Southold, NY 55+ active adult communities & homes for sale - Page 5

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes

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

Want to learn more about 55+ communities in Southold? 55places can help!

Questions? Call us: (631) 407-2675

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

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 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

New and Resale | 55+ age-restricted | Built 1959 - present | 588 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.

The Manors at The Colony ...

$300ks - $400ks

The Manors at The Colony ..., Shirley, NY

New Construction | 55+ age-restricted | Built 2013 - present | 150 homes

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | 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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 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...

$600ks

The Villages at Mount Sin..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes

Want to learn more about 55+ communities in Southold? 55places can help!

Questions? Call us: (631) 407-2675

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 | 228 homes

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

New Construction | 55+ age-restricted | Built 2024 - present | 152 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

The Vineyards at Miller P...

$500ks

The Vineyards at Miller P..., Miller Place, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes

Whitney Glen

$500ks - $600ks

Whitney Glen, Westport, CT

Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes

Hopmeadow Place

$200ks - $300ks

Hopmeadow Place, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes

Want to learn more about 55+ communities in Southold? 55places can help!

Questions? Call us: (631) 407-2675

Evergreen

$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

Beckley Farms

$300ks - $400ks

Beckley Farms, Berlin, CT

New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes

The Seasons at Elwood

$800ks - $900ks

The Seasons at Elwood, East Northport, NY

Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

New Construction | 55+ age-restricted | Built 2023 - present | 70 homes

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 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? 55places can help!

Questions? Call us: (631) 407-2675

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes

1 2...3

Leisure Village

116 B EXMORE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$285,000

2 beds

1 baths

875 sq ft

Condo

116 B EXMORE CT, BROOKHAVEN, NY, 11961

Community: Leisure Village

Leisure Village

373 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$414,500

2 beds

1 baths

1,171 sq ft

Condo

373 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...

164 VILLAGE CIR, BROOKHAVEN, NY, 11949

Condo

244 RIVER DR, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

Want to learn more about 55+ communities in Southold? 55places can help!

Questions? Call us: (631) 407-2675

The Vineyards at Miller Place

48 AVERY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764

$659,900

2 beds

3 baths

1,486 sq ft

Condo

48 AVERY LN, BROOKHAVEN, NY, 11764

Community: The Vineyards at Miller Place

Glenwood Village

1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ..., Riverhead, NY 11901

$149,000

2 beds

1 baths

840 sq ft

Mobile Home

1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ...

Community: Glenwood Village

Heritage Village

902 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$379,900

2 beds

2 baths

1,398 sq ft

Condo

902 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Westhampton Pines

112 ASHLEY DR, SOUTHAMPTON, NY, 11977, Southampton, NY 11977

$1,295,000

3 beds

3 baths

2,306 sq ft

Condo

112 ASHLEY DR, SOUTHAMPTON, NY, 11977

Community: Westhampton Pines

Heritage Village

643 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$314,900

2 beds

2 baths

1,398 sq ft

Condo

643 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

740 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$409,000

2 beds

2 baths

1,432 sq ft

Condo

740 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

1097 ST ANDREWS DR 9, OXFORD, CT, 06478, Oxford, CT 06478

$780,580

2 beds

3 baths

2,536 sq ft

Condo

1097 ST ANDREWS DR 9, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$780,580

2 beds

3 baths

2,536 sq ft

Condo

1097 ST ANDREWS DR 9, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

1 2 3 4 5

Frequently Asked Questions

What size 55+ communities are there in Southold?

In Southold, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Southold?

The smallest 55+ community in Southold has 92 homes, the largest has 92 homes, and the average community consists of 92 homes.

Are there gated 55+ communities in Southold?

No, there are no gated 55+ communities in Southold.

How long do listings in 55+ communities in Southold typically stay on the market, and what is the average price of homes for sale?

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.

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Want to learn more about 55+ communities in Southold?

Call us: (631) 407-2675

184 homes

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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: May 14, 2026.
This application does not include information on all of the properties available for sale at this time.

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Southold, NY 55+ active adult communities & homes for sale - Page 5

95 communities near Southold

184 homes near Southold

2 beds

1 baths

875 sq ft

Condo

2 beds

1 baths

1,171 sq ft

Condo

2 beds

2 baths

1,323 sq ft

Condo

2 beds

1 baths

1,074 sq ft

Condo

2 beds

2 baths

938 sq ft

Condo

2 beds

2 baths

1,341 sq ft

Condo

2 beds

3 baths

2,331 sq ft

Condo

3 beds

2 baths

1,839 sq ft

Condo

2 beds

2 baths

1,147 sq ft

Condo

2 beds

2 baths

2,150 sq ft

Condo

2 beds

2 baths

871 sq ft

Condo

2 beds

2 baths

2,141 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,758 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,960 sq ft

Condo

2 beds

3 baths

1,486 sq ft

Condo

2 beds

1 baths

840 sq ft

Mobile Home

2 beds

2 baths

1,398 sq ft

Condo

3 beds