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

86 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
3 rating (2 reviews) Heritage Hills
$400ks - $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
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
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
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
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 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
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 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) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 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 Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
Harmony Place
$400ks - $500ks
Harmony Place, Rutland, MA
New Construction | 55+ age-restricted | Built 2023 - present | 142 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 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.
Applegate Estates
$500ks - $400ks
Applegate Estates, Southington, CT
New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes
The Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 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
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 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
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
The Gardens of Wilbraham
$200ks - $400ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
Windcrest East
$400ks - $500ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 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.
Meadow Brook Estates
$300ks - $400ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
Regency Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
Newbury Village
$400ks - $500ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
5 rating (2 reviews) Benson Woods
$400ks - $600ks
Benson Woods, Middlebury, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes
Villas at Seminary Hill
$200ks - $300ks
Villas at Seminary Hill, Carmel, NY
New Construction | 55+ age-restricted | Built 2018 - present | 50 homes
3.5 rating (2 reviews) Harvest Pointe
$800ks - $3Ms
Harvest Pointe, Cutchogue, NY
New Construction | 55+ age-restricted | Built 2017 - present | 124 homes
Stoneleigh Woods at Carme...
$400ks
Stoneleigh Woods at Carme..., Carmel, NY
Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Founders Village
$400ks - $500ks
Founders Village, Southold, NY
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 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 701 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

701 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$589,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New The Village at Oxford Greens 157 COUNTRY CLUB DR 157, OXFORD, CT, 064..., Oxford, CT 06478
$649,900

3 beds

|

3 baths

|

2,008 sq ft

|

Condo

157 COUNTRY CLUB DR 157, OXFORD, CT, 064...
New Overlook 2059 SUMMIT LOOP 97, CARMEL, NY, 10512, Carmel, NY 10512
$920,000

2 beds

|

3 baths

|

2,873 sq ft

|

Condo

2059 SUMMIT LOOP 97, CARMEL, NY, 10512
Community: Overlook
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
New Overlook 2057 SUMMIT LOOP 96, CARMEL, NY, 10512, Carmel, NY 10512
$885,000

2 beds

|

2 baths

|

1,948 sq ft

|

Condo

2057 SUMMIT LOOP 96, CARMEL, NY, 10512
Community: Overlook
New Overlook 4091 FAIRWAYS DR 146, CARMEL, NY, 10512, Carmel, NY 10512
$772,000

3 beds

|

4 baths

|

2,131 sq ft

|

Condo

4091 FAIRWAYS DR 146, CARMEL, NY, 10512
Community: Overlook
New Overlook 2003 SUMMIT LOOP 82, CARMEL, NY, 10512, Carmel, NY 10512
$799,000

2 beds

|

2 baths

|

1,948 sq ft

|

Condo

2003 SUMMIT LOOP 82, CARMEL, NY, 10512
Community: Overlook
New Overlook 4085 FAIRWAYS DR 143, CARMEL, NY, 10512, Carmel, NY 10512
$727,000

3 beds

|

3 baths

|

1,931 sq ft

|

Condo

4085 FAIRWAYS DR 143, CARMEL, NY, 10512
Community: Overlook
New Overlook 4087 FAIRWAYS DR 144, CARMEL, NY, 10512, Carmel, NY 10512
$699,000

3 beds

|

4 baths

|

2,141 sq ft

|

Condo

4087 FAIRWAYS DR 144, CARMEL, NY, 10512
Community: Overlook
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 Village 24-B HERITAGE CRST B, SOUTHBURY, CT, 064..., Southbury, CT 06488
$419,900

2 beds

|

2 baths

|

1,217 sq ft

|

Condo

24-B HERITAGE CRST B, SOUTHBURY, CT, 064...
Community: Heritage Village
New Heritage Village 593 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$205,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

593 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
New Stoneleigh Woods at Carmel 205 EGRETS LNDG 205, CARMEL, NY, 10512, Carmel, NY 10512
$475,000

2 beds

|

2 baths

|

1,344 sq ft

|

Condo

205 EGRETS LNDG 205, CARMEL, NY, 10512
New Heritage Village 147 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$235,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

147 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 22 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$204,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

22 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Leisure Village 258 NEWCASTLE CT F, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$299,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

258 NEWCASTLE CT F, BROOKHAVEN, NY, 1196...
Community: Leisure Village
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Liberty at Newtown 76 SUZIE DR 76, NEWTOWN, CT, 06470, Newtown, CT 06470
$648,000

2 beds

|

3 baths

|

2,341 sq ft

|

Condo

76 SUZIE DR 76, NEWTOWN, CT, 06470
Community: Liberty at Newtown
Heritage Village 804 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$259,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

804 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 89 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$649,000

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

89 S TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
Oak Meadow Estates 197 OAK MEADOW LN 197, TORRINGTON, CT, 0..., Torrington, CT 06790
$399,000

2 beds

|

2 baths

|

1,419 sq ft

|

Condo

197 OAK MEADOW LN 197, TORRINGTON, CT, 0...
Community: Oak Meadow Estates
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 Knoll 338 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$419,990

2 beds

|

1 baths

|

960 sq ft

|

Condo

338 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Billingsgate 14 BILLINGSGATE DR 14, SIMSBURY, CT, 060..., Simsbury, CT 06070
$750,000

2 beds

|

3 baths

|

2,729 sq ft

|

Condo

14 BILLINGSGATE DR 14, SIMSBURY, CT, 060...
Community: Billingsgate
Leisure Village 312 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$239,000

1 beds

|

1 baths

|

684 sq ft

|

Condo

312 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...
Community: Leisure Village
Heritage Village 184 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$209,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

184 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 333 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$335,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

333 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Hills 334 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$659,000

2 beds

|

2 baths

|

1,428 sq ft

|

Condo

334 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Sunken Pond Estates 102 WINGED FOOT WAY, RIVERHEAD, NY, 1190..., Riverhead, NY 11901
$515,000

2 beds

|

3 baths

|

1,350 sq ft

|

Condo

102 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
Heritage Hills 103 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$780,000

3 beds

|

2 baths

|

1,780 sq ft

|

Condo

103 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Leisure Village 158 FALMOUTH CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$228,888

2 beds

|

1 baths

|

836 sq ft

|

Condo

158 FALMOUTH CT A, BROOKHAVEN, NY, 11961
Community: Leisure Village
The Village at Oxford Greens 443 TEE SHOT DR 443, OXFORD, CT, 06478, Oxford, CT 06478
$689,900

3 beds

|

3 baths

|

2,759 sq ft

|

Condo

443 TEE SHOT DR 443, 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.
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
Heritage Hills 606 HERITAGE HILLS DR C, SOMERS, NY, 105..., Somers, NY 10589
$825,000

3 beds

|

2 baths

|

1,905 sq ft

|

Condo

606 HERITAGE HILLS DR C, SOMERS, NY, 105...
Community: Heritage Hills
Hopmeadow Place 1 W ST 310, SIMSBURY, CT, 06070, Simsbury, CT 06070
$385,000

2 beds

|

2 baths

|

1,430 sq ft

|

Condo

1 W ST 310, SIMSBURY, CT, 06070
Community: Hopmeadow Place
Leisure Knoll 152B LAURANCE LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$374,000

1 beds

|

1 baths

|

530 sq ft

|

Condo

152B LAURANCE LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Oronoque Village 448 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614
$525,000

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

448 HAMMERSTONE LN B, STRATFORD, CT, 066...
Community: Oronoque Village
The Powder Forest Homes 6 RONAN WAY 6, SIMSBURY, CT, 06070, Simsbury, CT 06070
$739,900

2 beds

|

3 baths

|

1,864 sq ft

6 RONAN WAY 6, SIMSBURY, CT, 06070
Saddle Lakes 174 ADELE CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$675,000

2 beds

|

2 baths

|

1,631 sq ft

|

Condo

174 ADELE CT, RIVERHEAD, NY, 11901
Community: Saddle Lakes
Newtown Woods 832 BROOKSIDE CT 832, NEWTOWN, CT, 06470, Newtown, CT 06470
$585,000

2 beds

|

2 baths

|

1,807 sq ft

|

Condo

832 BROOKSIDE CT 832, NEWTOWN, CT, 06470
Community: Newtown Woods
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Leisure Village 133 EASTBOURNE CT F, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$349,000

2 beds

|

1 baths

|

836 sq ft

|

Condo

133 EASTBOURNE CT F, BROOKHAVEN, NY, 119...
Community: Leisure Village
Sunken Pond Estates 2803 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$499,000

2 beds

|

3 baths

|

1,350 sq ft

|

Condo

2803 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
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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