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

95 communities 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

New The Villages at Mount Sinai Park

10 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$749,000

3 beds

3 baths

2,500 sq ft

House

10 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

New Leisure Knoll

225 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$540,000

2 beds

2 baths

1,094 sq ft

House

225 KINGSTON DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New The Villages at Mount Sinai Park

54 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$929,000

3 beds

3 baths

2,816 sq ft

House

54 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

New The Villages at Mount Sinai Park

68 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$839,999

2 beds

2 baths

1,736 sq ft

House

68 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

New Saddle Lakes

156 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$629,000

3 beds

3 baths

1,837 sq ft

Condo

156 SCENIC LAKE DR, RIVERHEAD, NY, 11901

Community: Saddle Lakes

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

Questions? Call us: (631) 407-2675

New Encore at Lake Grove

8 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755

$634,000

2 beds

3 baths

1,378 sq ft

Condo

8 SYMPHONY DR, BROOKHAVEN, NY, 11755

Community: Encore at Lake Grove

New Leisure Knoll

257 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$399,000

2 beds

2 baths

1,000 sq ft

Condo

257 EDINBURGH DR, BROOKHAVEN, NY, 11961

1302 BALTUSROL BLVD, RIVERHEAD, NY, 1190...

Community: Stoneleigh Woods at Riverhead

New Oronoque Village

664 OSAGE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$499,000

1 beds

3 baths

1,438 sq ft

664 OSAGE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Oronoque Village

543 N TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$585,000

1 beds

3 baths

1,426 sq ft

Condo

543 N TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

New Encore at Lake Grove

176 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755

$609,000

2 beds

2 baths

1,429 sq ft

Condo

176 SYMPHONY DR, BROOKHAVEN, NY, 11755

Community: Encore at Lake Grove

New Regency at Prospect

196 SYCAMORE DR 196, PROSPECT, CT, 06712, Prospect, CT 06712

$307,127

3 beds

2 baths

1,500 sq ft

Condo

196 SYCAMORE DR 196, PROSPECT, CT, 06712

Condo

541 STRATFORD LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

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

Questions? Call us: (631) 407-2675

Heritage Village

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

$309,000

3 beds

2 baths

1,716 sq ft

Condo

847 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

132 BISON LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$470,000

1 beds

3 baths

1,426 sq ft

Condo

132 BISON LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$405,000

2 beds

2 baths

1,432 sq ft

Condo

648 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Fairfield at St. James

309 FLAIR DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$454,000

1 beds

2 baths

983 sq ft

Condo

309 FLAIR DR, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Foxwood Village

1407 MIDDLE RD 253, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$449,000

3 beds

2 baths

1,753 sq ft

House

1407 MIDDLE RD 253, RIVERHEAD, NY, 11933

Community: Foxwood Village

Leisure Village

265 NEWCASTLE CT B, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$335,000

2 beds

1 baths

875 sq ft

Condo

265 NEWCASTLE CT B, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Fairfield at St. James

607 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$529,000

1 beds

2 baths

950 sq ft

Condo

607 CABOT CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Stone Ridge Estates

170 LARRY LN, HUNTINGTON, NY, 11746, Huntington, NY 11746

$789,000

2 beds

2 baths

1,415 sq ft

Condo

170 LARRY LN, HUNTINGTON, NY, 11746

Community: Stone Ridge Estates

Fairfield at St. James

604 CABOT CT 604, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$499,000

2 beds

2 baths

10 sq ft

Condo

604 CABOT CT 604, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Whitney Glen

32 WHITNEY GLN 32, WESTPORT, CT, 06880, Westport, CT 06880

$459,000

1 beds

2 baths

949 sq ft

Condo

32 WHITNEY GLN 32, WESTPORT, CT, 06880

Community: Whitney Glen

Encore at Lake Grove

58 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755

$629,990

2 beds

3 baths

Condo

58 SYMPHONY DR, BROOKHAVEN, NY, 11755

Community: Encore at Lake Grove

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

Questions? Call us: (631) 407-2675

South Pond Village

20 REED CT 20, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$245,000

2 beds

2 baths

1,202 sq ft

Condo

20 REED CT 20, BLOOMFIELD, CT, 06002

Community: South Pond Village

Pond Spring Village

35 OCTOBER LN 35, BEACON FALLS, CT, 0646..., Beacon Falls, CT 06468

$420,000

2 beds

3 baths

1,328 sq ft

Condo

35 OCTOBER LN 35, BEACON FALLS, CT, 0646...

Community: Pond Spring Village

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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95 communities

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

95 communities near Southold

184 homes near Southold

3 beds

3 baths

2,500 sq ft

House

2 beds

2 baths

1,094 sq ft

House

3 beds

3 baths

2,816 sq ft

House

2 beds

2 baths

1,736 sq ft

House

3 beds

3 baths

1,837 sq ft

Condo

2 beds

3 baths

1,378 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

3 beds

3 baths

2,652 sq ft

Condo

2 beds

3 baths

1,942 sq ft

Condo

2 beds

3 baths

2,820 sq ft

Condo

2 beds

2 baths

1,944 sq ft

Condo

2 beds

3 baths

1,350 sq ft

Condo

1 beds

3 baths

1,438 sq ft

1 beds

3 baths

1,426 sq ft

Condo

2 beds

2 baths

1,429 sq ft

Condo

3 beds

2 baths

1,500 sq ft

Condo

2 beds

3 baths

2,256 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths