Southold, NY 55+ active adult communities & homes for sale - Page 2

95 communities near Southold

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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

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

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

The Village at Hunt Glen

$300ks

The Village at Hunt Glen, Granby, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 homes

O'Meara Farm

$400ks

O'Meara Farm, Farmington, CT

Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

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

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Questions? Call us: (631) 407-2675

Shaker Heights

$400ks - $500ks

Shaker Heights, Enfield, CT

New Construction | 55+ age-restricted | Built 2018 - present | 77 homes

Bramble Ridge

$300ks

Bramble Ridge, Suffield, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 homes

Autumn Fields

$200ks - $300ks

Autumn Fields, Enfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 homes

Beckley Farms

$300ks - $400ks

Beckley Farms, Berlin, CT

New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 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.

Jessup's Landing

$1Ms

Jessup's Landing, Quogue, NY

New and Resale | 55+ age-restricted | Built 2009 - 2016 | 31 homes

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes

Clockmaker's Hill

$100ks

Clockmaker's Hill, Winsted, CT

Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes

Whitney Glen

$500ks - $600ks

Whitney Glen, Westport, CT

Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes

Cobblestone Court

$400ks - $500ks

Cobblestone Court, Essex, CT

New and Resale | 55+ age-restricted | Built 2017 - present | 8 homes

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

Questions? Call us: (631) 407-2675

Summer Wind Estates

$300ks - $400ks

Summer Wind Estates, North Haven, CT

New Construction | 55+ age-restricted | Built 2015 - present | 18 homes

RiverBend Estates

$400ks

RiverBend Estates, Oxford, CT

New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

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

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes

Eastport Meadows

$400ks

Eastport Meadows, Eastport, NY

Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 homes

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

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

Gloria Commons

$200ks - $300ks

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

RiverWalk

$500ks - $600ks

RiverWalk, Branford, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes

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

Questions? Call us: (631) 407-2675

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

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

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

Fieldstone Village

$500ks - $800ks

Fieldstone Village, Orange, CT

Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes

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

The Pines at Bohemia

$400ks - $500ks

The Pines at Bohemia, Bohemia, NY

New Construction | 55+ age-restricted | Built 2019 - present | 20 homes

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

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

The Polo Club at Islandia

$600ks - $700ks

The Polo Club at Islandia, Islandia, NY

New Construction | 55+ age-restricted | Built 2019 - present | 72 homes

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

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

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

Questions? Call us: (631) 407-2675

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

The Bridges at Oxford Gre...

$600ks

The Bridges at Oxford Gre..., Oxford, CT

New Construction | 55+ age-restricted | Built 2025 - present | 99 homes

1 2...3

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 Heritage Village

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

$385,000

2 beds

2 baths

1,432 sq ft

Condo

972 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New The Village at Oxford Greens

349 NIBLICK LN, OXFORD, CT, 06478, Oxford, CT 06478

$689,000

3 beds

2 baths

2,152 sq ft

349 NIBLICK LN, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Heritage Village

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

$289,900

2 beds

2 baths

1,044 sq ft

Condo

176 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

New Spring Lake Village

21 HICKORY HL 21, SOUTHINGTON, CT, 06489, Southington, CT 06489

$248,000

2 beds

2 baths

1,285 sq ft

Condo

21 HICKORY HL 21, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

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

Questions? Call us: (631) 407-2675

New The Manors at The Colony Preserve

33 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967

$510,000

2 beds

2 baths

1,557 sq ft

Condo

33 GREENTREE CT, BROOKHAVEN, NY, 11967

Community: The Manors at The Colony Preserve

New The Waterways at Moriches

632 WATER WAY 32, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955

$799,000

2 beds

3 baths

1,874 sq ft

Condo

632 WATER WAY 32, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

New The Seasons at Elwood

178 SUMMER CIR, HUNTINGTON, NY, 11731, Huntington, NY 11731

$1,688,000

2 beds

3 baths

2,900 sq ft

Condo

178 SUMMER CIR, HUNTINGTON, NY, 11731

Community: The Seasons at Elwood

New Vineyards at Blue Point

174 HALLEY DR, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772

$829,900

2 beds

2 baths

1,928 sq ft

Condo

174 HALLEY DR, BROOKHAVEN, NY, 11772

Community: Vineyards at Blue Point

New Greenwood Village

5131 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$135,000

2 beds

2 baths

987 sq ft

House

5131 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

New Fairfield at St. James

1205 GOTHAM DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$649,000

2 beds

2 baths

948 sq ft

Condo

1205 GOTHAM DR, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

New Country Pointe Preserve

118 JUNIPER LN 31, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980

$865,000

2 beds

3 baths

1,998 sq ft

Condo

118 JUNIPER LN 31, BROOKHAVEN, NY, 11980

Community: Country Pointe Preserve

New Vineyards at Blue Point

32 AVERY WAY, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772

$799,000

2 beds

3 baths

2,168 sq ft

Condo

32 AVERY WAY, BROOKHAVEN, NY, 11772

Community: Vineyards at Blue Point

New Fairfield at St. James

606 FLAIR CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$429,000

1 beds

1 baths

752 sq ft

Condo

606 FLAIR CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

New Oronoque Village

46 BUCKSKIN LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$559,900

1 beds

2 baths

1,375 sq ft

Condo

46 BUCKSKIN LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Vineyards at Moriches

20 EMILIE DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934

$759,000

2 beds

3 baths

1,984 sq ft

Condo

20 EMILIE DR, BROOKHAVEN, NY, 11934

Community: Vineyards at Moriches

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

Questions? Call us: (631) 407-2675

New Leisure Glen

187 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$525,000

2 beds

2 baths

1,451 sq ft

Condo

187 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New The Waterways at Moriches

216 RIVER DR, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955

$510,000

2 beds

2 baths

1,544 sq ft

Condo

216 RIVER DR, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

New Heritage Village

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

$275,000

2 beds

2 baths

1,432 sq ft

Condo

874 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Greenwood Village

16 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$299,999

2 beds

2 baths

1,288 sq ft

Condo

16 DOGWOOD LN, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Vineyards at Moriches

27 EMILIE DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934

$785,000

2 beds

3 baths

2,335 sq ft

Condo

27 EMILIE DR, BROOKHAVEN, NY, 11934

Community: Vineyards at Moriches

Heritage Village

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

$399,900

2 beds

2 baths

1,398 sq ft

Condo

701 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$589,900

3 beds

2 baths

1,716 sq ft

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

157 COUNTRY CLUB DR 157, OXFORD, CT, 064..., Oxford, CT 06478

$649,900

3 beds

3 baths

2,008 sq ft

Condo

157 COUNTRY CLUB DR 157, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Windmill Gate

7 DARIA DR, ISLIP, NY, 11769, Islip, NY 11769

$633,000

2 beds

2 baths

1,175 sq ft

Condo

7 DARIA DR, ISLIP, NY, 11769

Community: Windmill Gate

Sunrise Village

113 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782

$479,000

2 beds

2 baths

1,141 sq ft

Condo

113 REVERE DR, ISLIP, NY, 11782

Community: Sunrise Village

Heritage Village

24-B HERITAGE CRST B, SOUTHBURY, CT, 064..., Southbury, CT 06488

$419,900

2 beds

2 baths

1,217 sq ft

Condo

24-B HERITAGE CRST B, SOUTHBURY, CT, 064...

Community: Heritage Village

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

Questions? Call us: (631) 407-2675

Heritage Village

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

$205,000

2 beds

2 baths

1,044 sq ft

Condo

593 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$235,000

2 beds

2 baths

1,076 sq ft

Condo

147 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$204,000

2 beds

2 baths

1,032 sq ft

Condo

22 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Greenwood Village

130 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$129,000

2 beds

2 baths

1,177 sq ft

Condo

130 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Leisure Village

258 NEWCASTLE CT F, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$299,000

2 beds

1 baths

875 sq ft

Condo

258 NEWCASTLE CT F, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Heritage Village

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

$259,000

2 beds

2 baths

1,432 sq ft

Condo

804 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Strathmore Gate East

4 FLAIR WAY, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$495,000

2 beds

2 baths

1,112 sq ft

House

4 FLAIR WAY, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

Oronoque Village

89 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$649,000

1 beds

3 baths

1,438 sq ft

Condo

89 S TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

Oak Meadow Estates

197 OAK MEADOW LN 197, TORRINGTON, CT, 0..., Torrington, CT 06790

$399,000

2 beds

2 baths

1,419 sq ft

Condo

197 OAK MEADOW LN 197, TORRINGTON, CT, 0...

Community: Oak Meadow Estates

Strathmore Gate East

9 FREEDOM LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$289,000

1 beds

1 baths

728 sq ft

Condo

9 FREEDOM LN, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

Leisure Knoll

338 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$419,990

2 beds

1 baths

960 sq ft

Condo

338 EDINBURGH DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

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

Questions? Call us: (631) 407-2675

Greenwood Village

5127 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$227,000

2 beds

2 baths

1,291 sq ft

Condo

5127 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Billingsgate

$750,000

2 beds

3 baths

2,729 sq ft

Condo

14 BILLINGSGATE DR 14, SIMSBURY, CT, 060...

Community: Billingsgate

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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95 communities

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Southold, NY 55+ active adult communities & homes for sale - Page 2

95 communities near Southold

184 homes near Southold

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

1,432 sq ft

Condo

3 beds

2 baths

2,152 sq ft

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,285 sq ft

Condo

2 beds

2 baths

1,557 sq ft

Condo

2 beds

3 baths

1,874 sq ft

Condo

2 beds

3 baths

2,900 sq ft

Condo

2 beds

2 baths

1,928 sq ft

Condo

2 beds

2 baths

987 sq ft

House

2 beds

2 baths

948 sq ft

Condo

2 beds

3 baths

1,998 sq ft

Condo

2 beds

3 baths

2,168 sq ft

Condo

1 beds

1 baths

752 sq ft

Condo

1 beds

2 baths

1,375 sq ft

Condo

2 beds

3 baths

1,984 sq ft

Condo

2 beds

2 baths

1,451 sq ft

Condo

2 beds

2 baths

1,544 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths