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Simsbury, CT 55+ active adult communities & homes for sale - Page 2

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
Meadow Brook Estates 169 MEADOW BROOK RD 169, OXFORD, CT, 064..., Oxford, CT 06478
$625,000

2 beds

|

3 baths

|

1,821 sq ft

|

Condo

169 MEADOW BROOK RD 169, OXFORD, CT, 064...
Spring Lake Village 116 TIMBER RDG, SOUTHINGTON, CT, 06489, Southington, CT 06489
$304,900

2 beds

|

2 baths

|

1,128 sq ft

|

Condo

116 TIMBER RDG, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Heritage Hills 537 HERITAGE HILLS DR F, SOMERS, NY, 105..., Somers, NY 10589
$629,000

2 beds

|

2 baths

|

1,265 sq ft

|

Condo

537 HERITAGE HILLS DR F, SOMERS, NY, 105...
Community: Heritage Hills
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
Heritage Hills 159 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$569,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

159 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Oronoque Village 511 OPA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$589,900

2 beds

|

2 baths

|

1,620 sq ft

|

Condo

511 OPA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
The Vineyards at Mount Sinai 72 FARM ACRE CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$999,999

2 beds

|

4 baths

|

3,736 sq ft

|

Condo

72 FARM ACRE CIR, BROOKHAVEN, NY, 11766
Heritage Village 643 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$374,500

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

643 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Autumn Fields 37 QUAIL HOLW 37, ENFIELD, CT, 06082, Enfield, CT 06082
$419,000

2 beds

|

3 baths

|

1,679 sq ft

|

Condo

37 QUAIL HOLW 37, ENFIELD, CT, 06082
Community: Autumn Fields
Leisure Glen 276 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$585,000

2 beds

|

2 baths

|

1,666 sq ft

|

Condo

276 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
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.
Glenwood Village 1661 OLD COUNTRY RD 254, RIVERHEAD, NY, ..., Riverhead, NY 11901
$185,000

2 beds

|

2 baths

|

1,036 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 254, RIVERHEAD, NY, ...
Community: Glenwood Village
Rivington 215 CENTER MEADOW LN 215, DANBURY, CT, 0..., Danbury, CT 06810
$499,000

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

215 CENTER MEADOW LN 215, DANBURY, CT, 0...
Community: Rivington
Heritage Village 4 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$245,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

4 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Leisure Knoll 7 AVON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$479,999

2 beds

|

2 baths

|

1,070 sq ft

|

Condo

7 AVON CT, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Leisure Knoll 545 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$429,000

2 beds

|

2 baths

|

1,172 sq ft

|

Condo

545 STRATFORD LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Overlook 2040 SUMMIT LOOP 57, CARMEL, NY, 10512, Carmel, NY 10512
$899,000

2 beds

|

2 baths

|

1,948 sq ft

|

Condo

2040 SUMMIT LOOP 57, CARMEL, NY, 10512
Community: Overlook
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Glenwood Village 1661 OLD COUNTRY RD 476, RIVERHEAD, NY, ..., Riverhead, NY 11901
$349,000

2 beds

|

2 baths

|

960 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 476, RIVERHEAD, NY, ...
Community: Glenwood Village
Leisure Knoll 254 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$450,000

2 beds

|

1 baths

|

1,020 sq ft

|

Condo

254 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Regency at Woodbridge 27 HERITAGE LN, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525
$599,900

3 beds

|

3 baths

|

Condo

27 HERITAGE LN, WOODBRIDGE, CT, 06525
Heritage Hills 813 HERITAGE HLS, SOMERS, NY, 10589, Somers, NY 10589
$899,000

2 beds

|

2 baths

|

1,663 sq ft

|

Condo

813 HERITAGE HLS, 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.
The Village at Oxford Greens 1159 ST ANDREWS DR 80, OXFORD, CT, 06478, Oxford, CT 06478
$799,900

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1159 ST ANDREWS DR 80, OXFORD, CT, 06478
Fairview at Oxford Greens 1159 ST ANDREWS DR 80, OXFORD, CT, 06478, Oxford, CT 06478
$799,900

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1159 ST ANDREWS DR 80, OXFORD, CT, 06478
Fieldstone Village 101 SUNRISE HILL CIR 101, ORANGE, CT, 06..., Orange, CT 06477
$875,000

2 beds

|

3 baths

|

2,350 sq ft

|

Condo

101 SUNRISE HILL CIR 101, ORANGE, CT, 06...
Community: Fieldstone Village
Glenwood Village 1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ..., Riverhead, NY 11901
$375,000

3 beds

|

2 baths

|

1,317 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ...
Community: Glenwood Village
Harmony Place 21 FIDELITY DR 73, RUTLAND, MA, 01543, Rutland, MA 01543
$489,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

21 FIDELITY DR 73, RUTLAND, MA, 01543
Community: Harmony Place
Harmony Place 23 FIDELITY DR 74, RUTLAND, MA, 01543, Rutland, MA 01543
$489,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

23 FIDELITY DR 74, RUTLAND, MA, 01543
Community: Harmony Place
Harmony Place 19 FIDELITY DR 72, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

19 FIDELITY DR 72, RUTLAND, MA, 01543
Community: Harmony Place
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Harmony Place 17 FIDELITY DR 71, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

17 FIDELITY DR 71, RUTLAND, MA, 01543
Community: Harmony Place
Leisure Village 232 BLACKPOOL CT F, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$349,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

232 BLACKPOOL CT F, BROOKHAVEN, NY, 1196...
Community: Leisure Village
The Retreat at Carmel 8 ATKINS CT, CARMEL, NY, 10512, Carmel, NY 10512
$690,000

2 beds

|

3 baths

|

2,148 sq ft

|

Condo

8 ATKINS CT, 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.
Leisure Glen 29 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$549,900

2 beds

|

2 baths

|

1,314 sq ft

|

Condo

29 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Spring Lake Village 142 TIMBER RDG 142, SOUTHINGTON, CT, 064..., Southington, CT 06489
$359,900

2 beds

|

3 baths

|

1,601 sq ft

|

Condo

142 TIMBER RDG 142, SOUTHINGTON, CT, 064...
Community: Spring Lake Village
Heritage Village 399 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$165,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

399 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Chatfield Farms 6 WOODLAND PATH 6, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403
$799,000

3 beds

|

4 baths

|

2,600 sq ft

|

Condo

6 WOODLAND PATH 6, BEACON FALLS, CT, 064...
Community: Chatfield Farms
Leisure Village 179 VENTRY CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$319,000

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

179 VENTRY CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
Glenwood Village 1661 OLD COUNTRY RD 189, RIVERHEAD, NY, ..., Riverhead, NY 11901
$205,000

2 beds

|

2 baths

|

1,036 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 189, RIVERHEAD, NY, ...
Community: Glenwood Village
Heritage Village 1003 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$325,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

1003 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
Spring Lake Village 253 CARRIAGE DR 253, SOUTHINGTON, CT, 06..., Southington, CT 06489
$309,900

2 beds

|

2 baths

|

1,152 sq ft

|

Condo

253 CARRIAGE DR 253, SOUTHINGTON, CT, 06...
Community: Spring Lake Village
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Heritage Hills 456 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$640,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

456 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Liberty at Newtown 16 FRANKLIN CT 16, NEWTOWN, CT, 06470, Newtown, CT 06470
$599,000

2 beds

|

3 baths

|

1,940 sq ft

|

Condo

16 FRANKLIN CT 16, NEWTOWN, CT, 06470
Community: Liberty at Newtown
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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