Call us at (860) 238-3620 to learn more about active adult communities near Winchester Area
Winchester Area, CT 55+ active adult communities & homes for sale
92 communities near Winchester Area
180 homes near Winchester Area
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$100Ks
Clockmaker's Hill, Winsted, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2014
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38 homes
$200Ks
- $400Ks
Oak Meadow Estates, Torrington, CT
New and Resale
|
55+ age-restricted
|
Built 2013 - present
|
31 homes
3 rating (2 reviews)
![Heritage Hills]()
$300Ks
- $900Ks
Heritage Hills, Somers, NY
Resale Only
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Age-targeted
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Built 1974 - 2006
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2,600 homes
3.6 rating (7 reviews)
![Heritage Village]()
$200Ks
- $500Ks
Heritage Village, Southbury, CT
Resale Only
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55+ age-restricted
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Built 1967 - 2005
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2,580 homes
$200Ks
- $400Ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
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Built 1969 - 1986
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1,500 homes
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$400Ks
- $600Ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
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1,050 homes
4 rating (1 reviews)
![Jefferson Village]()
$200Ks
- $600Ks
Jefferson Village, Yorktown Heights, NY
Resale Only
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55+ age-restricted
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Built 1967 - 1982
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1,000 homes
$200Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
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55+ age-restricted
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Built 1971 - 1977
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929 homes
$500Ks
- $600Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
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55+ age-restricted
|
Built 2004 - present
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835 homes
$300Ks
- $400Ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
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Built 1972 - 1982
|
701 homes
Download the Ultimate 55+ Homebuying Guide
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$200Ks
Spring Lake Village, Southington, CT
Resale Only
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55+ age-restricted
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Built 1970 - 2004
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640 homes
4 rating (8 reviews)
![Glenwood Village]()
$100Ks
- $400Ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
$300Ks
- $500Ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
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379 homes
$400Ks
- $600Ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
|
312 homes
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3.5 rating (2 reviews)
![Foxwood Village]()
$300Ks
- $400Ks
Foxwood Village, Calverton, NY
Resale Only
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55+ age-restricted
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Built 1986 - 2007
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294 homes
1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only
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55+ age-restricted
|
Built 2006 - 2013
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285 homes
$500Ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
$600Ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 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.
4.9 rating (14 reviews)
![Chatfield Farms]()
$500Ks
- $600Ks
Chatfield Farms, Beacon Falls, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
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231 homes
$400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
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55+ age-restricted
|
Built 1974 - 1985
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226 homes
$600Ks
- $700Ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only
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55+ age-restricted
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Built 2014 - 2020
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225 homes
5 rating (1 reviews)
![Sunken Pond Estates]()
$400Ks
- $500Ks
Sunken Pond Estates, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
194 homes
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5 rating (1 reviews)
![The Villages at Mount Sin...]()
$600Ks
- $700Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
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Built 2005 - 2007
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185 homes
$600Ks
- $700Ks
The Powder Forest Homes, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2016
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182 homes
5 rating (1 reviews)
![Newtown Woods]()
$400Ks
- $500Ks
Newtown Woods, Newtown, CT
New and Resale
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55+ age-restricted
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Built 2011 - present
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178 homes
$500Ks
- $600Ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only
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55+ age-restricted
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Built 2007 - 2016
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176 homes
$300Ks
- $400Ks
Beckley Farms, Berlin, CT
New and Resale
|
55+ age-restricted
|
Built 2010 - present
|
170 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.
$400Ks
- $500Ks
Regency at Fishkill, Fishkill, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2020
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164 homes
$100Ks
- $200Ks
South Pond Village, Bloomfield, CT
Resale Only
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55+ age-restricted
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Built 1999 - 2005
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151 homes
$600Ks
- $700Ks
Setauket Meadows, Setauket, NY
Resale Only
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55+ age-restricted
|
Built 2005 - 2007
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150 homes
$500Ks
- $800Ks
Fieldstone Village, Orange, CT
Resale Only
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55+ age-restricted
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Built 2010 - 2018
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142 homes
$500Ks
North Woods of Colchester, Colchester, CT
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
140 homes
Want to learn more about 55+ communities in Winchester Area?
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Questions? Call us:
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$600Ks
Windcrest East, Calverton, NY
Resale Only
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55+ age-restricted
|
Built 2004 - 2005
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126 homes
$600Ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
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55+ age-restricted
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Built 2019 - present
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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
$600Ks
- $700Ks
Newbury Village, Brookfield, CT
New and Resale
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55+ age-restricted
|
Built 2005 - present
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120 homes
Overlook
![4073 FAIRWAYS DR # 137, CARMEL, NY, 1051..., Carmel, NY 10512]()
3 beds
|3 baths
|1,914 sq ft
|Condo
4073 FAIRWAYS DR # 137, CARMEL, NY, 1051...
Community: Overlook
MLS 925922 • Toll Brothers Real Estate Inc., Thom...
Leisure Village
![416 WEYMOUTH CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|2 baths
|1,200 sq ft
|Condo
416 WEYMOUTH CT A, RIDGE, NY, 11961
Community: Leisure Village
MLS 927362 • Douglas Elliman Real Estate, Lisa F....
Overlook
![1037 COTTAGE DR 18, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 889837 • Toll Brothers Real Estate Inc., Thom...
Overlook
![4071 FAIRWAYS DR 136, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 920677 • Toll Brothers Real Estate Inc., Thom...
Leisure Village
![169 VENTRY CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 932590 • Leisure Living Realty Inc, Paulina R...
Want to learn more about 55+ communities in Winchester Area?
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Questions? Call us:
(860) 238-3620
Jefferson Village
![34 WARWICK PL D, YORKTOWN HEIGHTS, NY, 1..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|970 sq ft
|Condo
34 WARWICK PL D, YORKTOWN HEIGHTS, NY, 1...
Community: Jefferson Village
MLS 933020 • Douglas Elliman Real Estate, Margare...
Heritage Hills
![349 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,484 sq ft
|Condo
349 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 927340 • Billingsley Realty, William F. Reill...
Jefferson Village
![108 VILLAGE RD B, YORKTOWN HEIGHTS, NY, ..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,200 sq ft
|Condo
108 VILLAGE RD B, YORKTOWN HEIGHTS, NY, ...
Community: Jefferson Village
MLS 884476 • William Raveis Real Estate, Heather ...
Jefferson Village
![159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,300 sq ft
|Condo
159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
MLS 935455 • Glilos, Yoel Schwartz
Leisure Village
![259 NEWCASTLE CT E, RIDGE, NY, 11961, Ridge, NY 11961]()
1 beds
|1 baths
|875 sq ft
|Condo
259 NEWCASTLE CT E, RIDGE, NY, 11961
Community: Leisure Village
MLS 878336 • Barons Real Estate Associates, David...
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
Stoneleigh Woods at Riverhead
![53 GOOSE NECK LN, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|2 baths
|1,383 sq ft
|Condo
53 GOOSE NECK LN, RIVERHEAD, NY, 11901
Community: Stoneleigh Woods at Riverhead
MLS 933743 • Douglas Elliman Real Estate, Oscar C...
Heritage Hills
![262 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,427 sq ft
|Condo
262 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 933592 • William Raveis-New York LLC, Hope Ro...
Glenwood Village
![1661 OLD COUNTRY RD 434, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,144 sq ft
|Mobile Home
1661 OLD COUNTRY RD 434, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 923306 • NGC Realty Group, Allison Diem
Windcrest East
![41 GOLDEN SPRUCE DR, CALVERTON, NY, 1193..., Calverton, NY 11933]()
3 beds
|3 baths
|2,091 sq ft
|Condo
41 GOLDEN SPRUCE DR, CALVERTON, NY, 1193...
Community: Windcrest East
MLS 939196 • Compass Greater NY LLC, Heather L. K...
Leisure Knoll
![145 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 936582 • Frontline Realty Group LLC, Nicholas...
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Leisure Village
![310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119..., Ridge, NY 11961]()
2 beds
|1 baths
|1,278 sq ft
|Condo
310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119...
Community: Leisure Village
MLS 889288 • Coldwell Banker American Homes, Kath...
Heritage Hills
![390 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,559 sq ft
|Condo
390 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 937071 • Houlihan Lawrence Inc., Lynn Conway
Heritage Hills
![129 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
1 beds
|1 baths
|1,055 sq ft
|Condo
129 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 887993 • William Raveis-New York LLC, Daniel ...
Heritage Hills
![798 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,296 sq ft
|Condo
798 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
MLS 899317 • Houlihan Lawrence Inc., Donna O'Conn...
Regency at Fishkill
![736 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524]()
1 beds
|2 baths
|1,543 sq ft
|Condo
736 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 937630 • BHHS Hudson Valley Properties, Marga...
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.
Jefferson Village
![156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598]()
1 beds
|1 baths
|850 sq ft
|Condo
156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
MLS 823393 • Houlihan Lawrence Inc., Nancy Kenned...
Glassbury Court at Cold Spring
![43 YESTERDAY DR, COLD SPRING, NY, 10516, Cold Spring, NY 10516]()
2 beds
|3 baths
|2,620 sq ft
|Condo
43 YESTERDAY DR, COLD SPRING, NY, 10516
Community: Glassbury Court at Cold Spring
MLS 912195 • Coldwell Banker Realty, Audra Maccar...
Jefferson Village
![41 JEFFERSON OVAL B, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
41 JEFFERSON OVAL B, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
MLS 824285 • Houlihan Lawrence Inc., Barbara J. N...
The Villages at Mount Sinai Park
![68 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
2 beds
|2 baths
|1,736 sq ft
|Condo
68 LOUDEN LOOP, MOUNT SINAI, NY, 11766
Community: The Villages at Mount Sinai Park
MLS 910234 • Island Advantage Realty LLC, Todd A....
Glassbury Court at Cold Spring
![11 REVOLUTION RD, COLD SPRING, NY, 10516, Cold Spring, NY 10516]()
2 beds
|3 baths
|1,806 sq ft
|Condo
11 REVOLUTION RD, COLD SPRING, NY, 10516
Community: Glassbury Court at Cold Spring
MLS 935000 • Robert A. McCaffrey Realty Inc, Bill...
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Questions? Call us:
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Leisure Village
![215 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,085 sq ft
|Condo
215 WOODBRIDGE DR A, RIDGE, NY, 11961
Community: Leisure Village
MLS 933663 • Leisure Living Realty Inc, Paulina R...
Heritage Hills
![593 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,470 sq ft
|Condo
593 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 933299 • Houlihan Lawrence Inc., Linda Crispi...
Glenwood Village
![1661 OLD COUNTRY RD 506, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,232 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 506, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 930276 • Signature Premier Properties, Noreen...
Heritage Hills
![356 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,435 sq ft
|Condo
356 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 927509 • Houlihan Lawrence Inc., Teresa Chang
Stoneleigh Woods at Riverhead
![159 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|3 baths
|2,175 sq ft
|Condo
159 STONELEIGH DR, RIVERHEAD, NY, 11901
Community: Stoneleigh Woods at Riverhead
MLS 925846 • Douglas Elliman Real Estate, Mercede...
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 Hills
![882 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|1,909 sq ft
|Condo
882 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 930280 • Coldwell Banker Realty, Natasha Pazd...
Leisure Village
![474 DARWEN DR B, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 911211 • Douglas Elliman Real Estate, Nicole ...
Jefferson Village
![98 MOLLY PITCHER LN A, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
98 MOLLY PITCHER LN A, YORKTOWN HEIGHTS,...
Community: Jefferson Village
MLS 927228 • Houlihan Lawrence Inc., Jo-Ella Deli...
Jefferson Village
![2 HAMPTON CT A, YORKTOWN HEIGHTS, NY, 10..., Yorktown Heights, NY 10598]()
1 beds
|1 baths
|800 sq ft
|Condo
2 HAMPTON CT A, YORKTOWN HEIGHTS, NY, 10...
Community: Jefferson Village
MLS 902554 • Houlihan Lawrence Inc., Jo-Ella Deli...
Foxwood Village
![1407 MIDDLE RD UNIT 258, CALVERTON, NY, ..., Calverton, NY 11933]()
3 beds
|2 baths
|1,568 sq ft
|Manufactured Home
1407 MIDDLE RD UNIT 258, CALVERTON, NY, ...
Community: Foxwood Village
MLS 928912 • Signature Premier Properties, Heathe...
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Stoneleigh Woods at Riverhead
![4 HAVERTON CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|3 baths
|2,175 sq ft
|Condo
4 HAVERTON CT, RIVERHEAD, NY, 11901
Community: Stoneleigh Woods at Riverhead
MLS 928263 • Exit Realty Liberty, Maureen A. Kler...
Glenwood Village
![1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1..., Riverhead, NY 11901]()
2 beds
|2 baths
|924 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1...
Community: Glenwood Village
MLS 927346 • Keystone Realty USA Corp, Cynthia Mc...
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...
Stoneleigh Woods at Riverhead
![67 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|3 baths
|1,972 sq ft
|Condo
67 STONELEIGH DR, RIVERHEAD, NY, 11901
Community: Stoneleigh Woods at Riverhead
MLS 917715 • Douglas Elliman Real Estate, Mary El...
Heritage Hills
![438 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,470 sq ft
|Condo
438 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 911228 • Keller Williams Realty Partner, Mark...
Frequently Asked Questions
In the Winchester Area, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.
The smallest 55+ communities in the Winchester Area has 31 homes, the largest has 38 homes, and the average communities consists of 34 homes.
Yes, there is new 55+ home available in the Winchester Area. The most recent communities started in the Winchester Area include Oak Meadow Estates, Clockmaker's Hill. There is also 1 communities in the Winchester Area that offers new construction homes, including Oak Meadow Estates.
No, there are no gated 55+ communities in the Winchester Area.
On average, listings in 55+ communities in the Winchester Area stay on the market for around 788 days. The average price of homes for sale in these communities is approximately $389,900, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Oak Meadow Estates average around $389,900.
Want to learn more about 55+ communities in the Winchester Area?
- Insights and market stats
- Instant new home alerts
- Answers from local 55+ experts
Want to learn more about 55+ communities in Winchester Area?
92
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© 2025 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: Dec 02, 2025.
This application does not include information on all of the properties available for sale at this time.
