Southold, NY 55+ active adult communities & homes for sale - Page 3

201 homes 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

5 rating (2 reviews)

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

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

Questions? Call us: (631) 407-2675

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 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

The Manors at The Colony ...

$300ks - $400ks

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

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

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

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Questions? Call us: (631) 407-2675

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

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

4.6 rating (9 reviews)

Meadowbrook Pointe Links ...

$300ks - $700ks

Meadowbrook Pointe Links ..., Medford, NY

New and Resale | 55+ age-restricted | Built 2010 - present | 280 homes

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 Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes

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

Questions? Call us: (631) 407-2675

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

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

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

The Vineyards at Mount Si...

$800ks - $1Ms

The Vineyards at Mount Si..., Mount Sinai, NY

New Construction | 55+ age-restricted | Built 2020 - present | 91 homes

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

The Seasons at Elwood

$800ks - $900ks

The Seasons at Elwood, East Northport, NY

Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes

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

Questions? Call us: (631) 407-2675

Stone Ridge Estates

$500ks - $600ks

Stone Ridge Estates, Dix Hills, NY

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

1 2...3

Fieldstone Village

101 SUNRISE HILL CIR 101, ORANGE, CT, 06..., Orange, CT 06477

$875,000

2 beds

3 baths

2,350 sq ft

Condo

101 SUNRISE HILL CIR 101, ORANGE, CT, 06...

Community: Fieldstone Village

Glenwood Village

1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ..., Riverhead, NY 11901

$375,000

3 beds

2 baths

1,317 sq ft

Manufactured Home

1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ...

Community: Glenwood Village

Leisure Village

232 BLACKPOOL CT F, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$349,000

2 beds

1 baths

875 sq ft

Condo

232 BLACKPOOL CT F, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Vineyards at Brookfield

61 AVERY DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934

$695,000

2 beds

2 baths

1,557 sq ft

Condo

61 AVERY DR, BROOKHAVEN, NY, 11934

Community: Vineyards at Brookfield

Leisure Glen

29 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$549,900

2 beds

2 baths

1,314 sq ft

Condo

29 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

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

Questions? Call us: (631) 407-2675

Spring Lake Village

142 TIMBER RDG 142, SOUTHINGTON, CT, 064..., Southington, CT 06489

$359,900

2 beds

3 baths

1,601 sq ft

Condo

142 TIMBER RDG 142, SOUTHINGTON, CT, 064...

Community: Spring Lake Village

Heritage Village

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

$165,000

2 beds

2 baths

1,076 sq ft

Condo

399 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Country Pointe Preserve

3 JUNIPER LN 94, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980

$980,000

2 beds

3 baths

2,389 sq ft

Condo

3 JUNIPER LN 94, BROOKHAVEN, NY, 11980

Community: Country Pointe Preserve

Chatfield Farms

6 WOODLAND PATH 6, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403

$799,000

3 beds

4 baths

2,600 sq ft

Condo

6 WOODLAND PATH 6, BEACON FALLS, CT, 064...

Community: Chatfield Farms

The Waterways at Moriches

606 BAY VIEW CIR 6, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955

$699,000

2 beds

3 baths

1,860 sq ft

Condo

606 BAY VIEW CIR 6, BROOKHAVEN, NY, 1195...

Community: The Waterways at Moriches

Leisure Village

179 VENTRY CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$319,000

2 beds

1 baths

1,085 sq ft

Condo

179 VENTRY CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

Glenwood Village

1661 OLD COUNTRY RD 189, RIVERHEAD, NY, ..., Riverhead, NY 11901

$205,000

2 beds

2 baths

1,036 sq ft

Manufactured Home

1661 OLD COUNTRY RD 189, RIVERHEAD, NY, ...

Community: Glenwood Village

Spring Lake Village

253 CARRIAGE DR 253, SOUTHINGTON, CT, 06..., Southington, CT 06489

$309,900

2 beds

2 baths

1,152 sq ft

Condo

253 CARRIAGE DR 253, SOUTHINGTON, CT, 06...

Community: Spring Lake Village

Meadowbrook Pointe Links & Spa

250 SAND HILLS LN, BROOKHAVEN, NY, 11763, Brookhaven, NY 11763

$324,100

2 beds

2 baths

1,133 sq ft

Condo

250 SAND HILLS LN, BROOKHAVEN, NY, 11763

Community: Meadowbrook Pointe Links & Spa

Greenwood Village

69 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$139,000

2 beds

2 baths

1,134 sq ft

Condo

69 DOGWOOD LN, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Encore Atlantic Shores

228 SONATA CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$749,000

2 beds

2 baths

1,605 sq ft

Condo

228 SONATA CT, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

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

Questions? Call us: (631) 407-2675

The Village at Oxford Greens

1129 ST ANDREWS DR 49, OXFORD, CT, 06478, Oxford, CT 06478

$709,555

2 beds

3 baths

2,454 sq ft

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$709,555

2 beds

3 baths

2,454 sq ft

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

Fairview at Oxford Greens

1111 ST ANDREWS DR 16, OXFORD, CT, 06478, Oxford, CT 06478

$778,585

2 beds

3 baths

2,454 sq ft

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$778,585

2 beds

3 baths

2,454 sq ft

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478

Community: The Village at Oxford Greens

The Village at Oxford Greens

1138 ST ANDREWS DR 90, OXFORD, CT, 06478, Oxford, CT 06478

$754,150

2 beds

3 baths

1,955 sq ft

Condo

Community: The Waterways at Moriches

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

Questions? Call us: (631) 407-2675

Vineyards at Blue Point

37 HALLEY DR 17, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772

$660,000

2 beds

2 baths

1,220 sq ft

Condo

37 HALLEY DR 17, BROOKHAVEN, NY, 11772

Community: Vineyards at Blue Point

Heritage Village

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

$342,500

2 beds

2 baths

1,398 sq ft

Condo

581 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Windcrest East

5 GREEN ASH ST, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$775,000

3 beds

3 baths

2,449 sq ft

House

5 GREEN ASH ST, RIVERHEAD, NY, 11933

Community: Windcrest East

Oronoque Village

383 SEQUOIA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$485,000

1 beds

3 baths

1,360 sq ft

Condo

383 SEQUOIA LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$349,900

2 beds

2 baths

1,398 sq ft

Condo

895 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Stoneleigh Woods at Riverhead

159 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$674,999

2 beds

3 baths

2,172 sq ft

Condo

159 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

Heritage Village

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

$389,900

2 beds

2 baths

1,432 sq ft

Condo

16 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

626 OVERLOOK PATH 626, SOUTHINGTON, CT, ..., Southington, CT 06489

$350,000

2 beds

2 baths

1,230 sq ft

Condo

626 OVERLOOK PATH 626, SOUTHINGTON, CT, ...

Community: Spring Lake Village

Heritage Village

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

$299,900

2 beds

2 baths

1,032 sq ft

Condo

38 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

407 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$439,000

1 beds

2 baths

1,360 sq ft

Condo

407 MONTAUK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Baldwin Station

15 JASMINE CIR 15, MILFORD, CT, 06461, Milford, CT 06461

$599,000

2 beds

3 baths

2,331 sq ft

Condo

15 JASMINE CIR 15, MILFORD, CT, 06461

Community: Baldwin Station

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

Questions? Call us: (631) 407-2675

Fairview at Oxford Greens

941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478

$699,900

2 beds

2 baths

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$699,900

2 beds

2 baths

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478

Community: The Village at Oxford Greens

1 2 3 4 5…6

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 462 days. The average price of homes for sale in this community is approximately $525,806, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Founders Village average around $525,806.

Want more information about active adult communities around Southold?

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201 homes

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REIN updates its listings on a daily basis. Data last updated: Aug 27, 2026.
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Southold, NY 55+ active adult communities & homes for sale - Page 3

95 communities near Southold

201 homes near Southold

2 beds

3 baths

2,350 sq ft

Condo

3 beds

2 baths

1,317 sq ft

Manufactured Home

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

1,557 sq ft

Condo

2 beds

2 baths

1,314 sq ft

Condo

2 beds

3 baths

1,601 sq ft

Condo

2 beds

2 baths

1,076 sq ft

Condo

2 beds

3 baths

2,389 sq ft

Condo

3 beds

4 baths

2,600 sq ft

Condo

2 beds

3 baths

1,860 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds

2 baths

1,036 sq ft

Manufactured Home

2 beds

2 baths

1,152 sq ft

Condo

2 beds

2 baths

1,133 sq ft

Condo

2 beds

2 baths

1,134 sq ft

Condo

2 beds

2 baths

1,605 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds