
New Plymouth Estates at Mount Sinai 98 ANDREW DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$599,990

2 beds

|

2 baths

|

1,820 sq ft

|

Condo

98 ANDREW DR, BROOKHAVEN, NY, 11766
New Heritage Village 170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$349,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Oronoque Village 488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$575,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
New Plymouth Estates at Mount Sinai 26 ROSE LN, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$595,000

2 beds

|

2 baths

|

1,563 sq ft

|

Condo

26 ROSE LN, BROOKHAVEN, NY, 11766
New Heritage Village 2 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$357,500

2 beds

|

2 baths

|

1,572 sq ft

|

Condo

2 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Hills 567 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$469,900

1 beds

|

2 baths

|

967 sq ft

|

Condo

567 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
New Heritage Village 926 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$310,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

926 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Hills 586 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$600,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

586 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 The Villages at Mount Sinai Park 10 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$749,000

3 beds

|

3 baths

|

2,500 sq ft

|

House

10 LOUDEN LOOP, BROOKHAVEN, NY, 11766
New Leisure Knoll 225 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$540,000

2 beds

|

2 baths

|

1,094 sq ft

|

House

225 KINGSTON DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New The Villages at Mount Sinai Park 54 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$929,000

3 beds

|

3 baths

|

2,816 sq ft

|

House

54 LOUDEN LOOP, BROOKHAVEN, NY, 11766
New The Villages at Mount Sinai Park 68 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$839,999

2 beds

|

2 baths

|

1,736 sq ft

|

House

68 LOUDEN LOOP, BROOKHAVEN, NY, 11766
New Saddle Lakes 156 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$629,000

3 beds

|

3 baths

|

1,837 sq ft

|

Condo

156 SCENIC LAKE DR, RIVERHEAD, NY, 11901
Community: Saddle Lakes
New Leisure Knoll 257 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$399,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

257 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
New The Village at Oxford Greens 505 TRADITIONS CT 505, OXFORD, CT, 06478, Oxford, CT 06478
$775,000

3 beds

|

3 baths

|

2,652 sq ft

|

Condo

505 TRADITIONS CT 505, OXFORD, CT, 06478
New Stoneleigh Woods at Riverhead 47 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$699,000

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

47 STONELEIGH DR, RIVERHEAD, NY, 11901
New Heritage Hills 415 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$875,000

3 beds

|

2 baths

|

1,909 sq ft

|

Condo

415 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
New Baldwin Station 69 JASMINE CIR 69, MILFORD, CT, 06461, Milford, CT 06461
$820,000

2 beds

|

3 baths

|

2,820 sq ft

|

Condo

69 JASMINE CIR 69, MILFORD, CT, 06461
Community: Baldwin Station
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 Overlook 2084 SUMMIT LOOP 77, CARMEL, NY, 10512, Carmel, NY 10512
$779,000

2 beds

|

3 baths

|

2,214 sq ft

|

Condo

2084 SUMMIT LOOP 77, CARMEL, NY, 10512
Community: Overlook
New Stoneleigh Woods at Riverhead 1302 BALTUSROL BLVD, RIVERHEAD, NY, 1190..., Riverhead, NY 11901
$515,000

2 beds

|

3 baths

|

1,350 sq ft

|

Condo

1302 BALTUSROL BLVD, RIVERHEAD, NY, 1190...
New Oronoque Village 664 OSAGE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$499,000

1 beds

|

3 baths

|

1,438 sq ft

664 OSAGE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
New Oronoque Village 543 N TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$585,000

1 beds

|

3 baths

|

1,426 sq ft

|

Condo

543 N TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
Regency at Prospect 196 SYCAMORE DR 196, PROSPECT, CT, 06712, Prospect, CT 06712
$307,127

3 beds

|

2 baths

|

1,500 sq ft

|

Condo

196 SYCAMORE DR 196, PROSPECT, CT, 06712
Community: Regency at Prospect
Heritage Village 916 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$390,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

916 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 96 SEMINOLE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$469,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

96 SEMINOLE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Leisure Knoll 1 AVON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$489,999

2 beds

|

2 baths

|

1,070 sq ft

|

Condo

1 AVON CT, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Leisure Village 54 AYLESBURY CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$349,000

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

54 AYLESBURY CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
Setauket Meadows 100 COVE LN 100, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733
$769,000

2 beds

|

3 baths

|

1,820 sq ft

|

Condo

100 COVE LN 100, BROOKHAVEN, NY, 11733
Community: Setauket Meadows
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.
Oronoque Village 315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$549,000

2 beds

|

3 baths

|

1,434 sq ft

|

Condo

315 NAVAJO LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Leisure Village 395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ..., Brookhaven, NY 11961
$299,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ...
Community: Leisure Village
Heritage Village 14 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$269,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

14 HERITAGE CIR B, SOUTHBURY, CT, 06488
Community: Heritage Village
Leisure Knoll 541 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$529,000

3 beds

|

2 baths

|

1,412 sq ft

|

Condo

541 STRATFORD LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Heritage Village 847 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$309,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

847 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 132 BISON LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$470,000

1 beds

|

3 baths

|

1,426 sq ft

|

Condo

132 BISON LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Hills 969 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$490,000

1 beds

|

2 baths

|

967 sq ft

|

Condo

969 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Village 648 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$405,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

648 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 Gardens of Wilbraham 56 CHERRY DR 56, WILBRAHAM, MA, 01095, Wilbraham, MA 01095
$419,000

2 beds

|

2 baths

|

1,213 sq ft

|

Condo

56 CHERRY DR 56, WILBRAHAM, MA, 01095
Foxwood Village 1407 MIDDLE RD 253, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$449,000

3 beds

|

2 baths

|

1,753 sq ft

|

House

1407 MIDDLE RD 253, RIVERHEAD, NY, 11933
Community: Foxwood 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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