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

94 communities near Southold

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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

3.7 rating (3 reviews)

Greenwood Village

<$100k - $200Ks

Greenwood Village, Manorville, NY

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

The Village at Oxford Gre...

$600Ks - $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

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The Waterways at Moriches

$400Ks - $500Ks

The Waterways at Moriches, Moriches, NY

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

4 rating (8 reviews)

Glenwood Village

$100Ks - $200Ks

Glenwood Village, Riverhead, NY

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

Fairview at Oxford Greens

$600Ks - $700Ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 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.

Regency at Woodbridge

$600Ks - $700Ks

Regency at Woodbridge, Woodbridge, CT

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

5 rating (1 reviews)

Encore Atlantic Shores

$700Ks

Encore Atlantic Shores, Eastport, NY

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

Leisure Glen

$400Ks - $500Ks

Leisure Glen, Ridge, NY

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

Stone Ridge Estates

$700Ks

Stone Ridge Estates, Dix Hills, NY

Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes

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Questions? Call us: (631) 407-2675

The Vineyards at Miller P...

$600Ks

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

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

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

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Questions? Call us: (631) 407-2675

Stoneleigh Woods at River...

$500Ks - $600Ks

Stoneleigh Woods at River..., Riverhead, NY

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

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

Leisure Knoll

$400Ks

Leisure Knoll, Ridge, NY

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

Spring Lake Village

$200Ks - $300Ks

Spring Lake Village, Southington, CT

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

The Manors at The Colony ...

$500Ks

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

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

4.9 rating (14 reviews)

Chatfield Farms

$500Ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

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5 rating (1 reviews)

Westhampton Pines

$1Ms

Westhampton Pines, Westhampton, NY

Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes

Oak Meadow Estates

$400Ks

Oak Meadow Estates, Torrington, CT

New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes

Bartlett Hill

$500Ks

Bartlett Hill, Portland, CT

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

Eagles Walk at East Quogu...

$500Ks

Eagles Walk at East Quogu..., East Quogue, NY

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 homes

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Country Village Estates

$400Ks

Country Village Estates, Coram, NY

Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes

3.5 rating (2 reviews)

Foxwood Village

$400Ks - $500Ks

Foxwood Village, Calverton, NY

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

Baldwin Station

$400Ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

Strathmore Gate East

$300Ks - $400Ks

Strathmore Gate East, Coram, NY

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

South Pond Village

$200Ks - $400Ks

South Pond Village, Bloomfield, CT

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

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Questions? Call us: (631) 407-2675

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

Granite Woods

$600Ks - $700Ks

Granite Woods, Middlebury, CT

New Construction | 55+ age-restricted | Built 2020 - present | 24 homes

Evergreen

$500Ks

Evergreen, Cromwell, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 52 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

Long Hill Village

$300Ks - $400Ks

Long Hill Village, Trumbull, CT

Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes

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Hopmeadow Place

$200Ks - $300Ks

Hopmeadow Place, Simsbury, CT

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

Gloria Commons

$400Ks

Gloria Commons, Milford, CT

Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes

Boulder Brook

$200Ks

Boulder Brook, Prospect, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes

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Questions? Call us: (631) 407-2675

Billingsgate

$400Ks - $600Ks

Billingsgate, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes

Castle Heights of Cheshir...

$500Ks - $600Ks

Castle Heights of Cheshir..., Cheshire, CT

Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes

1 2...3

New Leisure Knoll

475 STRATFORD LN, RIDGE, NY, 11961, Ridge, NY 11961

$519,000

3 beds

2 baths

1,592 sq ft

House

475 STRATFORD LN, RIDGE, NY, 11961

Community: Leisure Knoll

New Glenwood Village

1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190..., Riverhead, NY 11901

$245,000

2 beds

2 baths

1,156 sq ft

Manufactured Home

1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190...

162 THISTLE POND DR # 162, BLOOMFIELD, C...

Community: South Pond Village

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New The Village at Oxford Greens

117 COUNTRY CLUB DR # 117, OXFORD, CT, 0..., Oxford, CT 06478

$649,900

3 beds

3 baths

2,666 sq ft

117 COUNTRY CLUB DR # 117, OXFORD, CT, 0...

Community: The Village at Oxford Greens

New The Seasons at East Northport

142 AUGUST CIR, HUNTINGTON, NY, 11731, Huntington, NY 11731

$790,302

2 beds

2 baths

1,536 sq ft

Condo

142 AUGUST CIR, HUNTINGTON, NY, 11731

Community: The Seasons at East Northport

New Leisure Glen

77 GLEN DR, RIDGE, NY, 11961, Ridge, NY 11961

$499,000

2 beds

2 baths

1,699 sq ft

House

77 GLEN DR, RIDGE, NY, 11961

Community: Leisure Glen

New The Manors at The Colony Preserve

34 GREENTREE CT, SHIRLEY, NY, 11967, Shirley, NY 11967

$515,000

2 beds

2 baths

1,357 sq ft

Condo

34 GREENTREE CT, SHIRLEY, NY, 11967

Community: The Manors at The Colony Preserve

New The Village at Oxford Greens

301 FAIRWAY DR # 301, OXFORD, CT, 06478, Oxford, CT 06478

$649,000

2 beds

2 baths

2,080 sq ft

Condo

301 FAIRWAY DR # 301, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Meadowbrook Pointe Links & Spa

146 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763

$749,990

2 beds

3 baths

2,047 sq ft

Condo

146 AUGUSTA DR, MEDFORD, NY, 11763

Community: Meadowbrook Pointe Links & Spa

New Westhampton Pines

39 KIMBERLY DR # 39, WESTHAMPTON, NY, 11..., Westhampton, NY 11977

$1,495,000

3 beds

2 baths

2,500 sq ft

Condo

39 KIMBERLY DR # 39, WESTHAMPTON, NY, 11...

Community: Westhampton Pines

New Granite Woods

35 NUTMEG RD D1, MIDDLEBURY, CT, 06762, Middlebury, CT 06762

$229,000

1 beds

1 baths

889 sq ft

Condo

35 NUTMEG RD D1, MIDDLEBURY, CT, 06762

Community: Granite Woods

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

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New Oronoque Village

635 NORTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$420,000

1 beds

3 baths

1,454 sq ft

Condo

635 NORTH TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$195,000

2 beds

2 baths

1,032 sq ft

Condo

73 HERITAGE VLG B, SOUTHBURY, CT, 06488

Condo

13 ALGONQUIN LN C, STRATFORD, CT, 06614

Community: Oronoque Village

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Greenwood Village

42 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$99,000

2 beds

2 baths

960 sq ft

Condo

42 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

Heritage Village

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

$365,000

2 beds

2 baths

1,432 sq ft

Condo

595 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

185 COUNTRY CLUB DR # 185, OXFORD, CT, 0..., Oxford, CT 06478

$645,000

3 beds

3 baths

2,595 sq ft

Condo

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

Community: The Village at Oxford Greens

Greenwood Village

82 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$189,900

2 beds

2 baths

1,110 sq ft

Condo

82 VILLAGE CIR, MANORVILLE, NY, 11949

3 EDGEWOOD WAY # 26, WOODBRIDGE, CT, 065...

Community: Regency at Woodbridge

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Regency at Woodbridge

5 WHISPER RIDGE WAY # 49, WOODBRIDGE, CT..., Woodbridge, CT 06525

$749,000

3 beds

3 baths

Condo

5 WHISPER RIDGE WAY # 49, WOODBRIDGE, CT...

Community: Regency at Woodbridge

Regency at Woodbridge

5 EDGEWOOD WAY # 25, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525

2 beds

2 baths

1,497 sq ft

Condo

554 MIRROR POND CT, MORICHES, NY, 11955

Community: The Waterways at Moriches

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

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Oronoque Village

446 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614

$635,000

3 beds

3 baths

1,426 sq ft

Condo

446 HAMMERSTONE LN B, STRATFORD, CT, 066...

Community: Oronoque Village

Oronoque Village

151 SOUTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$480,000

1 beds

3 baths

1,426 sq ft

Condo

151 SOUTH TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

761 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$339,900

2 beds

2 baths

1,063 sq ft

Condo

761 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (631) 407-2675

Stoneleigh Woods at Riverhead

23 GOOSE NECK LN, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$585,000

2 beds

3 baths

1,631 sq ft

Condo

23 GOOSE NECK LN, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

Fairfield at St. James

901 FENWAY RD, SAINT JAMES, NY, 11780, Saint James, NY 11780

$499,000

2 beds

2 baths

1,230 sq ft

Condo

901 FENWAY RD, SAINT JAMES, NY, 11780

Community: Fairfield at St. James

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

3 beds

2 baths

1,592 sq ft

House

2 beds

2 baths

1,156 sq ft

Manufactured Home

2 beds

3 baths

1,700 sq ft

Condo

2 beds

3 baths

2,054 sq ft

Condo

2 beds

2 baths

1,341 sq ft

Condo

3 beds

3 baths

2,666 sq ft

2 beds

2 baths

1,536 sq ft

Condo

2 beds

2 baths

1,699 sq ft

House

2 beds

2 baths

1,357 sq ft

Condo

2 beds

2 baths

2,080 sq ft

Condo

2 beds

3 baths

2,047 sq ft

Condo

3 beds

2 baths

2,500 sq ft

Condo

1 beds

1 baths

889 sq ft

Condo

1 beds

3 baths

1,454 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

3 beds

3 baths

2,731 sq ft

Condo

1 beds

2 baths

900 sq ft

Condo

2 beds

2 baths

1,134 sq ft

Condo

1 beds

2 baths

929 sq ft

Condo

2 beds

2 baths