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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

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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

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

The Manors at The Colony ...

$300ks - $400ks

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

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

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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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

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Questions? Call us: (631) 407-2675

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

New Construction | 55+ age-restricted | Built 2024 - present | 152 homes

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

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

1 rating (1 reviews)

Plymouth Estates at Mount...

$400ks - $500ks

Plymouth Estates at Mount..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes

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Questions? Call us: (631) 407-2675

Hopmeadow Place

$200ks - $300ks

Hopmeadow Place, Simsbury, CT

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

New Construction | 55+ age-restricted | Built 2019 - present | 146 homes

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 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

The Vineyards at Miller P...

$500ks

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

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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes

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

Questions? Call us: (631) 407-2675

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes

1 2...3

New Heritage Village

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

$289,000

2 beds

2 baths

1,365 sq ft

Condo

877 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Greenwood Village

11 A DOGWOOD LN 11 A, BROOKHAVEN, NY, 11..., Brookhaven, NY 11949

$199,000

2 beds

2 baths

1,032 sq ft

Condo

11 A DOGWOOD LN 11 A, BROOKHAVEN, NY, 11...

Community: Greenwood Village

New The Manors at The Colony Preserve

40 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967

$540,000

2 beds

2 baths

1,360 sq ft

Condo

40 GREENTREE CT, BROOKHAVEN, NY, 11967

Community: The Manors at The Colony Preserve

New Pond Spring Village

37 SEPTEMBER LN 37, BEACON FALLS, CT, 06..., Beacon Falls, CT 06403

$450,000

2 beds

3 baths

1,328 sq ft

Condo

37 SEPTEMBER LN 37, BEACON FALLS, CT, 06...

Community: Pond Spring Village

New The Waterways at Moriches

188 RIVER DR, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955

$729,000

2 beds

2 baths

2,100 sq ft

Condo

188 RIVER DR, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

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Questions? Call us: (631) 407-2675

New Heritage Village

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

$525,000

3 beds

3 baths

1,716 sq ft

Condo

657 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Heritage Village

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

$215,000

2 beds

2 baths

1,044 sq ft

Condo

343 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

New Glenwood Village

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901

$419,000

2 beds

2 baths

1,624 sq ft

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...

Community: Glenwood Village

New Leisure Knoll

379 LARCHMONT CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$539,000

2 beds

2 baths

1,070 sq ft

Condo

379 LARCHMONT CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Chatfield Farms

24 BAYBERRY CT 24, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403

$725,000

3 beds

3 baths

1,981 sq ft

Condo

24 BAYBERRY CT 24, BEACON FALLS, CT, 064...

Community: Chatfield Farms

New The Seasons at Elwood

53 WINTER PL 53, HUNTINGTON, NY, 11731, Huntington, NY 11731

$979,900

2 beds

3 baths

1,500 sq ft

Condo

53 WINTER PL 53, HUNTINGTON, NY, 11731

Community: The Seasons at Elwood

New The Seasons at Elwood

240 FALL CT, HUNTINGTON, NY, 11731, Huntington, NY 11731

$1,299,999

2 beds

3 baths

2,329 sq ft

Condo

240 FALL CT, HUNTINGTON, NY, 11731

Community: The Seasons at Elwood

New Leisure Knoll

220 BELFAST LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$539,999

2 beds

2 baths

1,445 sq ft

Condo

220 BELFAST LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Leisure Glen

515 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$560,000

2 beds

2 baths

1,434 sq ft

House

515 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Meadow Brook Estates

223 MEADOW BROOK RD 223, OXFORD, CT, 064..., Oxford, CT 06478

$589,900

2 beds

2 baths

1,480 sq ft

Condo

223 MEADOW BROOK RD 223, OXFORD, CT, 064...

Community: Meadow Brook Estates

Greenwood Village

40 WILLOW CT, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$249,999

2 beds

2 baths

1,151 sq ft

Manufactured On Land

40 WILLOW CT, BROOKHAVEN, NY, 11949

Community: Greenwood Village

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

Questions? Call us: (631) 407-2675

Oronoque Village

261 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614

$550,000

2 beds

3 baths

1,620 sq ft

Condo

261 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

Woodridge Strathmore Terrace

54 STANDISH DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$549,999

2 beds

2 baths

1,335 sq ft

Condo

54 STANDISH DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

Heritage Village

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

$479,000

2 beds

2 baths

1,432 sq ft

Condo

899 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

209 ACORN LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$599,000

1 beds

3 baths

1,438 sq ft

Condo

209 ACORN LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Vineyards at Brookfield

69 AVERY DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934

$709,999

2 beds

3 baths

2,254 sq ft

Condo

69 AVERY DR, BROOKHAVEN, NY, 11934

Community: Vineyards at Brookfield

The Powder Forest Homes

9 ASHTON CIR, SIMSBURY, CT, 06070, Simsbury, CT 06070

$700,000

2 beds

2 baths

1,809 sq ft

Condo

9 ASHTON CIR, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

Applegate Estates

90 APPLE GATE 190, SOUTHINGTON, CT, 0648..., Southington, CT 06489

$450,000

2 beds

2 baths

1,350 sq ft

Condo

90 APPLE GATE 190, SOUTHINGTON, CT, 0648...

Community: Applegate Estates

The Village at Oxford Greens

71 LINKS WAY 71, OXFORD, CT, 06478, Oxford, CT 06478

$598,000

2 beds

2 baths

1,590 sq ft

Condo

71 LINKS WAY 71, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Heritage Village

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

$264,999

2 beds

2 baths

1,432 sq ft

Condo

397 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Waterways at Moriches

377 QUARRY POND CT, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955

$599,999

3 beds

2 baths

2,141 sq ft

Condo

377 QUARRY POND CT, BROOKHAVEN, NY, 1195...

Community: The Waterways at Moriches

Woodridge Strathmore Terrace

58 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$435,000

2 beds

2 baths

1,025 sq ft

Condo

58 HEARTHSIDE DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

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

Questions? Call us: (631) 407-2675

Greenwood Village

131 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$165,000

2 beds

2 baths

1,062 sq ft

Manufactured Home

131 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

The Waterways at Moriches

629 WATER WAY 29, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955

$715,000

2 beds

3 baths

1,611 sq ft

Condo

629 WATER WAY 29, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

Regency Meadows

108 IMPERIAL CT 108, TRUMBULL, CT, 06611, Trumbull, CT 06611

$739,000

2 beds

3 baths

2,891 sq ft

Condo

108 IMPERIAL CT 108, TRUMBULL, CT, 06611

Community: Regency Meadows

Heritage Village

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

$409,000

2 beds

2 baths

1,432 sq ft

Condo

139 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Foxwood Village

1407 MIDDLE RD 83, BROOKHAVEN, NY, 11933, Brookhaven, NY 11933

$425,000

2 beds

2 baths

1,444 sq ft

Manufactured Home

1407 MIDDLE RD 83, BROOKHAVEN, NY, 11933

Community: Foxwood Village

Heritage Village

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

$365,000

2 beds

2 baths

1,398 sq ft

Condo

738 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$289,900

2 beds

2 baths

1,044 sq ft

Condo

69 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$354,000

2 beds

2 baths

1,432 sq ft

Condo

122 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$324,900

2 beds

2 baths

1,398 sq ft

Condo

47 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Knoll

491 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$489,000

2 beds

2 baths

976 sq ft

Condo

491 STRATFORD LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Heritage Village

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

$424,900

2 beds

2 baths

1,398 sq ft

Condo

553 HERITAGE VLG B, 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

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

$270,000

2 beds

2 baths

1,044 sq ft

Condo

69 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$349,900

2 beds

2 baths

1,432 sq ft

Condo

170 HERITAGE VLG B, 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 442 days. The average price of homes for sale in this community is approximately $523,750, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Founders Village average around $523,750.

Want more information about active adult communities around Southold?

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95 communities

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REIN updates its listings on a daily basis. Data last updated: May 29, 2026.
This application does not include information on all of the properties available for sale at this time.

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

95 communities near Southold

192 homes near Southold

2 beds

2 baths

1,365 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

2 beds

2 baths

1,360 sq ft

Condo

2 beds

3 baths

1,328 sq ft

Condo

2 beds

2 baths

2,100 sq ft

Condo

3 beds

3 baths

1,716 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

1,070 sq ft

Condo

3 beds

3 baths

1,981 sq ft

Condo

2 beds

3 baths

1,500 sq ft

Condo

2 beds

3 baths

2,329 sq ft

Condo

2 beds

2 baths

1,445 sq ft

Condo

2 beds

2 baths

1,434 sq ft

House

2 beds

2 baths

1,480 sq ft

Condo

2 beds

2 baths

1,151 sq ft

Manufactured On Land

2 beds

3 baths

1,620 sq ft

Condo

2 beds

2 baths

1,335 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

1 beds