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
230 homes near Cheshire
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3.6 rating (7 reviews)
![Heritage Village]()
$200ks
- $500ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
$100ks
- $300ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
3 rating (2 reviews)
![Heritage Hills]()
$400ks
- $1Ms
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1974 - 2006
|
2,600 homes
$200ks
- $400ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
3.7 rating (3 reviews)
![Greenwood Village]()
$100ks
Greenwood Village, Manorville, NY
Resale Only
|
55+ age-restricted
|
Built 1980 - 2000
|
512 homes
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(475) 244-9781
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(475) 244-9781
$600ks
- $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 1994 - 2005
|
1,200 homes
4 rating (1 reviews)
![Jefferson Village]()
$100ks
- $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
$400ks
- $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
4 rating (8 reviews)
![Glenwood Village]()
$100ks
- $200ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 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.
$700ks
- $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2016
|
720 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.
$200ks
- $400ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 homes
$300ks
- $800ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
|
312 homes
$300ks
- $600ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
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(475) 244-9781
5 rating (2 reviews)
![Fairfield at St. James]()
$300ks
- $500ks
Fairfield at St. James, St. James, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1989
|
653 homes
5 rating (1 reviews)
![Encore Atlantic Shores]()
$500ks
- $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 homes
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(475) 244-9781
$500ks
- $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
70 homes
$400ks
- $600ks
The Seasons at East Meado..., East Meadow, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2012
|
404 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.
$100ks
- $200ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
$400ks
- $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
125 homes
$300ks
- $500ks
Dutchgate, Valley Stream, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2015
|
348 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.
$300ks
- $400ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
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(475) 244-9781
5 rating (1 reviews)
![Westhampton Pines]()
$900ks
- $1Ms
Westhampton Pines, Westhampton, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2013
|
189 homes
5 rating (1 reviews)
![Encore at Lake Grove]()
$500ks
- $700ks
Encore at Lake Grove, Lake Grove, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2007
|
228 homes
5 rating (1 reviews)
![Newtown Woods]()
$300ks
- $500ks
Newtown Woods, Newtown, CT
New and Resale
|
55+ age-restricted
|
Built 2011 - present
|
178 homes
$1Ms
Kensington Estates, Woodbury, NY
New Construction
|
55+ age-restricted
|
Built 2019 - 2021
|
80 homes
Want to learn more about 55+ rental communities in Cheshire?
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Questions? Call us:
(475) 244-9781
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.
$700ks
- $1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 homes
$300ks
- $900ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
$500ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2005
|
85 homes
$500ks
The Coves at Melville, Melville, NY
Resale Only
|
62+ age-restricted
|
Built 2004 - 2005
|
175 homes
$500ks
- $600ks
Stone Ridge Estates, Dix Hills, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2013
|
76 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
Village Estates, Amityville, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2008
|
138 homes
$300ks
- $400ks
South Pond Village, Bloomfield, CT
Resale Only
|
55+ age-restricted
|
Built 1999 - 2005
|
151 homes
$400ks
The Villas at Narraganset..., Lindenhurst, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2005
|
138 homes
$300ks
Strathmore Gate East, Coram, NY
Resale Only
|
55+ age-restricted
|
Built 1970 - 1975
|
174 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
Bartlett Hill, Portland, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2011
|
82 homes
Want to learn more about 55+ rental communities in Cheshire?
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Questions? Call us:
(475) 244-9781
$300ks
- $400ks
Liberty at Newtown, Newtown, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2007
|
96 homes
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2016
|
176 homes
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
$300ks
- $400ks
North Woods of Colchester, Colchester, CT
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
140 homes
New
Heritage Hills
![343 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,484 sq ft
|Condo
343 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 960438 • Mancini Realty Inc., Joan Mancini
New
North Woods of Colchester
![11 NORTH CT # 11, COLCHESTER, CT, 06415, Colchester, CT 06415]()
2 beds
|2 baths
|1,751 sq ft
|Condo
11 NORTH CT # 11, COLCHESTER, CT, 06415
Community: North Woods of Colchester
MLS 24153882 • Williams Realty Services, Dawn Cas...
New
The Seasons at East Meadow
![479 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554]()
2 beds
|2 baths
|1,358 sq ft
|Condo
479 SPRING DR, EAST MEADOW, NY, 11554
Community: The Seasons at East Meadow
MLS 961177 • LAFFEY REAL ESTATE, Peter D. Guadagn...
New
Leisure Knoll
![206 BELFAST LN, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 960634 • Leisure Living Realty Inc, Paulina R...
New
Glenwood Village
![1661 OLD COUNTRY RD 275, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,050 sq ft
|Mobile Home
1661 OLD COUNTRY RD 275, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 960267 • Old Orchard Estates R E Inc, Matthew...
Want to learn more about 55+ communities in Cheshire?
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Questions? Call us:
(475) 244-9781
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55places can help!
Questions? Call us:
(475) 244-9781
New
Leisure Glen
![530 LEISURE DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 957040 • Signature Premier Properties, Mildre...
New
Spring Lake Village
![40 HICKORY HL # 40, SOUTHINGTON, CT, 064..., Southington, CT 06489]()
2 beds
|2 baths
|1,211 sq ft
|Condo
40 HICKORY HL # 40, SOUTHINGTON, CT, 064...
Community: Spring Lake Village
MLS 24153678 • Realty 3 CT, Shelly Meister Zamudi...
New
Woodridge Strathmore Terrace
![27 HEARTHSIDE DR, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
1 beds
|1 baths
|844 sq ft
|Condo
27 HEARTHSIDE DR, MOUNT SINAI, NY, 11766
Community: Woodridge Strathmore Terrace
MLS 960957 • BERKSHIRE HATHAWAY, Michelle Madtes
New
Leisure Village
![418 WEYMOUTH CT C, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,036 sq ft
|Condo
418 WEYMOUTH CT C, RIDGE, NY, 11961
Community: Leisure Village
MLS 960927 • Signature Premier Properties, Adela ...
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
Dutchgate
![203 WILLOW LN, VALLEY STREAM, NY, 11580, Valley Stream, NY 11580]()
MLS 960893 • First Class Realty Enterprises, Josh...
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
Heritage Hills
![40 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,139 sq ft
|Condo
40 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 954097 • Houlihan Lawrence Inc., Janet Ferran...
New
The Greens at Half Hollow
![833 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747]()
2 beds
|2 baths
|1,150 sq ft
|Condo
833 MADEIRA BLVD, HUNTINGTON, NY, 11747
Community: The Greens at Half Hollow
MLS 960544 • Signature Premier Properties, Janice...
New
Meadowbrook Pointe Athletic Club & Spa
![366 ROOSEVELT WAY, NORTH HEMPSTEAD, NY, ..., North Hempstead, NY 11590]()
2 beds
|2 baths
|1,342 sq ft
|Condo
366 ROOSEVELT WAY, NORTH HEMPSTEAD, NY, ...
Community: Meadowbrook Pointe Athletic Club & Spa
MLS 960433 • Daniel Gale Sothebys Intl Rlty, Kari...
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(475) 244-9781
New
Fairfield at St. James
![203 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
1 beds
|1 baths
|841 sq ft
|Condo
203 CABOT CT, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 955663 • Signature Premier Properties, Bryn G...
New
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 24152837 • Drakeley Real Estate, Inc., Shelle...
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(475) 244-9781
New
Breton Hills
![709 BRETON WAY, GLEN COVE, NY, 11542, Glen Cove, NY 11542]()
MLS 955832 • JMRENY, Joseph A. Maselli
New
Stratford Park
![106 VICTORIA PL, HUNTINGTON, NY, 11747, Huntington, NY 11747]()
3 beds
|3 baths
|2,100 sq ft
|Condo
106 VICTORIA PL, HUNTINGTON, NY, 11747
Community: Stratford Park
MLS 960314 • Signature Premier Properties, Janice...
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 Village
![701 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
701 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24153612 • Century 21 Limitless, Kyle Seyboth
New
Leisure Village
![430 FALMOUTH CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|2 baths
|1,200 sq ft
|House
430 FALMOUTH CT A, RIDGE, NY, 11961
Community: Leisure Village
MLS 960353 • OverSouth LLC, Sean Manning
New
Leisure Village
![258 NEWCASTLE CT F, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|875 sq ft
|Condo
258 NEWCASTLE CT F, RIDGE, NY, 11961
Community: Leisure Village
MLS 958463 • Leisure Living Realty Inc, Paulina R...
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
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 24153507 • Northwest CT Realty, Leslie Tapia-...
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(475) 244-9781
New
The Greens at Half Hollow
![843 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747]()
2 beds
|2 baths
|1,150 sq ft
|Condo
843 MADEIRA BLVD, HUNTINGTON, NY, 11747
Community: The Greens at Half Hollow
MLS 957971 • Compass Greater NY LLC, Andrea L. Co...
New
South Pond Village
![81 SILO WAY 81, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002]()
2 beds
|2 baths
|1,204 sq ft
|Condo
81 SILO WAY 81, BLOOMFIELD, CT, 06002
Community: South Pond Village
MLS 24151413 • Berkshire Hathaway NE Prop., Sandy...
New
The Coves at Melville
![54 MORLEY CIR, HUNTINGTON, NY, 11747, Huntington, NY 11747]()
2 beds
|2 baths
|1,162 sq ft
|Condo
54 MORLEY CIR, HUNTINGTON, NY, 11747
Community: The Coves at Melville
MLS 959161 • Your Home Sold Guaranteed Rlty, Susa...
New
Heritage Hills
![680 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589]()
1 beds
|2 baths
|1,296 sq ft
|Condo
680 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
MLS 959581 • Houlihan Lawrence Inc., Donna O'Conn...
Want to learn more about 55+ rental communities in Cheshire?
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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.
New
Villas at Seminary Hill
![7102 PANKIN DR, CARMEL, NY, 10512, Carmel, NY 10512]()
2 beds
|2 baths
|1,144 sq ft
|Condo
7102 PANKIN DR, CARMEL, NY, 10512
Community: Villas at Seminary Hill
MLS 959423 • River Realty Services, Inc., Ernest ...
New
Leisure Knoll
![304 KINGSTON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,000 sq ft
|Condo
304 KINGSTON CT, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 959588 • Howard Hanna Coach, Kalliopi C. Suar...
New
Heritage Hills
![243 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|1,689 sq ft
|Condo
243 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 956550 • Houlihan Lawrence Inc., Donna O'Conn...
Oronoque Village
![133 BANNOCK LN, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|2,038 sq ft
|Condo
133 BANNOCK LN, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24153059 • William Raveis Real Estate, Joseph...
Heritage Village
![914 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,144 sq ft
|Condo
914 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24152900 • Coldwell Banker Realty, Douglas Co...
Want to learn more about 55+ communities in Cheshire?
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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.
Chatfield Farms
![8 WOODLAND PATH 8, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403]()
3 beds
|4 baths
|2,610 sq ft
|Condo
8 WOODLAND PATH 8, BEACON FALLS, CT, 064...
Community: Chatfield Farms
MLS 24153080 • KW Legacy Partners, Mela Veltri Ca...
Heritage Village
![419 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
419 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24152323 • Berkshire Hathaway NE Prop., Jesse...
Greenwood Village
![16 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949]()
2 beds
|2 baths
|1,164 sq ft
|Condo
16 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 958616 • Realty Connect USA L I Inc, Naomi A....
Leisure Village
![230 BLACKPOOL CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|836 sq ft
|Condo
230 BLACKPOOL CT A, RIDGE, NY, 11961
Community: Leisure Village
MLS 958476 • Aliano Real Estate, Nicholas R. Alia...
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.
Encore at Lake Grove
![17 SONATA CT, LAKE GROVE, NY, 11755, Lake Grove, NY 11755]()
2 beds
|3 baths
|1,486 sq ft
|Condo
17 SONATA CT, LAKE GROVE, NY, 11755
Community: Encore at Lake Grove
MLS 958702 • Howard Hanna Coach, Francine Saer CB...
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Meadow Brook Estates
![215 MEADOW BROOK RD # 215, OXFORD, CT, 0..., Oxford, CT 06478]()
3 beds
|3 baths
|2,207 sq ft
|Condo
215 MEADOW BROOK RD # 215, OXFORD, CT, 0...
Community: Meadow Brook Estates
MLS 24152665 • William Pitt Sotheby's Int'l, Erik...
Leisure Village
![406 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961]()
1 beds
|1 baths
|704 sq ft
|Condo
406 WOODBRIDGE DR B, RIDGE, NY, 11961
Community: Leisure Village
MLS 957458 • Signature Premier Properties, Bryn G...
Long Hill Village
![71 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611]()
1 beds
|3 baths
|1,370 sq ft
|Condo
71 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill Village
MLS 24152135 • Higgins Group Real Estate, Fredda ...
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Leisure Knoll
![190 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|1 baths
|913 sq ft
|House
190 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 958383 • Frontline Realty Group LLC, Nicholas...
Village Estates
![34 SARAH CT, AMITYVILLE, NY, 11701, Amityville, NY 11701]()
2 beds
|2 baths
|1,251 sq ft
|Condo
34 SARAH CT, AMITYVILLE, NY, 11701
Community: Village Estates
MLS 958123 • Coldwell Banker American Homes, Jose...
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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REIN updates its listings on a daily basis. Data last updated: Feb 13, 2026.
This application does not include information on all of the properties available for sale at this time.
