Call us at (631) 407-2675 to learn more about active adult communities in Southold

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

201 homes near Southold

Sort by:

Relevance

Relevance

3.6 rating (7 reviews) Heritage Village
$200ks - $500ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes
5 rating (2 reviews) Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
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
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 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
The Manors at The Colony ...
$300ks - $400ks
The Manors at The Colony ..., Shirley, NY
New Construction | 55+ age-restricted | Built 2013 - present | 150 homes
Leisure Glen
$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.
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 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
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
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
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
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
Eagles Walk at East Quogu...
$300ks - $400ks
Eagles Walk at East Quogu..., East Quogue, NY
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 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
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
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
Vineyards at Brookfield
$400ks - $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
Windcrest East
$400ks - $500ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Meadow Brook Estates
$300ks - $400ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
Country Village Estates
$300ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes
Founders Village
$400ks - $500ks
Founders Village, Southold, NY
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 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) Sunrise Village
$400ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes
Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes
Setauket Meadows
$500ks - $600ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes
The Vineyards at Mount Si...
$800ks - $1Ms
The Vineyards at Mount Si..., Mount Sinai, NY
New Construction | 55+ age-restricted | Built 2020 - present | 91 homes
Village Vistas
$800ks - $1Ms
Village Vistas, Port Jefferson, NY
Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 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
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 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
Stone Ridge Estates
$500ks - $600ks
Stone Ridge Estates, Dix Hills, NY
Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 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
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
Glenwood Village 1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,..., Riverhead, NY 11901
$469,000

2 beds

|

2 baths

|

1,500 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,...
Community: Glenwood Village
Heritage Village 1008 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$518,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

1008 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
Greenwood Village 89 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$89,000

1 beds

|

1 baths

|

812 sq ft

|

Condo

89 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Heritage Village 773 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$235,000

2 beds

|

2 baths

|

1,071 sq ft

|

Condo

773 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Glenwood Village 1661 OLD COUNTRY RD 233, RIVERHEAD, NY, ..., Riverhead, NY 11901
$239,999

2 beds

|

2 baths

|

980 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 233, RIVERHEAD, NY, ...
Community: Glenwood Village
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Pond Spring Village 111 PONDVIEW CIR, BEACON FALLS, CT, 0640..., Beacon Falls, CT 06403
$438,000

2 beds

|

2 baths

|

1,328 sq ft

|

Condo

111 PONDVIEW CIR, BEACON FALLS, CT, 0640...
Community: Pond Spring Village
The Village at Oxford Greens 349 NIBLICK LN 349, OXFORD, CT, 06478, Oxford, CT 06478
$658,000

3 beds

|

2 baths

|

2,008 sq ft

|

Condo

349 NIBLICK LN 349, OXFORD, CT, 06478
Heritage Village 972 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$360,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

972 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 349 NIBLICK LN, OXFORD, CT, 06478, Oxford, CT 06478
$658,000

3 beds

|

2 baths

|

2,152 sq ft

349 NIBLICK LN, OXFORD, CT, 06478
Heritage Village 176 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$284,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

176 HERITAGE VLG D, 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 33 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$510,000

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

33 GREENTREE CT, BROOKHAVEN, NY, 11967
The Waterways at Moriches 632 WATER WAY 32, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$799,000

2 beds

|

3 baths

|

1,874 sq ft

|

Condo

632 WATER WAY 32, BROOKHAVEN, NY, 11955
The Seasons at Elwood 178 SUMMER CIR, HUNTINGTON, NY, 11731, Huntington, NY 11731
$1,599,000

2 beds

|

3 baths

|

2,900 sq ft

|

Condo

178 SUMMER CIR, HUNTINGTON, NY, 11731
Greenwood Village 5131 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$135,000

2 beds

|

2 baths

|

987 sq ft

|

House

5131 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Fairfield at St. James 1205 GOTHAM DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$649,000

2 beds

|

2 baths

|

948 sq ft

|

Condo

1205 GOTHAM DR, SMITHTOWN, NY, 11780
Oronoque Village 46 BUCKSKIN LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$559,900

1 beds

|

2 baths

|

1,375 sq ft

|

Condo

46 BUCKSKIN LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Vineyards at Moriches 20 EMILIE DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934
$759,000

2 beds

|

3 baths

|

1,984 sq ft

|

Condo

20 EMILIE DR, BROOKHAVEN, NY, 11934
Heritage Village 701 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

701 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$589,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 24-B HERITAGE CRST B, SOUTHBURY, CT, 064..., Southbury, CT 06488
$398,500

2 beds

|

2 baths

|

1,217 sq ft

|

Condo

24-B HERITAGE CRST B, SOUTHBURY, CT, 064...
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 147 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$215,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

147 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 22 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$180,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

22 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Greenwood Village 130 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$119,000

2 beds

|

2 baths

|

1,177 sq ft

|

Condo

130 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Billingsgate 14 BILLINGSGATE DR 14, SIMSBURY, CT, 060..., Simsbury, CT 06070
$750,000

2 beds

|

3 baths

|

2,729 sq ft

|

Condo

14 BILLINGSGATE DR 14, SIMSBURY, CT, 060...
Community: Billingsgate
Encore Atlantic Shores 11 OVATION PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$885,000

2 beds

|

3 baths

|

2,900 sq ft

|

Condo

11 OVATION PL, BROOKHAVEN, NY, 11941
Heritage Village 184 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$209,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

184 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Manors at The Colony Preserve 22 CRICKET CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$425,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

22 CRICKET CT, BROOKHAVEN, NY, 11967
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Heritage Village 333 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$315,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

333 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Hopmeadow Place 1 W ST 310, SIMSBURY, CT, 06070, Simsbury, CT 06070
$385,000

2 beds

|

2 baths

|

1,430 sq ft

|

Condo

1 W ST 310, SIMSBURY, CT, 06070
Community: Hopmeadow Place
Oronoque Village 448 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614
$525,000

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

448 HAMMERSTONE LN B, STRATFORD, CT, 066...
Community: Oronoque 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.
Saddle Lakes 174 ADELE CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$649,000

2 beds

|

2 baths

|

1,631 sq ft

|

Condo

174 ADELE CT, RIVERHEAD, NY, 11901
Community: Saddle Lakes
Westhampton Pines 171 JONATHAN LN, SOUTHAMPTON, NY, 11977, Southampton, NY 11977
$1,345,000

3 beds

|

3 baths

|

2,310 sq ft

|

Condo

171 JONATHAN LN, SOUTHAMPTON, NY, 11977
Community: Westhampton Pines
Meadowbrook Pointe Links & Spa 163 AUGUSTA DR 163, BROOKHAVEN, NY, 1176..., Brookhaven, NY 11763
$699,990

2 beds

|

3 baths

|

1,558 sq ft

|

Condo

163 AUGUSTA DR 163, BROOKHAVEN, NY, 1176...
Heritage Village 945 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$398,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

945 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Vineyards at Brookfield 104 ARI LN, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934
$869,000

2 beds

|

4 baths

|

2,718 sq ft

|

Condo

104 ARI LN, BROOKHAVEN, NY, 11934
Country Village Estates 110 THEODORE DR 110, BROOKHAVEN, NY, 117..., Brookhaven, NY 11727
$475,000

2 beds

|

2 baths

|

1,261 sq ft

|

Condo

110 THEODORE DR 110, BROOKHAVEN, NY, 117...
The Powder Forest Homes 15 BANTRY RD 15, SIMSBURY, CT, 06070, Simsbury, CT 06070
$899,000

4 beds

|

3 baths

|

1,878 sq ft

15 BANTRY RD 15, SIMSBURY, CT, 06070
Oronoque Village 283 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614
$625,000

2 beds

|

3 baths

|

1,415 sq ft

|

Condo

283 AGAWAM DR A, 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 10 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$353,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

10 HERITAGE CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 1 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$225,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

1 HERITAGE VLG C, 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.
12345…6

Frequently Asked Questions


Want more information about active adult communities around Southold?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting optout@55places.com. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Southold?

Call us: (631) 407-2675
201 homes
Remove Boundaries ×
Map Satellite

Reinmlsx

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 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: Aug 27, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top