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

95 communities near Southold

Sort by:

Relevance

3.6 rating (7 reviews)

Heritage Village

$200ks - $500ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

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

Questions? Call us: (631) 407-2675

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

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)

The Villages at Mount Sin...

$600ks

The Villages at Mount Sin..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

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

Questions? Call us: (631) 407-2675

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

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

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

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

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

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

Questions? Call us: (631) 407-2675

The Vineyards at Miller P...

$500ks

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

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

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

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

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

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

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

Stone Ridge Estates

$500ks - $600ks

Stone Ridge Estates, Dix Hills, NY

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

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

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

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

Questions? Call us: (631) 407-2675

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

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

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

174 ADELE CT, RIVERHEAD, NY, 11901

Community: Saddle Lakes

New Spring Lake Village

402 LAKEVIEW DR 402, SOUTHINGTON, CT, 06..., Southington, CT 06489

$324,900

2 beds

2 baths

1,188 sq ft

Condo

402 LAKEVIEW DR 402, SOUTHINGTON, CT, 06...

Community: Spring Lake Village

New Westhampton Pines

171 JONATHAN LN, SOUTHAMPTON, NY, 11977, Southampton, NY 11977

$1,345,000

3 beds

3 baths

2,310 sq ft

Condo

171 JONATHAN LN, SOUTHAMPTON, NY, 11977

339 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (631) 407-2675

New The Village at Oxford Greens

567 INVERNESS CT 567, OXFORD, CT, 06478, Oxford, CT 06478

$665,000

2 beds

2 baths

2,008 sq ft

567 INVERNESS CT 567, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New The Powder Forest Homes

15 BANTRY RD 15, SIMSBURY, CT, 06070, Simsbury, CT 06070

$949,000

4 beds

3 baths

1,878 sq ft

15 BANTRY RD 15, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

New Oronoque Village

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

$625,000

2 beds

3 baths

1,415 sq ft

Condo

283 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

New The Seasons at Elwood

35 WINTER PL, HUNTINGTON, NY, 11731, Huntington, NY 11731

$949,000

2 beds

3 baths

1,500 sq ft

Condo

35 WINTER PL, HUNTINGTON, NY, 11731

Community: The Seasons at Elwood

Encore Atlantic Shores

176 MELODY CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$899,000

2 beds

3 baths

2,800 sq ft

Condo

176 MELODY CT, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

The Waterways at Moriches

605 BAY VIEW CIR 5, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955

$649,000

2 beds

3 baths

1,485 sq ft

Condo

605 BAY VIEW CIR 5, BROOKHAVEN, NY, 1195...

Community: The Waterways at Moriches

Meadow Brook Estates

211 MEADOW BROOK RD 211, OXFORD, CT, 064..., Oxford, CT 06478

$625,000

3 beds

3 baths

2,201 sq ft

Condo

211 MEADOW BROOK RD 211, OXFORD, CT, 064...

Community: Meadow Brook Estates

Heritage Village

10 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$364,000

3 beds

2 baths

1,716 sq ft

Condo

10 HERITAGE CIR A, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

342 SONGBIRD LN 342, SOUTHINGTON, CT, 06..., Southington, CT 06489

$259,900

2 beds

1 baths

912 sq ft

Condo

342 SONGBIRD LN 342, SOUTHINGTON, CT, 06...

Community: Spring Lake Village

Leisure Village

134 EASTBOURNE CT D, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$329,000

2 beds

1 baths

875 sq ft

Condo

134 EASTBOURNE CT D, BROOKHAVEN, NY, 119...

Community: Leisure Village

Heritage Village

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

$248,000

2 beds

2 baths

1,044 sq ft

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (631) 407-2675

Encore Atlantic Shores

203 BACH CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$759,000

2 beds

2 baths

1,889 sq ft

Condo

203 BACH CT, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

Heritage Village

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

$237,000

2 beds

2 baths

1,076 sq ft

Condo

24 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$249,000

2 beds

2 baths

1,076 sq ft

Condo

59 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

93 SEMINOLE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$559,000

2 beds

3 baths

2,542 sq ft

Condo

93 SEMINOLE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Westhampton Pines

112 ASHLEY, SOUTHAMPTON, NY, 11977, Southampton, NY 11977

$1,225,000

3 beds

3 baths

2,304 sq ft

Condo

112 ASHLEY, SOUTHAMPTON, NY, 11977

Community: Westhampton Pines

Heritage Village

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

$229,900

2 beds

2 baths

1,044 sq ft

Condo

196 HERITAGE VLG E, SOUTHBURY, CT, 06488

Community: Heritage Village

Fairfield at St. James

703 DREW DR D7, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$429,999

1 beds

1 baths

752 sq ft

Condo

703 DREW DR D7, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Leisure Knoll

183 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$415,000

2 beds

1 baths

960 sq ft

Condo

183 KINGSTON DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Regency at Prospect

6 LILAC LN 6, PROSPECT, CT, 06712, Prospect, CT 06712

$474,900

2 beds

3 baths

1,552 sq ft

Condo

6 LILAC LN 6, PROSPECT, CT, 06712

Community: Regency at Prospect

Leisure Village

200 NEWCASTLE CT E, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$255,000

1 beds

1 baths

684 sq ft

Condo

200 NEWCASTLE CT E, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Windcrest East

116 GOLDEN SPRUCE DR, RIVERHEAD, NY, 119..., Riverhead, NY 11933

$774,900

3 beds

3 baths

2,200 sq ft

House

116 GOLDEN SPRUCE DR, RIVERHEAD, NY, 119...

Community: Windcrest East

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

Questions? Call us: (631) 407-2675

Woodridge Strathmore Terrace

32 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$549,990

2 beds

2 baths

Condo

32 HEARTHSIDE DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

Heritage Village

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

$359,000

3 beds

2 baths

1,716 sq ft

Condo

912 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 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?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Southold?

Call us: (631) 407-2675

95 communities

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Jun 18, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

95 communities near Southold

186 homes near Southold

2 beds

2 baths

1,102 sq ft

Condo

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

1,631 sq ft

Condo

2 beds

2 baths

1,188 sq ft

Condo

3 beds

3 baths

2,310 sq ft

Condo

2 beds

2 baths

954 sq ft

Condo

2 beds

3 baths

1,558 sq ft

Condo

2 beds

2 baths

1,450 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

2 beds

3 baths

1,350 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

4 baths

2,718 sq ft

Condo

2 beds

2 baths

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,261 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

2,008 sq ft

4 beds

3 baths

1,878 sq ft

2 beds

3 baths

1,415 sq ft

Condo

2 beds

3 baths

1,500 sq ft

Condo