Call us at (475) 244-9781 to learn more about active adult communities near Cheshire
Cheshire, CT 55+ active adult communities & homes for sale
129 communities near Cheshire
228 homes near Cheshire
Sort by:
Relevance
$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
$200Ks
- $400Ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
$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?
55places can help!
Questions? Call us:
(475) 244-9781
$400Ks
- $600Ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
4 rating (1 reviews)
![Jefferson Village]()
$200Ks
- $600Ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
$200Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
$500Ks
- $700Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
$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.
$300Ks
- $400Ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 homes
$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
$200Ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
Want to learn more about 55+ communities in Cheshire?
55places can help!
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
$500Ks
- $600Ks
The Seasons at East Meado..., East Meadow, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2012
|
404 homes
$300Ks
- $500Ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
$400Ks
- $500Ks
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.
$400Ks
- $600Ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
$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]()
$400Ks
- $500Ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 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
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(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
Vineyards at Blue Point, Blue Point, NY
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
280 homes
$900Ks
- $1Ms
HarborView, Port Washington, NY
Resale Only
|
55+ age-restricted
|
Built 2002 - 2004
|
270 homes
$500Ks
The Club at Melville, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2017
|
261 homes
$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.
$500Ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
5 rating (1 reviews)
![Encore Atlantic Shores]()
$700Ks
- $800Ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 homes
$600Ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 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
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?
55places can help!
Questions? Call us:
(475) 244-9781
$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
$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
![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 24139552 • William Pitt Sotheby's Int'l, Mela...
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 24112399 • William Raveis Real Estate, Joseph...
Heritage Village
![1008 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
1008 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24136244 • Dave Jones Realty, LLC, Gregory Mi...
Heritage Village
![889 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
889 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24137432 • Coldwell Banker Realty, Maryanne B...
Heritage Village
![643 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
643 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24119411 • Drakeley Real Estate, Inc., Timoth...
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
The Village at Oxford Greens
![709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0..., Oxford, CT 06478]()
2 beds
|2 baths
|1,532 sq ft
|Condo
709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0...
Community: The Village at Oxford Greens
MLS 24135415 • Berkshire Hathaway NE Prop., Bonni...
Fairview at Oxford Greens
![709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0..., Oxford, CT 06478]()
2 beds
|2 baths
|1,532 sq ft
|Condo
709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0...
Community: Fairview at Oxford Greens
MLS 24135415 • Berkshire Hathaway NE Prop., Bonni...
The Summit at Bethel
![17 BRIAR RIDGE DR # 17, BETHEL, CT, 0680..., Bethel, CT 06801]()
3 beds
|4 baths
|3,012 sq ft
|Condo
17 BRIAR RIDGE DR # 17, BETHEL, CT, 0680...
Community: The Summit at Bethel
MLS 24137209 • William Raveis Real Estate, Jackie...
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
![890 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
890 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24121230 • Berkshire Hathaway NE Prop., Scott...
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
![214 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,076 sq ft
|Condo
214 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24135527 • Realty ONE Group Connect, Susan Ho...
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
![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...
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 ...
Heritage Village
![73 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
73 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24136386 • Alpine Realty, Gary Gilroy
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
Heritage Village
![114 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
114 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24128139 • Telesh Realty LLC, Igor Teleshevsk...
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
![1 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
1 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24128891 • Coldwell Banker Realty, Demaree Co...
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...
Leisure Knoll
![145 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 936582 • Frontline Realty Group LLC, Nicholas...
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 Village
![215 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,085 sq ft
|Condo
215 WOODBRIDGE DR A, RIDGE, NY, 11961
Community: Leisure Village
MLS 933663 • Leisure Living Realty Inc, Paulina R...
Heritage Hills
![593 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,470 sq ft
|Condo
593 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 933299 • Houlihan Lawrence Inc., Linda Crispi...
Stoneleigh Woods at Riverhead
![4 HAVERTON CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|3 baths
|2,175 sq ft
|Condo
4 HAVERTON CT, RIVERHEAD, NY, 11901
Community: Stoneleigh Woods at Riverhead
MLS 928263 • Exit Realty Liberty, Maureen A. Kler...
Glenwood Village
![1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1..., Riverhead, NY 11901]()
2 beds
|2 baths
|924 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1...
Community: Glenwood Village
MLS 927346 • Keystone Realty USA Corp, Cynthia Mc...
Greenwood Village
![99 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|1,487 sq ft
|Condo
99 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 927020 • Douglas Elliman Real Estate, Valerie...
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
The Greens at Half Hollow
![677 BALFOUR PL, MELVILLE, NY, 11747, Melville, NY 11747]()
2 beds
|3 baths
|1,900 sq ft
|Condo
677 BALFOUR PL, MELVILLE, NY, 11747
Community: The Greens at Half Hollow
MLS 937930 • Charles Rutenberg Realty Inc, Michel...
Heritage Hills
![798 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,296 sq ft
|Condo
798 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
MLS 899317 • Houlihan Lawrence Inc., Donna O'Conn...
Breton Hills
![209 BRETON WAY, GLEN COVE, NY, 11542, Glen Cove, NY 11542]()
MLS 934232 • BERKSHIRE HATHAWAY, Mary A. Stanco A...
The Greens at Half Hollow
![445 BARDINI DR, MELVILLE, NY, 11747, Melville, NY 11747]()
2 beds
|3 baths
|1,941 sq ft
|Condo
445 BARDINI DR, MELVILLE, NY, 11747
Community: The Greens at Half Hollow
MLS 939187 • Signature Premier Properties, Janice...
New
Leisure Village
![380 WOODBRIDGE DR D, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|2 baths
|1,405 sq ft
|Condo
380 WOODBRIDGE DR D, RIDGE, NY, 11961
Community: Leisure Village
MLS 942060 • Exit Realty Achieve, Diane Mascellar...
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.
Jefferson Village
![175 LONG HILL DR B, YORKTOWN HEIGHTS, NY..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,159 sq ft
|Condo
175 LONG HILL DR B, YORKTOWN HEIGHTS, NY...
Community: Jefferson Village
MLS 935088 • Houlihan Lawrence Inc., Kathleen O'D...
Leisure Village
![412 WEYMOUTH CT UNIT B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,100 sq ft
|Condo
412 WEYMOUTH CT UNIT B, RIDGE, NY, 11961
Community: Leisure Village
MLS 924555 • Keller Williams Rlty Landmark, Anton...
The Villages at Mount Sinai Park
![68 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
2 beds
|2 baths
|1,736 sq ft
|Condo
68 LOUDEN LOOP, MOUNT SINAI, NY, 11766
Community: The Villages at Mount Sinai Park
MLS 910234 • Island Advantage Realty LLC, Todd A....
Greenwood Village
![91 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|938 sq ft
|Condo
91 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 935628 • Signature Premier Properties, Linda ...
Overlook
![1037 COTTAGE DR 18, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 889837 • Toll Brothers Real Estate Inc., Thom...
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
Overlook
![4071 FAIRWAYS DR 136, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 920677 • Toll Brothers Real Estate Inc., Thom...
Overlook
![4073 FAIRWAYS DR # 137, CARMEL, NY, 1051..., Carmel, NY 10512]()
3 beds
|3 baths
|1,914 sq ft
|Condo
4073 FAIRWAYS DR # 137, CARMEL, NY, 1051...
Community: Overlook
MLS 925922 • Toll Brothers Real Estate Inc., Thom...
New
The Greens at Half Hollow
![159 ALTESSA BLVD, MELVILLE, NY, 11747, Melville, NY 11747]()
2 beds
|2 baths
|2,500 sq ft
|Condo
159 ALTESSA BLVD, MELVILLE, NY, 11747
Community: The Greens at Half Hollow
MLS 940204 • BERKSHIRE HATHAWAY, Jodi Locke
Encore Atlantic Shores
![113 OVERTURE PL, EASTPORT, NY, 11941, Eastport, NY 11941]()
2 beds
|3 baths
|3,037 sq ft
|Condo
113 OVERTURE PL, EASTPORT, NY, 11941
Community: Encore Atlantic Shores
MLS 926369 • Corcoran, Merle Buff
Strathmore Gate East
![53 FREEDOM LN, CORAM, NY, 11727, Coram, NY 11727]()
2 beds
|1 baths
|1,036 sq ft
|Condo
53 FREEDOM LN, CORAM, NY, 11727
Community: Strathmore Gate East
MLS 924175 • Douglas Elliman Real Estate, Lisa Ge...
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?
228
homes
near Cheshire
Remove Boundaries ×
Map
Satellite
The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2025 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Dec 09, 2025.
This application does not include information on all of the properties available for sale at this time.
