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Essex, CT 55+ active adult communities & homes for sale - Page 2
105 communities near Essex
163 homes near Essex
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$500Ks
- $800Ks
Fieldstone Village, Orange, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2018
|
142 homes
$500Ks
North Woods of Colchester, Colchester, CT
New and Resale
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55+ age-restricted
|
Built 2007 - present
|
140 homes
$600Ks
Upton Ridge, Upton, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
139 homes
$600Ks
Windcrest East, Calverton, NY
Resale Only
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55+ age-restricted
|
Built 2004 - 2005
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126 homes
$600Ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
125 homes
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3.5 rating (2 reviews)
![Harvest Pointe]()
$800Ks
- $3Ms
Harvest Pointe, Cutchogue, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
124 homes
$400Ks
- $500Ks
The Village at Orchard Me..., Shrewsbury, MA
Resale Only
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55+ age-restricted
|
Built 2002 - 2007
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114 homes
$300Ks
- $400Ks
Windmill Gate, Oakdale, NY
Resale Only
|
55+ age-restricted
|
Built 1989 - 1991
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110 homes
$500Ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale
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55+ age-restricted
|
Built 2005 - present
|
108 homes
$400Ks
- $500Ks
O'Meara Farm, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 1998 - 2005
|
104 homes
Download the Ultimate 55+ Homebuying Guide
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$400Ks
New England Commons, Webster, MA
New and Resale
|
55+ age-restricted
|
Built 2005 - present
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100 homes
$600Ks
Orchard Hill, Westborough, MA
Resale Only
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55+ age-restricted
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Built 2002 - 2010
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100 homes
$600Ks
- $700Ks
The Villages at Walker Me..., Westborough, MA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2000
|
100 homes
$600Ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
99 homes
$500Ks
- $400Ks
Applegate Estates, Southington, CT
New and Resale
|
55+ age-restricted
|
Built 2010 - 2025
|
94 homes
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$300Ks
Pond Spring Village, Beacon Falls, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
92 homes
$500Ks
- $600Ks
Founders Village, Southold, NY
Resale Only
|
55+ age-restricted
|
Built 1981 - 1985
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92 homes
$700Ks
Vineyards at Moriches, Center Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2014
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92 homes
$800Ks
- $1Ms
The Vineyards at Mount Si..., Mount Sinai, NY
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
91 homes
$800Ks
- $900Ks
Adams Farm, Shrewsbury, MA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2013
|
90 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.
$500Ks
- $600Ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only
|
55+ age-restricted
|
Built 2007 - 2022
|
88 homes
$600Ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only
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55+ age-restricted
|
Built 2004 - 2005
|
85 homes
5 rating (2 reviews)
![Benson Woods]()
$400Ks
- $600Ks
Benson Woods, Middlebury, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
79 homes
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$400Ks
- $500Ks
Shaker Heights, Enfield, CT
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
77 homes
5 rating (3 reviews)
![Founders Ridge]()
$500Ks
- $600Ks
Founders Ridge, Middletown, CT
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
75 homes
$600Ks
The Polo Club at Islandia, Islandia, NY
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
72 homes
$300Ks
- $400Ks
Long Hill Village, Trumbull, CT
Resale Only
|
55+ age-restricted
|
Built 1997 - 1999
|
71 homes
$600Ks
- $700Ks
Southwinds, South Kingstown, RI
Resale Only
|
55+ age-restricted
|
Built 2005 - 2010
|
70 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.
$300Ks
- $400Ks
Bella Vista, Glocester, RI
Resale Only
|
55+ age-restricted
|
Built 2015 - 2021
|
70 homes
$500Ks
- $600Ks
Regency at Woodbridge, Woodbridge, CT
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
70 homes
$300Ks
The Village at Hunt Glen, Granby, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2006
|
69 homes
$500Ks
Eagles Walk at East Quogu..., East Quogue, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2014
|
67 homes
Want to learn more about 55+ communities in Essex?
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(959) 265-7852
$200Ks
- $300Ks
Hopmeadow Place, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2005
|
66 homes
$500Ks
- $600Ks
RiverWalk, Branford, CT
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
60 homes
$600Ks
- $700Ks
Rockwood Meadows, Upton, MA
New Construction
|
55+ age-restricted
|
Built 2016 - present
|
58 homes
$500Ks
- $600Ks
The Village at Buckingham, Avon, CT
Resale Only
|
55+ age-restricted
|
Built 2002 - 2006
|
56 homes
Regency at Prospect
![11 POPLAR DR # 11, PROSPECT, CT, 06712, Prospect, CT 06712]()
3 beds
|3 baths
|2,058 sq ft
|Condo
11 POPLAR DR # 11, PROSPECT, CT, 06712
Community: Regency at Prospect
MLS 24129091 • Pavlik Real Estate LLC, Deborah Ri...
Oronoque Village
![766 NYACK LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,438 sq ft
|Condo
766 NYACK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24143831 • Coldwell Banker Realty, Christine ...
Heritage Village
![132 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
132 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24118807 • William Raveis Real Estate, Ron Ne...
Spring Lake Village
![373 LAKEVIEW DR # 373, SOUTHINGTON, CT, ..., Southington, CT 06489]()
2 beds
|2 baths
|1,188 sq ft
|Condo
373 LAKEVIEW DR # 373, SOUTHINGTON, CT, ...
Community: Spring Lake Village
MLS 24138533 • Stacy Blake Realty LLC, Linda Faga...
Oronoque Village
![195 BAYFIELD LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,575 sq ft
|Condo
195 BAYFIELD LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24128861 • Property Choices Real Estate, Paul...
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(959) 265-7852
Heritage Village
![902 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
902 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24126334 • 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...
Oronoque Village
![617 CHEROKEE LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,438 sq ft
|Condo
617 CHEROKEE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24132771 • William Raveis Real Estate, Kenny ...
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 Trails
![14 WATERVILLE LN # 14, HOPKINTON, MA, 01..., Hopkinton, MA 01748]()
2 beds
|3 baths
|2,274 sq ft
|Condo
14 WATERVILLE LN # 14, HOPKINTON, MA, 01...
Community: The Trails
MLS 73460639 • Realty Executives Boston West, Kar...
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 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...
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...
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...
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(959) 265-7852
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...
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...
Oronoque Village
![289 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,620 sq ft
|Condo
289 AGAWAM DR B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24138784 • Oronoque Real Estate, Monica Dalto...
Oronoque Village
![183 APACHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,426 sq ft
|Condo
183 APACHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24143262 • Preston Gray Real Estate, Tina Gam...
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
![383 SEQUOIA LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,360 sq ft
|Condo
383 SEQUOIA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24140690 • Coldwell Banker Realty, Mary Kelle...
Oronoque Village
![736 QUINNIPIAC LN B, STRATFORD, CT, 0661..., Stratford, CT 06614]()
1 beds
|3 baths
|1,426 sq ft
|Condo
736 QUINNIPIAC LN B, STRATFORD, CT, 0661...
Community: Oronoque Village
MLS 24127108 • Coldwell Banker Realty, Larry Vecc...
Oronoque Village
![516 OPA LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|2 baths
|1,426 sq ft
|Condo
516 OPA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24139775 • Oronoque Real Estate, Monica Dalto...
New
Heritage Village
![930 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
930 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24145189 • William Raveis Real Estate, Tom Gr...
Gloria Commons
![10 LUCIUS CT # 10, MILFORD, CT, 06461, Milford, CT 06461]()
2 beds
|3 baths
|2,061 sq ft
|Condo
10 LUCIUS CT # 10, MILFORD, CT, 06461
Community: Gloria Commons
MLS 24144529 • Preston Gray Real Estate, Katie Da...
Want to learn more about 55+ communities in Essex?
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(959) 265-7852
Oronoque Village
![151 SOUTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|2 baths
|1,426 sq ft
|Condo
151 SOUTH TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24144658 • Preston Gray Real Estate, Katie Da...
Oronoque Village
![488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,438 sq ft
|Condo
488 COMMANCHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24134368 • Higgins Group Real Estate, Carmen ...
Heritage Village
![876 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
876 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24139573 • William Raveis Real Estate, Ruth Z...
Heritage Village
![701 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
701 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24137961 • Coldwell Banker Realty, Claudia Fo...
Long Hill Village
![5 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611]()
2 beds
|2 baths
|1,370 sq ft
|Condo
5 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill Village
MLS 24144185 • Higgins Group Real Estate, Fredda ...
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
![12 WHISPER RIDGE WAY # 45, WOODBRIDGE, C..., Woodbridge, CT 06525]()
3 beds
|3 baths
|Condo
12 WHISPER RIDGE WAY # 45, WOODBRIDGE, C...
Community: Regency at Woodbridge
MLS 24136328 • Thomas Jacovino, Kathy Childs
Regency at Woodbridge
![21 HERITAGE LN # 60, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525]()
3 beds
|3 baths
|Condo
21 HERITAGE LN # 60, WOODBRIDGE, CT, 065...
Community: Regency at Woodbridge
MLS 24136335 • Thomas Jacovino, Kathy Childs
Oronoque Village
![87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,454 sq ft
|Condo
87 CREEK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24140020 • Oronoque Real Estate, Monica Dalto...
Oronoque Village
![133 BANNOCK LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
3 beds
|3 baths
|1,438 sq ft
|Condo
133 BANNOCK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24142372 • Coldwell Banker Realty, Mark Pires
Heritage Village
![39 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
39 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24139075 • William Raveis Real Estate, Ruth Z...
Want to learn more about 55+ communities in Essex?
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(959) 265-7852
Heritage Village
![953 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
953 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24142233 • Realty ONE Group Connect, Paul Duh
Heritage Village
![20 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,000 sq ft
|Condo
20 HERITAGE CIR B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24144129 • Drakeley Real Estate, Inc., Joyce ...
The Village at Buckingham
![8 KENINGTON RD # 8, AVON, CT, 06001, Avon, CT 06001]()
3 beds
|3 baths
|2,430 sq ft
|Condo
8 KENINGTON RD # 8, AVON, CT, 06001
Community: The Village at Buckingham
MLS 24142060 • Berkshire Hathaway NE Prop., Becky...
Heritage Village
![7 HERITAGE CRST B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,447 sq ft
|Condo
7 HERITAGE CRST B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24136069 • Showcase Realty, Inc., Darlene Gel...
Oronoque Village
![164 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,175 sq ft
|Condo
164 BISON LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24139444 • Stacy Blake Realty LLC, Celina Cuo...
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 18, 2025.
This application does not include information on all of the properties available for sale at this time.
