Call us at (631) 407-2675 to learn more about active adult communities in Southold

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

Living in Southold

Southold is one of four towns in Suffolk County, New York, located in the northeast corner of the state. Its prime location and coastal scenery have made it an enticing option…

Southold is one of four towns in Suffolk County, New York, located in the northeast corner of the state. Its prime location and coastal scenery have made it an enticing option for retirees. The town is also home to a quaint, relaxed environment, which is ideal for those in search of a comfortable lifestyle.

Climate & Geography

Located on the North Fork peninsula of Long Island, Southold lies in a transitional zone between a humid subtropical climate and a humid continental climate. Summers in the region are hot and humid while winters can be cold and snowy, although they are milder than the rest of the state because of the town's coastal location. There is regular precipitation throughout the year, with more rainfall than the national average, an average amount of snowfall, and approximately 206 days of sunshine throughout the year.

Recreation, Culture & Entertainment

Residents in search of outdoor recreation such as hiking, camping, hunting, fishing, canoeing, and more, will find plenty of opportunities in the nature areas around Southold. It's home to plenty of wildlife and coastal habitats including: Fisher Island Beaches, Pine Islands and Shallows, and Golfsmith Inlet and Beach. Aside from these, there are also six large vineyards across the town, which offer fine tasting wine and fascinating scenery.

Southold is known for its small-town charm and neighborly feel. Their downtown is defined by local shops and businesses, such as antique stores, art galleries, restaurants, and breweries. Not to mention, its location on Long Island is convenient for residents who want to explore even more amenities, beaches, and attractions. Residents can also reach New York City in two hours by car or three hours on public transit, perfect for a day trip or a weekend getaway.

Cost of Living & Taxes

Much like the majority of New York, the overall cost of living in Southold is significantly higher than national average. This can be attributed to the cost of housing which is well above the U.S median.

Health Care

Southold is in driving distance of Port Jefferson where residents can find two hospitals and medical centers. One of these facilities, John T. Mather Memorial Hospital, is rated high performing by U.S News in 3 adult specialties and 2 other procedures.

Frequently Asked Questions


95 communities near Southold

Sort by:

Relevance

Relevance

Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Country Village Estates
$300ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes
Long Hill Village
$300ks - $400ks
Long Hill Village, Trumbull, CT
Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes
Founders Village
$400ks - $500ks
Founders Village, Southold, NY
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes
Setauket Meadows
$500ks - $600ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Bidwell Village
$300ks - $400ks
Bidwell Village, Coventry, CT
New Construction | 55+ age-restricted | Built 2020 - present | 37 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
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Country Pointe Preserve
$600ks - $900ks
Country Pointe PreserveYaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 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.
Bella Vista
$300ks - $400ks
Bella Vista, Glocester, RI
Resale Only | 55+ age-restricted | Built 2015 - 2021 | 70 homes
Applegate Estates
$500ks - $400ks
Applegate Estates, Southington, CT
New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes
Eastport Meadows
$400ks
Eastport Meadows, Eastport, NY
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 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
Village Vistas
$800ks - $1Ms
Village Vistas, Port Jefferson, NY
Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes
Windmill Gate
$300ks - $400ks
Windmill Gate, Oakdale, NY
Resale Only | 55+ age-restricted | Built 1989 - 1991 | 110 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
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
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.
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
5 rating (2 reviews) Benson Woods
$400ks - $600ks
Benson Woods, Middlebury, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes
Clockmaker's Hill
$100ks
Clockmaker's Hill, Winsted, CT
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes
Bartlett Hill
$300ks - $400ks
Bartlett Hill, Portland, CT
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes
Fieldstone Village
$500ks - $800ks
Fieldstone Village, Orange, CT
Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Castle Heights of Cheshir...
$500ks - $600ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 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
North Woods of Colchester
$300ks - $400ks
North Woods of Colchester, Colchester, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 140 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.
Chimney Hill
$500ks - $700ks
Chimney Hill, Farmington, CT
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes
RiverWalk
$500ks - $600ks
RiverWalk, Branford, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes
Newington Ridge Preserve
$300ks - $400ks
Newington Ridge Preserve, Newington, CT
New Construction | 55+ age-restricted | Built 2014 - present | 16 homes
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
The Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
Bartlett Hollow
$200ks - $400ks
Bartlett Hollow, Middletown, CT
New Construction | 55+ age-restricted | Built 2015 - present | 25 homes
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
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
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
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.
Greenwood Village 201 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$250,000

2 beds

|

2 baths

|

1,078 sq ft

|

Condo

201 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Greenwood Village 201 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$250,000

2 beds

|

2 baths

|

1,078 sq ft

|

Condo

201 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
New Heritage Village 170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$339,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 778 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$420,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

778 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 176 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$274,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

176 HERITAGE VLG D, 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 Leisure Village 387 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$499,000

2 beds

|

2 baths

|

1,767 sq ft

|

Condo

387 WOODBRIDGE DR A, BROOKHAVEN, NY, 119...
Community: Leisure Village
New Leisure Village 387 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$499,000

2 beds

|

2 baths

|

1,767 sq ft

|

Condo

387 WOODBRIDGE DR A, BROOKHAVEN, NY, 119...
Community: Leisure Village
New Glenwood Village 1661 OLD COUNTRY RD 77, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$335,000

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 77, RIVERHEAD, NY, 1...
Community: Glenwood Village
New Glenwood Village 1661 OLD COUNTRY RD 77, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$335,000

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 77, RIVERHEAD, NY, 1...
Community: Glenwood Village
New Glenwood Village 1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901
$410,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
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.
New Glenwood Village 1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901
$410,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
New Meadow Brook Estates 802 SAGE HILL DR 802, OXFORD, CT, 06478, Oxford, CT 06478
$675,000

2 beds

|

3 baths

|

2,258 sq ft

|

Condo

802 SAGE HILL DR 802, OXFORD, CT, 06478
New Meadow Brook Estates 802 SAGE HILL DR 802, OXFORD, CT, 06478, Oxford, CT 06478
$675,000

2 beds

|

3 baths

|

2,258 sq ft

|

Condo

802 SAGE HILL DR 802, OXFORD, CT, 06478
New Leisure Knoll 346 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$419,000

2 beds

|

1 baths

|

1,050 sq ft

|

Condo

346 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New Leisure Knoll 346 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$419,000

2 beds

|

1 baths

|

1,050 sq ft

|

Condo

346 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New Sunken Pond Estates 3102 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$525,000

2 beds

|

2 baths

|

1,587 sq ft

|

Condo

3102 AMEN COR, RIVERHEAD, NY, 11901
Community: Sunken Pond Estates
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
New Sunken Pond Estates 3102 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$525,000

2 beds

|

2 baths

|

1,587 sq ft

|

Condo

3102 AMEN COR, RIVERHEAD, NY, 11901
Community: Sunken Pond Estates
New Leisure Knoll 177 CANTERBURY DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$379,900

2 beds

|

1 baths

|

1,116 sq ft

|

Condo

177 CANTERBURY DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New Leisure Knoll 177 CANTERBURY DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$379,900

2 beds

|

1 baths

|

1,116 sq ft

|

Condo

177 CANTERBURY DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New Sunrise Village 152 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782
$519,990

2 beds

|

2 baths

|

1,230 sq ft

|

Condo

152 REVERE DR, ISLIP, NY, 11782
Community: Sunrise Village
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.
New Sunrise Village 152 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782
$519,990

2 beds

|

2 baths

|

1,230 sq ft

|

Condo

152 REVERE DR, ISLIP, NY, 11782
Community: Sunrise Village
New Strathmore Gate East 46 FORGE LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$429,999

2 beds

|

2 baths

|

1,112 sq ft

|

House

46 FORGE LN, BROOKHAVEN, NY, 11727
New Strathmore Gate East 46 FORGE LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$429,999

2 beds

|

2 baths

|

1,112 sq ft

|

House

46 FORGE LN, BROOKHAVEN, NY, 11727
Foxwood Village 1407 MIDDLE RD 271, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$465,000

3 beds

|

2 baths

|

1,792 sq ft

|

Manufactured Home

1407 MIDDLE RD 271, RIVERHEAD, NY, 11933
Community: Foxwood Village
Foxwood Village 1407 MIDDLE RD 271, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$465,000

3 beds

|

2 baths

|

1,792 sq ft

|

Manufactured Home

1407 MIDDLE RD 271, RIVERHEAD, NY, 11933
Community: Foxwood Village
Granite Woods 35 NUTMEG RD B5, MIDDLEBURY, CT, 06762, Middlebury, CT 06762
$250,000

2 beds

|

1 baths

|

890 sq ft

|

Condo

35 NUTMEG RD B5, MIDDLEBURY, CT, 06762
Community: Granite Woods
Granite Woods 35 NUTMEG RD B5, MIDDLEBURY, CT, 06762, Middlebury, CT 06762
$250,000

2 beds

|

1 baths

|

890 sq ft

|

Condo

35 NUTMEG RD B5, MIDDLEBURY, CT, 06762
Community: Granite Woods
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Greenwood Village 33 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$225,000

2 beds

|

2 baths

|

1,134 sq ft

|

House

33 DOGWOOD LN, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Greenwood Village 33 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$225,000

2 beds

|

2 baths

|

1,134 sq ft

|

House

33 DOGWOOD LN, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Windcrest East 90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193..., Riverhead, NY 11933
$799,000

3 beds

|

3 baths

|

2,620 sq ft

|

Condo

90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...
Community: Windcrest East
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.
Windcrest East 90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193..., Riverhead, NY 11933
$799,000

3 beds

|

3 baths

|

2,620 sq ft

|

Condo

90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...
Community: Windcrest East
Windcrest East 29 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193..., Riverhead, NY 11933
$799,990

3 beds

|

3 baths

|

2,531 sq ft

|

Condo

29 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...
Community: Windcrest East
Windcrest East 29 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193..., Riverhead, NY 11933
$799,990

3 beds

|

3 baths

|

2,531 sq ft

|

Condo

29 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...
Community: Windcrest East
Leisure Glen 9 AMAGANSETT CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$519,900

2 beds

|

2 baths

|

1,476 sq ft

|

Condo

9 AMAGANSETT CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Leisure Glen 9 AMAGANSETT CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$519,900

2 beds

|

2 baths

|

1,476 sq ft

|

Condo

9 AMAGANSETT CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Long Hill Village 48 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611
$499,900

2 beds

|

2 baths

|

1,070 sq ft

|

Condo

48 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill Village
Long Hill Village 48 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611
$499,900

2 beds

|

2 baths

|

1,070 sq ft

|

Condo

48 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill Village
Meadow Brook Estates 130 MEADOW BROOK RD 130, OXFORD, CT, 064..., Oxford, CT 06478
$599,000

2 beds

|

3 baths

|

1,920 sq ft

|

Condo

130 MEADOW BROOK RD 130, OXFORD, CT, 064...
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Meadow Brook Estates 130 MEADOW BROOK RD 130, OXFORD, CT, 064..., Oxford, CT 06478
$599,000

2 beds

|

3 baths

|

1,920 sq ft

|

Condo

130 MEADOW BROOK RD 130, OXFORD, CT, 064...
Greenwood Village 10 GREENWOOD BLVD, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$179,999

2 beds

|

1 baths

|

938 sq ft

|

Condo

10 GREENWOOD BLVD, BROOKHAVEN, NY, 11949
Community: Greenwood Village
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.

Frequently Asked Questions


Want more information about active adult communities around Southold?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
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

Reinmlsx

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: Oct 13, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top