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Southold, NY 55+ active adult communities & homes for sale

228 homes near Southold

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No reviews yet Founders Village
$500Ks - $500Ks
Founders Village, Southold, NY
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes
3.6 rating (7 reviews) Heritage Village
$100Ks - $400Ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes
No reviews yet Leisure Village
$200Ks - $400Ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
No reviews yet Oronoque Village
$400Ks - $600Ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
No reviews yet The Village at Oxford Gre...
$500Ks - $600Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes
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No reviews yet Leisure Knoll
$300Ks - $500Ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
5 rating (1 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 - $500Ks
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
4 rating (8 reviews) Glenwood Village
$100Ks - $400Ks
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.
3.7 rating (3 reviews) Greenwood Village
<$100k - $200Ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
No reviews yet Regency at Prospect
$400Ks - $400Ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
No reviews yet The Waterways at Moriches
$400Ks - $600Ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
4 rating (5 reviews) South Shore Village
$600Ks - $800Ks
South Shore Village, South Kingstown, RI
New and Resale | 55+ age-restricted | Built 2016 - present | 303 homes
3.5 rating (2 reviews) Foxwood Village
$300Ks - $400Ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
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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
4.6 rating (9 reviews) Meadowbrook Pointe Links ...
$600Ks - $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
$600Ks - $900Ks
Vineyards at Blue Point, Blue Point, NY
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 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
No reviews yet Meadow Brook Estates
$500Ks - $500Ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 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) Encore Atlantic Shores
$700Ks - $800Ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
4.9 rating (14 reviews) Chatfield Farms
$500Ks - $500Ks
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
No reviews yet Woodridge Strathmore Terr...
$300Ks - $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
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Questions? Call us: (631) 407-2675
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
$400Ks - $400Ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes
5 rating (1 reviews) Sunken Pond Estates
$400Ks - $400Ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
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) The Villages at Mount Sin...
$700Ks - $800Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 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 Powder Forest Homes
$600Ks - $700Ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
No reviews yet Stoneleigh Woods at River...
$400Ks - $600Ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
No reviews yet Strathmore Gate East
$300Ks - $300Ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes
No reviews yet Beckley Farms
$300Ks - $400Ks
Beckley Farms, Berlin, CT
New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes
No reviews yet South Pond Village
$200Ks - $400Ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
No reviews yet Setauket Meadows
$600Ks - $700Ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes
No reviews yet The Manors at The Colony ...
$400Ks - $500Ks
The Manors at The Colony ..., Shirley, NY
New Construction | 55+ age-restricted | Built 2013 - present | 150 homes
No reviews yet Vineyards at Brookfield
$600Ks - $600Ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
No reviews yet Fieldstone Village
$500Ks - $800Ks
Fieldstone Village, Orange, CT
Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes
No reviews yet North Woods of Colchester
$300Ks - $400Ks
North Woods of Colchester, Colchester, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes
Heritage Village 9B HERITAGE CIR # 9, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$279,900

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

9B HERITAGE CIR # 9, SOUTHBURY, CT, 0648...
Community: Heritage Village
Heritage Village 225 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$185,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

225 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
Bartlett Hill 5 PEAR ORCHARD RD # 5, PORTLAND, CT, 064..., Portland, CT 06480
$589,900

2 beds

|

3 baths

|

2,208 sq ft

5 PEAR ORCHARD RD # 5, PORTLAND, CT, 064...
Community: Bartlett Hill
Oronoque Village 607 CHEROKEE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$318,000

1 beds

|

2 baths

|

1,454 sq ft

|

Condo

607 CHEROKEE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 224 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$349,000

2 beds

|

3 baths

|

1,572 sq ft

|

Condo

224 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Heritage Village 16 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$426,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

16 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 53 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$312,500

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

53 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Spring Lake Village 443 LAKEVIEW DR # 443, SOUTHINGTON, CT, ..., Southington, CT 06489
$289,900

2 beds

|

2 baths

|

1,188 sq ft

|

Condo

443 LAKEVIEW DR # 443, SOUTHINGTON, CT, ...
Community: Spring Lake Village
Heritage Village 93 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$247,000

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

93 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 682 CHAMPIONSHIP DR # 682, OXFORD, CT, 0..., Oxford, CT 06478
$559,900

2 beds

|

2 baths

|

1,592 sq ft

|

Condo

682 CHAMPIONSHIP DR # 682, OXFORD, CT, 0...
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 191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$419,900

2 beds

|

2 baths

|

1,716 sq ft

|

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 634 NORTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614
$529,900

2 beds

|

3 baths

|

1,454 sq ft

|

Condo

634 NORTH TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 685 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$379,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

685 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 164 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$320,000

1 beds

|

2 baths

|

1,175 sq ft

|

Condo

164 BISON LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Oronoque Village 173 MIDWOOD TRL B, STRATFORD, CT, 06614, Stratford, CT 06614
$650,000

2 beds

|

2 baths

|

1,454 sq ft

|

Condo

173 MIDWOOD TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Heritage Village 769 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$280,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

769 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Fairview at Oxford Greens 922 TILLINGHAST DR # 922, OXFORD, CT, 06..., Oxford, CT 06478
$599,900

2 beds

|

2 baths

|

1,688 sq ft

|

Condo

922 TILLINGHAST DR # 922, OXFORD, CT, 06...
The Village at Oxford Greens 922 TILLINGHAST DR # 922, OXFORD, CT, 06..., Oxford, CT 06478
$599,900

2 beds

|

2 baths

|

1,688 sq ft

|

Condo

922 TILLINGHAST DR # 922, OXFORD, CT, 06...
Founders Ridge UNIT 2-45 WEBSTER LN, MIDDLETOWN, CT, 06..., Middletown, CT 06457
$669,995

2 beds

|

2 baths

|

1,555 sq ft

UNIT 2-45 WEBSTER LN, MIDDLETOWN, CT, 06...
Community: Founders Ridge
Heritage Village 672 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$359,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

672 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
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 929 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$339,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

929 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 794 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$442,500

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

794 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 389 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

389 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 702 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$599,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

702 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 96 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

96 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
The Village at Oxford Greens 696 CHAMPIONSHIP DR # 696, OXFORD, CT, 0..., Oxford, CT 06478
$534,000

2 beds

|

2 baths

|

1,496 sq ft

|

Condo

696 CHAMPIONSHIP DR # 696, OXFORD, CT, 0...
New Glenwood Village 1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190..., Riverhead, NY 11901
$259,900

2 beds

|

2 baths

|

1,088 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190...
Community: Glenwood Village
Leisure Village 28 TRENT CT B, RIDGE, NY, 11961, Ridge, NY 11961
$379,999

2 beds

|

1 baths

|

1,200 sq ft

|

Condo

28 TRENT CT B, RIDGE, NY, 11961
Community: Leisure Village
Foxwood Village 1407 MIDDLE RD 203, CALVERTON, NY, 11933, Calverton, NY 11933
$420,000

3 beds

|

2 baths

|

1,568 sq ft

|

Manufactured Home

1407 MIDDLE RD 203, CALVERTON, NY, 11933
Community: Foxwood Village
Leisure Knoll 561 STRATFORD LN # 561, RIDGE, NY, 11961, Ridge, NY 11961
$485,000

2 beds

|

2 baths

|

1,150 sq ft

|

Condo

561 STRATFORD LN # 561, RIDGE, NY, 11961
Community: Leisure Knoll
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.
Greenwood Village 71 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949
$238,000

2 beds

|

2 baths

|

1,123 sq ft

|

Condo

71 DOGWOOD LN, MANORVILLE, NY, 11949
Community: Greenwood Village
New Stoneleigh Woods at Riverhead 8 LAKEVIEW CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$615,000

3 beds

|

3 baths

|

2,000 sq ft

|

Condo

8 LAKEVIEW CT, RIVERHEAD, NY, 11901
Vineyards at Moriches 30 TONI CT # 30, CENTER MORICHES, NY, 11..., Center Moriches, NY 11934
$725,000

2 beds

|

3 baths

|

2,204 sq ft

|

Condo

30 TONI CT # 30, CENTER MORICHES, NY, 11...
Leisure Knoll 365 SHEFFIELD CT, RIDGE, NY, 11961, Ridge, NY 11961
$369,999

2 beds

|

1 baths

|

963 sq ft

|

Condo

365 SHEFFIELD CT, RIDGE, NY, 11961
Community: Leisure Knoll
Encore at Lake Grove 3 CONCERTO DR, LAKE GROVE, NY, 11755, Lake Grove, NY 11755
$820,000

2 beds

|

3 baths

|

1,835 sq ft

|

Condo

3 CONCERTO DR, LAKE GROVE, NY, 11755
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Greenwood Village 10 ORANGE TREE CT, MANORVILLE, NY, 11949, Manorville, NY 11949
$210,000

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

10 ORANGE TREE CT, MANORVILLE, NY, 11949
Community: Greenwood Village
Greenwood Village 132 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$214,990

2 beds

|

2 baths

|

1,375 sq ft

|

Condo

132 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Meadowbrook Pointe Links & Spa 142 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763
$729,990

2 beds

|

3 baths

|

1,691 sq ft

|

Condo

142 AUGUSTA DR, MEDFORD, NY, 11763
Meadowbrook Pointe Links & Spa 42 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763
$649,990

2 beds

|

3 baths

|

1,534 sq ft

|

Condo

42 AUGUSTA DR, MEDFORD, NY, 11763
New Saddle Lakes 107 SCENIC LAKE DR # 107, RIVERHEAD, NY,..., Riverhead, NY 11901
$639,000

2 beds

|

2 baths

|

1,631 sq ft

|

Condo

107 SCENIC LAKE DR # 107, RIVERHEAD, NY,...
Community: Saddle Lakes

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228 homes near Southold
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