Call us at (475) 244-9781 to learn more about active adult communities in Cheshire
Cheshire, CT 55+ active adult communities & homes for sale
129 communities near Cheshire
224 homes near Cheshire
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3.6 rating (7 reviews)
![Heritage Village]()
$100Ks
- $500Ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
$200Ks
- $400Ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
3 rating (2 reviews)
![Heritage Hills]()
$300Ks
- $900Ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1974 - 2006
|
2,600 homes
$200Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
3.7 rating (3 reviews)
![Greenwood Village]()
<$100k
- $200Ks
Greenwood Village, Manorville, NY
Resale Only
|
55+ age-restricted
|
Built 1980 - 2000
|
512 homes
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4 rating (1 reviews)
![Jefferson Village]()
$200Ks
- $500Ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
$600Ks
- $700Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 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
$600Ks
- $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 1994 - 2005
|
1,200 homes
Download the Ultimate 55+ Homebuying Guide
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$400Ks
- $500Ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$400Ks
- $700Ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
|
312 homes
$600Ks
- $700Ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
125 homes
$600Ks
- $700Ks
Regency at Woodbridge, Woodbridge, CT
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
70 homes
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(475) 244-9781
$1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 homes
4 rating (8 reviews)
![Glenwood Village]()
$100Ks
- $200Ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
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(475) 244-9781
$700Ks
- $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2016
|
720 homes
$400Ks
- $800Ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 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.
$400Ks
- $500Ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
5 rating (1 reviews)
![Westhampton Pines]()
$1Ms
Westhampton Pines, Westhampton, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2013
|
189 homes
5 rating (1 reviews)
![The Villages at Mount Sin...]()
$500Ks
- $700Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
185 homes
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$500Ks
The Manors at The Colony ..., Shirley, NY
New Construction
|
55+ age-restricted
|
Built 2013 - present
|
150 homes
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(475) 244-9781
$500Ks
- $600Ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2016
|
176 homes
$700Ks
Stone Ridge Estates, Dix Hills, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2013
|
76 homes
$200Ks
- $300Ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
5 rating (1 reviews)
![Newtown Woods]()
$400Ks
- $500Ks
Newtown Woods, Newtown, CT
New and Resale
|
55+ age-restricted
|
Built 2011 - present
|
178 homes
Want to learn more about 55+ rental communities in Cheshire?
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(475) 244-9781
Download the Ultimate 55+ Homebuying Guide
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$500Ks
- $600Ks
The Villas at Narraganset..., Lindenhurst, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2005
|
138 homes
5 rating (1 reviews)
![Encore Atlantic Shores]()
$700Ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 homes
1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
285 homes
$600Ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2005
|
85 homes
$800Ks
- $2Ms
Kensington Estates, Woodbury, NY
New Construction
|
55+ age-restricted
|
Built 2019 - 2021
|
80 homes
Want to learn more about 55+ communities in Cheshire?
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Questions? Call us:
(475) 244-9781
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$300Ks
- $400Ks
Strathmore Gate East, Coram, NY
Resale Only
|
55+ age-restricted
|
Built 1970 - 1975
|
174 homes
$600Ks
- $700Ks
The Seasons at Plainview, Plainview, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2007
|
134 homes
$600Ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 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
The Seasons at East Meado..., East Meadow, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2012
|
404 homes
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3.5 rating (2 reviews)
![Foxwood Village]()
$400Ks
- $500Ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
$400Ks
- $500Ks
Dutchgate, Valley Stream, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2015
|
348 homes
4.9 rating (14 reviews)
![Chatfield Farms]()
$500Ks
- $600Ks
Chatfield Farms, Beacon Falls, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
231 homes
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$400Ks
Oak Meadow Estates, Torrington, CT
New and Resale
|
55+ age-restricted
|
Built 2013 - present
|
31 homes
New
Kensington Estates
![48 PLAINVIEW RD, WOODBURY, NY, 11797, Woodbury, NY 11797]()
6 beds
|5 baths
|4,333 sq ft
|House
48 PLAINVIEW RD, WOODBURY, NY, 11797
Community: Kensington Estates
MLS 955214 • SRG Residential LLC, Jared Sarney
New
Heritage Hills
![339 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|3 baths
|1,550 sq ft
|Condo
339 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 954783 • Keller Williams Realty Partner, Anne...
New
South Pond Village
![162 THISTLE POND DR # 162, BLOOMFIELD, C..., Bloomfield, CT 06002]()
2 beds
|2 baths
|1,341 sq ft
|Condo
162 THISTLE POND DR # 162, BLOOMFIELD, C...
Community: South Pond Village
MLS 24151340 • Hill Top Real Estate, LLC, Craig I...
New
Heritage Hills
![882 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|3 baths
|1,666 sq ft
|Condo
882 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
MLS 934009 • Houlihan Lawrence Inc., Gary Parker
New
The Retreat at Carmel
![18 WHEELER CT, CARMEL, NY, 10512, Carmel, NY 10512]()
2 beds
|3 baths
|2,035 sq ft
|Condo
18 WHEELER CT, CARMEL, NY, 10512
Community: The Retreat at Carmel
MLS 953121 • Keller Williams Realty Partner, Rand...
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New
The Village at Oxford Greens
![117 COUNTRY CLUB DR # 117, OXFORD, CT, 0..., Oxford, CT 06478]()
3 beds
|3 baths
|2,666 sq ft
117 COUNTRY CLUB DR # 117, OXFORD, CT, 0...
Community: The Village at Oxford Greens
MLS 24151623 • Real Estate Two, Karen Berwick
New
Meadowbrook Pointe Athletic Club & Spa
![568 PACING WAY # 568, WESTBURY, NY, 1159..., Westbury, NY 11590]()
2 beds
|2 baths
|1,328 sq ft
|Condo
568 PACING WAY # 568, WESTBURY, NY, 1159...
Community: Meadowbrook Pointe Athletic Club & Spa
MLS 954126 • Douglas Elliman Real Estate, Tiffany...
New
Heritage Hills
![744 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,525 sq ft
|Condo
744 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 949289 • Coldwell Banker Realty, Patricia Mai...
New
Heritage Hills
![578 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589]()
1 beds
|2 baths
|967 sq ft
|Condo
578 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
MLS 950188 • Houlihan Lawrence Inc., Harding Maso...
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.
New
The Seasons at East Northport
![142 AUGUST CIR, HUNTINGTON, NY, 11731, Huntington, NY 11731]()
2 beds
|2 baths
|1,536 sq ft
|Condo
142 AUGUST CIR, HUNTINGTON, NY, 11731
Community: The Seasons at East Northport
MLS 956156 • Steven M Roberts Management, Zachary...
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
New
Leisure Glen
![77 GLEN DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 952676 • Signature Premier Properties, Lisa M...
New
The Manors at The Colony Preserve
![34 GREENTREE CT, SHIRLEY, NY, 11967, Shirley, NY 11967]()
2 beds
|2 baths
|1,357 sq ft
|Condo
34 GREENTREE CT, SHIRLEY, NY, 11967
Community: The Manors at The Colony Preserve
MLS 955814 • Howard Hanna Coach, Heather N. Malon...
New
The Village at Oxford Greens
![301 FAIRWAY DR # 301, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|2 baths
|2,080 sq ft
|Condo
301 FAIRWAY DR # 301, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24151318 • Coldwell Banker Realty, Carl Deman...
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New
Meadowbrook Pointe Links & Spa
![146 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763]()
2 beds
|3 baths
|2,047 sq ft
|Condo
146 AUGUSTA DR, MEDFORD, NY, 11763
Community: Meadowbrook Pointe Links & Spa
MLS 955710 • Signature Premier Properties, Matthe...
New
Westhampton Pines
![39 KIMBERLY DR # 39, WESTHAMPTON, NY, 11..., Westhampton, NY 11977]()
3 beds
|2 baths
|2,500 sq ft
|Condo
39 KIMBERLY DR # 39, WESTHAMPTON, NY, 11...
Community: Westhampton Pines
MLS 953821 • Nest Seekers International LLC, Robe...
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New
Granite Woods
![35 NUTMEG RD D1, MIDDLEBURY, CT, 06762, Middlebury, CT 06762]()
1 beds
|1 baths
|889 sq ft
|Condo
35 NUTMEG RD D1, MIDDLEBURY, CT, 06762
Community: Granite Woods
MLS 24150979 • Showcase Realty, Inc., Karen Stanc...
New
Oronoque Village
![635 NORTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,454 sq ft
|Condo
635 NORTH TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24148329 • Coldwell Banker Realty, Wendy Barr...
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.
New
Heritage Hills
![656 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,296 sq ft
|Condo
656 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
MLS 950592 • Houlihan Lawrence Inc., Donna O'Conn...
New
Heritage Village
![73 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
73 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24150969 • RE/MAX Right Choice, Kimberly Came...
New
The Village at Oxford Greens
![607 CHAMPIONSHIP DR # 607, OXFORD, CT, 0..., Oxford, CT 06478]()
3 beds
|3 baths
|2,731 sq ft
|Condo
607 CHAMPIONSHIP DR # 607, OXFORD, CT, 0...
Community: The Village at Oxford Greens
MLS 24150582 • Coldwell Banker Realty, Stephanie ...
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
New
Country Pointe Plainview
![28301 SPRUCE POND CIR, PLAINVIEW, NY, 11..., Plainview, NY 11803]()
2 beds
|2 baths
|1,379 sq ft
|Condo
28301 SPRUCE POND CIR, PLAINVIEW, NY, 11...
Community: Country Pointe Plainview
MLS 955202 • Coldwell Banker American Homes, Jacq...
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Meadowbrook Pointe Athletic Club & Spa
![428 TROTTING LN # 428, WESTBURY, NY, 115..., Westbury, NY 11590]()
2 beds
|3 baths
|2,628 sq ft
|Condo
428 TROTTING LN # 428, WESTBURY, NY, 115...
Community: Meadowbrook Pointe Athletic Club & Spa
MLS 954156 • Compass Greater NY LLC, Luis Barreto
Fairfield at St. James
![101 FLAIR CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
1 beds
|2 baths
|900 sq ft
|Condo
101 FLAIR CT, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 954627 • Signature Premier Properties, Lori Z...
Snug Harbor
![170 HARBOR, AMITYVILLE, NY, 11701, Amityville, NY 11701]()
MLS 954471 • Signature Premier Properties, Phylli...
Greenwood Village
![54 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|1,134 sq ft
|Condo
54 DOGWOOD LN, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 954790 • Fiore Real Estate Sales Corp, Anna M...
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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.
Fairfield at St. James
![1107 CABOT CT N, SAINT JAMES, NY, 11780, Saint James, NY 11780]()
1 beds
|2 baths
|929 sq ft
|Condo
1107 CABOT CT N, SAINT JAMES, NY, 11780
Community: Fairfield at St. James
MLS 954779 • Signature Premier Properties, Amanda...
Heritage Village
![198 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
198 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24149422 • Coldwell Banker Realty, James Wood
The Summit at Bethel
![12 BRIAR RIDGE DR # 12, BETHEL, CT, 0680..., Bethel, CT 06801]()
2 beds
|3 baths
|2,023 sq ft
|Condo
12 BRIAR RIDGE DR # 12, BETHEL, CT, 0680...
Community: The Summit at Bethel
MLS 24149812 • Cheryl Scott-Daniels Realty, Chery...
Oronoque Village
![13 ALGONQUIN LN C, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,330 sq ft
|Condo
13 ALGONQUIN LN C, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24150570 • William Raveis Real Estate, Marta ...
Greenwood Village
![42 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|960 sq ft
|Condo
42 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 954479 • Coldwell Banker M&D Good Life, Sandr...
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Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Heritage Village
![595 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
595 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24149941 • Berkshire Hathaway NE Prop., Bonni...
Heritage Hills
![140 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|1,689 sq ft
|Condo
140 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 947181 • Houlihan Lawrence Inc., Harding Maso...
The Village at Oxford Greens
![185 COUNTRY CLUB DR # 185, OXFORD, CT, 0..., Oxford, CT 06478]()
3 beds
|3 baths
|2,595 sq ft
|Condo
185 COUNTRY CLUB DR # 185, OXFORD, CT, 0...
Community: The Village at Oxford Greens
MLS 24150423 • Coldwell Banker Realty, Joseph Pau...
Greenwood Village
![82 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|1,110 sq ft
|Condo
82 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 953477 • Gateway to The Hamptons R E, Vivian ...
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
![423 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
423 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24147877 • KEY Real Estate Services LLC, Oliv...
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The Bel Aire at East Meadow
![50 MERRICK AVE 119, EAST MEADOW, NY, 115..., East Meadow, NY 11554]()
2 beds
|2 baths
|941 sq ft
|Condo
50 MERRICK AVE 119, EAST MEADOW, NY, 115...
Community: The Bel Aire at East Meadow
MLS 929819 • Daniel Gale Sothebys Intl Rlty, Susa...
Oronoque Village
![315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,590 sq ft
|Condo
315 NAVAJO LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24148423 • eXp Realty, Tracey Jefferson
Leisure Village
![278 BERWICK CT UNIT B B, RIDGE, NY, 1196..., Ridge, NY 11961]()
2 beds
|1 baths
|875 sq ft
|Condo
278 BERWICK CT UNIT B B, RIDGE, NY, 1196...
Community: Leisure Village
MLS 953317 • Leisure Living Realty Inc, Laura Ruh...
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Heritage Village
![813 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
813 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24149937 • Berkshire Hathaway NE Prop., Bonni...
Regency at Woodbridge
![3 EDGEWOOD WAY # 26, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525]()
3 beds
|3 baths
|Condo
3 EDGEWOOD WAY # 26, WOODBRIDGE, CT, 065...
Community: Regency at Woodbridge
MLS 24149912 • Thomas Jacovino, Kathy Childs
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?
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