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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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 - $700Ks

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

1 2...3

Leisure Glen

12 BALDWIN CT, RIDGE, NY, 11961, Ridge, NY 11961

$489,990

2 beds

2 baths

1,542 sq ft

Condo

12 BALDWIN CT, RIDGE, NY, 11961

Community: Leisure Glen

Glenwood Village

1661 OLD COUNTRY OLD COUNTRY RD, RIVERHE..., Riverhead, NY 11901

$285,000

2 beds

2 baths

1,232 sq ft

Manufactured Home

1661 OLD COUNTRY OLD COUNTRY RD, RIVERHE...

Community: Glenwood Village

Oronoque Village

375 PIUTE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$450,000

2 beds

3 baths

1,550 sq ft

Condo

375 PIUTE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

$450,000

2 beds

3 baths

1,550 sq ft

Condo

375 PIUTE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New Heritage Village

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

$390,000

2 beds

2 baths

1,398 sq ft

Condo

876 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (631) 407-2675

New Heritage Village

$390,000

2 beds

2 baths

1,398 sq ft

Condo

876 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

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

$254,900

1 beds

1 baths

875 sq ft

Condo

Community: Oronoque Village

Leisure Village

$259,000

1 beds

1 baths

680 sq ft

House

166 VENTRY CT B, RIDGE, NY, 11961

Community: Leisure Village

Heritage Village

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

$374,500

2 beds

2 baths

1,398 sq ft

Condo

889 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

$374,500

2 beds

2 baths

1,398 sq ft

Condo

889 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$539,000

3 beds

2 baths

1,716 sq ft

Condo

644 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

$539,000

3 beds

2 baths

1,716 sq ft

Condo

644 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (631) 407-2675

Heritage Village

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

$349,900

2 beds

2 baths

1,398 sq ft

Condo

643 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$335,000

2 beds

2 baths

1,432 sq ft

Condo

Community: Heritage Village

Heritage Village

$350,000

2 beds

2 baths

1,398 sq ft

Condo

966 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

643 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

1034 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$259,999

1 beds

1 baths

928 sq ft

Condo

1034 HERITAGE VLG B, SOUTHBURY, CT, 0648...

Community: Heritage Village

Heritage Village

$259,999

1 beds

1 baths

928 sq ft

Condo

1034 HERITAGE VLG B, SOUTHBURY, CT, 0648...

Community: Heritage Village

Greenwood Village

53 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$275,000

2 beds

2 baths

1,100 sq ft

Condo

Community: Fairfield at St. James

Leisure Glen

$479,990

2 beds

2 baths

1,542 sq ft

Condo

12 BALDWIN CT, RIDGE, NY, 11961

Condo

509 OAK BLUFF CT, MORICHES, NY, 11955

Community: The Waterways at Moriches

1 2 3 4 5 6 7 8 9 10…11

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.

Want more information about active adult communities around Southold?

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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 15, 2025.
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Southold, NY 55+ active adult communities & homes for sale

94 communities near Southold

403 homes near Southold

2 beds

2 baths

1,542 sq ft

Condo

2 beds

2 baths

1,232 sq ft

Manufactured Home

2 beds

3 baths

1,550 sq ft

Condo

2 beds

3 baths

1,550 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

1 beds

1 baths

875 sq ft

Condo

1 beds

1 baths

875 sq ft

Condo

1 beds

1 baths

680 sq ft

House

2 beds

3 baths

1,620 sq ft

Condo

1 beds

1 baths

680 sq ft

House

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,440 sq ft

Condo

2 beds