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

85 communities near Simsbury

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Liberty at Newtown
$300Ks - $400Ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Applegate Estates
$500Ks - $400Ks
Applegate Estates, Southington, CT
New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes
Pond Spring Village
$300Ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
Founders Village
$500Ks - $600Ks
Founders Village, Southold, NY
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 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
Want to learn more about 55+ communities in Simsbury? 55places can help!
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Castle Heights of Cheshir...
$500Ks - $600Ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes
The Vineyards at Miller P...
$600Ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes
Baldwin Station
$400Ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
Bartlett Hill
$500Ks
Bartlett Hill, Portland, CT
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes
5 rating (2 reviews) Benson Woods
$400Ks - $600Ks
Benson Woods, Middlebury, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 79 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.
Shaker Heights
$400Ks - $500Ks
Shaker Heights, Enfield, CT
New Construction | 55+ age-restricted | Built 2018 - present | 77 homes
5 rating (3 reviews) Founders Ridge
$500Ks - $600Ks
Founders Ridge, Middletown, CT
New Construction | 55+ age-restricted | Built 2017 - present | 75 homes
Long Hill Village
$300Ks - $400Ks
Long Hill Village, Trumbull, CT
Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes
Regency at Woodbridge
$500Ks - $600Ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 homes
The Village at Hunt Glen
$300Ks
The Village at Hunt Glen, Granby, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 homes
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Sonoma Woods
$300Ks
Sonoma Woods, Middletown, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes
Stoneleigh Woods at Carme...
$400Ks
Stoneleigh Woods at Carme..., Carmel, NY
Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes
Whitney Glen
$500Ks - $600Ks
Whitney Glen, Westport, CT
Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes
RiverWalk
$500Ks - $600Ks
RiverWalk, Branford, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes
The Atrium of Portland
<$100k
The Atrium of Portland, Portland, CT
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 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.
Autumn Fields
$200Ks - $300Ks
Autumn Fields, Enfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 homes
The Village at Buckingham
$500Ks - $600Ks
The Village at Buckingham, Avon, CT
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes
77 Sunset Lane
$400Ks - $700Ks
77 Sunset Lane, Ridgefield, CT
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes
Evergreen
$500Ks
Evergreen, Cromwell, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes
Regency Meadows
$500Ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
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Questions? Call us: (860) 784-7675
Gloria Commons
$400Ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes
Villas at Seminary Hill
$400Ks
Villas at Seminary Hill, Carmel, NY
New Construction | 55+ age-restricted | Built 2018 - present | 50 homes
Bramble Ridge
$400Ks - $500Ks
Bramble Ridge, Suffield, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 homes
Chimney Hill
$500Ks - $700Ks
Chimney Hill, Farmington, CT
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes
Village Vistas
$800Ks - $1Ms
Village Vistas, Port Jefferson, NY
Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 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.
Forest Mews
$300Ks - $400Ks
Forest Mews, Avon, CT
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 homes
Clockmaker's Hill
$100Ks
Clockmaker's Hill, Winsted, CT
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes
Bidwell Village
$300Ks - $400Ks
Bidwell Village, Coventry, CT
New Construction | 55+ age-restricted | Built 2020 - present | 37 homes
Boulder Brook
$200Ks
Boulder Brook, Prospect, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes
The Woods at Dunham Pond
$400Ks - $500Ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Oak Meadow Estates
$200Ks - $400Ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
Autumn Estates
$500Ks - $600Ks
Autumn Estates, Farmington, CT
Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes
The Coach Homes at Ridgef...
$200Ks - $500Ks
The Coach Homes at Ridgef..., Ridgefield, CT
New Construction | 55+ age-restricted | Built 2019 - present | 30 homes
RiverBend Estates
$400Ks
RiverBend Estates, Oxford, CT
New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes
Bartlett Hollow
$200Ks - $400Ks
Bartlett Hollow, Middletown, CT
New Construction | 55+ age-restricted | Built 2015 - present | 25 homes
Oronoque Village 164 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$479,999

1 beds

|

2 baths

|

1,175 sq ft

|

Condo

164 BISON LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 44 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488
$239,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

44 HERITAGE VLG F, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$439,900

1 beds

|

2 baths

|

1,454 sq ft

|

Condo

87 CREEK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 723 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$259,900

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

723 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 859 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$380,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

859 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
Oronoque Village 488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$619,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 865 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$369,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

865 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Hills 262 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$525,000

2 beds

|

2 baths

|

1,427 sq ft

|

Condo

262 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Stoneleigh Woods at Riverhead 4 HAVERTON CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$660,000

2 beds

|

3 baths

|

2,175 sq ft

|

Condo

4 HAVERTON CT, RIVERHEAD, NY, 11901
Overlook 4071 FAIRWAYS DR 136, CARMEL, NY, 10512, Carmel, NY 10512
$668,000

3 beds

|

3 baths

|

1,914 sq ft

|

Condo

4071 FAIRWAYS DR 136, 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.
Overlook 4073 FAIRWAYS DR # 137, CARMEL, NY, 1051..., Carmel, NY 10512
$665,000

3 beds

|

3 baths

|

1,914 sq ft

|

Condo

4073 FAIRWAYS DR # 137, CARMEL, NY, 1051...
Community: Overlook
The Village at Oxford Greens 413 MULLIGAN DR # 413, OXFORD, CT, 06478, Oxford, CT 06478
$539,000

2 beds

|

2 baths

|

1,590 sq ft

|

Condo

413 MULLIGAN DR # 413, OXFORD, CT, 06478
Heritage Village 568A HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488
$409,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

568A HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 39 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$238,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

39 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Gloria Commons 10 LUCIUS CT # 10, MILFORD, CT, 06461, Milford, CT 06461
$450,000

2 beds

|

3 baths

|

2,061 sq ft

|

Condo

10 LUCIUS CT # 10, MILFORD, CT, 06461
Community: Gloria Commons
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
New Stoneleigh Woods at Riverhead 53 GOOSE NECK LN, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$590,000

2 beds

|

2 baths

|

1,383 sq ft

|

Condo

53 GOOSE NECK LN, RIVERHEAD, NY, 11901
Leisure Village 416 WEYMOUTH CT A, RIDGE, NY, 11961, Ridge, NY 11961
$389,000

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

416 WEYMOUTH CT A, RIDGE, NY, 11961
Community: Leisure Village
Overlook 1037 COTTAGE DR 18, CARMEL, NY, 10512, Carmel, NY 10512
$889,000

2 beds

|

3 baths

|

2,496 sq ft

|

Condo

1037 COTTAGE DR 18, CARMEL, NY, 10512
Community: Overlook
Spring Lake Village 1 COACH DR # 1, SOUTHINGTON, CT, 06489, Southington, CT 06489
$280,000

2 beds

|

2 baths

|

1,323 sq ft

|

Condo

1 COACH DR # 1, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Glenwood Village 1661 OLD COUNTRY RD 434, RIVERHEAD, NY, ..., Riverhead, NY 11901
$219,000

2 beds

|

2 baths

|

1,144 sq ft

|

Mobile Home

1661 OLD COUNTRY RD 434, RIVERHEAD, NY, ...
Community: Glenwood 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.
Windcrest East 41 GOLDEN SPRUCE DR, CALVERTON, NY, 1193..., Calverton, NY 11933
$649,000

3 beds

|

3 baths

|

2,091 sq ft

|

Condo

41 GOLDEN SPRUCE DR, CALVERTON, NY, 1193...
Community: Windcrest East
Leisure Knoll 145 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961
$499,999

2 beds

|

2 baths

|

913 sq ft

|

House

145 EDINBURGH DR, RIDGE, NY, 11961
Community: Leisure Knoll
Leisure Village 310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119..., Ridge, NY 11961
$342,000

2 beds

|

1 baths

|

1,278 sq ft

|

Condo

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119...
Community: Leisure Village
Heritage Hills 390 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$699,000

2 beds

|

2 baths

|

1,559 sq ft

|

Condo

390 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Hills 129 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$414,900

1 beds

|

1 baths

|

1,055 sq ft

|

Condo

129 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
Leisure Village 169 VENTRY CT A, RIDGE, NY, 11961, Ridge, NY 11961
$295,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

169 VENTRY CT A, RIDGE, NY, 11961
Community: Leisure Village
Heritage Hills 798 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$619,000

2 beds

|

2 baths

|

1,296 sq ft

|

Condo

798 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Hills 349 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$625,000

2 beds

|

2 baths

|

1,484 sq ft

|

Condo

349 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
The Villages at Mount Sinai Park 68 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766
$657,000

2 beds

|

2 baths

|

1,736 sq ft

|

Condo

68 LOUDEN LOOP, MOUNT SINAI, NY, 11766
Leisure Village 215 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961
$319,000

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

215 WOODBRIDGE DR A, RIDGE, NY, 11961
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.
Heritage Hills 593 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$585,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

593 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Glenwood Village 1661 OLD COUNTRY RD 506, RIVERHEAD, NY, ..., Riverhead, NY 11901
$329,999

2 beds

|

2 baths

|

1,232 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 506, RIVERHEAD, NY, ...
Community: Glenwood Village
Heritage Hills 356 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$750,000

2 beds

|

2 baths

|

1,435 sq ft

|

Condo

356 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Stoneleigh Woods at Riverhead 159 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$680,000

2 beds

|

3 baths

|

2,175 sq ft

|

Condo

159 STONELEIGH DR, RIVERHEAD, NY, 11901
Heritage Hills 882 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$825,000

3 beds

|

2 baths

|

1,909 sq ft

|

Condo

882 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
Leisure Village 474 DARWEN DR B, RIDGE, NY, 11961, Ridge, NY 11961
$400,000

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

474 DARWEN DR B, RIDGE, NY, 11961
Community: Leisure Village
Foxwood Village 1407 MIDDLE RD UNIT 258, CALVERTON, NY, ..., Calverton, NY 11933
$525,000

3 beds

|

2 baths

|

1,568 sq ft

|

Manufactured Home

1407 MIDDLE RD UNIT 258, CALVERTON, NY, ...
Community: Foxwood Village
Glenwood Village 1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$239,999

2 beds

|

2 baths

|

924 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1...
Community: Glenwood Village
Leisure Village 405 WOODBRIDGE DR D, RIDGE, NY, 11961, Ridge, NY 11961
$290,000

2 beds

|

1 baths

|

874 sq ft

|

Condo

405 WOODBRIDGE DR D, RIDGE, NY, 11961
Community: Leisure Village
Stoneleigh Woods at Riverhead 67 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$640,000

2 beds

|

3 baths

|

1,972 sq ft

|

Condo

67 STONELEIGH DR, RIVERHEAD, NY, 11901
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85 communities near Simsbury
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