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

$200Ks - $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

$400Ks

Leisure Knoll, Ridge, NY

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

5 rating (2 reviews)

Fairfield at St. James

$400Ks - $500Ks

Fairfield at St. James, St. James, NY

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

Leisure Glen

$500Ks

Leisure Glen, Ridge, NY

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

Spring Lake Village

$200Ks

Spring Lake Village, Southington, CT

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

4 rating (8 reviews)

Glenwood Village

$100Ks - $200Ks

Glenwood Village, Riverhead, NY

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

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.

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

$400Ks - $500Ks

Regency at Prospect, Prospect, CT

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

The Waterways at Moriches

$400Ks - $500Ks

The Waterways at Moriches, Moriches, NY

Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes

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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

$400Ks - $500Ks

Foxwood Village, Calverton, NY

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

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1 rating (1 reviews)

Plymouth Estates at Mount...

$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

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

Meadow Brook Estates, Oxford, CT

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

5 rating (1 reviews)

Encore Atlantic Shores

$700Ks - $800Ks

Encore Atlantic Shores, Eastport, NY

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

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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

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

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Saddle Lakes

$400Ks

Saddle Lakes, Riverhead, NY

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

Country Village Estates

$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

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

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5 rating (1 reviews)

The Villages at Mount Sin...

$500Ks - $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

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+ rental 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

The Manors at The Colony ...

$400Ks - $500Ks

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

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

Setauket Meadows

$600Ks - $700Ks

Setauket Meadows, Setauket, NY

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

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Questions? Call us: (631) 407-2675

Vineyards at Brookfield

$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

Oronoque Village

164 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$465,000

1 beds

2 baths

1,175 sq ft

Condo

164 BISON LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Long Hill Village

4 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611

2 beds

2 baths

1,590 sq ft

Condo

520 TRADITIONS CT N # 520, OXFORD, CT, 0...

Community: The Village at Oxford Greens

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Questions? Call us: (631) 407-2675

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New Regency at Woodbridge

10 HILLCREST DR # 5, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525

2 beds

3 baths

2,365 sq ft

930 TILLINGHAST DR # 930, OXFORD, CT, 06...

Community: The Village at Oxford Greens

Heritage Village

331 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488

$275,500

2 beds

2 baths

1,365 sq ft

Condo

331 HERITAGE VLG E, SOUTHBURY, CT, 06488

Community: Heritage Village

New Heritage Village

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

$367,900

3 beds

2 baths

1,716 sq ft

Condo

859 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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Heritage Village

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

$329,000

3 beds

2 baths

1,716 sq ft

Condo

701 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Fieldstone Village

323 GOOSE LN # 323, ORANGE, CT, 06477, Orange, CT 06477

$848,500

3 beds

4 baths

1,962 sq ft

Condo

323 GOOSE LN # 323, ORANGE, CT, 06477

Community: Fieldstone Village

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Heritage Village

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

$329,000

2 beds

2 baths

1,432 sq ft

Condo

98 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$285,000

2 beds

2 baths

1,432 sq ft

Condo

132 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

889 GLACIER WAY # 889, SOUTHINGTON, CT, ..., Southington, CT 06489

$399,900

3 beds

2 baths

1,923 sq ft

Condo

889 GLACIER WAY # 889, SOUTHINGTON, CT, ...

Community: Spring Lake Village

Baldwin Station

7 FIRE THORN LN # 7, MILFORD, CT, 06461, Milford, CT 06461

$689,950

2 beds

3 baths

2,331 sq ft

Condo

7 FIRE THORN LN # 7, MILFORD, CT, 06461

Community: Baldwin Station

Oronoque Village

766 NYACK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$649,000

1 beds

3 baths

1,438 sq ft

Condo

766 NYACK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

1 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$249,900

2 beds

2 baths

1,044 sq ft

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (631) 407-2675

South Pond Village

81 SILO WAY # 81, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$274,900

2 beds

2 baths

1,204 sq ft

Condo

81 SILO WAY # 81, BLOOMFIELD, CT, 06002

Community: South Pond Village

Regency at Woodbridge

8 WHISPER RIDGE WAY # 43, WOODBRIDGE, CT..., Woodbridge, CT 06525

$668,000

3 beds

3 baths

Condo

8 WHISPER RIDGE WAY # 43, WOODBRIDGE, CT...

Community: Regency at Woodbridge

Heritage Village

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

$264,900

1 beds

1 baths

928 sq ft

Condo

953 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

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

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Spring Lake Village

621 OVERLOOK PATH # 621, SOUTHINGTON, CT..., Southington, CT 06489

$340,000

2 beds

3 baths

1,133 sq ft

Condo

621 OVERLOOK PATH # 621, SOUTHINGTON, CT...

Community: Spring Lake Village

Oronoque Village

195 BAYFIELD LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$499,000

1 beds

3 baths

1,575 sq ft

Condo

195 BAYFIELD LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Fairview at Oxford Greens

712 CHAMPIONSHIP DR # 712, OXFORD, CT, 0..., Oxford, CT 06478

$615,000

2 beds

2 baths

1,546 sq ft

Condo

712 CHAMPIONSHIP DR # 712, OXFORD, CT, 0...

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$615,000

2 beds

2 baths

1,546 sq ft

Condo

712 CHAMPIONSHIP DR # 712, OXFORD, CT, 0...

Community: The Village at Oxford Greens

Oronoque Village

617 CHEROKEE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$524,900

1 beds

3 baths

1,438 sq ft

Condo

617 CHEROKEE LN 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

Heritage Village

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

$225,000

1 beds

1 baths

928 sq ft

Condo

917 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage 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

568A HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488

$409,900

2 beds

2 baths

1,432 sq ft

Condo

568A HERITAGE VLG, SOUTHBURY, CT, 06488

Community: Heritage Village

Regency at Woodbridge

1 WHISPER RIDGE WAY # 51, WOODBRIDGE, CT..., Woodbridge, CT 06525

$749,000

3 beds

3 baths

2,180 sq ft

Condo

1 WHISPER RIDGE WAY # 51, WOODBRIDGE, CT...

Community: Regency at Woodbridge

Oronoque Village

289 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614

$639,900

1 beds

3 baths

1,620 sq ft

Condo

289 AGAWAM DR B, STRATFORD, CT, 06614

Condo

383 SEQUOIA LN A, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (631) 407-2675

Spring Lake Village

85 CLEARVIEW CT # 85, SOUTHINGTON, CT, 0..., Southington, CT 06489

$289,900

1 beds

2 baths

1,028 sq ft

Condo

85 CLEARVIEW CT # 85, SOUTHINGTON, CT, 0...

Community: Spring Lake Village

Heritage Village

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

$389,900

2 beds

2 baths

1,398 sq ft

Condo

902 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage 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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94 communities

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

94 communities near Southold

153 homes near Southold

1 beds

2 baths

1,175 sq ft

Condo

2 beds

2 baths

1,400 sq ft

2 beds

2 baths

1,365 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,590 sq ft

Condo

3 beds

3 baths

Condo

1 beds

3 baths

1,175 sq ft

Condo

2 beds

3 baths

1,404 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

2 beds

3 baths

2,365 sq ft

2 beds

2 baths

1,365 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

3 beds

4 baths

1,962 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

2 baths

1,923 sq ft

Condo

2 beds

3 baths

2,331 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo