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

276 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 - $500Ks
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
$500Ks - $900Ks
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 - $700Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes
No reviews yet Leisure Knoll
$200Ks - $400Ks
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
$300Ks - $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 ...
$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 - $700Ks
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
$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 - $600Ks
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 - $500Ks
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 - $500Ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
Heritage Village 4 HERITAGE CRST A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$420,000

3 beds

|

2 baths

|

1,735 sq ft

|

Condo

4 HERITAGE CRST A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 926 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$325,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

926 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 192 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$229,500

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

192 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 122 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$384,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

122 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 331 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,000

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

331 HERITAGE VLG E, 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 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
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
Heritage Village 583 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$389,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

583 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage 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
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
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.
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
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 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 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
New New England Commons 16 CONCORD CT # 16, WEBSTER, MA, 01570, Webster, MA 01570
$469,900

3 beds

|

2 baths

|

1,649 sq ft

|

Condo

16 CONCORD CT # 16, WEBSTER, MA, 01570
Community: New England Commons
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
The Village at Westminster Place 33 TEA PARTY CIR # 33, HOLDEN, MA, 01520, Holden, MA 01520
$609,000

3 beds

|

3 baths

|

1,832 sq ft

|

House

33 TEA PARTY CIR # 33, HOLDEN, MA, 01520
Brierly Pond Village 103 HORNE WAY # 103, MILLBURY, MA, 01527, Millbury, MA 01527
$479,900

2 beds

|

3 baths

|

2,100 sq ft

|

Condo

103 HORNE WAY # 103, MILLBURY, MA, 01527
The Gardens of Wilbraham 45 IVY CIR # 45, WILBRAHAM, MA, 01095, Wilbraham, MA 01095
$475,000

2 beds

|

3 baths

|

1,752 sq ft

|

Condo

45 IVY CIR # 45, WILBRAHAM, MA, 01095
Harmony Place 8 FIDELITY DR # 4, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

8 FIDELITY DR # 4, RUTLAND, MA, 01543
Community: Harmony Place
Harmony Place 6 FIDELITY DR # 3, RUTLAND, MA, 01543, Rutland, MA 01543
$512,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

6 FIDELITY DR # 3, 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.
Harmony Place 4 FIDELITY DR # 2, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

4 FIDELITY DR # 2, RUTLAND, MA, 01543
Community: Harmony Place
Fairfield at St. James 302 ELTON CT, SAINT JAMES, NY, 11780, Saint James, NY 11780
$599,000

2 beds

|

2 baths

|

1,246 sq ft

|

Condo

302 ELTON CT, SAINT JAMES, NY, 11780
Leisure Village 166 VENTRY CT B, RIDGE, NY, 11961, Ridge, NY 11961
$259,000

1 beds

|

1 baths

|

680 sq ft

|

House

166 VENTRY CT B, RIDGE, NY, 11961
Community: Leisure Village
Greenwood Village 164 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$174,990

2 beds

|

2 baths

|

938 sq ft

|

Manufactured Home

164 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Leisure Glen 293 GLEN DR, RIDGE, NY, 11961, Ridge, NY 11961
$499,900

2 beds

|

2 baths

|

1,290 sq ft

|

Condo

293 GLEN DR, RIDGE, NY, 11961
Community: Leisure Glen
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
Sunrise Village 136 REVERE DR, SAYVILLE, NY, 11782, Sayville, NY 11782
$459,999

2 beds

|

2 baths

|

1,664 sq ft

|

Condo

136 REVERE DR, SAYVILLE, NY, 11782
Community: Sunrise Village
New Encore at Lake Grove 159 SYMPHONY DR, LAKE GROVE, NY, 11755, Lake Grove, NY 11755
$599,999

2 beds

|

3 baths

|

1,378 sq ft

|

Condo

159 SYMPHONY DR, LAKE GROVE, NY, 11755
Village Estates 26 SARAH CT, AMITYVILLE, NY, 11701, Amityville, NY 11701
$549,000

2 beds

|

2 baths

|

1,243 sq ft

|

Condo

26 SARAH CT, AMITYVILLE, NY, 11701
Community: Village Estates
The Waterways at Moriches 276 DOCKSIDE CT, MORICHES, NY, 11955, Moriches, NY 11955
$649,000

2 beds

|

2 baths

|

1,875 sq ft

|

Condo

276 DOCKSIDE CT, MORICHES, NY, 11955
The Seasons at East Meadow 319 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554
$619,000

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

319 SPRING DR, EAST MEADOW, NY, 11554
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.
Greenwood Village 96 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$214,000

2 beds

|

2 baths

|

1,110 sq ft

|

Condo

96 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Leisure Knoll 187 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961
$395,000

2 beds

|

2 baths

|

913 sq ft

|

Condo

187 EDINBURGH DR, RIDGE, NY, 11961
Community: Leisure Knoll
Leisure Glen 12 BALDWIN CT, RIDGE, NY, 11961, Ridge, NY 11961
$489,990

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

12 BALDWIN CT, RIDGE, NY, 11961
Community: Leisure Glen
Leisure Knoll 379 LARCHMONT CT # 379, RIDGE, NY, 11961, Ridge, NY 11961
$405,000

2 beds

|

2 baths

|

976 sq ft

|

Condo

379 LARCHMONT CT # 379, RIDGE, NY, 11961
Community: Leisure Knoll
Leisure Glen 240 GLEN DR, RIDGE, NY, 11961, Ridge, NY 11961
$499,900

2 beds

|

2 baths

|

1,451 sq ft

|

Condo

240 GLEN DR, RIDGE, NY, 11961
Community: Leisure Glen
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (860) 854-8527
The Villages at Mount Sinai Park 13 GRAYCREST CT, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766
$815,000

2 beds

|

2 baths

|

2,016 sq ft

|

Condo

13 GRAYCREST CT, MOUNT SINAI, NY, 11766
Greenwood Village 57 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949
$159,999

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

57 DOGWOOD LN, MANORVILLE, NY, 11949
Community: Greenwood Village
The Villages at Mount Sinai Park 109 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766
$749,900

2 beds

|

2 baths

|

1,736 sq ft

|

Condo

109 LOUDEN LOOP, MOUNT SINAI, NY, 11766
Encore Atlantic Shores 226 SONATA CT, EASTPORT, NY, 11941, Eastport, NY 11941
$689,000

2 beds

|

2 baths

|

1,605 sq ft

|

Condo

226 SONATA CT, EASTPORT, NY, 11941
New Leisure Glen 25 DOUGLASTON CT, RIDGE, NY, 11961, Ridge, NY 11961
$509,990

2 beds

|

2 baths

|

1,451 sq ft

|

Condo

25 DOUGLASTON CT, RIDGE, NY, 11961
Community: Leisure Glen
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276 homes near Middletown
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