Call us at (475) 244-9781 to learn more about active adult communities in Cheshire
Cheshire, CT 55+ active adult communities & homes for sale
125 communities near Cheshire
291 homes near Cheshire
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![Castle Heights of Cheshir...]()
$500Ks
- $600Ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only
|
55+ age-restricted
|
Built 2007 - 2022
|
88 homes
3 rating (2 reviews)
![Heritage Hills]()
$300Ks
- $900Ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1974 - 2006
|
2,600 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
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
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(475) 244-9781
No reviews yet
![Rivington]()
$400Ks
- $1Ms
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
4 rating (1 reviews)
![Jefferson Village]()
$300Ks
- $500Ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
No reviews yet
![Oronoque Village]()
$400Ks
- $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
![Meadowbrook Pointe Athlet...]()
$800Ks
- $800Ks
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2016
|
720 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
![Leisure Knoll]()
$300Ks
- $500Ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 homes
No reviews yet
![Country Pointe Plainview]()
$800Ks
- $1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 homes
5 rating (1 reviews)
![Fairfield at St. James]()
$500Ks
- $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
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(475) 244-9781
4 rating (8 reviews)
![Glenwood Village]()
$100Ks
- $400Ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
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
![Dutchgate]()
$400Ks
- $400Ks
Dutchgate, Valley Stream, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2015
|
348 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
![The Waterways at Moriches]()
$400Ks
- $600Ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
No reviews yet
![The Retreat at Carmel]()
$300Ks
- $600Ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
|
312 homes
3.5 rating (2 reviews)
![Foxwood Village]()
$300Ks
- $400Ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
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 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
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Questions? Call us:
(475) 244-9781
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
No reviews yet
![HarborView]()
$900Ks
- $1Ms
HarborView, Port Washington, NY
Resale Only
|
55+ age-restricted
|
Built 2002 - 2004
|
270 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
No reviews yet
![Meadow Brook Estates]()
$500Ks
- $500Ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 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)
![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]()
$700Ks
- $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]()
$600Ks
- $800Ks
Encore at Lake Grove, Lake Grove, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2007
|
228 homes
No reviews yet
![Woodridge Strathmore Terr...]()
$300Ks
- $400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 1974 - 1985
|
226 homes
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
5 rating (1 reviews)
![Sunrise Village]()
$400Ks
- $500Ks
Sunrise Village, Sayville, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1990
|
213 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
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
The Gardens of Wilbraham
![39 IVY CIR # 39, WILBRAHAM, MA, 01095, Wilbraham, MA 01095]()
1 beds
|2 baths
|1,218 sq ft
|Condo
39 IVY CIR # 39, WILBRAHAM, MA, 01095
Community: The Gardens of Wilbraham
MLS 73276030 • Witalisz & Associates, Inc., JoAnn...
The Gardens of Wilbraham
![45 IVY CIR # 45, WILBRAHAM, MA, 01095, Wilbraham, MA 01095]()
2 beds
|3 baths
|1,752 sq ft
|Condo
45 IVY CIR # 45, WILBRAHAM, MA, 01095
Community: The Gardens of Wilbraham
MLS 73328184 • Coldwell Banker Realty - Western M...
Greenwood Village
![71 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|1,123 sq ft
|Condo
71 DOGWOOD LN, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 816229 • Your Team D&G Realty Ltd, Debra R. L...
Villas at Seminary Hill
![3202 PANKIN DR, CARMEL, NY, 10512, Carmel, NY 10512]()
2 beds
|2 baths
|1,275 sq ft
|Condo
3202 PANKIN DR, CARMEL, NY, 10512
Community: Villas at Seminary Hill
MLS 826879 • Briante Realty Group, LLC, Lynn Stoe...
Rivington
![802 CENTER MEADOW LN # 802, DANBURY, CT,..., Danbury, CT 06810]()
2 beds
|3 baths
|1,312 sq ft
|Condo
802 CENTER MEADOW LN # 802, DANBURY, CT,...
Community: Rivington
MLS 24102913 • Berkshire Hathaway NE Prop., Bonni...
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Questions? Call us:
(475) 244-9781
Jefferson Village
![6 DEVON CT B, YORKTOWN HEIGHTS, NY, 1059..., Yorktown Heights, NY 10598]()
2 beds
|1 baths
|1,000 sq ft
|Condo
6 DEVON CT B, YORKTOWN HEIGHTS, NY, 1059...
Community: Jefferson Village
MLS 865906 • Keller Williams Realty Partner, Rose...
Heritage Village
![57 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
57 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24098902 • Berkshire Hathaway NE Prop., Bonni...
Oronoque Village
![515 OPA LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,454 sq ft
|Condo
515 OPA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24099312 • Coldwell Banker Realty, Lynda Linl...
New
Rivington
![17 WILDERSWOOD WAY # 17, DANBURY, CT, 06..., Danbury, CT 06810]()
3 beds
|3 baths
|2,305 sq ft
|Condo
17 WILDERSWOOD WAY # 17, DANBURY, CT, 06...
Community: Rivington
MLS 24103966 • Coldwell Banker Realty, Vikktoria ...
Heritage Village
![32 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
32 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24104023 • Coldwell Banker Realty, Cindy Seve...
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
![264 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
264 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24084870 • Joseph Bette REALTORS Inc, Deborah...
Leisure Village
![192 VENTRY CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 867626 • Realty One Group First, Magdalena Ko...
HarborView
![100 HARBOR VIEW DR 335, PORT WASHINGTON,..., Port Washington, NY 11050]()
3 beds
|3 baths
|2,216 sq ft
|Condo
100 HARBOR VIEW DR 335, PORT WASHINGTON,...
Community: HarborView
MLS 862122 • Evelyn Richards Inc, Maria Giacalone
The Waterways at Moriches
![276 DOCKSIDE CT, MORICHES, NY, 11955, Moriches, NY 11955]()
2 beds
|2 baths
|1,875 sq ft
|Condo
276 DOCKSIDE CT, MORICHES, NY, 11955
Community: The Waterways at Moriches
MLS 866339 • Douglas Elliman Real Estate, Jo Ann ...
Sunrise Village
![24 REVERE DR, SAYVILLE, NY, 11782, Sayville, NY 11782]()
MLS 867420 • Realty Connect USA L I Inc, Chris Jo...
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
New
The Waterways at Moriches
![279 DOCKSIDE CT, MORICHES, NY, 11955, Moriches, NY 11955]()
2 beds
|2 baths
|1,480 sq ft
|Condo
279 DOCKSIDE CT, MORICHES, NY, 11955
Community: The Waterways at Moriches
MLS 877043 • Douglas Elliman Real Estate, Jo Ann ...
Leisure Village
![404B WOODBRIDGE DR 404B, BROOKHAVEN, NY,..., Brookhaven, NY 11961]()
2 beds
|1 baths
|907 sq ft
|Condo
404B WOODBRIDGE DR 404B, BROOKHAVEN, NY,...
Community: Leisure Village
MLS 867426 • Leisure Living Realty Inc, Laura Ruh...
New
Leisure Glen
![5 SAYVILLE CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 875382 • RE/MAX Integrity Leaders, Stephen Be...
Leisure Village
![411A WEYMOUTH CT # 411A, RIDGE, NY, 1196..., Ridge, NY 11961]()
2 beds
|1 baths
|1,000 sq ft
|Condo
411A WEYMOUTH CT # 411A, RIDGE, NY, 1196...
Community: Leisure Village
MLS 867323 • Leisure Living Realty Inc, Laura Ruh...
Encore Atlantic Shores
![68 ENCORE, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941]()
2 beds
|3 baths
|3,000 sq ft
|Condo
68 ENCORE, BROOKHAVEN, NY, 11941
Community: Encore Atlantic Shores
MLS 851829 • Realty Connect USA LI Inc, Deanna Em...
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.
Leisure Knoll
![215 KINGSTON DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 876845 • Signature Premier Properties, Jodie ...
Regency at Woodbridge
![29 HERITAGE LN # 56, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525]()
3 beds
|3 baths
|2,239 sq ft
|Condo
29 HERITAGE LN # 56, WOODBRIDGE, CT, 065...
Community: Regency at Woodbridge
MLS 24064372 • Thomas Jacovino, Jessica Alburquer...
Heritage Village
![699 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
699 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24092608 • William Raveis Real Estate, Joan K...
Heritage Village
![133 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
133 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24100967 • William Raveis Real Estate, Ron Ne...
Heritage Village
![9 HERITAGE CIR D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,071 sq ft
|Condo
9 HERITAGE CIR D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24090141 • Berkshire Hathaway NE Prop., Lori ...
Want to learn more about 55+ communities in Cheshire?
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Questions? Call us:
(475) 244-9781
Heritage Village
![106 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
106 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24101757 • Berkshire Hathaway NE Prop., Jacqu...
New
Jefferson Village
![4 DEVON CT B, YORKTOWN HEIGHTS, NY, 1059..., Yorktown Heights, NY 10598]()
2 beds
|1 baths
|975 sq ft
|Condo
4 DEVON CT B, YORKTOWN HEIGHTS, NY, 1059...
Community: Jefferson Village
MLS 878738 • William Raveis Real Estate, Noreen P...
Encore Atlantic Shores
![226 SONATA CT, EASTPORT, NY, 11941, Eastport, NY 11941]()
2 beds
|2 baths
|1,605 sq ft
|Condo
226 SONATA CT, EASTPORT, NY, 11941
Community: Encore Atlantic Shores
MLS 873046 • Coldwell Banker Reliable R E, Kather...
Whitney Glen
![34 WHITNEY GLN # 34, WESTPORT, CT, 06880, Westport, CT 06880]()
2 beds
|3 baths
|1,400 sq ft
|Condo
34 WHITNEY GLN # 34, WESTPORT, CT, 06880
Community: Whitney Glen
MLS 24075720 • Coldwell Banker Realty, Darlene Le...
Heritage Hills
![331 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
1 beds
|1 baths
|955 sq ft
|Condo
331 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 876082 • Coldwell Banker Realty, Laura Sterli...
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
![1005 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
1005 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24103141 • Coldwell Banker Realty, Cindy Seve...
Heritage Village
![793 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
793 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24101885 • Joseph Bette REALTORS Inc, Justin ...
Heritage Village
![79 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
79 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24091089 • Keller Williams Realty, Gabby Addi...
The Summit at Bethel
![81 GREAT HILL DR # 81, BETHEL, CT, 06801, Bethel, CT 06801]()
3 beds
|3 baths
|2,447 sq ft
|Condo
81 GREAT HILL DR # 81, BETHEL, CT, 06801
Community: The Summit at Bethel
MLS 24087672 • Redfin Corporation, Luke Julius Jo...
Bartlett Hollow
![39 BARTLETT HOLW # 39, MIDDLETOWN, CT, 0..., Middletown, CT 06457]()
2 beds
|3 baths
|3,147 sq ft
39 BARTLETT HOLW # 39, MIDDLETOWN, CT, 0...
Community: Bartlett Hollow
MLS 24100834 • William Raveis Real Estate, Siobha...
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
Spring Lake Village
![6 LAKEVIEW DR # 6, SOUTHINGTON, CT, 0648..., Southington, CT 06489]()
3 beds
|3 baths
|1,471 sq ft
|Condo
6 LAKEVIEW DR # 6, SOUTHINGTON, CT, 0648...
Community: Spring Lake Village
MLS 24061909 • RE/MAX RISE, Michael Albert
Rivington
![302 CENTER MEADOW LN # 302, DANBURY, CT,..., Danbury, CT 06810]()
2 beds
|2 baths
|1,312 sq ft
|Condo
302 CENTER MEADOW LN # 302, DANBURY, CT,...
Community: Rivington
MLS 24101712 • Coldwell Banker Realty, Antonio Za...
Newtown Woods
![411 BROOKSIDE CT # 411, NEWTOWN, CT, 064..., Newtown, CT 06470]()
2 beds
|2 baths
|1,483 sq ft
|Condo
411 BROOKSIDE CT # 411, NEWTOWN, CT, 064...
Community: Newtown Woods
MLS 24091809 • Higgins Group Real Estate, Amanda ...
Encore at Lake Grove
![10 SYMPHONY DR, LAKE GROVE, NY, 11755, Lake Grove, NY 11755]()
2 beds
|2 baths
|1,390 sq ft
|Condo
10 SYMPHONY DR, LAKE GROVE, NY, 11755
Community: Encore at Lake Grove
MLS 853018 • RE/MAX Integrity Leaders, Robert J....
Heritage Village
![224 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|3 baths
|1,572 sq ft
|Condo
224 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24082989 • Berkshire Hathaway NE Prop., Maria...
Frequently Asked Questions
In Cheshire, there is 1 small community with less than 500 homes.
The smallest 55+ community in Cheshire has 88 homes, the largest has 88 homes, and the average community consists of 88 homes.
No, there are no gated 55+ communities in Cheshire.
Want more information about active adult communities around Cheshire?
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