Call us at (475) 244-9781 to learn more about active adult communities near Cheshire
Cheshire, CT 55+ active adult communities & homes for sale
128 communities near Cheshire
294 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]()
$200Ks
- $500Ks
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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No reviews yet
![Rivington]()
$400Ks
- $500Ks
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]()
$200Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
No reviews yet
![The Village at Oxford Gre...]()
$500Ks
- $700Ks
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]()
$1Ms
- $1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 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
No reviews yet
![Leisure Glen]()
$400Ks
- $400Ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
No reviews yet
![Spring Lake Village]()
$200Ks
- $200Ks
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]()
$300Ks
- $500Ks
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
- $700Ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
No reviews yet
![The Retreat at Carmel]()
$400Ks
- $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
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(475) 244-9781
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
- $800Ks
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
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
![Meadow Brook Estates]()
$500Ks
- $500Ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
5 rating (1 reviews)
![Encore Atlantic Shores]()
$600Ks
- $900Ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 homes
No reviews yet
![The Summit at Bethel]()
$600Ks
- $600Ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 homes
4.9 rating (14 reviews)
![Chatfield Farms]()
$600Ks
- $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
Want to learn more about 55+ communities in Cheshire?
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Questions? Call us:
(475) 244-9781
No reviews yet
![Woodridge Strathmore Terr...]()
$400Ks
- $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
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]()
$300Ks
- $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
Heritage Village
![746 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,063 sq ft
|Condo
746 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24133138 • Keller Williams Realty, Donna Doyl...
Oronoque Village
![617 CHEROKEE LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
3 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 Village at Oxford Greens
![578 PUTTING GREEN LN # 578, OXFORD, CT, ..., Oxford, CT 06478]()
2 beds
|3 baths
|2,008 sq ft
|Condo
578 PUTTING GREEN LN # 578, OXFORD, CT, ...
Community: The Village at Oxford Greens
MLS 24119430 • William Pitt Sotheby's Int'l, Tom ...
Spring Lake Village
![18 COACH DR # 18, SOUTHINGTON, CT, 06489, Southington, CT 06489]()
2 beds
|2 baths
|1,178 sq ft
|Condo
18 COACH DR # 18, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
MLS 24121584 • Realty 3 CT, Shelly Meister Zamudi...
Heritage Village
![313 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
313 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24117831 • The Washington Agency, Joanne Donn...
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Questions? Call us:
(475) 244-9781
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...
Heritage Village
![920 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
920 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24127321 • Coldwell Banker Realty, Karen Cons...
Heritage Village
![1034 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
1034 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24132420 • Emerald Glen Associates, Wendy Kud...
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 24116195 • William Raveis Real Estate, Daniel...
Chatfield Farms
![81 FIELDSTONE LN # 81, BEACON FALLS, CT,..., Beacon Falls, CT 06403]()
2 beds
|2 baths
|1,988 sq ft
|Condo
81 FIELDSTONE LN # 81, BEACON FALLS, CT,...
Community: Chatfield Farms
MLS 24133207 • Century 21 AllPoints Realty, Kim L...
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.
Chatfield Farms
![18 FIELDSTONE LN # 18, BEACON FALLS, CT,..., Beacon Falls, CT 06403]()
2 beds
|3 baths
|2,719 sq ft
18 FIELDSTONE LN # 18, BEACON FALLS, CT,...
Community: Chatfield Farms
MLS 24120361 • Drakeley Real Estate, Inc., Joyce ...
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...
Heritage Village
![26 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,217 sq ft
|Condo
26 HERITAGE CRST C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24123450 • Joseph Bette REALTORS Inc, Justin ...
Autumn Fields
![39 QUAIL HOLW # 39, ENFIELD, CT, 06082, Enfield, CT 06082]()
2 beds
|3 baths
|1,764 sq ft
|Condo
39 QUAIL HOLW # 39, ENFIELD, CT, 06082
Community: Autumn Fields
MLS 24123157 • Coldwell Banker Realty, Claudette ...
New
Heritage Village
![176 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
176 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24133427 • Keller Williams Realty Group, Lisa...
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
Bartlett Hill
![19 PLUMROSE CT # 19, PORTLAND, CT, 06480, Portland, CT 06480]()
MLS 24129113 • Houlihan Lawrence WD, Georgia Newc...
Heritage Village
![127 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
127 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24122657 • eXp Realty, Mark Mermelstein
Heritage Village
![999 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
999 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24062145 • eXp Realty, Mark Mermelstein
Heritage Village
![12 HERITAGE CRST A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,735 sq ft
|Condo
12 HERITAGE CRST A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24126040 • Around Town Real Estate LLC, Danie...
Heritage Village
![626 HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
626 HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24126430 • Coldwell Banker Realty, Kary Apano...
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
![916 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
916 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24133580 • Keller Williams Realty, Debi Orr
Oak Meadow Estates
![65 OAK MEADOW LN # 65, HARWINTON, CT, 06..., Harwinton, CT 06791]()
2 beds
|4 baths
|2,164 sq ft
|Condo
65 OAK MEADOW LN # 65, HARWINTON, CT, 06...
Community: Oak Meadow Estates
MLS 24121807 • Northwest CT Realty, Leslie Tapia-...
Heritage Village
![69 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
69 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24133619 • Joseph Bette REALTORS Inc, Justin ...
North Woods of Colchester
![50 CENTER CT # 50, COLCHESTER, CT, 06415, Colchester, CT 06415]()
2 beds
|2 baths
|1,744 sq ft
50 CENTER CT # 50, COLCHESTER, CT, 06415
Community: North Woods of Colchester
MLS 24128725 • Williams Realty Services, Dawn Cas...
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...
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
Heritage Village
![53 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
53 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24083817 • Joseph Bette REALTORS Inc, Cynthia...
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
![1011 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
1011 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24131215 • Joseph Bette REALTORS Inc, Justin ...
Heritage Village
![665 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
665 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24121072 • Joseph Bette REALTORS Inc, Justin ...
Heritage Village
![8 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,076 sq ft
|Condo
8 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24124173 • Joseph Bette REALTORS Inc, Justin ...
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
![122 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
122 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24092348 • Berkshire Hathaway NE Prop., Miche...
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 24127879 • Realty ONE Group Connect, Paul Duh
Heritage Village
![401 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
401 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24128837 • Real Broker CT, LLC, Steven Scarna...
Heritage Village
![786 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,063 sq ft
|Condo
786 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24111149 • Berkshire Hathaway NE Prop., Miche...
Regency at Woodbridge
![13 HERITAGE LN # 64, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525]()
3 beds
|3 baths
|2,239 sq ft
|Condo
13 HERITAGE LN # 64, WOODBRIDGE, CT, 065...
Community: Regency at Woodbridge
MLS 24096886 • Thomas Jacovino, Kathy Childs
Want to learn more about 55+ communities in Cheshire?
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Questions? Call us:
(475) 244-9781
Bidwell Village
![94 STONEHOUSE RD UNIT 10, COVENTRY, CT, ..., Coventry, CT 06238]()
3 beds
|3 baths
|1,717 sq ft
94 STONEHOUSE RD UNIT 10, COVENTRY, CT, ...
Community: Bidwell Village
MLS 24128107 • ERA Blanchard & Rossetto, Cheri Tr...
Oronoque Village
![543 NORTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,426 sq ft
|Condo
543 NORTH TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24130846 • William Pitt Sotheby's Int'l, Susa...
Oronoque Village
![193 BAYFIELD LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,620 sq ft
|Condo
193 BAYFIELD LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24120963 • Coldwell Banker Realty, Sue Varron...
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 24109763 • William Pitt Sotheby's Int'l, Mela...
Regency at Prospect
![9 LILAC LN # 9, PROSPECT, CT, 06712, Prospect, CT 06712]()
2 beds
|2 baths
|1,503 sq ft
|Condo
9 LILAC LN # 9, PROSPECT, CT, 06712
Community: Regency at Prospect
MLS 24111897 • Dave Jones Realty, LLC, Dave Jones
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?
Want to learn more about 55+ communities in Cheshire?
294
homes
near Cheshire
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