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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!
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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 - $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
Founders Village 2555 YOUNGS AVE 11D, SOUTHOLD, NY, 11971, Southold, NY 11971
$527,500

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

2555 YOUNGS AVE 11D, SOUTHOLD, NY, 11971
Community: Founders Village
Vineyards at Brookfield 56 AVERY DR N, CENTER MORICHES, NY, 1193..., Center Moriches, NY 11934
$639,000

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

56 AVERY DR N, CENTER MORICHES, NY, 1193...
Greenwood Village 77 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$165,000

2 beds

|

1 baths

|

1,000 sq ft

|

Condo

77 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Greenwood Village 22 LIMETREE DR, MANORVILLE, NY, 11949, Manorville, NY 11949
$141,000

2 beds

|

2 baths

|

920 sq ft

|

Condo

22 LIMETREE DR, MANORVILLE, NY, 11949
Community: Greenwood Village
Leisure Village 419 WEYMOUTH CT F, RIDGE, NY, 11961, Ridge, NY 11961
$283,000

1 beds

|

1 baths

|

782 sq ft

|

Condo

419 WEYMOUTH CT F, RIDGE, NY, 11961
Community: Leisure Village
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Leisure Village 332 WOODBRIDGE DR UNIT C WOODBRIDGE DR, ..., Ridge, NY 11961
$369,000

2 beds

|

1 baths

|

1,000 sq ft

|

Condo

332 WOODBRIDGE DR UNIT C WOODBRIDGE DR, ...
Community: Leisure Village
Foxwood Village 1407-54 MIDDLE RD 54, RIVERHEAD, NY, 119..., Riverhead, NY 11933
$324,999

2 beds

|

2 baths

|

1,280 sq ft

|

House

1407-54 MIDDLE RD 54, RIVERHEAD, NY, 119...
Community: Foxwood Village
Encore Atlantic Shores 68 ENCORE, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$849,999

2 beds

|

3 baths

|

3,000 sq ft

|

Condo

68 ENCORE, BROOKHAVEN, NY, 11941
The Seasons at East Meadow 315 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554
$588,000

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

315 SPRING DR, EAST MEADOW, NY, 11554
The Waterways at Moriches 107 E MIDLAND POND CT, MORICHES, NY, 119..., Moriches, NY 11955
$539,000

2 beds

|

2 baths

|

2,141 sq ft

|

Condo

107 E MIDLAND POND CT, MORICHES, NY, 119...
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.
Country Pointe Plainview 18205 ASPENWOOD DR, PLAINVIEW, NY, 11803, Plainview, NY 11803
$1,200,000

2 beds

|

2 baths

|

1,474 sq ft

|

Condo

18205 ASPENWOOD DR, PLAINVIEW, NY, 11803
Leisure Knoll 385 LARCHMONT CT, RIDGE, NY, 11961, Ridge, NY 11961
$419,999

2 beds

|

1 baths

|

1,050 sq ft

|

Condo

385 LARCHMONT CT, RIDGE, NY, 11961
Community: Leisure Knoll
Leisure Knoll 2 LAMONT RD # 2, RIDGE, NY, 11961, Ridge, NY 11961
$515,000

2 beds

|

2 baths

|

1,646 sq ft

|

Condo

2 LAMONT RD # 2, RIDGE, NY, 11961
Community: Leisure Knoll
The Powder Forest Homes 30 CARSON WAY # 30, SIMSBURY, CT, 06070, Simsbury, CT 06070
$674,900

3 beds

|

4 baths

|

1,862 sq ft

30 CARSON WAY # 30, SIMSBURY, CT, 06070
Heritage Village 106 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$424,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

106 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 15 HERITAGE LN # 63, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$729,000

3 beds

|

3 baths

|

2,486 sq ft

|

Condo

15 HERITAGE LN # 63, WOODBRIDGE, CT, 065...
Regency at Woodbridge 29 HERITAGE LN # 56, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$719,000

3 beds

|

3 baths

|

2,239 sq ft

|

Condo

29 HERITAGE LN # 56, WOODBRIDGE, CT, 065...
Regency at Woodbridge 13 HERITAGE LN # 64, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$669,000

3 beds

|

3 baths

|

2,239 sq ft

|

Condo

13 HERITAGE LN # 64, WOODBRIDGE, CT, 065...
Regency at Woodbridge 3 HERITAGE LN # 69, WOODBRIDGE, CT, 0652..., Woodbridge, CT 06525
$659,000

3 beds

|

3 baths

|

Condo

3 HERITAGE LN # 69, WOODBRIDGE, CT, 0652...
Regency at Woodbridge 11 HERITAGE LN # 65, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$659,000

3 beds

|

3 baths

|

2,028 sq ft

|

Condo

11 HERITAGE LN # 65, WOODBRIDGE, CT, 065...
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 Woodbridge 5 HERITAGE LN # 68, WOODBRIDGE, CT, 0652..., Woodbridge, CT 06525
$599,995

3 beds

|

3 baths

|

2,006 sq ft

|

Condo

5 HERITAGE LN # 68, WOODBRIDGE, CT, 0652...
New Heritage Village 170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$404,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Summit at Bethel 81 GREAT HILL DR # 81, BETHEL, CT, 06801, Bethel, CT 06801
$699,000

3 beds

|

3 baths

|

2,447 sq ft

|

Condo

81 GREAT HILL DR # 81, BETHEL, CT, 06801
Whitney Glen 34 WHITNEY GLN # 34, WESTPORT, CT, 06880, Westport, CT 06880
$815,000

2 beds

|

3 baths

|

1,400 sq ft

|

Condo

34 WHITNEY GLN # 34, WESTPORT, CT, 06880
Community: Whitney Glen
New Oronoque Village 186 APACHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$475,000

3 beds

|

3 baths

|

1,438 sq ft

|

Condo

186 APACHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Heritage Village 143 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$387,500

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

143 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 760 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$424,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

760 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 633 CHAMPIONSHIP DR # 633, OXFORD, CT, 0..., Oxford, CT 06478
$619,900

2 beds

|

3 baths

|

1,983 sq ft

|

Condo

633 CHAMPIONSHIP DR # 633, OXFORD, CT, 0...
Heritage Village 920 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$389,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

920 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 953 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$279,900

1 beds

|

1 baths

|

928 sq ft

|

Condo

953 HERITAGE VLG A, 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 16 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$426,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

16 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
Heritage Village 133 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$349,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

133 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 21 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$170,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

21 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 1022 COUNTRY VIEW RD # 1022, DANBURY, CT..., Danbury, CT 06810
$489,900

2 beds

|

2 baths

|

1,330 sq ft

|

Condo

1022 COUNTRY VIEW RD # 1022, DANBURY, CT...
Community: Rivington
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Sonoma Woods 46 SONOMA LN # 46, MIDDLETOWN, CT, 06457, Middletown, CT 06457
$689,900

2 beds

|

3 baths

|

2,515 sq ft

46 SONOMA LN # 46, MIDDLETOWN, CT, 06457
Community: Sonoma Woods
Heritage Village 701 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$380,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

701 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 644 CHAMPIONSHIP DR # 644, OXFORD, CT, 0..., Oxford, CT 06478
$659,000

2 beds

|

3 baths

|

2,197 sq ft

|

Condo

644 CHAMPIONSHIP DR # 644, OXFORD, CT, 0...
Oronoque Village 227 SHOSHONI LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$365,000

1 beds

|

2 baths

|

1,175 sq ft

|

Condo

227 SHOSHONI LN B, STRATFORD, CT, 06614
Community: Oronoque Village
The Village at Oxford Greens 403 MULLIGAN DR # 403, OXFORD, CT, 06478, Oxford, CT 06478
$679,000

2 beds

|

2 baths

|

2,080 sq ft

|

Condo

403 MULLIGAN DR # 403, OXFORD, CT, 06478

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252 homes near Middletown
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