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

94 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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

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Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

Spring Lake Village

$100ks - $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.

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Stone Ridge Estates

$500ks - $600ks

Stone Ridge Estates, Dix Hills, NY

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

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South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

4.9 rating (14 reviews)

Chatfield Farms

$400ks - $700ks

Chatfield Farms, Beacon Falls, CT

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

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

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

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The Seasons at East North...

$700ks

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

New Construction | 55+ age-restricted | Built 2023 - present | 190 homes

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

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

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Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

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Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

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

5 rating (1 reviews)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

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

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The Manors at The Colony ...

$300ks - $400ks

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

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

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes

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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

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes

1 2...3

New Heritage Village

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

$225,000

2 beds

2 baths

1,398 sq ft

Condo

411 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Sunrise Village

71 REVERE DR, SAYVILLE, NY, 11782, Sayville, NY 11782

$489,990

2 beds

3 baths

1,046 sq ft

Condo

71 REVERE DR, SAYVILLE, NY, 11782

Community: Sunrise Village

New Spring Lake Village

41 COACH DR # 41, SOUTHINGTON, CT, 06489, Southington, CT 06489

$249,900

2 beds

2 baths

1,232 sq ft

Condo

41 COACH DR # 41, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

New Heritage Village

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

$349,900

2 beds

2 baths

1,398 sq ft

Condo

865 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Regency at Prospect

50 LILAC LN # 50, PROSPECT, CT, 06712, Prospect, CT 06712

$489,000

2 beds

2 baths

1,503 sq ft

Condo

50 LILAC LN # 50, PROSPECT, CT, 06712

Community: Regency at Prospect

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Questions? Call us: (631) 407-2675

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New Leisure Knoll

498 CRANSTON LN, RIDGE, NY, 11961, Ridge, NY 11961

$479,000

2 beds

2 baths

1,412 sq ft

Condo

498 CRANSTON LN, RIDGE, NY, 11961

Community: Leisure Knoll

New Fairfield at St. James

1205 GOTHAM DR, SAINT JAMES, NY, 11780, Saint James, NY 11780

$449,990

1 beds

2 baths

750 sq ft

House

1205 GOTHAM DR, SAINT JAMES, NY, 11780

Community: Fairfield at St. James

New Heritage Village

1041 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$299,900

2 beds

2 baths

1,044 sq ft

Condo

1041 HERITAGE VLG A, SOUTHBURY, CT, 0648...

Community: Heritage Village

New Encore at Lake Grove

51 SYMPHONY DR, LAKE GROVE, NY, 11755, Lake Grove, NY 11755

$629,999

2 beds

3 baths

1,409 sq ft

Condo

51 SYMPHONY DR, LAKE GROVE, NY, 11755

Community: Encore at Lake Grove

New Leisure Village

306 TORQUAY CT E, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$239,000

1 beds

1 baths

684 sq ft

Condo

306 TORQUAY CT E, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Heritage Village

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

$285,000

2 beds

2 baths

1,432 sq ft

Condo

972 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Spring Lake Village

6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489, Southington, CT 06489

$320,000

3 beds

3 baths

1,471 sq ft

Condo

6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

New Woodridge Strathmore Terrace

35 CHIPPENDALE DR, MOUNT SINAI, NY, 1176..., Mount Sinai, NY 11766

$449,999

2 beds

2 baths

1,240 sq ft

Condo

35 CHIPPENDALE DR, MOUNT SINAI, NY, 1176...

Community: Woodridge Strathmore Terrace

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Questions? Call us: (631) 407-2675

New Glenwood Village

181 GLYNWOOD 181, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$265,000

2 beds

1 baths

1,100 sq ft

Manufactured On Land

181 GLYNWOOD 181, RIVERHEAD, NY, 11901

Community: Glenwood Village

Encore Atlantic Shores

179 MELODY CT, EASTPORT, NY, 11941, Eastport, NY 11941

$925,000

2 beds

3 baths

2,900 sq ft

Condo

179 MELODY CT, EASTPORT, NY, 11941

Community: Encore Atlantic Shores

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

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Oronoque Village

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

$599,000

1 beds

3 baths

2,199 sq ft

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$359,900

2 beds

2 baths

1,432 sq ft

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Knoll

206 BELFAST LN, RIDGE, NY, 11961, Ridge, NY 11961

$345,000

2 beds

1 baths

658 sq ft

Condo

206 BELFAST LN, RIDGE, NY, 11961

Community: Leisure Knoll

Glenwood Village

1661 OLD COUNTRY RD 275, RIVERHEAD, NY, ..., Riverhead, NY 11901

$249,850

2 beds

2 baths

1,050 sq ft

Mobile Home

1661 OLD COUNTRY RD 275, RIVERHEAD, NY, ...

Community: Glenwood Village

Leisure Glen

530 LEISURE DR, RIDGE, NY, 11961, Ridge, NY 11961

$595,000

2 beds

2 baths

1,434 sq ft

Condo

530 LEISURE DR, RIDGE, NY, 11961

Community: Leisure Glen

Spring Lake Village

40 HICKORY HL # 40, SOUTHINGTON, CT, 064..., Southington, CT 06489

$233,527

2 beds

2 baths

1,211 sq ft

Condo

40 HICKORY HL # 40, SOUTHINGTON, CT, 064...

Community: Spring Lake Village

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Woodridge Strathmore Terrace

27 HEARTHSIDE DR, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$399,000

1 beds

1 baths

844 sq ft

Condo

27 HEARTHSIDE DR, MOUNT SINAI, NY, 11766

Community: Woodridge Strathmore Terrace

Leisure Village

418 WEYMOUTH CT C, RIDGE, NY, 11961, Ridge, NY 11961

$349,999

2 beds

1 baths

1,036 sq ft

Condo

418 WEYMOUTH CT C, RIDGE, NY, 11961

Community: Leisure Village

Heritage Village

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

$399,000

3 beds

2 baths

1,716 sq ft

Condo

575 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$260,000

2 beds

2 baths

1,398 sq ft

Condo

701 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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Leisure Village

430 FALMOUTH CT A, RIDGE, NY, 11961, Ridge, NY 11961

$369,000

2 beds

2 baths

1,200 sq ft

House

430 FALMOUTH CT A, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

258 NEWCASTLE CT F, RIDGE, NY, 11961, Ridge, NY 11961

$279,000

2 beds

1 baths

875 sq ft

Condo

258 NEWCASTLE CT F, RIDGE, NY, 11961

Community: Leisure Village

Oak Meadow Estates

65 OAK MEADOW LN # 65, HARWINTON, CT, 06..., Harwinton, CT 06791

$495,000

2 beds

4 baths

2,164 sq ft

Condo

65 OAK MEADOW LN # 65, HARWINTON, CT, 06...

Community: Oak Meadow Estates

South Pond Village

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

$259,999

2 beds

2 baths

1,204 sq ft

Condo

81 SILO WAY 81, BLOOMFIELD, CT, 06002

Community: South Pond Village

Leisure Knoll

304 KINGSTON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$530,000

2 beds

2 baths

1,000 sq ft

Condo

304 KINGSTON CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

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Oronoque Village

133 BANNOCK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$635,000

2 beds

3 baths

2,038 sq ft

Condo

133 BANNOCK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$299,900

2 beds

2 baths

1,144 sq ft

Condo

914 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Chatfield Farms

8 WOODLAND PATH 8, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403

$699,900

3 beds

4 baths

2,610 sq ft

Condo

8 WOODLAND PATH 8, BEACON FALLS, CT, 064...

Community: Chatfield Farms

Heritage Village

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

$500,000

3 beds

2 baths

1,716 sq ft

Condo

419 HERITAGE VLG E, SOUTHBURY, CT, 06488

Community: Heritage Village

Greenwood Village

16 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$167,000

2 beds

2 baths

1,164 sq ft

Condo

16 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

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Leisure Village

230 BLACKPOOL CT A, RIDGE, NY, 11961, Ridge, NY 11961

$289,900

2 beds

1 baths

836 sq ft

Condo

230 BLACKPOOL CT A, RIDGE, NY, 11961

Community: Leisure Village

Meadow Brook Estates

215 MEADOW BROOK RD # 215, OXFORD, CT, 0..., Oxford, CT 06478

$589,000

3 beds

3 baths

2,207 sq ft

Condo

215 MEADOW BROOK RD # 215, OXFORD, CT, 0...

Community: Meadow Brook Estates

Leisure Village

406 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961

$245,000

1 beds

1 baths

704 sq ft

Condo

406 WOODBRIDGE DR B, RIDGE, NY, 11961

Community: Leisure Village

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Long Hill Village

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

$539,900

1 beds

3 baths

1,370 sq ft

Condo

71 CIDER MILL LN, TRUMBULL, CT, 06611

Community: Long Hill Village

Leisure Knoll

190 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$479,999

2 beds

1 baths

913 sq ft

House

190 EDINBURGH DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

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

156 homes near Southold

2 beds

2 baths

1,398 sq ft

Condo

2 beds

3 baths

1,046 sq ft

Condo

2 beds

2 baths

1,232 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,503 sq ft

Condo

2 beds

2 baths

1,412 sq ft

Condo

1 beds

2 baths

750 sq ft

House

2 beds

2 baths

1,044 sq ft

Condo

2 beds

3 baths

1,409 sq ft

Condo

1 beds

1 baths

684 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

3 baths

1,471 sq ft

Condo

2 beds

2 baths

1,240 sq ft

Condo

2 beds

1 baths

1,100 sq ft

Manufactured On Land

2 beds

3 baths

2,900 sq ft

Condo

1 beds

3 baths

2,199 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

1 baths

658 sq ft

Condo

2 beds

2 baths

1,050 sq ft

Mobile Home

2 beds