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 Village at Oxford Gre...

$400ks - $500ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

The Manors at The Colony ...

$300ks - $400ks

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

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

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.

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

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

Questions? Call us: (631) 407-2675

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

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

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

5 rating (1 reviews)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

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

Windmill Gate

$300ks - $400ks

Windmill Gate, Oakdale, NY

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

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

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

Questions? Call us: (631) 407-2675

Billingsgate

$400ks - $600ks

Billingsgate, Simsbury, CT

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

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

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

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

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

The Vineyards at Miller P...

$500ks

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

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

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

Questions? Call us: (631) 407-2675

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

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

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

$350,000

2 beds

2 baths

1,398 sq ft

Condo

581 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New 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

New Oronoque Village

212 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614

$319,000

1 beds

2 baths

1,426 sq ft

Condo

212 AGAWAM DR B, STRATFORD, CT, 06614

Community: Oronoque Village

New 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: Leisure 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

The Village 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: The Village at Oxford Greens

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

Questions? Call us: (631) 407-2675

Fairview at Oxford Greens

$699,900

2 beds

2 baths

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

Leisure Glen

581 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$625,000

2 beds

2 baths

1,685 sq ft

Condo

581 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Meadowbrook Pointe Links & Spa

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

$333,051

2 beds

2 baths

1,133 sq ft

Condo

252 SAND HILLS LN, BROOKHAVEN, NY, 11763

Community: Meadowbrook Pointe Links & Spa

Leisure Knoll

190 CANTERBURY DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$519,900

2 beds

1 baths

1,220 sq ft

Condo

190 CANTERBURY DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Glenwood Village

1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,..., Riverhead, NY 11901

$469,000

2 beds

2 baths

1,500 sq ft

Manufactured Home

1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,...

Community: Glenwood Village

Foxwood Village

1407 MIDDLE RD 277, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$515,000

2 beds

2 baths

1,568 sq ft

Manufactured Home

1407 MIDDLE RD 277, RIVERHEAD, NY, 11933

Community: Foxwood Village

Encore at Lake Grove

189 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755

$669,000

2 beds

3 baths

1,378 sq ft

Condo

189 SYMPHONY DR, BROOKHAVEN, NY, 11755

Community: Encore at Lake Grove

Heritage Village

1008 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$518,000

3 beds

2 baths

1,716 sq ft

Condo

1008 HERITAGE VLG A, SOUTHBURY, CT, 0648...

Community: Heritage Village

Heritage Village

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

$249,000

2 beds

2 baths

1,308 sq ft

Condo

76 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Greenwood Village

89 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$99,999

1 beds

1 baths

812 sq ft

Condo

89 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Setauket Meadows

66 BRIANNA DR, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733

$739,999

2 beds

3 baths

1,878 sq ft

Condo

66 BRIANNA DR, BROOKHAVEN, NY, 11733

Community: Setauket Meadows

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

Questions? Call us: (631) 407-2675

Heritage Village

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

$255,000

2 beds

2 baths

1,071 sq ft

Condo

773 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$449,000

2 beds

2 baths

1,432 sq ft

Condo

818 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

176 VENTRY CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$399,000

2 beds

1 baths

1,085 sq ft

Condo

176 VENTRY CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

Glenwood Village

1661 OLD COUNTRY RD 233, RIVERHEAD, NY, ..., Riverhead, NY 11901

$239,999

2 beds

2 baths

980 sq ft

Manufactured Home

1661 OLD COUNTRY RD 233, RIVERHEAD, NY, ...

Community: Glenwood Village

Pond Spring Village

111 PONDVIEW CIR, BEACON FALLS, CT, 0640..., Beacon Falls, CT 06403

$438,000

2 beds

2 baths

1,328 sq ft

Condo

111 PONDVIEW CIR, BEACON FALLS, CT, 0640...

Community: Pond Spring Village

Heritage Village

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

$310,000

2 beds

2 baths

1,398 sq ft

Condo

233 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

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

$689,000

3 beds

2 baths

2,008 sq ft

Condo

349 NIBLICK LN 349, OXFORD, CT, 06478

Community: The Village at Oxford Greens

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

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

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

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

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

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

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 optout@55places.com. 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: Jul 21, 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

190 homes near Southold

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

1,398 sq ft

Condo

3 beds

3 baths

2,449 sq ft

House

1 beds

2 baths

1,426 sq ft

Condo

1 beds

3 baths

1,360 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

3 baths

2,172 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Condo

2 beds

3 baths

1,503 sq ft

2 beds

2 baths

1,032 sq ft

Condo

1 beds

2 baths

1,360 sq ft

Condo

2 beds

1 baths

Condo

2 beds

3 baths

2,331 sq ft

Condo

2 beds

2 baths

1,682 sq ft

2 beds

2 baths

1,682 sq ft

2 beds

2 baths

1,685 sq ft

Condo

2 beds

2 baths

1,133 sq ft

Condo

2 beds

1 baths

1,220 sq ft

Condo

2 beds