not an image

Call us at (860) 784-7675 to learn more about active adult communities in Simsbury

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

183 homes near Simsbury

Sort by:

Relevance

Relevance

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
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
3 rating (2 reviews) Heritage Hills
$400ks - $900ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 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
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 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
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.
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 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
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
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 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) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 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 Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
The Retreat at Carmel
$300ks - $800ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
Pond Spring Village
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Villas at Seminary Hill
$200ks - $300ks
Villas at Seminary Hill, Carmel, NY
New Construction | 55+ age-restricted | Built 2018 - present | 50 homes
Regency at Woodbridge
$500ks - $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 homes
Bartlett Hill
$300ks - $400ks
Bartlett Hill, Portland, CT
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 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.
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 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
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 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!
Questions? Call us: (860) 784-7675
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
North Woods of Colchester
$300ks - $400ks
North Woods of Colchester, Colchester, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes
The Gardens of Wilbraham
$200ks - $400ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes
Oak Meadow Estates
$200ks - $300ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 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.
O'Meara Farm
$400ks
O'Meara Farm, Farmington, CT
Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes
Meadow Brook Estates
$300ks - $400ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
Evergreen
$400ks - $500ks
Evergreen, Cromwell, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Village Vistas
$800ks - $1Ms
Village Vistas, Port Jefferson, NY
Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes
The Atrium of Portland
<$100k
The Atrium of Portland, Portland, CT
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes
12...3
The Villages at Mount Sinai Park 3 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$675,000

2 beds

|

3 baths

|

1,736 sq ft

|

House

3 LOUDEN LOOP, BROOKHAVEN, NY, 11766
Regency at Prospect 104 CHERRY CIR 104, PROSPECT, CT, 06712, Prospect, CT 06712
$328,417

3 beds

|

2 baths

|

1,500 sq ft

|

Condo

104 CHERRY CIR 104, PROSPECT, CT, 06712
Community: Regency at Prospect
Rivington 131 WINDING RIDGE WAY 131, DANBURY, CT, ..., Danbury, CT 06810
$770,000

3 beds

|

3 baths

|

1,592 sq ft

|

Condo

131 WINDING RIDGE WAY 131, DANBURY, CT, ...
Community: Rivington
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
Castle Heights of Cheshire 151 VICTORIA DR, CHESHIRE, CT, 06410, Cheshire, CT 06410
$769,900

2 beds

|

4 baths

|

2,843 sq ft

|

Condo

151 VICTORIA DR, CHESHIRE, CT, 06410
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Glenwood Village 1661 OLD COUNTRY RD 251, RIVERHEAD, NY, ..., Riverhead, NY 11901
$130,000

2 beds

|

1 baths

|

720 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 251, RIVERHEAD, NY, ...
Community: Glenwood Village
Heritage Village 101 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$229,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

101 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 29 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$325,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

29 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
The Summit at Bethel 20 GREAT HILL DR 20, BETHEL, CT, 06801, Bethel, CT 06801
$649,000

3 beds

|

3 baths

|

2,159 sq ft

|

Condo

20 GREAT HILL DR 20, BETHEL, CT, 06801
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 39 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$440,000

2 beds

|

2 baths

|

1,427 sq ft

|

Condo

39 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Village 401 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$353,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

401 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Hills 415 HERITAGE HILLS DR D, SOMERS, NY, 105..., Somers, NY 10589
$875,000

2 beds

|

2 baths

|

1,663 sq ft

|

Condo

415 HERITAGE HILLS DR D, SOMERS, NY, 105...
Community: Heritage Hills
Leisure Glen 16 HUNTINGTON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$505,000

2 beds

|

2 baths

|

1,312 sq ft

|

Condo

16 HUNTINGTON CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Heritage Village 25 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$439,900

2 beds

|

2 baths

|

1,447 sq ft

|

Condo

25 HERITAGE CRST C, SOUTHBURY, CT, 06488
Community: Heritage Village
Sunken Pond Estates 3006 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$499,000

2 beds

|

2 baths

|

1,587 sq ft

|

Condo

3006 AMEN COR, RIVERHEAD, NY, 11901
Community: Sunken Pond Estates
South Pond Village 177 THISTLE POND DR 177, BLOOMFIELD, CT,..., Bloomfield, CT 06002
$465,000

3 beds

|

3 baths

|

2,243 sq ft

|

Condo

177 THISTLE POND DR 177, BLOOMFIELD, CT,...
Community: South Pond Village
The Village at Oxford Greens 523 PUTTING GREEN LN 523, OXFORD, CT, 06..., Oxford, CT 06478
$625,000

2 beds

|

2 baths

|

2,008 sq ft

|

Condo

523 PUTTING GREEN LN 523, OXFORD, CT, 06...
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 1016 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$225,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

1016 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
Oronoque Village 72 DAKOTA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$539,500

1 beds

|

3 baths

|

1,118 sq ft

|

Condo

72 DAKOTA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Oronoque Village 71 DAKOTA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$425,000

1 beds

|

2 baths

|

1,375 sq ft

|

Condo

71 DAKOTA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 977 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$520,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

977 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
The Village at Oxford Greens 731 CHAMPIONSHIP DR 731, OXFORD, CT, 064..., Oxford, CT 06478
$629,900

2 beds

|

2 baths

|

1,539 sq ft

|

Condo

731 CHAMPIONSHIP DR 731, OXFORD, CT, 064...
Heritage Village 151 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$214,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

151 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 79 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$229,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

79 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Leisure Village 207 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$499,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

207 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.
Leisure Village 395 WOODBRIDGE DR C, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$289,000

2 beds

|

1 baths

|

874 sq ft

|

Condo

395 WOODBRIDGE DR C, BROOKHAVEN, NY, 119...
Community: Leisure Village
Leisure Village 427 AYLESBURY CT A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$380,000

2 beds

|

2 baths

|

972 sq ft

|

Condo

427 AYLESBURY CT A, BROOKHAVEN, NY, 1196...
Community: Leisure Village
Heritage Village 644 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$509,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

644 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 86 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$535,000

2 beds

|

3 baths

|

2,734 sq ft

|

Condo

86 S TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
Oronoque Village 252 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614
$639,000

2 beds

|

3 baths

|

2,494 sq ft

|

Condo

252 AGAWAM DR A, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Simsbury? 55places can help!
Questions? Call us: (860) 784-7675
Heritage Village 78 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$280,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

78 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 424 CENTER MEADOW LN 424, DANBURY, CT, 0..., Danbury, CT 06810
$510,000

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

424 CENTER MEADOW LN 424, DANBURY, CT, 0...
Community: Rivington
Bartlett Hill 9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480, Portland, CT 06480
$479,900

2 beds

|

3 baths

|

1,404 sq ft

9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480
Community: Bartlett Hill
Oronoque Village 639 ONONDAGA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$629,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

639 ONONDAGA LN B, STRATFORD, CT, 06614
Community: Oronoque 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 Villages at Mount Sinai Park 10 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$749,000

3 beds

|

3 baths

|

2,455 sq ft

|

Condo

10 LOUDEN LOOP, BROOKHAVEN, NY, 11766
Sunken Pond Estates 1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$489,000

2 beds

|

3 baths

|

1,350 sq ft

|

Condo

1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
Leisure Knoll 506 LANCASTER CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$549,000

2 beds

|

2 baths

|

1,394 sq ft

|

House

506 LANCASTER CT, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Heritage Hills 392 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$979,000

3 beds

|

2 baths

|

1,793 sq ft

|

Condo

392 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
Heritage Village 41 E MEADOW RD, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,900

2 beds

|

3 baths

|

1,479 sq ft

|

Condo

41 E MEADOW RD, SOUTHBURY, CT, 06488
Community: Heritage Village
Overlook 3004 EASTVIEW DR 105, CARMEL, NY, 10512, Carmel, NY 10512
$722,000

2 beds

|

3 baths

|

2,040 sq ft

|

Condo

3004 EASTVIEW DR 105, CARMEL, NY, 10512
Community: Overlook
1234…5

Frequently Asked Questions


Want more information about active adult communities around Simsbury?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Simsbury?

Call us: (860) 784-7675
183 homes
Remove Boundaries ×
Map Satellite

Reinmlsx

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Apr 11, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top