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

180 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
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
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
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
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 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.
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
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
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
The Gardens of Wilbraham
$200ks - $400ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 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 Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
Stoneleigh Woods at Carme...
$400ks
Stoneleigh Woods at Carme..., Carmel, NY
Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes
Newbury Village
$400ks - $500ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes
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
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
The Vineyards at Miller P...
$500ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 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 Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 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.
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
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Oak Meadow Estates
$200ks - $300ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
The Retreat at Carmel
$300ks - $800ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
Bartlett Hill
$300ks - $400ks
Bartlett Hill, Portland, CT
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes
The Village at Buckingham
$300ks - $400ks
The Village at Buckingham, Avon, CT
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
77 Sunset Lane
$400ks - $700ks
77 Sunset Lane, Ridgefield, CT
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes
Clockmaker's Hill
$100ks
Clockmaker's Hill, Winsted, CT
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 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 Pond Spring Village 111 PONDVIEW CIR 111, BEACON FALLS, CT, ..., Beacon Falls, CT 06403
$438,000

2 beds

|

2 baths

|

1,328 sq ft

|

Condo

111 PONDVIEW CIR 111, BEACON FALLS, CT, ...
Community: Pond Spring Village
New 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
New The Village at Oxford Greens 349 NIBLICK LN 349, OXFORD, CT, 06478, Oxford, CT 06478
$689,000

3 beds

|

2 baths

|

2,008 sq ft

|

Condo

349 NIBLICK LN 349, OXFORD, CT, 06478
New Heritage Hills 600 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$599,000

2 beds

|

2 baths

|

1,265 sq ft

|

Condo

600 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
New Heritage Village 972 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$385,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

972 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New The Village at Oxford Greens 349 NIBLICK LN, OXFORD, CT, 06478, Oxford, CT 06478
$689,000

3 beds

|

2 baths

|

2,152 sq ft

349 NIBLICK LN, OXFORD, CT, 06478
New Heritage Village 176 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$289,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

176 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
New Spring Lake Village 21 HICKORY HL 21, SOUTHINGTON, CT, 06489, Southington, CT 06489
$248,000

2 beds

|

2 baths

|

1,285 sq ft

|

Condo

21 HICKORY HL 21, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
New Heritage Hills 34 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$625,000

2 beds

|

3 baths

|

1,545 sq ft

|

Condo

34 HERITAGE HLS C, 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 46 BUCKSKIN LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$559,900

1 beds

|

2 baths

|

1,375 sq ft

|

Condo

46 BUCKSKIN LN A, STRATFORD, CT, 06614
Community: Oronoque Village
New Leisure Glen 187 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$525,000

2 beds

|

2 baths

|

1,451 sq ft

|

Condo

187 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New The Retreat at Carmel 4 REESE CT, CARMEL, NY, 10512, Carmel, NY 10512
$699,000

2 beds

|

2 baths

|

1,979 sq ft

|

House

4 REESE CT, CARMEL, NY, 10512
New Heritage Hills 128 HERITAGE HILLS DR B, SOMERS, NY, 105..., Somers, NY 10589
$450,000

1 beds

|

1 baths

|

955 sq ft

|

Condo

128 HERITAGE HILLS DR B, SOMERS, NY, 105...
Community: Heritage Hills
New Heritage Hills 156 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$649,000

3 beds

|

2 baths

|

1,689 sq ft

|

Condo

156 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
New Heritage Village 874 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$275,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

874 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
The Gardens of Wilbraham 137 CHERRY DR 137, WILBRAHAM, MA, 01095, Wilbraham, MA 01095
$400,000

2 beds

|

2 baths

|

1,241 sq ft

|

Condo

137 CHERRY DR 137, WILBRAHAM, MA, 01095
Rivington 11 MERCY ST 11, DANBURY, CT, 06810, Danbury, CT 06810
$630,000

2 beds

|

4 baths

|

1,572 sq ft

11 MERCY ST 11, DANBURY, CT, 06810
Community: Rivington
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
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
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 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...
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
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
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
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
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
Overlook 4087 FAIRWAYS DR 144, CARMEL, NY, 10512, Carmel, NY 10512
$669,000

3 beds

|

4 baths

|

2,141 sq ft

|

Condo

4087 FAIRWAYS DR 144, CARMEL, NY, 10512
Community: Overlook
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
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
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
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
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 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
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
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
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
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
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
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
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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