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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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
- $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
Oronoque Village
![195 BAYFIELD LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,575 sq ft
|Condo
195 BAYFIELD LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24128861 • Property Choices Real Estate, Paul...
Rivington
![68 WARRINGTON ROUND # 68, DANBURY, CT, 0..., Danbury, CT 06810]()
2 beds
|3 baths
|1,600 sq ft
|Condo
68 WARRINGTON ROUND # 68, DANBURY, CT, 0...
Community: Rivington
MLS 24124873 • Howard Hanna Rand Realty, Kathleen...
Newtown Woods
![1024 BROOKSIDE CT # 1024, NEWTOWN, CT, 0..., Newtown, CT 06470]()
2 beds
|2 baths
|1,581 sq ft
|Condo
1024 BROOKSIDE CT # 1024, NEWTOWN, CT, 0...
Community: Newtown Woods
MLS 24129449 • Coldwell Banker Realty, Carrie Bar...
Heritage Village
![920 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
920 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24091615 • Coldwell Banker Realty, Lee Boyle
Regency at Prospect
![11 TAMARACK CT # 11, PROSPECT, CT, 06712, Prospect, CT 06712]()
2 beds
|3 baths
|1,848 sq ft
|Condo
11 TAMARACK CT # 11, PROSPECT, CT, 06712
Community: Regency at Prospect
MLS 24126654 • Coldwell Banker Realty, Jessica Da...
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Heritage Village
![773 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,063 sq ft
|Condo
773 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24125700 • Berkshire Hathaway NE Prop., Scott...
Heritage Village
![280 HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
280 HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24111199 • William Raveis Real Estate, Tom Gr...
Bartlett Hollow
![33 BARTLETT HOLW # 33, MIDDLETOWN, CT, 0..., Middletown, CT 06457]()
2 beds
|2 baths
|1,401 sq ft
|Condo
33 BARTLETT HOLW # 33, MIDDLETOWN, CT, 0...
Community: Bartlett Hollow
MLS 24122024 • Compass Connecticut, LLC, Deb Pach
Rivington
![1022 COUNTRY VIEW RD # 1022, DANBURY, CT..., Danbury, CT 06810]()
2 beds
|2 baths
|1,330 sq ft
|Condo
1022 COUNTRY VIEW RD # 1022, DANBURY, CT...
Community: Rivington
MLS 24093428 • Coldwell Banker Realty, Pamela Dos...
Spring Lake Village
![543 S FARMS TER # 543, SOUTHINGTON, CT, ..., Southington, CT 06489]()
2 beds
|3 baths
|1,782 sq ft
|Condo
543 S FARMS TER # 543, SOUTHINGTON, CT, ...
Community: Spring Lake Village
MLS 24102912 • Coldwell Banker Realty, Philip Gia...
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
![3 TIMBERLAND WAY # 3, BEACON FALLS, CT, ..., Beacon Falls, CT 06403]()
3 beds
|4 baths
|2,052 sq ft
3 TIMBERLAND WAY # 3, BEACON FALLS, CT, ...
Community: Chatfield Farms
MLS 24101359 • Dow Della Valle, E. Tyler Della Va...
Park Glen
![10 HARMONY TRL # 10, NEW MILFORD, CT, 06..., New Milford, CT 06776]()
2 beds
|3 baths
|4,023 sq ft
|Condo
10 HARMONY TRL # 10, NEW MILFORD, CT, 06...
Community: Park Glen
MLS 24109997 • Coldwell Banker Realty, Erin Porte...
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
![977 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
977 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24099168 • William Pitt Sotheby's Int'l, Mary...
Heritage Village
![825 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
825 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24124224 • Keller Williams Realty, Donna Doyl...
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Questions? Call us:
(475) 244-9781
Forest Mews
![17 CHERRY TREE LN # 17, AVON, CT, 06001, Avon, CT 06001]()
3 beds
|3 baths
|2,069 sq ft
|Condo
17 CHERRY TREE LN # 17, AVON, CT, 06001
Community: Forest Mews
MLS 24123671 • Coldwell Banker Realty, Barbara Au...
Newtown Woods
![603 BROOKSIDE CT # 603, NEWTOWN, CT, 064..., Newtown, CT 06470]()
2 beds
|2 baths
|1,504 sq ft
|Condo
603 BROOKSIDE CT # 603, NEWTOWN, CT, 064...
Community: Newtown Woods
MLS 24120267 • Coldwell Banker Realty, Pete Gille...
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...
Heritage Village
![98 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
98 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24101279 • Berkshire Hathaway NE Prop., Miche...
Heritage Village
![575 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
575 HERITAGE VLG A, 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.
Regency at Woodbridge
![4 WHISPER RIDGE WAY # 41, WOODBRIDGE, CT..., Woodbridge, CT 06525]()
3 beds
|3 baths
|Condo
4 WHISPER RIDGE WAY # 41, WOODBRIDGE, CT...
Community: Regency at Woodbridge
MLS 24112155 • Thomas Jacovino, Kathy Childs
The Village at Oxford Greens
![302 FAIRWAY DR # 302, OXFORD, CT, 06478, Oxford, CT 06478]()
3 beds
|3 baths
|2,750 sq ft
|Condo
302 FAIRWAY DR # 302, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24126623 • Coldwell Banker Realty, Pam McHenr...
Regency at Prospect
![8 HICKORY DR # 8, PROSPECT, CT, 06712, Prospect, CT 06712]()
3 beds
|2 baths
|1,500 sq ft
|Condo
8 HICKORY DR # 8, PROSPECT, CT, 06712
Community: Regency at Prospect
MLS 24128348 • Nolan Realty LLC, Mark Nolan
Heritage Village
![405 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
405 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24129966 • Mapleridge Realty, Tommy Dorso
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...
Want to learn more about 55+ communities in Cheshire?
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(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...
Oronoque Village
![133 BANNOCK LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,438 sq ft
|Condo
133 BANNOCK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24126564 • Coldwell Banker Realty, Mark Pires
Heritage Village
![139 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
139 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24112368 • Independent Realty Group, Tammi Li...
Heritage Village
![192 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,308 sq ft
|Condo
192 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24125904 • Coldwell Banker Realty, Claudia Fo...
Oronoque Village
![638 ONONDAGA LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|2,071 sq ft
|Condo
638 ONONDAGA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24123085 • Coldwell Banker Realty, Larry Vecc...
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.
Rivington
![416 CENTER MEADOW LN # 416, DANBURY, CT,..., Danbury, CT 06810]()
2 beds
|2 baths
|1,312 sq ft
|Condo
416 CENTER MEADOW LN # 416, DANBURY, CT,...
Community: Rivington
MLS 24123937 • Coldwell Banker Realty, Michele Is...
Oronoque Village
![408 MONTAUK LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,118 sq ft
|Condo
408 MONTAUK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24120413 • Weichert, Realtors-On The Mark, Gr...
Heritage Village
![132 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
132 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24118807 • William Raveis Real Estate, Ron Ne...
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...
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...
Want to learn more about 55+ communities in Cheshire?
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Questions? Call us:
(475) 244-9781
Greenwood Village
![164 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|938 sq ft
|Manufactured Home
164 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 887454 • Realty Connect USA L I Inc, Joseph I...
The Gardens of Wilbraham
![116 CHERRY DR # 116, WILBRAHAM, MA, 0109..., Wilbraham, MA 01095]()
2 beds
|2 baths
|1,634 sq ft
|Condo
116 CHERRY DR # 116, WILBRAHAM, MA, 0109...
Community: The Gardens of Wilbraham
MLS 73441478 • Coldwell Banker Realty - Western M...
Encore Atlantic Shores
![43 APPLAUSE DR, EASTPORT, NY, 11941, Eastport, NY 11941]()
2 beds
|3 baths
|3,037 sq ft
|Condo
43 APPLAUSE DR, EASTPORT, NY, 11941
Community: Encore Atlantic Shores
MLS 902647 • LAFFEY REAL ESTATE, Marcella Zack E-...
New
Jefferson Village
![34 WARWICK PL C, YORKTOWN HEIGHTS, NY, 1..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,000 sq ft
|Condo
34 WARWICK PL C, YORKTOWN HEIGHTS, NY, 1...
Community: Jefferson Village
MLS 922352 • RE/MAX Classic Realty, George Campo...
Heritage Hills
![438 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,470 sq ft
|Condo
438 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 911228 • Keller Williams Realty Partner, Mark...
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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