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Southold, NY 55+ active adult communities & homes for sale - Page 4

184 homes near Southold

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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
Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 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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The Village at Oxford Gre...
$400ks - $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes
The Manors at The Colony ...
$300ks - $400ks
The Manors at The Colony ..., Shirley, NY
New Construction | 55+ age-restricted | Built 2013 - present | 150 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
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 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
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 (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) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
Vineyards at Brookfield
$400ks - $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 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.
Country Pointe Preserve
$600ks - $900ks
Country Pointe PreserveYaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Stone Ridge Estates
$500ks - $600ks
Stone Ridge Estates, Dix Hills, NY
Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes
5 rating (1 reviews) Sunrise Village
$400ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes
Windmill Gate
$300ks - $400ks
Windmill Gate, Oakdale, NY
Resale Only | 55+ age-restricted | Built 1989 - 1991 | 110 homes
The Seasons at Elwood
$800ks - $900ks
The Seasons at Elwood, East Northport, NY
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Country Village Estates
$300ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes
The Vineyards at Miller P...
$500ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 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
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 Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
1 rating (1 reviews) Plymouth Estates at Mount...
$400ks - $500ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes
Meadow Brook Estates
$300ks - $400ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Regency Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 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
The Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
Oak Meadow Estates
$200ks - $300ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 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.
12...3
Plymouth Estates at Mount Sinai 26 ROSE LN, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$575,000

2 beds

|

2 baths

|

1,563 sq ft

|

Condo

26 ROSE LN, BROOKHAVEN, NY, 11766
Heritage Village 2 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$350,000

2 beds

|

2 baths

|

1,572 sq ft

|

Condo

2 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Villages at Mount Sinai Park 10 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$749,000

3 beds

|

3 baths

|

2,500 sq ft

|

House

10 LOUDEN LOOP, BROOKHAVEN, NY, 11766
The Villages at Mount Sinai Park 54 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$899,000

3 beds

|

3 baths

|

2,816 sq ft

|

House

54 LOUDEN LOOP, BROOKHAVEN, NY, 11766
The Villages at Mount Sinai Park 68 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$799,999

2 beds

|

2 baths

|

1,736 sq ft

|

House

68 LOUDEN LOOP, BROOKHAVEN, NY, 11766
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
The Village at Oxford Greens 505 TRADITIONS CT 505, OXFORD, CT, 06478, Oxford, CT 06478
$755,000

3 beds

|

3 baths

|

2,652 sq ft

|

Condo

505 TRADITIONS CT 505, OXFORD, CT, 06478
Stoneleigh Woods at Riverhead 47 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$659,000

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

47 STONELEIGH DR, RIVERHEAD, NY, 11901
Heritage Village 916 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$379,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

916 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$519,000

2 beds

|

3 baths

|

1,434 sq ft

|

Condo

315 NAVAJO LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 14 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$269,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

14 HERITAGE CIR B, 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.
The Manors at The Colony Preserve 17 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$559,000

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

17 GREENTREE CT, BROOKHAVEN, NY, 11967
Leisure Village 265 NEWCASTLE CT B, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$335,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

265 NEWCASTLE CT B, BROOKHAVEN, NY, 1196...
Community: Leisure Village
Heritage Village 551 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$239,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

551 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 149 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$219,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

149 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 59 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488
$219,900

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

59 HERITAGE VLG F, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 619 ERIE LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$635,000

1 beds

|

3 baths

|

1,583 sq ft

|

Condo

619 ERIE LN 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
Fairview at Oxford Greens 1126 ST ANDREWS DR 96, OXFORD, CT, 06478, Oxford, CT 06478
$801,070

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1126 ST ANDREWS DR 96, OXFORD, CT, 06478
The Village at Oxford Greens 1126 ST ANDREWS DR 96, OXFORD, CT, 06478, Oxford, CT 06478
$801,070

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1126 ST ANDREWS DR 96, OXFORD, CT, 06478
Heritage Village 953 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$260,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

953 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Stoneleigh Woods at Riverhead 156 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$649,000

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

156 STONELEIGH DR, RIVERHEAD, NY, 11901
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 638A ONONDAGA LN, STRATFORD, CT, 06614, Stratford, CT 06614
$510,000

1 beds

|

3 baths

|

1,175 sq ft

|

Condo

638A ONONDAGA LN, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 44 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488
$205,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

44 HERITAGE VLG F, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 12 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$239,900

1 beds

|

1 baths

|

928 sq ft

|

Condo

12 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Foxwood Village 1407 MIDDLE RD 265, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$469,000

3 beds

|

2 baths

|

1,792 sq ft

|

Manufactured Home

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933
Community: Foxwood Village
Oronoque Village 377 PIUTE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$465,000

1 beds

|

3 baths

|

2,025 sq ft

|

Condo

377 PIUTE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
The Villages at Mount Sinai Park 16 OAKHURST CT, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$789,000

2 beds

|

2 baths

|

1,929 sq ft

|

House

16 OAKHURST CT, BROOKHAVEN, NY, 11766
The Waterways at Moriches 485 WOODSCREEK CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$778,000

2 beds

|

3 baths

|

1,854 sq ft

|

Condo

485 WOODSCREEK CT, BROOKHAVEN, NY, 11955
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Glenwood Village 1661 OLD COUNTRY RD 417, RIVERHEAD, NY, ..., Riverhead, NY 11901
$329,000

2 beds

|

2 baths

|

1,344 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 417, RIVERHEAD, NY, ...
Community: Glenwood Village
Heritage Village 930 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$439,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

930 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Manors at The Colony Preserve 15 CRICKET CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$499,999

2 beds

|

2 baths

|

1,322 sq ft

|

Condo

15 CRICKET CT, BROOKHAVEN, NY, 11967
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 191 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$139,999

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

191 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
South Pond Village 78 SILO WAY 78, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002
$289,900

3 beds

|

3 baths

|

1,639 sq ft

|

Condo

78 SILO WAY 78, BLOOMFIELD, CT, 06002
Community: South Pond Village
Heritage Village 4 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

4 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Glenwood Village 1661 OLD COUNTRY RD 62, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$409,900

3 beds

|

2 baths

|

1,680 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 62, RIVERHEAD, NY, 1...
Community: Glenwood Village
Heritage Village 53 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$269,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

53 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Regency at Woodbridge 27 HERITAGE LN, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525
$599,900

3 beds

|

3 baths

|

Condo

27 HERITAGE LN, WOODBRIDGE, CT, 06525
Heritage Village 101 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$215,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

101 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Sunken Pond Estates 3006 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$460,000

2 beds

|

2 baths

|

1,587 sq ft

|

Condo

3006 AMEN COR, RIVERHEAD, NY, 11901
Community: Sunken Pond Estates
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Heritage Village 1016 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$225,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

1016 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
Heritage Village 22 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$325,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

22 HERITAGE CIR 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.
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