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

94 communities near Southold

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Founders Village

$500Ks - $600Ks

Founders Village, Southold, NY

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

3.6 rating (7 reviews)

Heritage Village

$100Ks - $500Ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

Leisure Village

$200Ks - $400Ks

Leisure Village, Ridge, NY

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

Oronoque Village

$200Ks - $600Ks

Oronoque Village, Stratford, CT

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

The Village at Oxford Gre...

$500Ks - $700Ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes

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Questions? Call us: (631) 407-2675

Leisure Knoll

$300Ks - $400Ks

Leisure Knoll, Ridge, NY

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

5 rating (2 reviews)

Fairfield at St. James

$400Ks - $400Ks

Fairfield at St. James, St. James, NY

Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes

Leisure Glen

$400Ks - $400Ks

Leisure Glen, Ridge, NY

Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes

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

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3.7 rating (3 reviews)

Greenwood Village

$100Ks - $200Ks

Greenwood Village, Manorville, NY

Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes

Regency at Prospect

$300Ks - $500Ks

Regency at Prospect, Prospect, CT

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

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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Questions? Call us: (631) 407-2675

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 ...

$300Ks - $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

$800Ks - $800Ks

Vineyards at Blue Point, Blue Point, NY

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes

The Seasons at Elwood

$800Ks - $900Ks

The Seasons at Elwood, East Northport, NY

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

Meadow Brook Estates

$500Ks - $500Ks

Meadow Brook Estates, Oxford, CT

Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes

5 rating (1 reviews)

Encore Atlantic Shores

$600Ks - $800Ks

Encore Atlantic Shores, Eastport, NY

Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes

4.9 rating (14 reviews)

Chatfield Farms

$500Ks - $600Ks

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

Woodridge Strathmore Terr...

$400Ks - $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

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

Questions? Call us: (631) 407-2675

Saddle Lakes

$400Ks - $400Ks

Saddle Lakes, Riverhead, NY

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

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 - $500Ks

Sunken Pond Estates, Riverhead, NY

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

The Seasons at East North...

$700Ks - $700Ks

The Seasons at East North..., East Northport, NY

New Construction | 55+ age-restricted | Built 2023 - present | 190 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 - $700Ks

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

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

The Powder Forest Homes

$600Ks - $700Ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes

Stoneleigh Woods at River...

$600Ks - $600Ks

Stoneleigh Woods at River..., Riverhead, NY

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

Strathmore Gate East

$300Ks - $400Ks

Strathmore Gate East, Coram, NY

Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes

Beckley Farms

$300Ks - $400Ks

Beckley Farms, Berlin, CT

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

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

Questions? Call us: (631) 407-2675

South Pond Village

$100Ks - $200Ks

South Pond Village, Bloomfield, CT

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

Setauket Meadows

$600Ks - $700Ks

Setauket Meadows, Setauket, NY

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

The Manors at The Colony ...

$400Ks - $500Ks

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

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

Vineyards at Brookfield

$700Ks - $700Ks

Vineyards at Brookfield, Center Moriches, NY

New Construction | 55+ age-restricted | Built 2019 - present | 146 homes

Fieldstone Village

$500Ks - $800Ks

Fieldstone Village, Orange, CT

Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes

643 HERITAGE VLG A, SOUTHBURY, CT, 06488

Condo

289 AGAWAM DR 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

Oronoque Village

488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$619,000

2 beds

3 baths

1,438 sq ft

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Spring Lake Village

373 LAKEVIEW DR # 373, SOUTHINGTON, CT, ..., Southington, CT 06489

$259,900

2 beds

2 baths

1,188 sq ft

Condo

373 LAKEVIEW DR # 373, SOUTHINGTON, CT, ...

Community: Spring Lake Village

Heritage Village

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

$535,000

3 beds

2 baths

1,716 sq ft

Condo

623 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$515,000

3 beds

2 baths

1,716 sq ft

Condo

977 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

1008 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$399,000

2 beds

2 baths

1,432 sq ft

Condo

1008 HERITAGE VLG B, SOUTHBURY, CT, 0648...

Community: Heritage Village

Chatfield Farms

18 FIELDSTONE LN # 18, BEACON FALLS, CT,..., Beacon Falls, CT 06403

$599,000

2 beds

3 baths

2,719 sq ft

44 HERITAGE VLG F, SOUTHBURY, CT, 06488

Condo

185 COUNTRY CLUB DR # 185, OXFORD, CT, 0...

Community: The Village at Oxford Greens

Leisure Village

259 NEWCASTLE CT E, RIDGE, NY, 11961, Ridge, NY 11961

$254,900

1 beds

1 baths

875 sq ft

Condo

259 NEWCASTLE CT E, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

120 EXMORE CT D, RIDGE, NY, 11961, Ridge, NY 11961

$239,990

1 beds

1 baths

684 sq ft

Condo

120 EXMORE CT D, RIDGE, NY, 11961

Community: Leisure Village

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

Questions? Call us: (631) 407-2675

Leisure Village

96 ENFIELD CT B, RIDGE, NY, 11961, Ridge, NY 11961

$424,000

2 beds

2 baths

1,486 sq ft

Condo

96 ENFIELD CT B, RIDGE, NY, 11961

Community: Leisure Village

Encore Atlantic Shores

113 OVERTURE PL, EASTPORT, NY, 11941, Eastport, NY 11941

$895,000

2 beds

3 baths

3,037 sq ft

Condo

113 OVERTURE PL, EASTPORT, NY, 11941

Community: Encore Atlantic Shores

New Vineyards at Moriches

134 HALLEY DR, CENTER MORICHES, NY, 1193..., Center Moriches, NY 11934

$735,000

3 beds

3 baths

2,933 sq ft

Condo

134 HALLEY DR, CENTER MORICHES, NY, 1193...

Community: Vineyards at Moriches

Glenwood Village

1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ..., Riverhead, NY 11901

$149,999

2 beds

1 baths

816 sq ft

Mobile Home

1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ...

Community: Glenwood Village

Leisure Village

280 BERWICK CT A, RIDGE, NY, 11961, Ridge, NY 11961

$359,900

2 beds

1 baths

836 sq ft

Condo

280 BERWICK CT A, RIDGE, NY, 11961

Community: Leisure Village

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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

94 communities near Southold

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REIN updates its listings on a daily basis. Data last updated: Nov 13, 2025.
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Southold, NY 55+ active adult communities & homes for sale

94 communities near Southold

199 homes near Southold

2 beds

2 baths

1,365 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,063 sq ft

Condo

3 beds

3 baths

1,545 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,758 sq ft

Condo

2 beds

3 baths

2,061 sq ft

Condo

2 beds

2 baths

1,314 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,447 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,308 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

3 baths

1,620 sq ft

Condo

2 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,188 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds