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Southold, NY 55+ active adult communities & homes for sale - Page 10

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


446 homes near Southold

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3.6 rating (7 reviews) Heritage Village
$200ks - $500ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
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5 rating (2 reviews) Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 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.
The Manors at The Colony ...
$300ks - $400ks
The Manors at The Colony ..., Shirley, NY
New Construction | 55+ age-restricted | Built 2013 - present | 150 homes
Meadow Brook Estates
$300ks - $400ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 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) Encore Atlantic Shores
$500ks - $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 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 (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
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 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
Windcrest East
$400ks - $500ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 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) Sunrise Village
$400ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 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
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
Granite Woods
$600ks - $700ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 homes
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
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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
Regency at Woodbridge
$500ks - $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 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.
Country Village Estates
$300ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes
Sonoma Woods
$300ks
Sonoma Woods, Middletown, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes
Setauket Meadows
$500ks - $600ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes
Pond Spring Village
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
The Seasons at Elwood
$800ks - $900ks
The Seasons at Elwood, East Northport, NY
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 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
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Vineyards at Brookfield
$400ks - $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 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
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.
12...3
Heritage Village 38 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

38 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 38 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

38 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 407 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$429,000

1 beds

|

2 baths

|

1,360 sq ft

|

Condo

407 MONTAUK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Oronoque Village 407 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$429,000

1 beds

|

2 baths

|

1,360 sq ft

|

Condo

407 MONTAUK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
The Village at Oxford Greens 941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478
$674,900

2 beds

|

2 baths

|

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
The Village at Oxford Greens 941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478
$674,900

2 beds

|

2 baths

|

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478
Fairview at Oxford Greens 941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478
$674,900

2 beds

|

2 baths

|

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478
Fairview at Oxford Greens 941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478
$674,900

2 beds

|

2 baths

|

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478
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
Glenwood Village 1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,..., Riverhead, NY 11901
$449,000

2 beds

|

2 baths

|

1,500 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 156D, 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.
Greenwood Village 89 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$79,000

1 beds

|

1 baths

|

812 sq ft

|

Condo

89 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Greenwood Village 89 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$79,000

1 beds

|

1 baths

|

812 sq ft

|

Condo

89 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood 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
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
Heritage Village 972 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$337,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

972 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 972 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$337,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

972 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage 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
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
The Seasons at Elwood 178 SUMMER CIR, HUNTINGTON, NY, 11731, Huntington, NY 11731
$1,499,000

2 beds

|

3 baths

|

2,900 sq ft

|

Condo

178 SUMMER CIR, HUNTINGTON, NY, 11731
The Seasons at Elwood 178 SUMMER CIR, HUNTINGTON, NY, 11731, Huntington, NY 11731
$1,499,000

2 beds

|

3 baths

|

2,900 sq ft

|

Condo

178 SUMMER CIR, HUNTINGTON, NY, 11731
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 5131 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$115,000

2 beds

|

2 baths

|

987 sq ft

|

House

5131 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Greenwood Village 5131 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$115,000

2 beds

|

2 baths

|

987 sq ft

|

House

5131 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
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
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
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
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
Heritage Village 191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$574,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

191 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
Heritage Village 191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$574,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Billingsgate 14 BILLINGSGATE DR 14, SIMSBURY, CT, 060..., Simsbury, CT 06070
$750,000

2 beds

|

3 baths

|

2,729 sq ft

|

Condo

14 BILLINGSGATE DR 14, SIMSBURY, CT, 060...
Community: Billingsgate
Billingsgate 14 BILLINGSGATE DR 14, SIMSBURY, CT, 060..., Simsbury, CT 06070
$750,000

2 beds

|

3 baths

|

2,729 sq ft

|

Condo

14 BILLINGSGATE DR 14, SIMSBURY, CT, 060...
Community: Billingsgate
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 Manors at The Colony Preserve 22 CRICKET CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$399,999

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

22 CRICKET CT, BROOKHAVEN, NY, 11967
The Manors at The Colony Preserve 22 CRICKET CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$399,999

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

22 CRICKET CT, BROOKHAVEN, NY, 11967
Saddle Lakes 174 ADELE CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$599,000

2 beds

|

2 baths

|

1,631 sq ft

|

Condo

174 ADELE CT, RIVERHEAD, NY, 11901
Community: Saddle Lakes
Saddle Lakes 174 ADELE CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$599,000

2 beds

|

2 baths

|

1,631 sq ft

|

Condo

174 ADELE CT, RIVERHEAD, NY, 11901
Community: Saddle Lakes
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
Community: Westhampton Pines
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
Community: Westhampton Pines
Meadowbrook Pointe Links & Spa 163 AUGUSTA DR 163, BROOKHAVEN, NY, 1176..., Brookhaven, NY 11763
$649,990

2 beds

|

3 baths

|

1,558 sq ft

|

Condo

163 AUGUSTA DR 163, BROOKHAVEN, NY, 1176...
Meadowbrook Pointe Links & Spa 163 AUGUSTA DR 163, BROOKHAVEN, NY, 1176..., Brookhaven, NY 11763
$649,990

2 beds

|

3 baths

|

1,558 sq ft

|

Condo

163 AUGUSTA DR 163, BROOKHAVEN, NY, 1176...
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
The Village at Oxford Greens 567 INVERNESS CT 567, OXFORD, CT, 06478, Oxford, CT 06478
$650,000

2 beds

|

2 baths

|

2,008 sq ft

|

Condo

567 INVERNESS CT 567, OXFORD, CT, 06478
The Village at Oxford Greens 567 INVERNESS CT 567, OXFORD, CT, 06478, Oxford, CT 06478
$650,000

2 beds

|

2 baths

|

2,008 sq ft

|

Condo

567 INVERNESS CT 567, OXFORD, CT, 06478
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.

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446 homes
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