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Southold, NY 55+ rental communities & homes for rent

1 communities near Southold

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The Cornerstone at Hauppa...
The Cornerstone at Hauppa...
$3,511.06 - $3,981.06 / mo
Base rent from $3,430
The Cornerstone at Hauppa..., Hauppauge, NY
New Construction | 55+ age-restricted | Built 2019 - 2020 | 96 rental homes
96 rental homes Attached & Apartments
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Heritage Village 345 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$386,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

345 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24196164 • Keller Williams Realty, Marvin Ben... • Keller Williams Realty
Greenwood Village 105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949
$245,000

2 beds

|

2 baths

|

1,130 sq ft

|

Condo

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1...
Community: Greenwood Village
MLS 1029061 • Gateway to The Hamptons R E, Janet ... • Gateway to The Hamptons R E
Glenwood Village 1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901
$419,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 1011541 • Gateway to The Hamptons R E, Vivian... • Gateway to The Hamptons R E
New Heritage Village 738 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$329,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

738 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24202019 • Lamacchia Realty, Stephanie Plaza • Lamacchia Realty
New Granite Woods 35 NUTMEG RD B2, MIDDLEBURY, CT, 06762, Middlebury, CT 06762
$239,900

1 beds

|

1 baths

|

889 sq ft

|

Condo

35 NUTMEG RD B2, MIDDLEBURY, CT, 06762
Community: Granite Woods
MLS 24202228 • RE/MAX RISE, Maria Pinheiro • RE/MAX RISE
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Questions? Call us: (631) 407-2675
New Woodridge Strathmore Terrace 6 COBBLESTONE WAY, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$430,000

2 beds

|

2 baths

|

1,151 sq ft

|

Condo

6 COBBLESTONE WAY, BROOKHAVEN, NY, 11766
Community: Woodridge Strathmore Terrace
MLS 1043235 • S & J Property Management Corp, Jen... • S & J Property Management Corp
New Oronoque Village 393 OTTAWA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$350,000

1 beds

|

3 baths

|

1,118 sq ft

|

Condo

393 OTTAWA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24202099 • Joy Real Estate, Richard Persico • Joy Real Estate
New Foxwood Village 1407 MIDDLE RD 265, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$469,999

3 beds

|

2 baths

|

1,792 sq ft

|

Manufactured Home

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933
Community: Foxwood Village
MLS 1043007 • Douglas Elliman Real Estate, Sheryl... • Douglas Elliman Real Estate
New Leisure Village 463 B OLDHAM CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$389,990

2 beds

|

1 baths

|

1,074 sq ft

|

Condo

463 B OLDHAM CT, BROOKHAVEN, NY, 11961
Community: Leisure Village
MLS 1042796 • Century 21 KR Realty, Jane A. Argir... • Century 21 KR Realty
New Leisure Village 472 DARWEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$408,000

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

472 DARWEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Village
MLS 1043048 • World Prop Intl Sea to Sky, Matthew... • World Prop Intl Sea to Sky
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 South Pond Village 78 SILO WAY 78, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002
$289,500

3 beds

|

3 baths

|

1,639 sq ft

|

Condo

78 SILO WAY 78, BLOOMFIELD, CT, 06002
Community: South Pond Village
MLS 24200832 • Berkshire Hathaway NE Prop., Karen... • Berkshire Hathaway NE Prop.
New Plymouth Estates at Mount Sinai 7 POND CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$665,000

2 beds

|

2 baths

|

1,274 sq ft

|

Condo

7 POND CIR, BROOKHAVEN, NY, 11766
Community: Plymouth Estates at Mount Sinai
MLS 1040452 • BH&G R E Realty Connect, Judith A. ... • BH&G R E Realty Connect
New Leisure Knoll 152A LAURANCE LN A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$399,999

2 beds

|

1 baths

|

724 sq ft

|

Condo

152A LAURANCE LN A, BROOKHAVEN, NY, 1196...
Community: Leisure Knoll
MLS 1042894 • Coldwell Banker American Homes, Mar... • Coldwell Banker American Homes
New Leisure Glen 6 OAKDALE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$559,000

2 beds

|

2 baths

|

1,666 sq ft

|

Condo

6 OAKDALE CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
MLS 1042317 • Leisure Living Realty Inc, Laura Ru... • Leisure Living Realty Inc
New Leisure Glen 428 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$649,000

2 beds

|

2 baths

|

1,652 sq ft

|

Condo

428 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
MLS 1042640 • Signature Premier Properties, Mildr... • Signature Premier Properties
New Oronoque Village 138 BISON LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$480,000

2 beds

|

3 baths

|

1,438 sq ft

138 BISON LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24201494 • Coldwell Banker Realty, Christine ... • Coldwell Banker Realty
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
New Leisure Village 134 EASTBOURNE CT A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$349,999

2 beds

|

1 baths

|

836 sq ft

|

Condo

134 EASTBOURNE CT A, BROOKHAVEN, NY, 119...
Community: Leisure Village
MLS 1042262 • Century 21 AA Realty, Mary E. Gugli... • Century 21 AA Realty
New Sunrise Village 17 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782
$439,999

2 beds

|

1 baths

|

871 sq ft

|

Condo

17 REVERE DR, ISLIP, NY, 11782
Community: Sunrise Village
MLS 1041823 • Douglas Elliman Real Estate, Michel... • Douglas Elliman Real Estate
New Leisure Glen 454 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$649,000

2 beds

|

2 baths

|

1,652 sq ft

|

Condo

454 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
MLS 1041411 • Manzoni Real Estate, Ray Manzoni CB... • Manzoni Real Estate
New Heritage Village 857 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$235,000

2 beds

|

2 baths

|

1,071 sq ft

|

Condo

857 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24200789 • Keller Williams Realty, Karen Dibb... • Keller Williams Realty
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 Heritage Village 9 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$275,000

2 beds

|

2 baths

|

1,071 sq ft

|

Condo

9 HERITAGE CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24201310 • Berkshire Hathaway NE Prop., Scott... • Berkshire Hathaway NE Prop.
New Heritage Village 353 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$329,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

353 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24201344 • Century 21 Bette Real Estate, Just... • Century 21 Bette Real Estate
New Woodridge Strathmore Terrace 89 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$409,999

1 beds

|

1 baths

|

720 sq ft

|

Condo

89 HEARTHSIDE DR, BROOKHAVEN, NY, 11766
Community: Woodridge Strathmore Terrace
MLS 1042035 • Coldwell Banker American Homes, Ric... • Coldwell Banker American Homes
New Heritage Village 559 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$315,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

559 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24200880 • Robert J. Drakeley, Broker, CT REO... • Robert J. Drakeley, Broker
Vineyards at Blue Point 132 HALLEY DR, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772
$879,999

2 beds

|

4 baths

|

2,290 sq ft

|

Condo

132 HALLEY DR, BROOKHAVEN, NY, 11772
Community: Vineyards at Blue Point
MLS 1040054 • Next Phase Realty LLC, Lamar Lanier... • Next Phase Realty LLC
Eagles Walk at East Quogue 1401 AERIE WAY, SOUTHAMPTON, NY, 11942, Southampton, NY 11942
$565,000

2 beds

|

2 baths

|

1,271 sq ft

|

Condo

1401 AERIE WAY, SOUTHAMPTON, NY, 11942
Community: Eagles Walk at East Quogue
MLS 1041260 • Signature Premier Properties, Jeane... • Signature Premier Properties
Heritage Village 397 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$424,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

397 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24200929 • Keller Williams Realty, Lou Capell... • Keller Williams Realty
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Shaker Heights 12 COPLEY CIR 12, ENFIELD, CT, 06082, Enfield, CT 06082
$589,900

2 beds

|

2 baths

|

1,897 sq ft

|

Condo

12 COPLEY CIR 12, ENFIELD, CT, 06082
Community: Shaker Heights
MLS 73563615 • Berkshire Hathaway HomeServices Re... • Berkshire Hathaway HomeServices Realty Professionals
Founders Village 2555 YOUNGS AVE 3C, SOUTHOLD, NY, 11971, Southold, NY 11971
$550,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

2555 YOUNGS AVE 3C, SOUTHOLD, NY, 11971
Community: Founders Village
MLS 1027409 • Thomas J McCarthy Real Estate, Thom... • Thomas J McCarthy Real Estate
Leisure Knoll 185 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$405,000

2 beds

|

1 baths

|

1,014 sq ft

|

Condo

185 KINGSTON DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 1041185 • Douglas Elliman Real Estate, Kennet... • Douglas Elliman Real Estate
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 549 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$164,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

549 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24200695 • Berkshire Hathaway NE Prop., Maris... • Berkshire Hathaway NE Prop.
Encore Atlantic Shores 101 MOZART CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$779,000

2 beds

|

2 baths

|

2,044 sq ft

|

House

101 MOZART CT, BROOKHAVEN, NY, 11941
Community: Encore Atlantic Shores
MLS 1040804 • Compass Greater NY LLC, Laura S. Ca... • Compass Greater NY LLC
Heritage Village 1041 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$244,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

1041 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24193096 • Carey & Guarrera Real Estate, Alet... • Carey & Guarrera Real Estate
Greenwood Village 205 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$125,000

2 beds

|

2 baths

|

1,138 sq ft

|

House

205 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 1040375 • Dream Select Realty Corp, Juan A. R... • Dream Select Realty Corp
The Village at Oxford Greens 521 PUTTING GREEN LN 521, OXFORD, CT, 06..., Oxford, CT 06478
$675,000

3 beds

|

3 baths

|

2,735 sq ft

|

Condo

521 PUTTING GREEN LN 521, OXFORD, CT, 06...
Community: The Village at Oxford Greens
MLS 24199321 • William Pitt Sotheby's Int'l, Tom ... • William Pitt Sotheby's Int'l
Setauket Meadows 2 EMILYS WAY, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733
$799,500

2 beds

|

3 baths

|

1,842 sq ft

|

Condo

2 EMILYS WAY, BROOKHAVEN, NY, 11733
Community: Setauket Meadows
MLS 1039552 • Daniel Gale Sothebys Intl Rlty, Lyn... • Daniel Gale Sothebys Intl Rlty
Oronoque Village 546 N TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$539,000

2 beds

|

3 baths

|

1,434 sq ft

|

Condo

546 N TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24199616 • Coldwell Banker Realty, Mark Pires • Coldwell Banker Realty
Greenwood Village 162 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$154,888

2 beds

|

2 baths

|

1,078 sq ft

|

Condo

162 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 1039145 • Coldwell Banker American Homes, Rya... • Coldwell Banker American Homes
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Leisure Glen 272 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$549,000

2 beds

|

2 baths

|

1,456 sq ft

|

Condo

272 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
MLS 1039018 • Signature Premier Properties, Mildr... • Signature Premier Properties
Woodridge Strathmore Terrace 62 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$425,000

2 beds

|

2 baths

|

1,105 sq ft

|

Condo

62 HEARTHSIDE DR, BROOKHAVEN, NY, 11766
Community: Woodridge Strathmore Terrace
MLS 1033093 • Douglas Elliman Real Estate, Christ... • Douglas Elliman Real Estate
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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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.

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