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Southold, NY 55+ active adult communities & homes for sale - Page 2
95 communities near Southold
201 homes near Southold
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$200ks
- $300ks
Hopmeadow Place, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2005
|
66 homes
$500ks
- $600ks
Stone Ridge Estates, Dix Hills, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2013
|
76 homes
$800ks
- $900ks
The Seasons at Elwood, East Northport, NY
Resale Only
|
55+ age-restricted
|
Built 2018 - 2020
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256 homes
$500ks
Regency Meadows, Trumbull, CT
Resale Only
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55+ age-restricted
|
Built 2003 - 2005
|
51 homes
$800ks
- $1Ms
The Vineyards at Mount Si..., Mount Sinai, NY
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
91 homes
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$400ks
- $500ks
Shaker Heights, Enfield, CT
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
77 homes
$600ks
- $700ks
Granite Woods, Middlebury, CT
New Construction
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55+ age-restricted
|
Built 2020 - present
|
24 homes
$500ks
- $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
70 homes
$300ks
- $400ks
Forest Mews, Avon, CT
Resale Only
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55+ age-restricted
|
Built 2001 - 2004
|
40 homes
$300ks
- $400ks
Bella Vista, Glocester, RI
Resale Only
|
55+ age-restricted
|
Built 2015 - 2021
|
70 homes
Download the Ultimate 55+ Homebuying Guide
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$400ks
Eastport Meadows, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2016
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50 homes
5 rating (1 reviews)
![Encore at Lake Grove]()
$500ks
- $700ks
Encore at Lake Grove, Lake Grove, NY
Resale Only
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55+ age-restricted
|
Built 2006 - 2007
|
228 homes
$300ks
- $400ks
Windmill Gate, Oakdale, NY
Resale Only
|
55+ age-restricted
|
Built 1989 - 1991
|
110 homes
3.5 rating (2 reviews)
![Harvest Pointe]()
$800ks
- $3Ms
Harvest Pointe, Cutchogue, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
124 homes
$1Ms
Jessup's Landing, Quogue, NY
New and Resale
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55+ age-restricted
|
Built 2009 - 2016
|
31 homes
$400ks
- $500ks
The Pines at Bohemia, Bohemia, NY
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
20 homes
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$600ks
- $700ks
The Polo Club at Islandia, Islandia, NY
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
72 homes
$600ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
99 homes
$700ks
The Seasons at East North..., East Northport, NY
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
190 homes
$500ks
- $400ks
Applegate Estates, Southington, CT
New and Resale
|
55+ age-restricted
|
Built 2010 - 2025
|
94 homes
Download the Ultimate 55+ Homebuying Guide
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$300ks
- $400ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
5 rating (2 reviews)
![Benson Woods]()
$400ks
- $600ks
Benson Woods, Middlebury, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
79 homes
$100ks
Clockmaker's Hill, Winsted, CT
Resale Only
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55+ age-restricted
|
Built 2005 - 2014
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38 homes
$300ks
- $400ks
The Village at Buckingham, Avon, CT
Resale Only
|
55+ age-restricted
|
Built 2002 - 2006
|
56 homes
$300ks
- $400ks
Bartlett Hill, Portland, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2011
|
82 homes
$300ks
Sonoma Woods, Middletown, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2015
|
68 homes
$500ks
- $800ks
Fieldstone Village, Orange, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2018
|
142 homes
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1 rating (1 reviews)
![Beckley Farms]()
$300ks
- $400ks
Beckley Farms, Berlin, CT
New and Resale
|
55+ age-restricted
|
Built 2010 - present
|
170 homes
$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
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.
$300ks
- $400ks
North Woods of Colchester, Colchester, CT
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
140 homes
$500ks
- $700ks
Chimney Hill, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
44 homes
$500ks
- $600ks
RiverWalk, Branford, CT
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
60 homes
$300ks
- $400ks
Newington Ridge Preserve, Newington, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
16 homes
$500ks
- $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2016
|
182 homes
5 rating (3 reviews)
![Founders Ridge]()
$300ks
- $400ks
Founders Ridge, Middletown, CT
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
75 homes
$200ks
- $400ks
Bartlett Hollow, Middletown, CT
New Construction
|
55+ age-restricted
|
Built 2015 - present
|
25 homes
$500ks
- $600ks
Autumn Estates, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 2011 - 2017
|
30 homes
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<$100k
The Atrium of Portland, Portland, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2004
|
56 homes
$200ks
Boulder Brook, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2006
|
35 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.
Heritage Village
![345 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
345 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24196164 • Keller Williams Realty, Marvin Ben... • Keller Williams Realty
Greenwood Village
![105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949]()
2 beds
|2 baths
|1,130 sq ft
|Condo
105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1...
Community: Greenwood Village
MLS 1029061 • Gateway to The Hamptons R E, Janet ... • Gateway to The Hamptons R E
Glenwood Village
![1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,624 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 1011541 • Gateway to The Hamptons R E, Vivian... • Gateway to The Hamptons R E
New
Heritage Village
![738 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
738 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24202019 • Lamacchia Realty, Stephanie Plaza • Lamacchia Realty
New
Granite Woods
![35 NUTMEG RD B2, MIDDLEBURY, CT, 06762, Middlebury, CT 06762]()
1 beds
|1 baths
|889 sq ft
|Condo
35 NUTMEG RD B2, MIDDLEBURY, CT, 06762
Community: Granite Woods
MLS 24202228 • RE/MAX RISE, Maria Pinheiro • RE/MAX RISE
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New
Woodridge Strathmore Terrace
![6 COBBLESTONE WAY, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766]()
2 beds
|2 baths
|1,151 sq ft
|Condo
6 COBBLESTONE WAY, BROOKHAVEN, NY, 11766
Community: Woodridge Strathmore Terrace
MLS 1043235 • S & J Property Management Corp, Jen... • S & J Property Management Corp
New
Oronoque Village
![393 OTTAWA LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,118 sq ft
|Condo
393 OTTAWA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24202099 • Joy Real Estate, Richard Persico • Joy Real Estate
New
Foxwood Village
![1407 MIDDLE RD 265, RIVERHEAD, NY, 11933, Riverhead, NY 11933]()
3 beds
|2 baths
|1,792 sq ft
|Manufactured Home
1407 MIDDLE RD 265, RIVERHEAD, NY, 11933
Community: Foxwood Village
MLS 1043007 • Douglas Elliman Real Estate, Sheryl... • Douglas Elliman Real Estate
New
Leisure Village
![463 B OLDHAM CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|1 baths
|1,074 sq ft
|Condo
463 B OLDHAM CT, BROOKHAVEN, NY, 11961
Community: Leisure Village
MLS 1042796 • Century 21 KR Realty, Jane A. Argir... • Century 21 KR Realty
New
Leisure Village
![472 DARWEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,200 sq ft
|Condo
472 DARWEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Village
MLS 1043048 • World Prop Intl Sea to Sky, Matthew... • World Prop Intl Sea to Sky
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
South Pond Village
![78 SILO WAY 78, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002]()
3 beds
|3 baths
|1,639 sq ft
|Condo
78 SILO WAY 78, BLOOMFIELD, CT, 06002
Community: South Pond Village
MLS 24200832 • Berkshire Hathaway NE Prop., Karen... • Berkshire Hathaway NE Prop.
New
Plymouth Estates at Mount Sinai
![7 POND CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766]()
2 beds
|2 baths
|1,274 sq ft
|Condo
7 POND CIR, BROOKHAVEN, NY, 11766
Community: Plymouth Estates at Mount Sinai
MLS 1040452 • BH&G R E Realty Connect, Judith A. ... • BH&G R E Realty Connect
New
Leisure Knoll
![152A LAURANCE LN A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961]()
2 beds
|1 baths
|724 sq ft
|Condo
152A LAURANCE LN A, BROOKHAVEN, NY, 1196...
Community: Leisure Knoll
MLS 1042894 • Coldwell Banker American Homes, Mar... • Coldwell Banker American Homes
New
Leisure Glen
![6 OAKDALE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
MLS 1042317 • Leisure Living Realty Inc, Laura Ru... • Leisure Living Realty Inc
New
Leisure Glen
![428 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,652 sq ft
|Condo
428 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
MLS 1042640 • Signature Premier Properties, Mildr... • Signature Premier Properties
New
Oronoque Village
![138 BISON LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
MLS 24201494 • Coldwell Banker Realty, Christine ... • Coldwell Banker Realty
Want to learn more about 55+ communities in Southold?
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Questions? Call us:
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New
Leisure Village
![134 EASTBOURNE CT A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961]()
2 beds
|1 baths
|836 sq ft
|Condo
134 EASTBOURNE CT A, BROOKHAVEN, NY, 119...
Community: Leisure Village
MLS 1042262 • Century 21 AA Realty, Mary E. Gugli... • Century 21 AA Realty
New
Sunrise Village
![17 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782]()
MLS 1041823 • Douglas Elliman Real Estate, Michel... • Douglas Elliman Real Estate
New
Leisure Glen
![454 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,652 sq ft
|Condo
454 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
MLS 1041411 • Manzoni Real Estate, Ray Manzoni CB... • Manzoni Real Estate
New
Heritage Village
![857 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,071 sq ft
|Condo
857 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24200789 • Keller Williams Realty, Karen Dibb... • Keller Williams Realty
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
Heritage Village
![9 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,071 sq ft
|Condo
9 HERITAGE CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24201310 • Berkshire Hathaway NE Prop., Scott... • Berkshire Hathaway NE Prop.
New
Heritage Village
![353 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
353 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24201344 • Century 21 Bette Real Estate, Just... • Century 21 Bette Real Estate
New
Woodridge Strathmore Terrace
![89 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766]()
1 beds
|1 baths
|720 sq ft
|Condo
89 HEARTHSIDE DR, BROOKHAVEN, NY, 11766
Community: Woodridge Strathmore Terrace
MLS 1042035 • Coldwell Banker American Homes, Ric... • Coldwell Banker American Homes
New
Heritage Village
![559 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
559 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24200880 • Robert J. Drakeley, Broker, CT REO... • Robert J. Drakeley, Broker
Vineyards at Blue Point
![132 HALLEY DR, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772]()
2 beds
|4 baths
|2,290 sq ft
|Condo
132 HALLEY DR, BROOKHAVEN, NY, 11772
Community: Vineyards at Blue Point
MLS 1040054 • Next Phase Realty LLC, Lamar Lanier... • Next Phase Realty LLC
Eagles Walk at East Quogue
![1401 AERIE WAY, SOUTHAMPTON, NY, 11942, Southampton, NY 11942]()
2 beds
|2 baths
|1,271 sq ft
|Condo
1401 AERIE WAY, SOUTHAMPTON, NY, 11942
Community: Eagles Walk at East Quogue
MLS 1041260 • Signature Premier Properties, Jeane... • Signature Premier Properties
Heritage Village
![397 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
397 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24200929 • Keller Williams Realty, Lou Capell... • Keller Williams Realty
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Shaker Heights
![12 COPLEY CIR 12, ENFIELD, CT, 06082, Enfield, CT 06082]()
2 beds
|2 baths
|1,897 sq ft
|Condo
12 COPLEY CIR 12, ENFIELD, CT, 06082
Community: Shaker Heights
MLS 73563615 • Berkshire Hathaway HomeServices Re... • Berkshire Hathaway HomeServices Realty Professionals
Founders Village
![2555 YOUNGS AVE 3C, SOUTHOLD, NY, 11971, Southold, NY 11971]()
2 beds
|2 baths
|1,100 sq ft
|Condo
2555 YOUNGS AVE 3C, SOUTHOLD, NY, 11971
Community: Founders Village
MLS 1027409 • Thomas J McCarthy Real Estate, Thom... • Thomas J McCarthy Real Estate
Leisure Knoll
![185 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|1 baths
|1,014 sq ft
|Condo
185 KINGSTON DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 1041185 • Douglas Elliman Real Estate, Kennet... • Douglas Elliman Real Estate
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.
Heritage Village
![549 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
549 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24200695 • Berkshire Hathaway NE Prop., Maris... • Berkshire Hathaway NE Prop.
Encore Atlantic Shores
![101 MOZART CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941]()
2 beds
|2 baths
|2,044 sq ft
|House
101 MOZART CT, BROOKHAVEN, NY, 11941
Community: Encore Atlantic Shores
MLS 1040804 • Compass Greater NY LLC, Laura S. Ca... • Compass Greater NY LLC
Heritage Village
![1041 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
2 beds
|2 baths
|1,000 sq ft
|Condo
1041 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24193096 • Carey & Guarrera Real Estate, Alet... • Carey & Guarrera Real Estate
Greenwood Village
![205 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949]()
2 beds
|2 baths
|1,138 sq ft
|House
205 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 1040375 • Dream Select Realty Corp, Juan A. R... • Dream Select Realty Corp
The Village at Oxford Greens
![521 PUTTING GREEN LN 521, OXFORD, CT, 06..., Oxford, CT 06478]()
3 beds
|3 baths
|2,735 sq ft
|Condo
521 PUTTING GREEN LN 521, OXFORD, CT, 06...
Community: The Village at Oxford Greens
MLS 24199321 • William Pitt Sotheby's Int'l, Tom ... • William Pitt Sotheby's Int'l
Setauket Meadows
![2 EMILYS WAY, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733]()
2 beds
|3 baths
|1,842 sq ft
|Condo
2 EMILYS WAY, BROOKHAVEN, NY, 11733
Community: Setauket Meadows
MLS 1039552 • Daniel Gale Sothebys Intl Rlty, Lyn... • Daniel Gale Sothebys Intl Rlty
Oronoque Village
![546 N TRL A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,434 sq ft
|Condo
546 N TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24199616 • Coldwell Banker Realty, Mark Pires • Coldwell Banker Realty
Greenwood Village
![162 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949]()
2 beds
|2 baths
|1,078 sq ft
|Condo
162 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 1039145 • Coldwell Banker American Homes, Rya... • Coldwell Banker American Homes
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Leisure Glen
![272 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
MLS 1039018 • Signature Premier Properties, Mildr... • Signature Premier Properties
Woodridge Strathmore Terrace
![62 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766]()
2 beds
|2 baths
|1,105 sq ft
|Condo
62 HEARTHSIDE DR, BROOKHAVEN, NY, 11766
Community: Woodridge Strathmore Terrace
MLS 1033093 • Douglas Elliman Real Estate, Christ... • Douglas Elliman Real Estate
Download the Ultimate 55+ Homebuying Guide
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Frequently Asked Questions
In Southold, there is 1 small community with less than 500 homes.
The smallest 55+ community in Southold has 92 homes, the largest has 92 homes, and the average community consists of 92 homes.
No, there are no gated 55+ communities in Southold.
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?
Want to learn more about 55+ communities in Southold?
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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: Aug 27, 2026.
This application does not include information on all of the properties available for sale at this time.
