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Southold, NY 55+ active adult communities & homes for sale
94 communities near Southold
192 homes near Southold
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$500Ks
- $600Ks
Founders Village, Southold, NY
Resale Only
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55+ age-restricted
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Built 1981 - 1985
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92 homes
3.6 rating (7 reviews)
![Heritage Village]()
$200Ks
- $500Ks
Heritage Village, Southbury, CT
Resale Only
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55+ age-restricted
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Built 1967 - 2005
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2,580 homes
$200Ks
- $400Ks
Leisure Village, Ridge, NY
Resale Only
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55+ age-restricted
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Built 1969 - 1986
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1,500 homes
$200Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
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55+ age-restricted
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Built 1971 - 1977
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929 homes
$500Ks
- $600Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
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55+ age-restricted
|
Built 2004 - present
|
835 homes
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$300Ks
- $400Ks
Leisure Knoll, Ridge, NY
Resale Only
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55+ age-restricted
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Built 1972 - 1982
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701 homes
5 rating (2 reviews)
![Fairfield at St. James]()
$400Ks
Fairfield at St. James, St. James, NY
Resale Only
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55+ age-restricted
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Built 1972 - 1989
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653 homes
$200Ks
Spring Lake Village, Southington, CT
Resale Only
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55+ age-restricted
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Built 1970 - 2004
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640 homes
4 rating (8 reviews)
![Glenwood Village]()
$100Ks
- $400Ks
Glenwood Village, Riverhead, NY
New and Resale
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55+ age-restricted
|
Built 1959 - present
|
588 homes
Download the Ultimate 55+ Homebuying Guide
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3.7 rating (3 reviews)
![Greenwood Village]()
$100Ks
- $200Ks
Greenwood Village, Manorville, NY
Resale Only
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55+ age-restricted
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Built 1980 - 2000
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512 homes
$300Ks
- $500Ks
Regency at Prospect, Prospect, CT
Resale Only
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55+ age-restricted
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Built 2006 - 2020
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379 homes
$400Ks
- $700Ks
The Waterways at Moriches, Moriches, NY
Resale Only
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55+ age-restricted
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Built 1985 - 1999
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343 homes
4 rating (5 reviews)
![South Shore Village]()
$600Ks
- $800Ks
South Shore Village, South Kingstown, RI
New and Resale
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55+ age-restricted
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Built 2016 - present
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303 homes
3.5 rating (2 reviews)
![Foxwood Village]()
$300Ks
- $400Ks
Foxwood Village, Calverton, NY
Resale Only
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55+ age-restricted
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Built 1986 - 2007
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294 homes
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1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only
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55+ age-restricted
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Built 2006 - 2013
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285 homes
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
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55+ age-restricted
|
Built 2016 - 2018
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280 homes
$800Ks
- $900Ks
The Seasons at Elwood, East Northport, NY
Resale Only
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55+ age-restricted
|
Built 2018 - 2020
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256 homes
$500Ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
Download the Ultimate 55+ Homebuying Guide
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5 rating (1 reviews)
![Encore Atlantic Shores]()
$600Ks
- $800Ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
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240 homes
4.9 rating (14 reviews)
![Chatfield Farms]()
$500Ks
- $600Ks
Chatfield Farms, Beacon Falls, CT
New Construction
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55+ age-restricted
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Built 2014 - present
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231 homes
5 rating (1 reviews)
![Encore at Lake Grove]()
$600Ks
- $800Ks
Encore at Lake Grove, Lake Grove, NY
Resale Only
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55+ age-restricted
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Built 2006 - 2007
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228 homes
$400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
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55+ age-restricted
|
Built 1974 - 1985
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226 homes
5 rating (1 reviews)
![Sunrise Village]()
$400Ks
- $500Ks
Sunrise Village, Sayville, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1990
|
213 homes
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$400Ks
Country Village Estates, Coram, NY
Resale Only
|
55+ age-restricted
|
Built 1993 - 2001
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195 homes
5 rating (1 reviews)
![Sunken Pond Estates]()
$400Ks
- $500Ks
Sunken Pond Estates, Riverhead, NY
Resale Only
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55+ age-restricted
|
Built 2003 - 2005
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194 homes
$700Ks
The Seasons at East North..., East Northport, NY
New Construction
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55+ age-restricted
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Built 2023 - present
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190 homes
5 rating (1 reviews)
![Westhampton Pines]()
$900Ks
- $1Ms
Westhampton Pines, Westhampton, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2013
|
189 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)
![The Villages at Mount Sin...]()
$600Ks
- $700Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only
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55+ age-restricted
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Built 2005 - 2007
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185 homes
$600Ks
- $700Ks
The Powder Forest Homes, Simsbury, CT
Resale Only
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55+ age-restricted
|
Built 2006 - 2016
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182 homes
$600Ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only
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55+ age-restricted
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Built 2007 - 2016
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176 homes
$300Ks
- $400Ks
Strathmore Gate East, Coram, NY
Resale Only
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55+ age-restricted
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Built 1970 - 1975
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174 homes
$300Ks
- $400Ks
Beckley Farms, Berlin, CT
New and Resale
|
55+ age-restricted
|
Built 2010 - present
|
170 homes
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$100Ks
- $200Ks
South Pond Village, Bloomfield, CT
Resale Only
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55+ age-restricted
|
Built 1999 - 2005
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151 homes
$600Ks
- $700Ks
Setauket Meadows, Setauket, NY
Resale Only
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55+ age-restricted
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Built 2005 - 2007
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150 homes
$400Ks
- $500Ks
The Manors at The Colony ..., Shirley, NY
New Construction
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55+ age-restricted
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Built 2013 - present
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150 homes
$700Ks
Vineyards at Brookfield, Center Moriches, NY
New Construction
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55+ age-restricted
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Built 2019 - present
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146 homes
Oronoque Village
![195 BAYFIELD LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 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...
Heritage Village
![44 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,308 sq ft
|Condo
44 HERITAGE VLG F, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24135482 • Joseph Bette REALTORS Inc, Deborah...
Evergreen
![34 WOODSBORO CIR # 34, CROMWELL, CT, 064..., Cromwell, CT 06416]()
2 beds
|2 baths
|1,758 sq ft
|Condo
34 WOODSBORO CIR # 34, CROMWELL, CT, 064...
Community: Evergreen
MLS 24134359 • Century 21 North East, Joselyn Val...
Heritage Village
![623 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
623 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24125367 • Showcase Realty, Inc., Jeff Colt
Heritage Village
![568A HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
568A HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24129707 • Showcase Realty, Inc., Jeff Colt
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Heritage Village
![191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24122871 • Joseph Bette REALTORS Inc, Justin ...
Heritage Village
![39 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
39 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24139075 • William Raveis Real Estate, Ruth Z...
Spring Lake Village
![85 CLEARVIEW CT # 85, SOUTHINGTON, CT, 0..., Southington, CT 06489]()
1 beds
|2 baths
|1,028 sq ft
|Condo
85 CLEARVIEW CT # 85, SOUTHINGTON, CT, 0...
Community: Spring Lake Village
MLS 24138605 • Century 21 AllPoints Realty, Jill ...
Heritage Village
![865 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
865 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24138526 • Showcase Realty, Inc., Gregory Bal...
Heritage Village
![60 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
60 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24137022 • William Raveis Real Estate, Ruth Z...
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.
Oronoque Village
![289 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,620 sq ft
|Condo
289 AGAWAM DR B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24138784 • Oronoque Real Estate, Monica Dalto...
The Village at Oxford Greens
![930 TILLINGHAST DR # 930, OXFORD, CT, 06..., Oxford, CT 06478]()
2 beds
|3 baths
|2,365 sq ft
930 TILLINGHAST DR # 930, OXFORD, CT, 06...
Community: The Village at Oxford Greens
MLS 24137749 • Real Estate Two, Karen Berwick
Heritage Village
![103 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
103 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24135394 • Joseph Bette REALTORS Inc, Justin ...
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 24137961 • Coldwell Banker Realty, Claudia Fo...
Bidwell Village
![94 STONEHOUSE RD UNIT 10, COVENTRY, CT, ..., Coventry, CT 06238]()
3 beds
|3 baths
|1,717 sq ft
94 STONEHOUSE RD UNIT 10, COVENTRY, CT, ...
Community: Bidwell Village
MLS 24128107 • ERA Blanchard & Rossetto, Cheri Tr...
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Oronoque Village
![164 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,175 sq ft
|Condo
164 BISON LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24139444 • Stacy Blake Realty LLC, Celina Cuo...
Heritage Village
![859 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
859 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24116487 • Litchfield County Real Estate, Cou...
Oronoque Village
![87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,454 sq ft
|Condo
87 CREEK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24140020 • Oronoque Real Estate, Monica Dalto...
Fieldstone Village
![206 DEERFIELD LN # 206, ORANGE, CT, 0647..., Orange, CT 06477]()
2 beds
|3 baths
|1,650 sq ft
|Condo
206 DEERFIELD LN # 206, ORANGE, CT, 0647...
Community: Fieldstone Village
MLS 24136607 • Coldwell Banker Realty, Judy Coope...
Gloria Commons
![10 LUCIUS CT # 10, MILFORD, CT, 06461, Milford, CT 06461]()
2 beds
|3 baths
|2,061 sq ft
|Condo
10 LUCIUS CT # 10, MILFORD, CT, 06461
Community: Gloria Commons
MLS 24125515 • Preston Gray Real Estate, Katie Da...
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
![259 NEWCASTLE CT E, RIDGE, NY, 11961, Ridge, NY 11961]()
1 beds
|1 baths
|875 sq ft
|Condo
259 NEWCASTLE CT E, RIDGE, NY, 11961
Community: Leisure Village
MLS 878336 • Barons Real Estate Associates, David...
Leisure Village
![166 VENTRY CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 895352 • Voro LLC, Lauren A. Granger
Leisure Knoll
![323 BROWNFIELD DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 919433 • Daniel Gale Sothebys Intl Rlty, Bonn...
New
Fairfield at St. James
![401 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
1 beds
|2 baths
|900 sq ft
|Condo
401 CABOT CT, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 935978 • Howard Hanna Coach, Patricia Gisbert
Leisure Village
![46 TRENT CT C, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 916420 • Frontline Realty Group LLC, Lisa Kne...
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Leisure Village
![280 BERWICK CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 927775 • Coldwell Banker M&D Good Life, Micha...
Fairfield at St. James
![914 FENWAY RD, SAINT JAMES, NY, 11780, Saint James, NY 11780]()
2 beds
|2 baths
|1,200 sq ft
|Condo
914 FENWAY RD, SAINT JAMES, NY, 11780
Community: Fairfield at St. James
MLS 886931 • Douglas Elliman Real Estate, Laura R...
Leisure Village
![169 VENTRY CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 932590 • Leisure Living Realty Inc, Paulina R...
Leisure Village
![474 DARWEN DR B, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 911211 • Douglas Elliman Real Estate, Nicole ...
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....
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
Encore at Lake Grove
![22 SONATA CT, LAKE GROVE, NY, 11755, Lake Grove, NY 11755]()
2 beds
|2 baths
|1,429 sq ft
|Condo
22 SONATA CT, LAKE GROVE, NY, 11755
Community: Encore at Lake Grove
MLS 933888 • Signature Premier Properties, Rowena...
Glenwood Village
![1661 OLD COUNTRY RD 506, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,232 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 506, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 930276 • Signature Premier Properties, Noreen...
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
Fairfield at St. James
![607 CABOT CT 607, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
1 beds
|2 baths
|929 sq ft
|Condo
607 CABOT CT 607, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 920102 • Howard Hanna Coach, Kathleen E. Beck...
Stoneleigh Woods at Riverhead
![159 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|3 baths
|2,172 sq ft
|House
159 STONELEIGH DR, RIVERHEAD, NY, 11901
Community: Stoneleigh Woods at Riverhead
MLS 901369 • Douglas Elliman Real Estate, Mercede...
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New
Leisure Knoll
![145 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 936582 • Frontline Realty Group LLC, Nicholas...
New
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...
New
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 ...
Setauket Meadows
![95 COVE LN, EAST SETAUKET, NY, 11733, East Setauket, NY 11733]()
2 beds
|3 baths
|1,991 sq ft
|Condo
95 COVE LN, EAST SETAUKET, NY, 11733
Community: Setauket Meadows
MLS 926626 • Shea & Sanders Real Estate Inc, John...
Foxwood Village
![1407 MIDDLE RD UNIT 258, CALVERTON, NY, ..., Calverton, NY 11933]()
3 beds
|2 baths
|1,568 sq ft
|Manufactured Home
1407 MIDDLE RD UNIT 258, CALVERTON, NY, ...
Community: Foxwood Village
MLS 928912 • Signature Premier Properties, Heathe...
Frequently Asked Questions
In Southold, there is 1 small community with less than 500 homes.
The smallest 55+ community in Southold has 92 homes, the largest has 92 homes, and the average community consists of 92 homes.
No, there are no gated 55+ communities in Southold.
On average, listings in 55+ community in Southold stay on the market for around 169 days. The average price of homes for sale in this community is approximately $527,500, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Founders Village average around $527,500.
Want more information about active adult communities around Southold?
Want to learn more about 55+ communities in Southold?
94
communities
near Southold
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© 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: Nov 20, 2025.
This application does not include information on all of the properties available for sale at this time.
