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
298 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]()
$400Ks
- $700Ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1975 - 2003
|
2,600 homes
3.6 rating (7 reviews)
![Heritage Village]()
$200Ks
- $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
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
- $600Ks
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
- $1Ms
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]()
$900Ks
- $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]()
$500Ks
- $700Ks
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
4.6 rating (9 reviews)
![Meadowbrook Pointe Links ...]()
$600Ks
- $700Ks
Meadowbrook Pointe Links ..., Medford, NY
New and Resale
|
55+ age-restricted
|
Built 2010 - present
|
280 homes
Want to learn more about 55+ communities in Cheshire?
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Questions? Call us:
(475) 244-9781
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
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]()
$700Ks
- $800Ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 homes
No reviews yet
![The Summit at Bethel]()
$700Ks
- $800Ks
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
- $400Ks
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
Breton Hills
![308 BRETON WAY # 308, GLEN COVE, NY, 115..., Glen Cove, NY 11542]()
2 beds
|2 baths
|1,500 sq ft
|Condo
308 BRETON WAY # 308, GLEN COVE, NY, 115...
Community: Breton Hills
MLS 862280 • Goldilocks Real Estate, Holly Gottli...
Leisure Glen
![229 GLEN DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 864444 • Coldwell Banker American Homes, Joy ...
Fairfield at St. James
![206 FLAIR CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
3 beds
|3 baths
|1,649 sq ft
|Condo
206 FLAIR CT, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 863947 • Realty Connect USA L I Inc, Danielle...
The Coves at Melville
![169 MORLEY CIR, MELVILLE, NY, 11747, Melville, NY 11747]()
2 beds
|2 baths
|1,170 sq ft
|Condo
169 MORLEY CIR, MELVILLE, NY, 11747
Community: The Coves at Melville
MLS 863214 • Compass Greater NY LLC, Jeffrey Mayo
Meadowbrook Pointe Links & Spa
![234 AUGUSTA DR # 234, MEDFORD, NY, 11763, Medford, NY 11763]()
2 beds
|3 baths
|1,627 sq ft
|Condo
234 AUGUSTA DR # 234, MEDFORD, NY, 11763
Community: Meadowbrook Pointe Links & Spa
MLS 860712 • Realty Connect USA L I Inc, Thomas P...
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
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....
Meadowbrooke Pointe East Meadow
![417 EMANUEL WAY # 417, EAST MEADOW, NY, ..., East Meadow, NY 11554]()
2 beds
|2 baths
|961 sq ft
|Condo
417 EMANUEL WAY # 417, EAST MEADOW, NY, ...
Community: Meadowbrooke Pointe East Meadow
MLS 841635 • Cosmo Group Realty, Jessica Alejo
Country Pointe Plainview
![40204 SILVER BIRCH LN, PLAINVIEW, NY, 11..., Plainview, NY 11803]()
2 beds
|2 baths
|2,000 sq ft
|Condo
40204 SILVER BIRCH LN, PLAINVIEW, NY, 11...
Community: Country Pointe Plainview
MLS 824864 • Realty Connect USA LLC, Amy Maximov
The Seasons at Plainview
![44 AUTUMN DR, PLAINVIEW, NY, 11803, Plainview, NY 11803]()
2 beds
|2 baths
|1,591 sq ft
|Condo
44 AUTUMN DR, PLAINVIEW, NY, 11803
Community: The Seasons at Plainview
MLS 838943 • Douglas Elliman Real Estate, Lorna J...
Leisure Knoll
![145 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS L3591120 • Century 21 Cor Ace Realty Inc, Glo...
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 Villages at Mount Sinai Park
![4 OAKHURST CT, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
3 beds
|3 baths
|2,850 sq ft
|Condo
4 OAKHURST CT, MOUNT SINAI, NY, 11766
Community: The Villages at Mount Sinai Park
MLS 856049 • Douglas Elliman Real Estate, Lisa A....
Heritage Hills
![446 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,265 sq ft
|Condo
446 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
MLS 837483 • Coldwell Banker Realty, Maryanne Dur...
Leisure Knoll
![209 KINGSTON DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 861828 • Coldwell Banker American Homes, Kath...
Leisure Village
![286 BERWICK CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,085 sq ft
|Condo
286 BERWICK CT A, RIDGE, NY, 11961
Community: Leisure Village
MLS 865765 • Peconic Realty Group LLC, Ryan Verba...
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...
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Questions? Call us:
(475) 244-9781
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 24092610 • William Raveis Real Estate, Joan K...
Newtown Woods
![18 BROOKSIDE CT # 18, NEWTOWN, CT, 06470, Newtown, CT 06470]()
2 beds
|3 baths
|2,001 sq ft
|Condo
18 BROOKSIDE CT # 18, NEWTOWN, CT, 06470
Community: Newtown Woods
MLS 24095329 • William Raveis Real Estate, Sandy ...
Meadow Brook Estates
![306 SPRUCE HILL DR, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|1,691 sq ft
|Condo
306 SPRUCE HILL DR, OXFORD, CT, 06478
Community: Meadow Brook Estates
MLS 24092226 • Rupwani Associates, Rosalie Averil...
Heritage Village
![664C HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,000 sq ft
|Condo
664C HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24091437 • William Raveis Real Estate, Ruth Z...
Heritage Village
![738 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
738 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24097299 • William Raveis Real Estate, Diane ...
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
![405 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
405 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24085607 • KW Legacy Partners, Leah Schroeder
Heritage Village
![607 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
607 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24090077 • Joseph Bette REALTORS Inc, Justin ...
Regency at Woodbridge
![1 HERITAGE LN # 70, WOODBRIDGE, CT, 0652..., Woodbridge, CT 06525]()
3 beds
|3 baths
|2,486 sq ft
|Condo
1 HERITAGE LN # 70, WOODBRIDGE, CT, 0652...
Community: Regency at Woodbridge
MLS 24097373 • Thomas Jacovino, Kathy Childs
South Pond Village
![175 THISTLE POND DR # 175, BLOOMFIELD, C..., Bloomfield, CT 06002]()
2 beds
|2 baths
|1,535 sq ft
|Condo
175 THISTLE POND DR # 175, BLOOMFIELD, C...
Community: South Pond Village
MLS 24084866 • Berkshire Hathaway NE Prop., Marga...
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 24076921 • Joseph Bette REALTORS Inc, Justin ...
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
Bramble Ridge
![56 BOYSENBERRY CT # 56, SUFFIELD, CT, 06..., Suffield, CT 06078]()
2 beds
|2 baths
|2,001 sq ft
|Condo
56 BOYSENBERRY CT # 56, SUFFIELD, CT, 06...
Community: Bramble Ridge
MLS 24095292 • Century 21 AllPoints Realty, Miche...
Billingsgate
![2 PENNINGTON DR # 2, SIMSBURY, CT, 06070, Simsbury, CT 06070]()
2 beds
|3 baths
|2,867 sq ft
|Condo
2 PENNINGTON DR # 2, SIMSBURY, CT, 06070
Community: Billingsgate
MLS 24085860 • William Pitt Sotheby's Int'l, Dian...
Regency at Woodbridge
![7 HERITAGE LN # 67, WOODBRIDGE, CT, 0652..., Woodbridge, CT 06525]()
3 beds
|3 baths
|2,486 sq ft
|Condo
7 HERITAGE LN # 67, WOODBRIDGE, CT, 0652...
Community: Regency at Woodbridge
MLS 24079730 • Thomas Jacovino, Kathy Childs
Regency at Woodbridge
![3 HERITAGE LN # 69, WOODBRIDGE, CT, 0652..., Woodbridge, CT 06525]()
3 beds
|3 baths
|Condo
3 HERITAGE LN # 69, WOODBRIDGE, CT, 0652...
Community: Regency at Woodbridge
MLS 24066347 • Thomas Jacovino, Kathy Childs
Regency at Woodbridge
![5 HERITAGE LN # 68, WOODBRIDGE, CT, 0652..., Woodbridge, CT 06525]()
3 beds
|3 baths
|2,006 sq ft
|Condo
5 HERITAGE LN # 68, WOODBRIDGE, CT, 0652...
Community: Regency at Woodbridge
MLS 24097354 • Thomas Jacovino, Kathy Childs
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
![740 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
740 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24092035 • Coldwell Banker Realty, Maryanne B...
Liberty at Newtown
![5 FRANKLIN CT # 5, NEWTOWN, CT, 06470, Newtown, CT 06470]()
2 beds
|3 baths
|2,407 sq ft
|Condo
5 FRANKLIN CT # 5, NEWTOWN, CT, 06470
Community: Liberty at Newtown
MLS 24097058 • Blackstone Properties of CT, Annma...
Heritage Village
![740 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
740 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24098094 • William Raveis Real Estate, Daniel...
Spring Lake Village
![762 KETTLE PATH # 762, SOUTHINGTON, CT, ..., Southington, CT 06489]()
2 beds
|2 baths
|1,230 sq ft
|Condo
762 KETTLE PATH # 762, SOUTHINGTON, CT, ...
Community: Spring Lake Village
MLS 24095461 • Century 21 AllPoints Realty, Marya...
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...
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
Park Glen
![15 HARMONY TRL # 15, NEW MILFORD, CT, 06..., New Milford, CT 06776]()
2 beds
|4 baths
|2,720 sq ft
|Condo
15 HARMONY TRL # 15, NEW MILFORD, CT, 06...
Community: Park Glen
MLS 24086114 • Coldwell Banker Realty, Bill Hunni...
Heritage Village
![345 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
345 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24098283 • Coldwell Banker Realty, Chris York
Spring Lake Village
![783 KETTLE PATH # 783, SOUTHINGTON, CT, ..., Southington, CT 06489]()
2 beds
|3 baths
|1,230 sq ft
|Condo
783 KETTLE PATH # 783, SOUTHINGTON, CT, ...
Community: Spring Lake Village
MLS 24075346 • Berkshire Hathaway NE Prop., Donal...
Heritage Village
![787 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
787 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24096092 • Berkshire Hathaway NE Prop., Miche...
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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