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

259 homes near Middletown

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5 rating (3 reviews) Founders Ridge
$500Ks - $600Ks
Founders Ridge, Middletown, CT
New Construction | 55+ age-restricted | Built 2017 - present | 75 homes
No reviews yet Sonoma Woods
$300Ks - $300Ks
Sonoma Woods, Middletown, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes
No reviews yet Bartlett Hollow
$200Ks - $400Ks
Bartlett Hollow, Middletown, CT
New Construction | 55+ age-restricted | Built 2015 - present | 25 homes
3.6 rating (7 reviews) Heritage Village
$200Ks - $500Ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes
No reviews yet Leisure Village
$200Ks - $400Ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
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No reviews yet The Greens at Half Hollow
$600Ks - $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only | 55+ age-restricted | Built 1994 - 2005 | 1,200 homes
No reviews yet Rivington
$400Ks - $500Ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
No reviews yet Oronoque Village
$200Ks - $600Ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
No reviews yet The Village at Oxford Gre...
$500Ks - $700Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes
No reviews yet Leisure Knoll
$300Ks - $500Ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 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.
No reviews yet Country Pointe Plainview
$1Ms - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
5 rating (2 reviews) Fairfield at St. James
$400Ks - $500Ks
Fairfield at St. James, St. James, NY
Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes
No reviews yet Leisure Glen
$400Ks - $400Ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
No reviews yet Spring Lake Village
$200Ks - $200Ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
4 rating (8 reviews) Glenwood Village
$100Ks - $400Ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
3.7 rating (3 reviews) Greenwood Village
$100Ks - $200Ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
No reviews yet The Seasons at East Meado...
$500Ks - $600Ks
The Seasons at East Meado..., East Meadow, NY
Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes
No reviews yet Regency at Prospect
$300Ks - $500Ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
No reviews yet The Waterways at Moriches
$400Ks - $700Ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
3.5 rating (2 reviews) Foxwood Village
$300Ks - $400Ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 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...
$500Ks - $500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes
4.6 rating (9 reviews) Meadowbrook Pointe Links ...
$300Ks - $700Ks
Meadowbrook Pointe Links ..., Medford, NY
New and Resale | 55+ age-restricted | Built 2010 - present | 280 homes
4 rating (1 reviews) Vineyards at Blue Point
$800Ks - $800Ks
Vineyards at Blue Point, Blue Point, NY
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes
No reviews yet The Club at Melville
$500Ks - $500Ks
The Club at Melville, Melville, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes
No reviews yet The Seasons at Elwood
$800Ks - $900Ks
The Seasons at Elwood, East Northport, NY
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
No reviews yet Meadow Brook Estates
$500Ks - $500Ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
5 rating (1 reviews) Encore Atlantic Shores
$600Ks - $900Ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
No reviews yet The Summit at Bethel
$600Ks - $600Ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
4.9 rating (14 reviews) Chatfield Farms
$600Ks - $600Ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 homes
5 rating (1 reviews) Encore at Lake Grove
$600Ks - $800Ks
Encore at Lake Grove, Lake Grove, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 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.
No reviews yet Woodridge Strathmore Terr...
$400Ks - $400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
5 rating (1 reviews) Sunrise Village
$400Ks - $500Ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes
No reviews yet Brierly Pond Village
$400Ks - $400Ks
Brierly Pond Village, Millbury, MA
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 homes
No reviews yet Saddle Lakes
$400Ks - $400Ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
No reviews yet Country Village Estates
$300Ks - $400Ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
5 rating (1 reviews) Sunken Pond Estates
$400Ks - $500Ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
No reviews yet The Seasons at East North...
$700Ks - $700Ks
The Seasons at East North..., East Northport, NY
New Construction | 55+ age-restricted | Built 2023 - present | 190 homes
5 rating (1 reviews) Westhampton Pines
$900Ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
5 rating (1 reviews) The Villages at Mount Sin...
$600Ks - $700Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes
No reviews yet The Powder Forest Homes
$600Ks - $700Ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
Heritage Village 786 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$295,000

2 beds

|

2 baths

|

1,063 sq ft

|

Condo

786 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Regency at Woodbridge 13 HERITAGE LN # 64, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$599,000

3 beds

|

3 baths

|

2,239 sq ft

|

Condo

13 HERITAGE LN # 64, WOODBRIDGE, CT, 065...
Bidwell Village 94 STONEHOUSE RD UNIT 10, COVENTRY, CT, ..., Coventry, CT 06238
$450,000

3 beds

|

3 baths

|

1,717 sq ft

94 STONEHOUSE RD UNIT 10, COVENTRY, CT, ...
Community: Bidwell Village
Oronoque Village 193 BAYFIELD LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$559,000

2 beds

|

3 baths

|

1,620 sq ft

|

Condo

193 BAYFIELD LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 737 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$369,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

737 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Regency at Prospect 9 LILAC LN # 9, PROSPECT, CT, 06712, Prospect, CT 06712
$454,900

2 beds

|

2 baths

|

1,503 sq ft

|

Condo

9 LILAC LN # 9, PROSPECT, CT, 06712
Community: Regency at Prospect
Oronoque Village 195 BAYFIELD LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$560,000

2 beds

|

3 baths

|

1,575 sq ft

|

Condo

195 BAYFIELD LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 920 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$360,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

920 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 68 WARRINGTON ROUND # 68, DANBURY, CT, 0..., Danbury, CT 06810
$585,000

2 beds

|

3 baths

|

1,600 sq ft

|

Condo

68 WARRINGTON ROUND # 68, DANBURY, CT, 0...
Community: Rivington
Newtown Woods 1024 BROOKSIDE CT # 1024, NEWTOWN, CT, 0..., Newtown, CT 06470
$525,000

2 beds

|

2 baths

|

1,581 sq ft

|

Condo

1024 BROOKSIDE CT # 1024, NEWTOWN, CT, 0...
Community: Newtown Woods
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 773 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$325,000

2 beds

|

2 baths

|

1,063 sq ft

|

Condo

773 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Regency at Prospect 11 TAMARACK CT # 11, PROSPECT, CT, 06712, Prospect, CT 06712
$539,900

2 beds

|

3 baths

|

1,848 sq ft

|

Condo

11 TAMARACK CT # 11, PROSPECT, CT, 06712
Community: Regency at Prospect
Heritage Village 280 HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488
$199,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

280 HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
Bartlett Hollow 33 BARTLETT HOLW # 33, MIDDLETOWN, CT, 0..., Middletown, CT 06457
$449,000

2 beds

|

2 baths

|

1,401 sq ft

|

Condo

33 BARTLETT HOLW # 33, MIDDLETOWN, CT, 0...
Community: Bartlett Hollow
Spring Lake Village 543 S FARMS TER # 543, SOUTHINGTON, CT, ..., Southington, CT 06489
$225,000

2 beds

|

3 baths

|

1,782 sq ft

|

Condo

543 S FARMS TER # 543, SOUTHINGTON, CT, ...
Community: Spring Lake Village
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Chatfield Farms 3 TIMBERLAND WAY # 3, BEACON FALLS, CT, ..., Beacon Falls, CT 06403
$629,900

3 beds

|

4 baths

|

2,052 sq ft

3 TIMBERLAND WAY # 3, BEACON FALLS, CT, ...
Community: Chatfield Farms
Rivington 1022 COUNTRY VIEW RD # 1022, DANBURY, CT..., Danbury, CT 06810
$499,900

2 beds

|

2 baths

|

1,330 sq ft

|

Condo

1022 COUNTRY VIEW RD # 1022, DANBURY, CT...
Community: Rivington
Park Glen 10 HARMONY TRL # 10, NEW MILFORD, CT, 06..., New Milford, CT 06776
$639,000

2 beds

|

3 baths

|

4,023 sq ft

|

Condo

10 HARMONY TRL # 10, NEW MILFORD, CT, 06...
Community: Park Glen
Heritage Village 198 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$365,000

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

198 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 825 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,900

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

825 HERITAGE VLG B, 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.
Heritage Village 977 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$515,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

977 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Forest Mews 17 CHERRY TREE LN # 17, AVON, CT, 06001, Avon, CT 06001
$549,000

3 beds

|

3 baths

|

2,069 sq ft

|

Condo

17 CHERRY TREE LN # 17, AVON, CT, 06001
Community: Forest Mews
Heritage Village 701 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$350,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

701 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Newtown Woods 603 BROOKSIDE CT # 603, NEWTOWN, CT, 064..., Newtown, CT 06470
$489,000

2 beds

|

2 baths

|

1,504 sq ft

|

Condo

603 BROOKSIDE CT # 603, NEWTOWN, CT, 064...
Community: Newtown Woods
Heritage Village 98 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$335,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

98 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Regency at Woodbridge 4 WHISPER RIDGE WAY # 41, WOODBRIDGE, CT..., Woodbridge, CT 06525
$569,000

3 beds

|

3 baths

|

Condo

4 WHISPER RIDGE WAY # 41, WOODBRIDGE, CT...
Heritage Village 575 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$430,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

575 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 405 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$219,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

405 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Regency at Prospect 8 HICKORY DR # 8, PROSPECT, CT, 06712, Prospect, CT 06712
$347,184

3 beds

|

2 baths

|

1,500 sq ft

|

Condo

8 HICKORY DR # 8, PROSPECT, CT, 06712
Community: Regency at Prospect
The Village at Oxford Greens 302 FAIRWAY DR # 302, OXFORD, CT, 06478, Oxford, CT 06478
$735,000

3 beds

|

3 baths

|

2,750 sq ft

|

Condo

302 FAIRWAY DR # 302, OXFORD, CT, 06478
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 1 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$279,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 114 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$305,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

114 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 139 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$424,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

139 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 192 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$260,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

192 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 416 CENTER MEADOW LN # 416, DANBURY, CT,..., Danbury, CT 06810
$489,000

2 beds

|

2 baths

|

1,312 sq ft

|

Condo

416 CENTER MEADOW LN # 416, DANBURY, CT,...
Community: Rivington
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Oronoque Village 638 ONONDAGA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$399,000

2 beds

|

3 baths

|

2,071 sq ft

|

Condo

638 ONONDAGA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Oronoque Village 408 MONTAUK LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$425,000

1 beds

|

2 baths

|

1,118 sq ft

|

Condo

408 MONTAUK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 643 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$369,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

643 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 132 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

132 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Park Glen 15 HARMONY TRL # 15, NEW MILFORD, CT, 06..., New Milford, CT 06776
$699,900

2 beds

|

4 baths

|

2,720 sq ft

|

Condo

15 HARMONY TRL # 15, NEW MILFORD, CT, 06...
Community: Park Glen
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259 homes near Middletown
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