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Southold, NY 55+ active adult communities & homes for sale - Page 2
94 communities near Southold
155 homes near Southold
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$500Ks
North Woods of Colchester, Colchester, CT
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
140 homes
$600Ks
Windcrest East, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2005
|
126 homes
$600Ks
- $700Ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
125 homes
3.5 rating (2 reviews)
![Harvest Pointe]()
$800Ks
- $3Ms
Harvest Pointe, Cutchogue, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
124 homes
$300Ks
- $400Ks
Windmill Gate, Oakdale, NY
Resale Only
|
55+ age-restricted
|
Built 1989 - 1991
|
110 homes
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$400Ks
- $500Ks
O'Meara Farm, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 1998 - 2005
|
104 homes
$600Ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
99 homes
$500Ks
- $400Ks
Applegate Estates, Southington, CT
New and Resale
|
55+ age-restricted
|
Built 2010 - 2025
|
94 homes
$700Ks
Vineyards at Moriches, Center Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2014
|
92 homes
Download the Ultimate 55+ Homebuying Guide
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$300Ks
Pond Spring Village, Beacon Falls, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
92 homes
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$800Ks
- $1Ms
The Vineyards at Mount Si..., Mount Sinai, NY
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
91 homes
$500Ks
- $600Ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only
|
55+ age-restricted
|
Built 2007 - 2022
|
88 homes
$600Ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2005
|
85 homes
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5 rating (2 reviews)
![Benson Woods]()
$400Ks
- $600Ks
Benson Woods, Middlebury, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
79 homes
$400Ks
- $500Ks
Shaker Heights, Enfield, CT
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
77 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.
$700Ks
Stone Ridge Estates, Dix Hills, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2013
|
76 homes
5 rating (3 reviews)
![Founders Ridge]()
$500Ks
- $600Ks
Founders Ridge, Middletown, CT
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
75 homes
$600Ks
The Polo Club at Islandia, Islandia, NY
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
72 homes
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$300Ks
- $400Ks
Long Hill Village, Trumbull, CT
Resale Only
|
55+ age-restricted
|
Built 1997 - 1999
|
71 homes
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$300Ks
- $400Ks
Bella Vista, Glocester, RI
Resale Only
|
55+ age-restricted
|
Built 2015 - 2021
|
70 homes
$600Ks
- $700Ks
Regency at Woodbridge, Woodbridge, CT
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
70 homes
$300Ks
The Village at Hunt Glen, Granby, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2006
|
69 homes
Want to learn more about 55+ rental communities in Southold?
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$500Ks
Eagles Walk at East Quogu..., East Quogue, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2014
|
67 homes
$200Ks
- $300Ks
Hopmeadow Place, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2005
|
66 homes
$500Ks
- $600Ks
Whitney Glen, Westport, CT
Resale Only
|
55+ age-restricted
|
Built 1982 - 1982
|
62 homes
$500Ks
- $600Ks
RiverWalk, Branford, CT
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
60 homes
<$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?
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Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$200Ks
- $300Ks
Autumn Fields, Enfield, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2006
|
56 homes
$500Ks
- $600Ks
The Village at Buckingham, Avon, CT
Resale Only
|
55+ age-restricted
|
Built 2002 - 2006
|
56 homes
$500Ks
Evergreen, Cromwell, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
52 homes
$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.
Want to learn more about 55+ rental communities in Southold?
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Questions? Call us:
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$400Ks
Eastport Meadows, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2016
|
50 homes
$400Ks
- $500Ks
Bramble Ridge, Suffield, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2015
|
47 homes
$500Ks
- $700Ks
Chimney Hill, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
44 homes
Want to learn more about 55+ communities in Southold?
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$800Ks
- $1Ms
Village Vistas, Port Jefferson, NY
Resale Only
|
55+ age-restricted
|
Built 2013 - 2017
|
43 homes
Stone Ridge Estates
![108 JOSEPH LN, DIX HILLS, NY, 11746, Dix Hills, NY 11746]()
2 beds
|2 baths
|1,695 sq ft
|Condo
108 JOSEPH LN, DIX HILLS, NY, 11746
Community: Stone Ridge Estates
MLS 903129 • Real Broker NY LLC, Matthew J. Lenne...
New
Fairfield at St. James
![101 FLAIR CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
1 beds
|2 baths
|900 sq ft
|Condo
101 FLAIR CT, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 954627 • Signature Premier Properties, Lori Z...
The Vineyards at Miller Place
![45 HALLEY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764]()
2 beds
|3 baths
|1,853 sq ft
|Condo
45 HALLEY LN, MILLER PLACE, NY, 11764
Community: The Vineyards at Miller Place
MLS 933352 • Coldwell Banker M&D Good Life, Steve...
New
Meadowbrook Pointe Links & Spa
![146 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763]()
2 beds
|3 baths
|2,047 sq ft
|Condo
146 AUGUSTA DR, MEDFORD, NY, 11763
Community: Meadowbrook Pointe Links & Spa
MLS 955710 • Signature Premier Properties, Matthe...
Leisure Village
![171B VENTRY CT 171B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961]()
1 beds
|1 baths
|679 sq ft
|Condo
171B VENTRY CT 171B, BROOKHAVEN, NY, 119...
Community: Leisure Village
MLS 904701 • Leisure Living Realty Inc, Laura Ruh...
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New
Westhampton Pines
![39 KIMBERLY DR # 39, WESTHAMPTON, NY, 11..., Westhampton, NY 11977]()
3 beds
|2 baths
|2,500 sq ft
|Condo
39 KIMBERLY DR # 39, WESTHAMPTON, NY, 11...
Community: Westhampton Pines
MLS 953821 • Nest Seekers International LLC, Robe...
The Manors at The Colony Preserve
![41 GREENTREE CT, SHIRLEY, NY, 11967, Shirley, NY 11967]()
2 beds
|2 baths
|1,800 sq ft
|Condo
41 GREENTREE CT, SHIRLEY, NY, 11967
Community: The Manors at The Colony Preserve
MLS 920956 • Leesa Byrnes Realty Inc, Leesa Byrne...
Leisure Village
![278 BERWICK CT UNIT B B, RIDGE, NY, 1196..., Ridge, NY 11961]()
2 beds
|1 baths
|875 sq ft
|Condo
278 BERWICK CT UNIT B B, RIDGE, NY, 1196...
Community: Leisure Village
MLS 953317 • Leisure Living Realty Inc, Laura Ruh...
Greenwood Village
![42 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|960 sq ft
|Condo
42 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 954479 • Coldwell Banker M&D Good Life, Sandr...
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
![82 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|1,110 sq ft
|Condo
82 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 953477 • Gateway to The Hamptons R E, Vivian ...
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Greenwood Village
![164 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|938 sq ft
|Condo
164 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 946958 • BERKSHIRE HATHAWAY, Geri M. Monzillo
Greenwood Village
![19 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|871 sq ft
|Condo
19 DOGWOOD LN, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 933453 • Gateway to The Hamptons R E, Vivian ...
Leisure Village
![418 WEYMOUTH CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,036 sq ft
|Condo
418 WEYMOUTH CT B, RIDGE, NY, 11961
Community: Leisure Village
MLS 953029 • Signature Premier Properties, Adela ...
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Foxwood Village
![1407 MIDDLE RD 275, CALVERTON, NY, 11933, Calverton, NY 11933]()
3 beds
|2 baths
|1,530 sq ft
|House
1407 MIDDLE RD 275, CALVERTON, NY, 11933
Community: Foxwood Village
MLS 941578 • Coldwell Banker American Homes, Kath...
Plymouth Estates at Mount Sinai
![166 IRA RD, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
2 beds
|2 baths
|1,820 sq ft
|House
166 IRA RD, MOUNT SINAI, NY, 11766
Community: Plymouth Estates at Mount Sinai
MLS 878423 • Aliano Real Estate, Nicholas A. Colo...
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New
Fairfield at St. James
![1107 CABOT CT N, SAINT JAMES, NY, 11780, Saint James, NY 11780]()
1 beds
|2 baths
|929 sq ft
|Condo
1107 CABOT CT N, SAINT JAMES, NY, 11780
Community: Fairfield at St. James
MLS 954779 • Signature Premier Properties, Amanda...
New
Greenwood Village
![54 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|1,134 sq ft
|Condo
54 DOGWOOD LN, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 954790 • Fiore Real Estate Sales Corp, Anna M...
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.
Leisure Village
![405 WOODBRIDGE DR D, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|874 sq ft
|Condo
405 WOODBRIDGE DR D, RIDGE, NY, 11961
Community: Leisure Village
MLS 920854 • Coldwell Banker American Homes, Kath...
Country Village Estates
![163 THEODORE DR, CORAM, NY, 11727, Coram, NY 11727]()
2 beds
|2 baths
|1,261 sq ft
|Condo
163 THEODORE DR, CORAM, NY, 11727
Community: Country Village Estates
MLS 909033 • Coldwell Banker American Homes, Ange...
Leisure Village
![423 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961]()
1 beds
|1 baths
|782 sq ft
|Condo
423 WOODBRIDGE DR B, RIDGE, NY, 11961
Community: Leisure Village
MLS 946602 • Realty Connect USA LI, Margaret Tsou...
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Leisure Glen
![10 OAKDALE CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 950788 • Signature Premier Properties, Mildre...
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Stone Ridge Estates
![153 CHRISTINE DR, DIX HILLS, NY, 11746, Dix Hills, NY 11746]()
2 beds
|2 baths
|1,415 sq ft
|Condo
153 CHRISTINE DR, DIX HILLS, NY, 11746
Community: Stone Ridge Estates
MLS 951036 • Charles Rutenberg Realty Inc, Diane ...
Greenwood Village
![91 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|938 sq ft
|Condo
91 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 935628 • Signature Premier Properties, Linda ...
The Waterways at Moriches
![554 MIRROR POND CT, MORICHES, NY, 11955, Moriches, NY 11955]()
2 beds
|2 baths
|1,497 sq ft
|Condo
554 MIRROR POND CT, MORICHES, NY, 11955
Community: The Waterways at Moriches
MLS 950265 • Keller Williams Realty Elite, Elizab...
Stoneleigh Woods at Riverhead
![23 GOOSE NECK LN, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|3 baths
|1,631 sq ft
|Condo
23 GOOSE NECK LN, RIVERHEAD, NY, 11901
Community: Stoneleigh Woods at Riverhead
MLS 952233 • Daniel Gale Sothebys Intl Rlty, Deni...
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Leisure Village
![169 VENTRY CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 932590 • Leisure Living Realty Inc, Paulina R...
Fairfield at St. James
![504 GOTHAM CT, SAINT JAMES, NY, 11780, Saint James, NY 11780]()
1 beds
|2 baths
|1,036 sq ft
|House
504 GOTHAM CT, SAINT JAMES, NY, 11780
Community: Fairfield at St. James
MLS 941087 • Realty Forward Inc, Eric Connolly
Fairfield at St. James
![901 FENWAY RD, SAINT JAMES, NY, 11780, Saint James, NY 11780]()
2 beds
|2 baths
|1,230 sq ft
|Condo
901 FENWAY RD, SAINT JAMES, NY, 11780
Community: Fairfield at St. James
MLS 951936 • Howard Hanna Coach, Cierra Dolan
Leisure Village
![128 EXMORE CT UNIT D, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,278 sq ft
|Condo
128 EXMORE CT UNIT D, RIDGE, NY, 11961
Community: Leisure Village
MLS 951533 • Coldwell Banker American Homes, Davi...
Encore Atlantic Shores
![6 OVATION PL, EASTPORT, NY, 11941, Eastport, NY 11941]()
2 beds
|2 baths
|2,150 sq ft
|Condo
6 OVATION PL, EASTPORT, NY, 11941
Community: Encore Atlantic Shores
MLS 951535 • Corcoran, Mary R. Clay
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Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Leisure Village
![116 EXMORE CT UNIT B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|875 sq ft
|Condo
116 EXMORE CT UNIT B, RIDGE, NY, 11961
Community: Leisure Village
MLS 945552 • Realty Connect USA L I Inc, James T....
Leisure Village
![164 FALMOUTH CT E, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 948284 • Douglas Elliman Real Estate, Joseph ...
Leisure Village
![186 VENTRY CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|900 sq ft
|Condo
186 VENTRY CT UNIT C, RIDGE, NY, 11961
Community: Leisure Village
MLS 950783 • Coldwell Banker American Homes, Ther...
The Waterways at Moriches
![414 LINDSAY LN, MORICHES, NY, 11955, Moriches, NY 11955]()
2 beds
|2 baths
|2,141 sq ft
|Condo
414 LINDSAY LN, MORICHES, NY, 11955
Community: The Waterways at Moriches
MLS 929881 • Daniel Gale Sothebys Intl Rlty, Dani...
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.
Stoneleigh Woods at Riverhead
![5 NEWCASTLE CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|3 baths
|1,942 sq ft
|Condo
5 NEWCASTLE CT, RIVERHEAD, NY, 11901
Community: Stoneleigh Woods at Riverhead
MLS 947474 • Douglas Elliman Real Estate, Michell...
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Leisure Knoll
![190 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 863784 • Coldwell Banker American Homes, Bonn...
Leisure Village
![373 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,171 sq ft
|Condo
373 WOODBRIDGE DR B, RIDGE, NY, 11961
Community: Leisure Village
MLS 948513 • Signature Premier Properties, Mildre...
Fairfield at St. James
![401 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
1 beds
|2 baths
|900 sq ft
|Condo
401 CABOT CT, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 935978 • Howard Hanna Coach, Patricia Gisbert
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The Villages at Mount Sinai Park
![4 OAKHURST CT, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
3 beds
|3 baths
|2,850 sq ft
|House
4 OAKHURST CT, MOUNT SINAI, NY, 11766
Community: The Villages at Mount Sinai Park
MLS 947993 • Douglas Elliman Real Estate, Lisa A....
Greenwood Village
![77 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|1 baths
|1,000 sq ft
|Condo
77 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 853523 • Gateway to The Hamptons R E, Janet R...
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 169 days. The average price of homes for sale in this community is approximately $527,500, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Founders Village average around $527,500.
Want more information about active adult communities around Southold?
Want to learn more about 55+ communities in Southold?
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© 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: Jan 28, 2026.
This application does not include information on all of the properties available for sale at this time.
