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Essex, CT 55+ active adult communities & homes for sale
105 communities near Essex
184 homes near Essex
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$400Ks
- $500Ks
Cobblestone Court, Essex, CT
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
8 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
$200Ks
- $400Ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
$200Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
$500Ks
- $600Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
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(959) 265-7852
$300Ks
- $400Ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 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
$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
Download the Ultimate 55+ Homebuying Guide
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3.7 rating (3 reviews)
![Greenwood Village]()
$100Ks
- $200Ks
Greenwood Village, Manorville, NY
Resale Only
|
55+ age-restricted
|
Built 1980 - 2000
|
512 homes
$300Ks
- $500Ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
$400Ks
- $600Ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
4 rating (5 reviews)
![South Shore Village]()
$600Ks
- $800Ks
South Shore Village, South Kingstown, RI
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
303 homes
3.5 rating (2 reviews)
![Foxwood Village]()
$400Ks
- $500Ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
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1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$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
Vineyards at Blue Point, Blue Point, NY
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
280 homes
$500Ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
5 rating (1 reviews)
![Encore Atlantic Shores]()
$700Ks
- $800Ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 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.
4.9 rating (14 reviews)
![Chatfield Farms]()
$500Ks
- $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
$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
$400Ks
Brierly Pond Village, Millbury, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
199 homes
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(959) 265-7852
$400Ks
Country Village Estates, Coram, NY
Resale Only
|
55+ age-restricted
|
Built 1993 - 2001
|
195 homes
5 rating (1 reviews)
![Sunken Pond Estates]()
$400Ks
- $500Ks
Sunken Pond Estates, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
194 homes
$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
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 (1 reviews)
![The Villages at Mount Sin...]()
$500Ks
- $700Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
185 homes
$600Ks
- $700Ks
The Powder Forest Homes, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2016
|
182 homes
$500Ks
- $600Ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2016
|
176 homes
$300Ks
- $400Ks
Strathmore Gate East, Coram, NY
Resale Only
|
55+ age-restricted
|
Built 1970 - 1975
|
174 homes
$800Ks
- $1Ms
The Trails, Hopkinton, MA
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
170 homes
Want to learn more about 55+ communities in Essex?
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(959) 265-7852
$300Ks
- $400Ks
Beckley Farms, Berlin, CT
New and Resale
|
55+ age-restricted
|
Built 2010 - present
|
170 homes
$100Ks
- $200Ks
South Pond Village, Bloomfield, CT
Resale Only
|
55+ age-restricted
|
Built 1999 - 2005
|
151 homes
$600Ks
- $700Ks
Setauket Meadows, Setauket, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
150 homes
$400Ks
- $500Ks
The Manors at The Colony ..., Shirley, NY
New Construction
|
55+ age-restricted
|
Built 2013 - present
|
150 homes
Brierly Pond Village
![32 HORNE WAY # 32, MILLBURY, MA, 01527, Millbury, MA 01527]()
2 beds
|2 baths
|1,420 sq ft
|Condo
32 HORNE WAY # 32, MILLBURY, MA, 01527
Community: Brierly Pond Village
MLS 73433720 • Lamacchia Realty, Inc, Diane Dabro...
The Trails
![30 WATERVILLE LN # 30, HOPKINTON, MA, 01..., Hopkinton, MA 01748]()
2 beds
|3 baths
|2,510 sq ft
|Condo
30 WATERVILLE LN # 30, HOPKINTON, MA, 01...
Community: The Trails
MLS 73458269 • Realty Executives Boston West, Phi...
The Villages at Walker Meadow
![9 SHAKER WAY # 9, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
2 beds
|2 baths
|2,090 sq ft
|Condo
9 SHAKER WAY # 9, WESTBOROUGH, MA, 01581
Community: The Villages at Walker Meadow
MLS 73429776 • Mathieu Newton Sotheby's Internati...
Orchard Hill
![5 BLOSSOM CT # 5, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
3 beds
|4 baths
|3,373 sq ft
|Condo
5 BLOSSOM CT # 5, WESTBOROUGH, MA, 01581
Community: Orchard Hill
MLS 73437675 • Berkshire Hathaway HomeServices Co...
Brierly Pond Village
![192 HORNE WAY # 192, MILLBURY, MA, 01527, Millbury, MA 01527]()
2 beds
|3 baths
|1,746 sq ft
|Condo
192 HORNE WAY # 192, MILLBURY, MA, 01527
Community: Brierly Pond Village
MLS 73457258 • Lamacchia Realty, Inc., Mulryan an...
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(959) 265-7852
Brierly Pond Village
![23 HORNE WAY # 23, MILLBURY, MA, 01527, Millbury, MA 01527]()
2 beds
|3 baths
|1,794 sq ft
|Condo
23 HORNE WAY # 23, MILLBURY, MA, 01527
Community: Brierly Pond Village
MLS 73456924 • Hillman Real Estate, Andrew Hillma...
The Trails
![13 BIRKDALE LN # 13, HOPKINTON, MA, 0174..., Hopkinton, MA 01748]()
2 beds
|3 baths
|2,277 sq ft
|Condo
13 BIRKDALE LN # 13, HOPKINTON, MA, 0174...
Community: The Trails
MLS 73430544 • Keller Williams Elite, Sue Sindoni
The Gardens of Wilbraham
![116 CHERRY DR # 116, WILBRAHAM, MA, 0109..., Wilbraham, MA 01095]()
2 beds
|2 baths
|1,634 sq ft
|Condo
116 CHERRY DR # 116, WILBRAHAM, MA, 0109...
Community: The Gardens of Wilbraham
MLS 73441478 • Coldwell Banker Realty - Western M...
Brierly Pond Village
![92 HORNE WAY # 92, MILLBURY, MA, 01527, Millbury, MA 01527]()
2 beds
|2 baths
|1,420 sq ft
|Condo
92 HORNE WAY # 92, MILLBURY, MA, 01527
Community: Brierly Pond Village
MLS 73454040 • RE/MAX Partners, Stephanie McNamar...
The Villages at Walker Meadow
![3 DOVER WAY # 3, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
2 beds
|2 baths
|1,874 sq ft
|Condo
3 DOVER WAY # 3, WESTBOROUGH, MA, 01581
Community: The Villages at Walker Meadow
MLS 73452352 • Mathieu Newton Sotheby's Internati...
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 Gardens of Wilbraham
![32 LODGE LN # 32, WILBRAHAM, MA, 01095, Wilbraham, MA 01095]()
2 beds
|2 baths
|1,610 sq ft
|Condo
32 LODGE LN # 32, WILBRAHAM, MA, 01095
Community: The Gardens of Wilbraham
MLS 73451919 • Coldwell Banker Realty - Western M...
The Trails
![71 WESTON LN # 71, HOPKINTON, MA, 01748, Hopkinton, MA 01748]()
2 beds
|4 baths
|3,258 sq ft
|Condo
71 WESTON LN # 71, HOPKINTON, MA, 01748
Community: The Trails
MLS 73444675 • RE/MAX Executive Realty, Erika Ste...
Orchard Hill
![9 BALDWIN CT # 9, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
3 beds
|3 baths
|2,793 sq ft
|Condo
9 BALDWIN CT # 9, WESTBOROUGH, MA, 01581
Community: Orchard Hill
MLS 73440395 • Mathieu Newton Sotheby's Internati...
The Trails
![10 WATERVILLE LN # 10, HOPKINTON, MA, 01..., Hopkinton, MA 01748]()
2 beds
|3 baths
|2,274 sq ft
|Condo
10 WATERVILLE LN # 10, HOPKINTON, MA, 01...
Community: The Trails
MLS 73410711 • Realty Executives Boston West, Kar...
The Village at Oxford Greens
![106 COUNTRY CLUB DR # 106, OXFORD, CT, 0..., Oxford, CT 06478]()
2 beds
|3 baths
|1,590 sq ft
|Condo
106 COUNTRY CLUB DR # 106, OXFORD, CT, 0...
Community: The Village at Oxford Greens
MLS 24119727 • William Pitt Sotheby's Int'l, Tom ...
Want to learn more about 55+ communities in Essex?
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Questions? Call us:
(959) 265-7852
Heritage Village
![170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
170 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24121047 • Joseph Bette REALTORS Inc, Justin ...
The Village at Oxford Greens
![930 TILLINGHAST DR # 930, OXFORD, CT, 06..., Oxford, CT 06478]()
2 beds
|3 baths
|2,365 sq ft
930 TILLINGHAST DR # 930, OXFORD, CT, 06...
Community: The Village at Oxford Greens
MLS 24137749 • Real Estate Two, Karen Berwick
Heritage Village
![103 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
103 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24135394 • Joseph Bette REALTORS Inc, Justin ...
Heritage Village
![644 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
644 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24125882 • Berkshire Hathaway NE Prop., Miche...
Heritage Village
![929 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
929 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24138393 • Pyramid R.E. & Mgmt Co., Jack Dani...
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
![825 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
825 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24124224 • Keller Williams Realty, Donna Doyl...
Heritage Village
![98 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
98 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24101279 • Berkshire Hathaway NE Prop., Miche...
Heritage Village
![977 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
977 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24099168 • William Pitt Sotheby's Int'l, Mary...
Heritage Village
![198 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
198 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24112399 • William Raveis Real Estate, Joseph...
The Village at Oxford Greens
![302 FAIRWAY DR # 302, OXFORD, CT, 06478, Oxford, CT 06478]()
3 beds
|3 baths
|2,750 sq ft
|Condo
302 FAIRWAY DR # 302, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24126623 • Coldwell Banker Realty, Pam McHenr...
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Heritage Village
![419 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
419 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24097056 • Joseph Bette REALTORS Inc, Deborah...
Heritage Village
![737 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
737 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24139552 • William Pitt Sotheby's Int'l, Mela...
Heritage Village
![1008 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
1008 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24136244 • Dave Jones Realty, LLC, Gregory Mi...
Heritage Village
![889 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
889 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24137432 • Coldwell Banker Realty, Maryanne B...
Heritage Village
![643 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
643 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24119411 • Drakeley Real Estate, Inc., Timoth...
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
Greenwood Village
![22 LIMETREE DR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|909 sq ft
|Condo
22 LIMETREE DR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 940248 • EXP Realty, Jennifer Nyx
New
Fairfield at St. James
![504 GOTHAM CT, SAINT JAMES, NY, 11780, Saint James, NY 11780]()
2 beds
|2 baths
|1,236 sq ft
|House
504 GOTHAM CT, SAINT JAMES, NY, 11780
Community: Fairfield at St. James
MLS 941087 • Realty Forward Inc, Eric Connolly
New
Foxwood Village
![1407 MIDDLE RD 275, CALVERTON, NY, 11933, Calverton, NY 11933]()
3 beds
|2 baths
|1,530 sq ft
|Manufactured Home
1407 MIDDLE RD 275, CALVERTON, NY, 11933
Community: Foxwood Village
MLS 941578 • Coldwell Banker American Homes, Kath...
New
Leisure Village
![276 BERWICK CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 940467 • Leisure Living Realty Inc, Paulina R...
Strathmore Gate East
![53 FREEDOM LN, CORAM, NY, 11727, Coram, NY 11727]()
2 beds
|1 baths
|1,036 sq ft
|Condo
53 FREEDOM LN, CORAM, NY, 11727
Community: Strathmore Gate East
MLS 924175 • Douglas Elliman Real Estate, Lisa Ge...
Want to learn more about 55+ communities in Essex?
55places can help!
Questions? Call us:
(959) 265-7852
Glenwood Village
![1661 OLD COUNTRY RD 434, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,144 sq ft
|Mobile Home
1661 OLD COUNTRY RD 434, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 923306 • NGC Realty Group, Allison Diem
Windcrest East
![41 GOLDEN SPRUCE DR, CALVERTON, NY, 1193..., Calverton, NY 11933]()
3 beds
|3 baths
|2,091 sq ft
|Condo
41 GOLDEN SPRUCE DR, CALVERTON, NY, 1193...
Community: Windcrest East
MLS 939196 • Compass Greater NY LLC, Heather L. K...
Encore Atlantic Shores
![177 MELODY CT, EASTPORT, NY, 11941, Eastport, NY 11941]()
2 beds
|2 baths
|2,150 sq ft
|Condo
177 MELODY CT, EASTPORT, NY, 11941
Community: Encore Atlantic Shores
MLS 939804 • Belzak & Bodkin Realty Corp, Rosemar...
Sunrise Village
![77 REVERE DR, SAYVILLE, NY, 11782, Sayville, NY 11782]()
MLS 937491 • Douglas Elliman Real Estate, Susan L...
Fairfield at St. James
![705 CABOT CT, SAINT JAMES, NY, 11780, Saint James, NY 11780]()
1 beds
|2 baths
|963 sq ft
|Condo
705 CABOT CT, SAINT JAMES, NY, 11780
Community: Fairfield at St. James
MLS 935580 • Signature Premier Properties, Debora...
Frequently Asked Questions
In Essex, there is 1 small community with less than 500 homes.
The smallest 55+ community in Essex has 8 homes, the largest has 8 homes, and the average community consists of 8 homes.
Yes, there is new 55+ home available in Essex. The most recent community started in Essex include Cobblestone Court. There is also 1 community in Essex that offers new construction homes, including Cobblestone Court.
No, there are no gated 55+ communities in Essex.
Want more information about active adult communities around Essex?
Want to learn more about 55+ communities in Essex?
105
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© 2025 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Dec 06, 2025.
This application does not include information on all of the properties available for sale at this time.
