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

95 communities near Southold

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Autumn Estates

$500ks - $600ks

Autumn Estates, Farmington, CT

Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

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

Billingsgate

$400ks - $600ks

Billingsgate, Simsbury, CT

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

Boulder Brook

$200ks

Boulder Brook, Prospect, CT

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

Gloria Commons

$200ks - $300ks

Gloria Commons, Milford, CT

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

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

Questions? Call us: (631) 407-2675

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

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

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

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

RiverBend Estates

$400ks

RiverBend Estates, Oxford, CT

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

Summer Wind Estates

$300ks - $400ks

Summer Wind Estates, North Haven, CT

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

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

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

Bidwell Village

$300ks - $400ks

Bidwell Village, Coventry, CT

New Construction | 55+ age-restricted | Built 2020 - present | 37 homes

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

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

Forest Mews

$300ks - $400ks

Forest Mews, Avon, CT

Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 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

Shaker Heights

$400ks - $500ks

Shaker Heights, Enfield, CT

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

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

Questions? Call us: (631) 407-2675

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

Cobblestone Court

$400ks - $500ks

Cobblestone Court, Essex, CT

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

Eastport Meadows

$400ks

Eastport Meadows, Eastport, NY

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

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

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

5 rating (1 reviews)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

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

Windmill Gate

$300ks - $400ks

Windmill Gate, Oakdale, NY

Resale Only | 55+ age-restricted | Built 1989 - 1991 | 110 homes

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

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

Questions? Call us: (631) 407-2675

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

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

Stone Ridge Estates

$500ks - $600ks

Stone Ridge Estates, Dix Hills, NY

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

3.5 rating (2 reviews)

Harvest Pointe

$800ks - $3Ms

Harvest Pointe, Cutchogue, NY

New Construction | 55+ age-restricted | Built 2017 - present | 124 homes

Jessup's Landing

$1Ms

Jessup's Landing, Quogue, NY

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

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

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

The Pines at Bohemia

$400ks - $500ks

The Pines at Bohemia, Bohemia, NY

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

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

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

The Bridges at Oxford Gre...

$600ks

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

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

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

Questions? Call us: (631) 407-2675

The Seasons at East North...

$700ks

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

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

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

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

1 2...3

New The Villages at Mount Sinai Park

10 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$749,000

3 beds

3 baths

2,500 sq ft

House

10 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

New Leisure Knoll

225 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$540,000

2 beds

2 baths

1,094 sq ft

House

225 KINGSTON DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New The Villages at Mount Sinai Park

54 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$929,000

3 beds

3 baths

2,816 sq ft

House

54 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

New The Villages at Mount Sinai Park

68 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$839,999

2 beds

2 baths

1,736 sq ft

House

68 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

New Saddle Lakes

156 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$629,000

3 beds

3 baths

1,837 sq ft

Condo

156 SCENIC LAKE DR, RIVERHEAD, NY, 11901

Community: Saddle Lakes

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

Questions? Call us: (631) 407-2675

New Encore at Lake Grove

8 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755

$634,000

2 beds

3 baths

1,378 sq ft

Condo

8 SYMPHONY DR, BROOKHAVEN, NY, 11755

Community: Encore at Lake Grove

New Leisure Knoll

257 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$399,000

2 beds

2 baths

1,000 sq ft

Condo

257 EDINBURGH DR, BROOKHAVEN, NY, 11961

1302 BALTUSROL BLVD, RIVERHEAD, NY, 1190...

Community: Stoneleigh Woods at Riverhead

New Oronoque Village

664 OSAGE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$499,000

1 beds

3 baths

1,438 sq ft

664 OSAGE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Oronoque Village

543 N TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$585,000

1 beds

3 baths

1,426 sq ft

Condo

543 N TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

New Encore at Lake Grove

176 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755

$609,000

2 beds

2 baths

1,429 sq ft

Condo

176 SYMPHONY DR, BROOKHAVEN, NY, 11755

Community: Encore at Lake Grove

New Regency at Prospect

196 SYCAMORE DR 196, PROSPECT, CT, 06712, Prospect, CT 06712

$307,127

3 beds

2 baths

1,500 sq ft

Condo

196 SYCAMORE DR 196, PROSPECT, CT, 06712

Condo

541 STRATFORD LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

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

Questions? Call us: (631) 407-2675

Heritage Village

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

$309,000

3 beds

2 baths

1,716 sq ft

Condo

847 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

132 BISON LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$470,000

1 beds

3 baths

1,426 sq ft

Condo

132 BISON LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$405,000

2 beds

2 baths

1,432 sq ft

Condo

648 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Fairfield at St. James

309 FLAIR DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$454,000

1 beds

2 baths

983 sq ft

Condo

309 FLAIR DR, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Foxwood Village

1407 MIDDLE RD 253, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$449,000

3 beds

2 baths

1,753 sq ft

House

1407 MIDDLE RD 253, RIVERHEAD, NY, 11933

Community: Foxwood Village

Leisure Village

265 NEWCASTLE CT B, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$335,000

2 beds

1 baths

875 sq ft

Condo

265 NEWCASTLE CT B, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Fairfield at St. James

607 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$529,000

1 beds

2 baths

950 sq ft

Condo

607 CABOT CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Stone Ridge Estates

170 LARRY LN, HUNTINGTON, NY, 11746, Huntington, NY 11746

$789,000

2 beds

2 baths

1,415 sq ft

Condo

170 LARRY LN, HUNTINGTON, NY, 11746

Community: Stone Ridge Estates

Fairfield at St. James

604 CABOT CT 604, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$499,000

2 beds

2 baths

10 sq ft

Condo

604 CABOT CT 604, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Whitney Glen

32 WHITNEY GLN 32, WESTPORT, CT, 06880, Westport, CT 06880

$459,000

1 beds

2 baths

949 sq ft

Condo

32 WHITNEY GLN 32, WESTPORT, CT, 06880

Community: Whitney Glen

Encore at Lake Grove

58 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755

$629,990

2 beds

3 baths

Condo

58 SYMPHONY DR, BROOKHAVEN, NY, 11755

Community: Encore at Lake Grove

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

Questions? Call us: (631) 407-2675

South Pond Village

20 REED CT 20, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$245,000

2 beds

2 baths

1,202 sq ft

Condo

20 REED CT 20, BLOOMFIELD, CT, 06002

Community: South Pond Village

Pond Spring Village

35 OCTOBER LN 35, BEACON FALLS, CT, 0646..., Beacon Falls, CT 06468

$420,000

2 beds

3 baths

1,328 sq ft

Condo

35 OCTOBER LN 35, BEACON FALLS, CT, 0646...

Community: Pond Spring 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 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.

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

3 beds

3 baths

2,500 sq ft

House

2 beds

2 baths

1,094 sq ft

House

3 beds

3 baths

2,816 sq ft

House

2 beds

2 baths

1,736 sq ft

House

3 beds

3 baths

1,837 sq ft

Condo

2 beds

3 baths

1,378 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

3 beds

3 baths

2,652 sq ft

Condo

2 beds

3 baths

1,942 sq ft

Condo

2 beds

3 baths

2,820 sq ft

Condo

2 beds

2 baths

1,944 sq ft

Condo

2 beds

3 baths

1,350 sq ft

Condo

1 beds

3 baths

1,438 sq ft

1 beds

3 baths

1,426 sq ft

Condo

2 beds

2 baths

1,429 sq ft

Condo

3 beds

2 baths

1,500 sq ft

Condo

2 beds

3 baths

2,256 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths