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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
Bartlett Hill
$500Ks
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
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 (2 reviews) Benson Woods
$400Ks - $600Ks
Benson Woods, Middlebury, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
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
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Regency at Woodbridge
$600Ks - $700Ks
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
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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
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
RiverWalk
$500Ks - $600Ks
RiverWalk, Branford, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes
The Village at Buckingham
$500Ks - $600Ks
The Village at Buckingham, Avon, CT
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
The Atrium of Portland
<$100k
The Atrium of Portland, Portland, CT
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes
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Autumn Fields
$200Ks - $300Ks
Autumn Fields, Enfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 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
Want to learn more about 55+ rental communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
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.
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
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
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
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 Woods at Dunham Pond
$400Ks - $500Ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes
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Questions? Call us: (860) 784-7675
Oak Meadow Estates
$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
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Bartlett Hollow
$200Ks - $400Ks
Bartlett Hollow, Middletown, CT
New Construction | 55+ age-restricted | Built 2015 - present | 25 homes
RiverBend Estates
$400Ks
RiverBend Estates, Oxford, CT
New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes
The Vineyards at Miller Place 48 AVERY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764
$679,900

2 beds

|

3 baths

|

1,486 sq ft

|

Condo

48 AVERY LN, MILLER PLACE, NY, 11764
The Gardens of Wilbraham 32 LODGE LN # 32, WILBRAHAM, MA, 01095, Wilbraham, MA 01095
$565,000

2 beds

|

2 baths

|

1,610 sq ft

|

Condo

32 LODGE LN # 32, WILBRAHAM, MA, 01095
Harmony Place 132 FIDELITY DR # 61, RUTLAND, MA, 01543, Rutland, MA 01543
$539,000

2 beds

|

2 baths

|

2,149 sq ft

|

Condo

132 FIDELITY DR # 61, RUTLAND, MA, 01543
Community: Harmony Place
Harmony Place 210 FIDELITY DR 84, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

210 FIDELITY DR 84, RUTLAND, MA, 01543
Community: Harmony Place
Harmony Place 12 FIDELITY DR # 6, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

12 FIDELITY DR # 6, RUTLAND, MA, 01543
Community: Harmony Place
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Want to learn more about 55+ rental communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Harmony Place 18 FIDELITY DR # 9, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

18 FIDELITY DR # 9, RUTLAND, MA, 01543
Community: Harmony Place
Harmony Place 212 FIDELITY DR 83, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

212 FIDELITY DR 83, RUTLAND, MA, 01543
Community: Harmony Place
Harmony Place 20 FIDELITY DR # 10, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

20 FIDELITY DR # 10, RUTLAND, MA, 01543
Community: Harmony Place
Harmony Place 10 FIDELITY DR # 5, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

10 FIDELITY DR # 5, RUTLAND, MA, 01543
Community: Harmony Place
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 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
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Leisure Village 289 CARDIFF CT B, RIDGE, NY, 11961, Ridge, NY 11961
$420,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

289 CARDIFF CT B, RIDGE, NY, 11961
Community: Leisure Village
Leisure Village 278 BERWICK CT UNIT B B, RIDGE, NY, 1196..., Ridge, NY 11961
$369,900

2 beds

|

1 baths

|

875 sq ft

|

Condo

278 BERWICK CT UNIT B B, RIDGE, NY, 1196...
Community: Leisure Village
New Heritage Hills 656 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$634,900

2 beds

|

2 baths

|

1,296 sq ft

|

Condo

656 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
The Retreat at Carmel 14 LANGDON GROVE, CARMEL, NY, 10512, Carmel, NY 10512
$699,900

3 beds

|

3 baths

|

3,000 sq ft

|

Condo

14 LANGDON GROVE, CARMEL, NY, 10512
Heritage Hills 55 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$675,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

55 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ rental communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Heritage Hills 182 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$475,000

2 beds

|

2 baths

|

1,205 sq ft

|

Condo

182 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Hills 443 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$625,000

2 beds

|

2 baths

|

1,559 sq ft

|

Condo

443 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.
The Vineyards at Miller Place 45 HALLEY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764
$650,000

2 beds

|

3 baths

|

1,853 sq ft

|

Condo

45 HALLEY LN, MILLER PLACE, NY, 11764
Leisure Village 418 WEYMOUTH CT B, RIDGE, NY, 11961, Ridge, NY 11961
$364,999

2 beds

|

1 baths

|

1,036 sq ft

|

Condo

418 WEYMOUTH CT B, RIDGE, NY, 11961
Community: Leisure Village
Foxwood Village 1407 MIDDLE RD 275, CALVERTON, NY, 11933, Calverton, NY 11933
$425,000

3 beds

|

2 baths

|

1,530 sq ft

|

House

1407 MIDDLE RD 275, CALVERTON, NY, 11933
Community: Foxwood Village
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
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
Plymouth Estates at Mount Sinai 166 IRA RD, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766
$579,999

2 beds

|

2 baths

|

1,820 sq ft

|

House

166 IRA RD, MOUNT SINAI, NY, 11766
The Retreat at Carmel 2 BLAIR HTS UNIT 3317, CARMEL, NY, 10512, Carmel, NY 10512
$465,000

2 beds

|

2 baths

|

1,323 sq ft

|

Condo

2 BLAIR HTS UNIT 3317, CARMEL, NY, 10512
The Retreat at Carmel 4 FROST CT, CARMEL, NY, 10512, Carmel, NY 10512
$759,900

2 beds

|

3 baths

|

2,035 sq ft

|

Condo

4 FROST CT, CARMEL, NY, 10512
Heritage Hills 140 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$645,000

3 beds

|

2 baths

|

1,689 sq ft

|

Condo

140 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ rental communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
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 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
Leisure Village 423 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961
$247,500

1 beds

|

1 baths

|

782 sq ft

|

Condo

423 WOODBRIDGE DR B, RIDGE, NY, 11961
Community: Leisure Village
Leisure Glen 10 OAKDALE CT, RIDGE, NY, 11961, Ridge, NY 11961
$599,900

2 beds

|

2 baths

|

1,666 sq ft

|

Condo

10 OAKDALE CT, RIDGE, NY, 11961
Community: Leisure Glen
Heritage Hills 798 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$609,000

2 beds

|

2 baths

|

1,296 sq ft

|

Condo

798 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Hills 348 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$596,000

2 beds

|

2 baths

|

1,428 sq ft

|

Condo

348 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
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Stoneleigh Woods at Riverhead 23 GOOSE NECK LN, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$585,000

2 beds

|

3 baths

|

1,631 sq ft

|

Condo

23 GOOSE NECK LN, RIVERHEAD, NY, 11901
Leisure Village 169 VENTRY CT A, RIDGE, NY, 11961, Ridge, NY 11961
$289,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

169 VENTRY CT A, RIDGE, NY, 11961
Community: Leisure Village
Leisure Village 128 EXMORE CT UNIT D, RIDGE, NY, 11961, Ridge, NY 11961
$319,900

2 beds

|

1 baths

|

1,278 sq ft

|

Condo

128 EXMORE CT UNIT D, RIDGE, NY, 11961
Community: Leisure Village
Leisure Village 116 EXMORE CT UNIT B, RIDGE, NY, 11961, Ridge, NY 11961
$299,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

116 EXMORE CT UNIT B, 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.
Leisure Village 164 FALMOUTH CT E, RIDGE, NY, 11961, Ridge, NY 11961
$279,000

2 beds

|

1 baths

|

819 sq ft

|

Condo

164 FALMOUTH CT E, RIDGE, NY, 11961
Community: Leisure Village
Want to learn more about 55+ rental communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Leisure Village 186 VENTRY CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961
$289,000

2 beds

|

1 baths

|

900 sq ft

|

Condo

186 VENTRY CT UNIT C, RIDGE, NY, 11961
Community: Leisure Village
Heritage Hills 537 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$600,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

537 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
Stoneleigh Woods at Riverhead 5 NEWCASTLE CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$635,000

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

5 NEWCASTLE CT, RIVERHEAD, NY, 11901
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Leisure Knoll 190 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961
$434,999

2 beds

|

1 baths

|

787 sq ft

|

Condo

190 CANTERBURY DR, RIDGE, NY, 11961
Community: Leisure Knoll
Leisure Village 373 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961
$415,000

2 beds

|

1 baths

|

1,171 sq ft

|

Condo

373 WOODBRIDGE DR B, RIDGE, NY, 11961
Community: Leisure Village

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