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
Want to learn more about 55+ communities in Cheshire?
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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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Questions? Call us:
(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
Bidwell Village
![94 STONEHOUSE RD UNIT 16, COVENTRY, CT, ..., Coventry, CT 06238]()
3 beds
|3 baths
|1,570 sq ft
|Condo
94 STONEHOUSE RD UNIT 16, COVENTRY, CT, ...
Community: Bidwell Village
MLS 24096493 • Lindlau Realty, Inc., Eric Lindlau
Founders Ridge
![20 WEBSTER LN # 20, MIDDLETOWN, CT, 0645..., Middletown, CT 06457]()
2 beds
|2 baths
|1,548 sq ft
|Condo
20 WEBSTER LN # 20, MIDDLETOWN, CT, 0645...
Community: Founders Ridge
MLS 24095287 • William Raveis Real Estate, Britta...
Rivington
![19 MILL RD # 19, DANBURY, CT, 06810, Danbury, CT 06810]()
MLS 24088160 • RE/MAX One, Shannon Muscara
Bartlett Hill
![107 CHESTNUT HILL RD # 107, PORTLAND, CT..., Portland, CT 06480]()
MLS 24096325 • Coldwell Banker Realty, Nancy Stet...
Regency at Prospect
![127 SYCAMORE DR # 127, PROSPECT, CT, 067..., Prospect, CT 06712]()
2 beds
|2 baths
|1,503 sq ft
|Condo
127 SYCAMORE DR # 127, PROSPECT, CT, 067...
Community: Regency at Prospect
MLS 24033507 • Huntsman,Meade & Partners Comp, Mi...
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Questions? Call us:
(475) 244-9781
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 24098523 • Complete Real Estate, Anthony La P...
The Village at Oxford Greens
![403 MULLIGAN DR # 403, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|2 baths
|2,080 sq ft
|Condo
403 MULLIGAN DR # 403, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24097841 • Around Town Real Estate LLC, Andre...
Bramble Ridge
![10 DEWBERRY WAY # 10, SUFFIELD, CT, 0607..., Suffield, CT 06078]()
2 beds
|2 baths
|2,001 sq ft
|Condo
10 DEWBERRY WAY # 10, SUFFIELD, CT, 0607...
Community: Bramble Ridge
MLS 24096968 • Chestnut Oak Associates, Donna Bla...
Rivington
![1026 COUNTRY VIEW RD # 1026, DANBURY, CT..., Danbury, CT 06810]()
2 beds
|2 baths
|1,312 sq ft
|Condo
1026 COUNTRY VIEW RD # 1026, DANBURY, CT...
Community: Rivington
MLS 24085507 • Keller Williams Realty Partner, La...
Heritage Village
![575A VILLAGE ST, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
575A VILLAGE ST, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24096747 • Klemm Real Estate Inc, Sallie Smit...
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
![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 ...
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...
The Woods at Dunham Pond
![48 HERON VIEW RD # 48, NEW FAIRFIELD, CT..., New Fairfield, CT 06812]()
1 beds
|3 baths
|1,550 sq ft
|Condo
48 HERON VIEW RD # 48, NEW FAIRFIELD, CT...
Community: The Woods at Dunham Pond
MLS 24095402 • William Raveis Real Estate, Kelley...
Oronoque Village
![635 NORTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,642 sq ft
|Condo
635 NORTH TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24095005 • Oronoque Real Estate, Monica Dalto...
Heritage Village
![9B HERITAGE CIR # 9, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
2 beds
|2 baths
|1,000 sq ft
|Condo
9B HERITAGE CIR # 9, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24091564 • Drakeley Real Estate, Inc., Mary A...
Want to learn more about 55+ communities in Cheshire?
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(475) 244-9781
Heritage Village
![725 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
725 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24071405 • William Raveis Real Estate, Amanda...
Heritage Village
![225 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
225 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24092359 • William Raveis Real Estate, Joan K...
Heritage Village
![151 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
151 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24097060 • Showcase Realty, Inc., Stephanie V...
Heritage Village
![976 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
976 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24096690 • William Pitt Sotheby's Int'l, Lind...
Bartlett Hill
![5 PEAR ORCHARD RD # 5, PORTLAND, CT, 064..., Portland, CT 06480]()
MLS 24096304 • Houlihan Lawrence WD, Georgia Newc...
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.
Pond Spring Village
![91 PONDVIEW CIR # 91, BEACON FALLS, CT, ..., Beacon Falls, CT 06403]()
3 beds
|3 baths
|1,328 sq ft
|Condo
91 PONDVIEW CIR # 91, BEACON FALLS, CT, ...
Community: Pond Spring Village
MLS 24096829 • Berkshire Hathaway NE Prop., Kevin...
Heritage Village
![143 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
143 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24076910 • Joseph Bette REALTORS Inc, Justin ...
Heritage Village
![128 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
128 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24086942 • Berkshire Hathaway NE Prop., Joan ...
Oronoque Village
![607 CHEROKEE LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,454 sq ft
|Condo
607 CHEROKEE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24090970 • William Raveis Real Estate, John S...
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, Jessica Alburquer...
Want to learn more about 55+ communities in Cheshire?
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Questions? Call us:
(475) 244-9781
Regency at Woodbridge
![15 HERITAGE LN # 63, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525]()
3 beds
|3 baths
|2,486 sq ft
|Condo
15 HERITAGE LN # 63, WOODBRIDGE, CT, 065...
Community: Regency at Woodbridge
MLS 24096880 • Thomas Jacovino, Jessica Alburquer...
Heritage Village
![1042 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
2 beds
|2 baths
|1,071 sq ft
|Condo
1042 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24080741 • Berkshire Hathaway NE Prop., Miche...
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
![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...
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...
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
![1000 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
1000 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24091531 • Around Town Real Estate LLC, James...
Heritage Village
![16 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
16 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24085195 • Joseph Bette REALTORS Inc, Cynthia...
Heritage Village
![331 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
331 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24091449 • Around Town Real Estate LLC, Andre...
Heritage Village
![134 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
134 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24060000 • Keller Williams Realty, Lou Capell...
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 24093072 • William Raveis Real Estate, Donna ...
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
The Village at Oxford Greens
![644 CHAMPIONSHIP DR # 644, OXFORD, CT, 0..., Oxford, CT 06478]()
2 beds
|3 baths
|2,296 sq ft
|Condo
644 CHAMPIONSHIP DR # 644, OXFORD, CT, 0...
Community: The Village at Oxford Greens
MLS 24096492 • Coldwell Banker Realty, Joseph Pau...
Rivington
![38 WINDING RIDGE WAY, DANBURY, CT, 06810, Danbury, CT 06810]()
3 beds
|3 baths
|1,767 sq ft
|Condo
38 WINDING RIDGE WAY, DANBURY, CT, 06810
Community: Rivington
MLS 24081996 • Houlihan Lawrence, Barbara Sawin
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 24089564 • Realty ONE Group Connect, Paul Duh
Oronoque Village
![513 OPA LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,454 sq ft
|Condo
513 OPA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24090671 • Coldwell Banker Realty, Jennifer L...
Heritage Village
![957A HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
957A HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24071514 • William Raveis Real Estate, Pat Ca...
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?
298
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