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

106 communities near Essex

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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
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
Want to learn more about 55+ communities in Essex? 55places can help!
Questions? Call us: (959) 265-7852
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
The Manors at The Colony ...
$300ks - $400ks
The Manors at The Colony ..., Shirley, NY
New Construction | 55+ age-restricted | Built 2013 - present | 150 homes
5 rating (1 reviews) Encore Atlantic Shores
$500ks - $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 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
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.
5 rating (2 reviews) Fairfield at St. James
$300ks - $500ks
Fairfield at St. James, St. James, NY
Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Upton Ridge
$400ks - $600ks
Upton Ridge, Upton, MA
New Construction | 55+ age-restricted | Built 2019 - present | 139 homes
The Village at Orchard Me...
$400ks - $500ks
The Village at Orchard Me..., Shrewsbury, MA
Resale Only | 55+ age-restricted | Built 2002 - 2007 | 114 homes
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Questions? Call us: (959) 265-7852
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
3.5 rating (2 reviews) Foxwood Village
$200ks - $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.
The Trails
$500ks - $700ks
The Trails, Hopkinton, MA
New Construction | 55+ age-restricted | Built 2017 - present | 170 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
Brierly Pond Village
$300ks - $400ks
Brierly Pond Village, Millbury, MA
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 homes
Orchard Hill
$500ks
Orchard Hill, Westborough, MA
Resale Only | 55+ age-restricted | Built 2002 - 2010 | 100 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
The Gardens of Wilbraham
$200ks - $400ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes
Vineyards at Brookfield
$400ks - $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
Want to learn more about 55+ communities in Essex? 55places can help!
Questions? Call us: (959) 265-7852
Country Pointe Preserve
$600ks - $900ks
Country Pointe PreserveYaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 homes
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
1 rating (1 reviews) Plymouth Estates at Mount...
$400ks - $500ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 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.
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
5 rating (1 reviews) Sunrise Village
$400ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes
Meadow Brook Estates
$300ks - $400ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
Regency Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
The Villages at Walker Me...
$600ks - $700ks
The Villages at Walker Me..., Westborough, MA
Resale Only | 55+ age-restricted | Built 1999 - 2000 | 100 homes
The Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
Want to learn more about 55+ communities in Essex? 55places can help!
Questions? Call us: (959) 265-7852
Oak Meadow Estates
$200ks - $300ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 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.
12...3
Glenwood Village 1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901
$419,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
New Upton Ridge 56 SHANNON WAY 56, UPTON, MA, 01568, Upton, MA 01568
$724,900

2 beds

|

3 baths

|

1,950 sq ft

|

Condo

56 SHANNON WAY 56, UPTON, MA, 01568
Community: Upton Ridge
New The Waterways at Moriches 632 WATER WAY 32, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$799,000

2 beds

|

3 baths

|

1,874 sq ft

|

Condo

632 WATER WAY 32, BROOKHAVEN, NY, 11955
New Vineyards at Blue Point 174 HALLEY DR, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772
$829,900

2 beds

|

2 baths

|

1,928 sq ft

|

Condo

174 HALLEY DR, BROOKHAVEN, NY, 11772
New Greenwood Village 5131 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$135,000

2 beds

|

2 baths

|

987 sq ft

|

House

5131 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Want to learn more about 55+ communities in Essex? 55places can help!
Questions? Call us: (959) 265-7852
New Fairfield at St. James 1205 GOTHAM DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$649,000

2 beds

|

2 baths

|

948 sq ft

|

Condo

1205 GOTHAM DR, SMITHTOWN, NY, 11780
New Country Pointe Preserve 118 JUNIPER LN 31, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980
$865,000

2 beds

|

3 baths

|

1,998 sq ft

|

Condo

118 JUNIPER LN 31, BROOKHAVEN, NY, 11980
New Vineyards at Blue Point 32 AVERY WAY, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772
$799,000

2 beds

|

3 baths

|

2,168 sq ft

|

Condo

32 AVERY WAY, BROOKHAVEN, NY, 11772
New Fairfield at St. James 606 FLAIR CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$429,000

1 beds

|

1 baths

|

752 sq ft

|

Condo

606 FLAIR CT, SMITHTOWN, NY, 11780
New Oronoque Village 46 BUCKSKIN LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$559,900

1 beds

|

2 baths

|

1,375 sq ft

|

Condo

46 BUCKSKIN LN A, 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.
New Vineyards at Moriches 20 EMILIE DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934
$759,000

2 beds

|

3 baths

|

1,984 sq ft

|

Condo

20 EMILIE DR, BROOKHAVEN, NY, 11934
New Leisure Glen 187 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$525,000

2 beds

|

2 baths

|

1,451 sq ft

|

Condo

187 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New The Waterways at Moriches 216 RIVER DR, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$510,000

2 beds

|

2 baths

|

1,544 sq ft

|

Condo

216 RIVER DR, BROOKHAVEN, NY, 11955
New Heritage Village 874 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$275,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

874 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Greenwood Village 16 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$299,999

2 beds

|

2 baths

|

1,288 sq ft

|

Condo

16 DOGWOOD LN, BROOKHAVEN, NY, 11949
Community: Greenwood Village
New Vineyards at Moriches 27 EMILIE DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934
$785,000

2 beds

|

3 baths

|

2,335 sq ft

|

Condo

27 EMILIE DR, BROOKHAVEN, NY, 11934
Want to learn more about 55+ communities in Essex? 55places can help!
Questions? Call us: (959) 265-7852
New The Gardens of Wilbraham 137 CHERRY DR 137, WILBRAHAM, MA, 01095, Wilbraham, MA 01095
$400,000

2 beds

|

2 baths

|

1,241 sq ft

|

Condo

137 CHERRY DR 137, WILBRAHAM, MA, 01095
Heritage Village 701 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

701 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$589,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 157 COUNTRY CLUB DR 157, OXFORD, CT, 064..., Oxford, CT 06478
$649,900

3 beds

|

3 baths

|

2,008 sq ft

|

Condo

157 COUNTRY CLUB DR 157, OXFORD, CT, 064...
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.
Windmill Gate 7 DARIA DR, ISLIP, NY, 11769, Islip, NY 11769
$633,000

2 beds

|

2 baths

|

1,175 sq ft

|

Condo

7 DARIA DR, ISLIP, NY, 11769
Community: Windmill Gate
Sunrise Village 113 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782
$479,000

2 beds

|

2 baths

|

1,141 sq ft

|

Condo

113 REVERE DR, ISLIP, NY, 11782
Community: Sunrise Village
Heritage Village 24-B HERITAGE CRST B, SOUTHBURY, CT, 064..., Southbury, CT 06488
$419,900

2 beds

|

2 baths

|

1,217 sq ft

|

Condo

24-B HERITAGE CRST B, SOUTHBURY, CT, 064...
Community: Heritage Village
Heritage Village 593 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$205,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

593 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 147 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$235,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

147 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 22 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$204,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

22 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Greenwood Village 130 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$129,000

2 beds

|

2 baths

|

1,177 sq ft

|

Condo

130 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Want to learn more about 55+ communities in Essex? 55places can help!
Questions? Call us: (959) 265-7852
Leisure Village 258 NEWCASTLE CT F, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$299,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

258 NEWCASTLE CT F, BROOKHAVEN, NY, 1196...
Community: Leisure Village
Heritage Village 804 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$259,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

804 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Strathmore Gate East 4 FLAIR WAY, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$495,000

2 beds

|

2 baths

|

1,112 sq ft

|

House

4 FLAIR WAY, BROOKHAVEN, NY, 11727
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.
Oronoque Village 89 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$649,000

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

89 S TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
Oak Meadow Estates 197 OAK MEADOW LN 197, TORRINGTON, CT, 0..., Torrington, CT 06790
$399,000

2 beds

|

2 baths

|

1,419 sq ft

|

Condo

197 OAK MEADOW LN 197, TORRINGTON, CT, 0...
Community: Oak Meadow Estates
Strathmore Gate East 9 FREEDOM LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$289,000

1 beds

|

1 baths

|

728 sq ft

|

Condo

9 FREEDOM LN, BROOKHAVEN, NY, 11727
Leisure Knoll 338 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$419,990

2 beds

|

1 baths

|

960 sq ft

|

Condo

338 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Greenwood Village 5127 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$227,000

2 beds

|

2 baths

|

1,291 sq ft

|

Condo

5127 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Billingsgate 14 BILLINGSGATE DR 14, SIMSBURY, CT, 060..., Simsbury, CT 06070
$750,000

2 beds

|

3 baths

|

2,729 sq ft

|

Condo

14 BILLINGSGATE DR 14, SIMSBURY, CT, 060...
Community: Billingsgate
Encore Atlantic Shores 11 OVATION PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$885,000

2 beds

|

3 baths

|

2,900 sq ft

|

Condo

11 OVATION PL, BROOKHAVEN, NY, 11941
Leisure Village 312 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$239,000

1 beds

|

1 baths

|

684 sq ft

|

Condo

312 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...
Community: Leisure Village
Want to learn more about 55+ communities in Essex? 55places can help!
Questions? Call us: (959) 265-7852
Orchard Hill 19 IMPERIAL CT 19, WESTBOROUGH, MA, 0158..., Westborough, MA 01581
$597,500

2 beds

|

3 baths

|

2,183 sq ft

|

Condo

19 IMPERIAL CT 19, WESTBOROUGH, MA, 0158...
Community: Orchard Hill
Heritage Village 184 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$209,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

184 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.

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