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Southold, NY 55+ active adult communities & homes for sale - Page 2
95 communities near Southold
184 homes near Southold
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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
$100ks
- $300ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
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Built 1969 - 1986
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1,500 homes
$200ks
- $400ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
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Built 1972 - 1982
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701 homes
$200ks
- $400ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
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929 homes
$400ks
- $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
Want to learn more about 55+ communities in Southold?
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$300ks
- $600ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
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Built 1985 - 1999
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343 homes
3.7 rating (3 reviews)
![Greenwood Village]()
$100ks
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
5 rating (2 reviews)
![Fairfield at St. James]()
$300ks
- $500ks
Fairfield at St. James, St. James, NY
Resale Only
|
55+ age-restricted
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Built 1972 - 1989
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653 homes
4 rating (8 reviews)
![Glenwood Village]()
$100ks
- $200ks
Glenwood Village, Riverhead, NY
New and Resale
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55+ age-restricted
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Built 1959 - present
|
588 homes
$300ks
- $400ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 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
The Manors at The Colony ..., Shirley, NY
New Construction
|
55+ age-restricted
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Built 2013 - present
|
150 homes
$400ks
- $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
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55+ age-restricted
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Built 2019 - present
|
125 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
$500ks
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
5 rating (1 reviews)
![Westhampton Pines]()
$900ks
- $1Ms
Westhampton Pines, Westhampton, NY
Resale Only
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55+ age-restricted
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Built 2005 - 2013
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189 homes
5 rating (1 reviews)
![The Villages at Mount Sin...]()
$600ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
185 homes
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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
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228 homes
3.5 rating (2 reviews)
![Foxwood Village]()
$200ks
- $400ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
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294 homes
$300ks
- $400ks
South Pond Village, Bloomfield, CT
Resale Only
|
55+ age-restricted
|
Built 1999 - 2005
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151 homes
$500ks
- $600ks
Setauket Meadows, Setauket, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
150 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
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55+ age-restricted
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Built 1970 - 2004
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640 homes
$600ks
- $900ks
Country Pointe PreserveYaphank, NY
New Construction
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55+ age-restricted
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Built 2024 - present
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152 homes
$300ks
- $400ks
Eagles Walk at East Quogu..., East Quogue, NY
Resale Only
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55+ age-restricted
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Built 2004 - 2014
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67 homes
$500ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only
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55+ age-restricted
|
Built 2004 - 2005
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85 homes
$500ks
- $600ks
Whitney Glen, Westport, CT
Resale Only
|
55+ age-restricted
|
Built 1982 - 1982
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62 homes
$400ks
- $500ks
Saddle Lakes, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2000 - 2002
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196 homes
$200ks
- $300ks
Hopmeadow Place, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2005
|
66 homes
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Questions? Call us:
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$400ks
- $500ks
Evergreen, Cromwell, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
52 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
$300ks
- $400ks
Beckley Farms, Berlin, CT
New and Resale
|
55+ age-restricted
|
Built 2010 - present
|
170 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
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
$800ks
- $1Ms
Village Vistas, Port Jefferson, NY
Resale Only
|
55+ age-restricted
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Built 2013 - 2017
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43 homes
$800ks
- $900ks
The Seasons at Elwood, East Northport, NY
Resale Only
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55+ age-restricted
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Built 2018 - 2020
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256 homes
5 rating (1 reviews)
![Sunken Pond Estates]()
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
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194 homes
$500ks
- $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction
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55+ age-restricted
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Built 2023 - present
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70 homes
$300ks
- $400ks
Bartlett Hill, Portland, CT
Resale Only
|
55+ age-restricted
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Built 2005 - 2011
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82 homes
4 rating (1 reviews)
![Vineyards at Blue Point]()
$500ks
- $700ks
Vineyards at Blue Point, Blue Point, NY
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
280 homes
Want to learn more about 55+ communities in Southold?
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Questions? Call us:
(631) 407-2675
$400ks
- $500ks
Founders Village, Southold, NY
Resale Only
|
55+ age-restricted
|
Built 1981 - 1985
|
92 homes
$200ks
- $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 1974 - 1985
|
226 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.
Leisure Knoll
![520 CRANSTON LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,574 sq ft
|Condo
520 CRANSTON LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 992872 • RE/MAX Signature Real Estate, Anthon...
Heritage Village
![551 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
551 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24171379 • William Raveis Real Estate, Tom Gr...
Oronoque Village
![298 BATON LN 298 A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,175 sq ft
|Condo
298 BATON LN 298 A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24168212 • BHGRE Gaetano Marra Homes, Daniell...
Fairfield at St. James
![604 GOTHAM DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
1 beds
|2 baths
|954 sq ft
|Condo
604 GOTHAM DR, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 993174 • Signature Premier Properties, Kerril...
Leisure Glen
![104 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
MLS 992607 • Douglas Elliman Real Estate, Donna W...
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Questions? Call us:
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Oronoque Village
![209 ACORN LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,438 sq ft
|Condo
209 ACORN LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24171201 • Sunset Creek Realty, LLC, Joseph F...
Leisure Village
![368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961]()
MLS 992407 • Figs Real Estate Group, Edward S. Fi...
Leisure Village
![110 EXMORE CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|1 baths
|1,085 sq ft
|Condo
110 EXMORE CT A, BROOKHAVEN, NY, 11961
Community: Leisure Village
MLS 992109 • Signature Premier Properties, Mildre...
Regency at Prospect
![156 SYCAMORE DR 156, PROSPECT, CT, 06712, Prospect, CT 06712]()
2 beds
|3 baths
|2,067 sq ft
|Condo
156 SYCAMORE DR 156, PROSPECT, CT, 06712
Community: Regency at Prospect
MLS 24170069 • Pavlik Real Estate LLC, Deborah Ri...
Heritage Village
![149 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
149 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24170635 • Coldwell Banker Realty, Maryanne B...
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.
Meadowbrook Pointe Links & Spa
![48 AUGUSTA DR, BROOKHAVEN, NY, 11763, Brookhaven, NY 11763]()
2 beds
|4 baths
|1,553 sq ft
|Condo
48 AUGUSTA DR, BROOKHAVEN, NY, 11763
Community: Meadowbrook Pointe Links & Spa
MLS 991344 • Signature Premier Properties, Matthe...
Heritage Village
![59 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,308 sq ft
|Condo
59 HERITAGE VLG F, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24170135 • Coldwell Banker Realty, Filomena R...
Oronoque Village
![619 ERIE LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,583 sq ft
|Condo
619 ERIE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24168547 • Coldwell Banker Realty, Christine ...
The Village at Oxford Greens
![1126 ST ANDREWS DR 96, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|1,955 sq ft
|Condo
1126 ST ANDREWS DR 96, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24170314 • EG Group Realty LLC, Shabnam Sadat
Fairview at Oxford Greens
![1126 ST ANDREWS DR 96, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|1,955 sq ft
|Condo
1126 ST ANDREWS DR 96, OXFORD, CT, 06478
Community: Fairview at Oxford Greens
MLS 24170314 • EG Group Realty LLC, Shabnam Sadat
Leisure Glen
![289 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
MLS 990561 • Howard Hanna Coach, Kalliopi C. Suar...
Want to learn more about 55+ communities in Southold?
55places can help!
Questions? Call us:
(631) 407-2675
Leisure Village
![323 A WOODBRIDGE DR, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961]()
2 beds
|2 baths
|1,278 sq ft
|Condo
323 A WOODBRIDGE DR, BROOKHAVEN, NY, 119...
Community: Leisure Village
MLS 989894 • Howard Hanna Coach, David Friedman
Heritage Village
![953 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
953 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24170076 • Realty ONE Group Connect, Paul Duh
Country Pointe Preserve
![3 JUNIPER LN 94, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980]()
2 beds
|3 baths
|2,389 sq ft
|Condo
3 JUNIPER LN 94, BROOKHAVEN, NY, 11980
Community: Country Pointe Preserve
MLS 990129 • Premier Prop At Meadowbrook Pt, Robe...
Stoneleigh Woods at Riverhead
![156 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|3 baths
|1,942 sq ft
|Condo
156 STONELEIGH DR, RIVERHEAD, NY, 11901
Community: Stoneleigh Woods at Riverhead
MLS 989122 • Northshore Properties Realty, Dylan ...
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 Glen
![155 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
MLS 988626 • Kerrigan Country Realty, Claire Vegl...
Oronoque Village
![564 PEQUOT LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|2 baths
|1,438 sq ft
|Condo
564 PEQUOT LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24169261 • Davis Owen Real Estate, Davis Owen
Hopmeadow Place
![1 W ST 223, SIMSBURY, CT, 06070, Simsbury, CT 06070]()
MLS 24169118 • Berkshire Hathaway NE Prop., Eilee...
Oronoque Village
![638A ONONDAGA LN, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,175 sq ft
|Condo
638A ONONDAGA LN, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24168699 • William Raveis Real Estate, Sailoz...
Encore Atlantic Shores
![11 OVATION PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941]()
2 beds
|3 baths
|3,037 sq ft
|House
11 OVATION PL, BROOKHAVEN, NY, 11941
Community: Encore Atlantic Shores
MLS 989209 • Blue Shark Realty Group Inc, Efthimi...
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 24168923 • Century 21 Bette Real Estate, Debo...
The Waterways at Moriches
![248 RIVER DR 248, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955]()
2 beds
|2 baths
|1,544 sq ft
|Condo
248 RIVER DR 248, BROOKHAVEN, NY, 11955
Community: The Waterways at Moriches
MLS 988378 • Corcoran, Mary R. Clay
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Heritage Village
![110 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
110 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24168738 • KW Legacy Partners, Scott Sasinous...
Heritage Village
![32 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
32 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24167676 • Keller Williams Realty, Lou Capell...
Heritage Village
![12 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
12 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24167926 • KW Legacy Partners, Mela Veltri Ca...
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.
Foxwood Village
![1407 MIDDLE RD 265, RIVERHEAD, NY, 11933, Riverhead, NY 11933]()
3 beds
|2 baths
|1,792 sq ft
|Manufactured Home
1407 MIDDLE RD 265, RIVERHEAD, NY, 11933
Community: Foxwood Village
MLS 986510 • Joanne Kane Gigantiello, Joanne Giga...
Leisure Glen
![82 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
MLS 981401 • Douglas Elliman Real Estate, Deirdre...
Leisure Knoll
![259 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,135 sq ft
|Condo
259 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 982740 • Realty Connect USA L I Inc, Sharon A...
Oronoque Village
![377 PIUTE LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|2,025 sq ft
|Condo
377 PIUTE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24167595 • House Real Estate, Maureen Greenbe...
The Villages at Mount Sinai Park
![16 OAKHURST CT, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766]()
2 beds
|2 baths
|1,929 sq ft
|House
16 OAKHURST CT, BROOKHAVEN, NY, 11766
Community: The Villages at Mount Sinai Park
MLS 984832 • Howard Hanna Coach, Julie P. Lapasot...
The Waterways at Moriches
![485 WOODSCREEK CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955]()
2 beds
|3 baths
|1,854 sq ft
|Condo
485 WOODSCREEK CT, BROOKHAVEN, NY, 11955
Community: The Waterways at Moriches
MLS 985436 • Realty Connect USA LLC, Roseann Bisc...
Leisure Village
![404 WOODBRIDGE RD B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961]()
2 beds
|1 baths
|907 sq ft
|Condo
404 WOODBRIDGE RD B, BROOKHAVEN, NY, 119...
Community: Leisure Village
MLS 985582 • Coldwell Banker M&D Good Life, Micha...
Gloria Commons
![32 LUCIUS CT 32, MILFORD, CT, 06460, Milford, CT 06460]()
2 beds
|3 baths
|2,079 sq ft
|Condo
32 LUCIUS CT 32, MILFORD, CT, 06460
Community: Gloria Commons
MLS 24165290 • Compass Connecticut, LLC, Katie O'...
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Beckley Farms
![13 CONCORD DR 13, BERLIN, CT, 06037, Berlin, CT 06037]()
MLS 24151720 • Coldwell Banker Realty, Sean Page
Glenwood Village
![1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,624 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 984954 • Joanne Kane Gigantiello, Joanne Giga...
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.
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?
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© 2026 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: May 14, 2026.
This application does not include information on all of the properties available for sale at this time.
