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

252 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
$100Ks - $400Ks
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!
Questions? Call us: (860) 854-8527
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 - $1Ms
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
No reviews yet Oronoque Village
$300Ks - $600Ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
No reviews yet The Village at Oxford Gre...
$500Ks - $600Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes
No reviews yet Leisure Knoll
$400Ks - $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 (1 reviews) Fairfield at St. James
$400Ks - $600Ks
Fairfield at St. James, St. James, NY
Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes
No reviews yet Leisure Glen
$400Ks - $500Ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
No reviews yet Spring Lake Village
$200Ks - $300Ks
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
$400Ks - $400Ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
No reviews yet The Waterways at Moriches
$400Ks - $600Ks
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 ...
$600Ks - $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
$600Ks - $900Ks
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 - $800Ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
No reviews yet The Summit at Bethel
$600Ks - $700Ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
4.9 rating (14 reviews) Chatfield Farms
$500Ks - $500Ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 homes
5 rating (1 reviews) Encore at Lake Grove
$500Ks - $700Ks
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 - $400Ks
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
$400Ks - $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
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...
$700Ks - $800Ks
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
5 rating (1 reviews) Newtown Woods
$400Ks - $400Ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
Meadow Brook Estates 306 SPRUCE HILL DR, OXFORD, CT, 06478, Oxford, CT 06478
$515,000

2 beds

|

3 baths

|

1,586 sq ft

|

Condo

306 SPRUCE HILL DR, OXFORD, CT, 06478
Heritage Village 13 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$240,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

13 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 17 WILDERSWOOD WAY # 17, DANBURY, CT, 06..., Danbury, CT 06810
$859,000

3 beds

|

3 baths

|

2,305 sq ft

|

Condo

17 WILDERSWOOD WAY # 17, DANBURY, CT, 06...
Community: Rivington
Heritage Village 948 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$259,900

2 beds

|

2 baths

|

1,071 sq ft

|

Condo

948 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 761 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$245,000

2 beds

|

2 baths

|

1,063 sq ft

|

Condo

761 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Rivington 45 WINDING RIDGE WAY # 45, DANBURY, CT, ..., Danbury, CT 06810
$925,000

3 beds

|

5 baths

|

2,592 sq ft

|

Condo

45 WINDING RIDGE WAY # 45, DANBURY, CT, ...
Community: Rivington
Heritage Village 21 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$290,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

21 HERITAGE CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 65 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$175,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

65 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 98 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$347,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

98 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 951 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$339,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

951 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 192 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

192 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Newtown Woods 231 BROOKSIDE CT 231, NEWTOWN, CT, 06470, Newtown, CT 06470
$499,999

2 beds

|

2 baths

|

1,483 sq ft

|

Condo

231 BROOKSIDE CT 231, NEWTOWN, CT, 06470
Community: Newtown Woods
Heritage Village 32 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$224,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

32 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 134 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$419,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

134 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 1036 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$499,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

1036 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Heritage Village 926 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$338,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

926 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 793 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,900

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

793 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
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
The Village at Oxford Greens 89 LINKS WAY # 89, OXFORD, CT, 06478, Oxford, CT 06478
$675,000

2 beds

|

2 baths

|

2,008 sq ft

|

Condo

89 LINKS WAY # 89, OXFORD, CT, 06478
Meadow Brook Estates 326 SPRUCE HILL DR # 326, OXFORD, CT, 06..., Oxford, CT 06478
$555,000

2 beds

|

3 baths

|

1,682 sq ft

|

Condo

326 SPRUCE HILL DR # 326, 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.
Regency at Prospect 127 SYCAMORE DR # 127, PROSPECT, CT, 067..., Prospect, CT 06712
$424,900

2 beds

|

2 baths

|

1,503 sq ft

|

Condo

127 SYCAMORE DR # 127, PROSPECT, CT, 067...
Community: Regency at Prospect
Heritage Village 345 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$439,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

345 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 8 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$269,900

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

8 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 10 OLD PASTURE DR # 10, DANBURY, CT, 068..., Danbury, CT 06810
$1,175,000

3 beds

|

4 baths

|

2,544 sq ft

|

Condo

10 OLD PASTURE DR # 10, DANBURY, CT, 068...
Community: Rivington
Heritage Village 669 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$300,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

669 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Heritage Village 331 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$315,000

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

331 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 231 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$265,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

231 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
The Coach Homes at Ridgefield 233 DANBURY RD A109, RIDGEFIELD, CT, 068..., Ridgefield, CT 06877
$539,000

1 beds

|

2 baths

|

1,000 sq ft

|

Condo

233 DANBURY RD A109, RIDGEFIELD, CT, 068...
Heritage Village 419 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$289,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

419 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Founders Ridge 20 WEBSTER LN # 20, MIDDLETOWN, CT, 0645..., Middletown, CT 06457
$550,000

2 beds

|

2 baths

|

1,548 sq ft

|

Condo

20 WEBSTER LN # 20, MIDDLETOWN, CT, 0645...
Community: Founders Ridge
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 12 HERITAGE CRST E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$485,000

2 beds

|

2 baths

|

1,447 sq ft

|

Condo

12 HERITAGE CRST E, SOUTHBURY, CT, 06488
Community: Heritage Village
Spring Lake Village 9 VILLAGE RD # 9, SOUTHINGTON, CT, 06489, Southington, CT 06489
$299,000

2 beds

|

2 baths

|

1,264 sq ft

|

Condo

9 VILLAGE RD # 9, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Heritage Village 881 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$409,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

881 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 92 SEMINOLE LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$639,000

3 beds

|

3 baths

|

1,438 sq ft

|

Condo

92 SEMINOLE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 740 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$430,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

740 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Heritage Village 79 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$205,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

79 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Bartlett Hollow 39 BARTLETT HOLW # 39, MIDDLETOWN, CT, 0..., Middletown, CT 06457
$579,900

3 beds

|

3 baths

|

3,147 sq ft

39 BARTLETT HOLW # 39, MIDDLETOWN, CT, 0...
Community: Bartlett Hollow
Founders Ridge UNIT 2-45 WEBSTER LN, MIDDLETOWN, CT, 06..., Middletown, CT 06457
$669,995

2 beds

|

2 baths

|

1,555 sq ft

UNIT 2-45 WEBSTER LN, MIDDLETOWN, CT, 06...
Community: Founders Ridge
Billingsgate 15 BILLINGSGATE DR # 15, SIMSBURY, CT, 0..., Simsbury, CT 06070
$675,000

2 beds

|

4 baths

|

2,729 sq ft

|

Condo

15 BILLINGSGATE DR # 15, SIMSBURY, CT, 0...
Community: Billingsgate
Heritage Village 1005 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$299,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

1005 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village

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252 homes near Middletown
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