Call us at (860) 238-3620 to learn more about active adult communities in Winchester Area
Winchester Area, CT 55+ active adult communities & homes for sale
89 communities near Winchester Area
207 homes near Winchester Area
Sort by:
Relevance
No reviews yet
![Clockmaker's Hill]()
$100Ks
- $100Ks
Clockmaker's Hill, Winsted, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2014
|
38 homes
No reviews yet
![Oak Meadow Estates]()
$200Ks
- $400Ks
Oak Meadow Estates, Torrington, CT
New and Resale
|
55+ age-restricted
|
Built 2013 - present
|
31 homes
3 rating (2 reviews)
![Heritage Hills]()
$400Ks
- $700Ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1975 - 2003
|
2,600 homes
3.6 rating (7 reviews)
![Heritage Village]()
$100Ks
- $400Ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
No reviews yet
![Leisure Village]()
$200Ks
- $400Ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
No reviews yet
![Rivington]()
$400Ks
- $1Ms
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
4 rating (1 reviews)
![Jefferson Village]()
$300Ks
- $600Ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
No reviews yet
![Oronoque Village]()
$400Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
No reviews yet
![The Village at Oxford Gre...]()
$500Ks
- $600Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
No reviews yet
![Leisure Knoll]()
$300Ks
- $500Ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 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.
No reviews yet
![Leisure Glen]()
$400Ks
- $500Ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
No reviews yet
![Spring Lake Village]()
$200Ks
- $200Ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
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
No reviews yet
![Regency at Prospect]()
$400Ks
- $400Ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
No reviews yet
![The Retreat at Carmel]()
$300Ks
- $600Ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
|
312 homes
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
3.5 rating (2 reviews)
![Foxwood Village]()
$300Ks
- $400Ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$500Ks
- $500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
285 homes
No reviews yet
![Meadow Brook Estates]()
$500Ks
- $500Ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
No reviews yet
![The Summit at Bethel]()
$700Ks
- $800Ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 homes
4.9 rating (14 reviews)
![Chatfield Farms]()
$500Ks
- $500Ks
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.
No reviews yet
![Woodridge Strathmore Terr...]()
$300Ks
- $400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 1974 - 1985
|
226 homes
No reviews yet
![Regency at Wappinger]()
$700Ks
- $800Ks
Regency at Wappinger, Wappingers Falls, NY
New and Resale
|
55+ age-restricted
|
Built 2014 - present
|
225 homes
No reviews yet
![Saddle Lakes]()
$400Ks
- $400Ks
Saddle Lakes, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2000 - 2002
|
196 homes
5 rating (1 reviews)
![Sunken Pond Estates]()
$400Ks
- $400Ks
Sunken Pond Estates, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
194 homes
5 rating (1 reviews)
![The Villages at Mount Sin...]()
$700Ks
- $800Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
185 homes
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
No reviews yet
![The Powder Forest Homes]()
$600Ks
- $700Ks
The Powder Forest Homes, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2016
|
182 homes
5 rating (1 reviews)
![Newtown Woods]()
$400Ks
- $500Ks
Newtown Woods, Newtown, CT
New and Resale
|
55+ age-restricted
|
Built 2011 - present
|
178 homes
No reviews yet
![Stoneleigh Woods at River...]()
$400Ks
- $600Ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2016
|
176 homes
No reviews yet
![Beckley Farms]()
$300Ks
- $400Ks
Beckley Farms, Berlin, CT
New and Resale
|
55+ age-restricted
|
Built 2010 - present
|
170 homes
No reviews yet
![Regency at Fishkill]()
$500Ks
- $500Ks
Regency at Fishkill, Fishkill, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2020
|
164 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.
No reviews yet
![South Pond Village]()
$200Ks
- $400Ks
South Pond Village, Bloomfield, CT
Resale Only
|
55+ age-restricted
|
Built 1999 - 2005
|
151 homes
No reviews yet
![Setauket Meadows]()
$600Ks
- $700Ks
Setauket Meadows, Setauket, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
150 homes
No reviews yet
![Fieldstone Village]()
$500Ks
- $800Ks
Fieldstone Village, Orange, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2018
|
142 homes
No reviews yet
![North Woods of Colchester]()
$300Ks
- $400Ks
North Woods of Colchester, Colchester, CT
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
140 homes
No reviews yet
![Windcrest East]()
$600Ks
- $600Ks
Windcrest East, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2005
|
126 homes
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
No reviews yet
![Fairview at Oxford Greens]()
$500Ks
- $600Ks
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
No reviews yet
![Newbury Village]()
$400Ks
- $500Ks
Newbury Village, Brookfield, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
120 homes
No reviews yet
![The Gardens of Wilbraham]()
$300Ks
- $400Ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
108 homes
No reviews yet
![O'Meara Farm]()
$400Ks
- $400Ks
O'Meara Farm, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 1998 - 2005
|
104 homes
The Villages at Mount Sinai Park
![105 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
2 beds
|2 baths
|1,971 sq ft
|Condo
105 LOUDEN LOOP, MOUNT SINAI, NY, 11766
Community: The Villages at Mount Sinai Park
MLS 867720 • Howard Hanna Coach, Julie P. Lapasot...
Villas at Seminary Hill
![3202 PANKIN DR, CARMEL, NY, 10512, Carmel, NY 10512]()
2 beds
|2 baths
|1,275 sq ft
|Condo
3202 PANKIN DR, CARMEL, NY, 10512
Community: Villas at Seminary Hill
MLS 826879 • Briante Realty Group, LLC, Lynn Stoe...
Jefferson Village
![6 DEVON CT B, YORKTOWN HEIGHTS, NY, 1059..., Yorktown Heights, NY 10598]()
2 beds
|1 baths
|1,000 sq ft
|Condo
6 DEVON CT B, YORKTOWN HEIGHTS, NY, 1059...
Community: Jefferson Village
MLS 865906 • Keller Williams Realty Partner, Rose...
Leisure Glen
![6 BROOKVILLE CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 858951 • Signature Premier Properties, Elaine...
Leisure Village
![346 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|2 baths
|1,300 sq ft
|Condo
346 WOODBRIDGE DR B, RIDGE, NY, 11961
Community: Leisure Village
MLS 837450 • Leisure Living Realty Inc, Paulina R...
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Leisure Village
![232A BLACKPOOL CT 232A, BROOKHAVEN, NY, ..., Brookhaven, NY 11961]()
2 beds
|1 baths
|836 sq ft
|Condo
232A BLACKPOOL CT 232A, BROOKHAVEN, NY, ...
Community: Leisure Village
MLS 858698 • Leisure Living Realty Inc, Heather B...
Leisure Village
![256 NEWCASTLE CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,184 sq ft
|Condo
256 NEWCASTLE CT B, RIDGE, NY, 11961
Community: Leisure Village
MLS 851233 • Coldwell Banker M&D Good Life, Micha...
Leisure Village
![192 VENTRY CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 867626 • Realty One Group First, Magdalena Ko...
Leisure Village
![411A WEYMOUTH CT # 411A, RIDGE, NY, 1196..., Ridge, NY 11961]()
2 beds
|1 baths
|1,000 sq ft
|Condo
411A WEYMOUTH CT # 411A, RIDGE, NY, 1196...
Community: Leisure Village
MLS 867323 • Leisure Living Realty Inc, Laura Ruh...
Leisure Village
![404B WOODBRIDGE DR 404B, BROOKHAVEN, NY,..., Brookhaven, NY 11961]()
2 beds
|1 baths
|907 sq ft
|Condo
404B WOODBRIDGE DR 404B, BROOKHAVEN, NY,...
Community: Leisure Village
MLS 867426 • Leisure Living Realty Inc, Laura Ruh...
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.
Villas at Seminary Hill
![2203 PANKIN DR, CARMEL, NY, 10512, Carmel, NY 10512]()
2 beds
|2 baths
|1,275 sq ft
|Condo
2203 PANKIN DR, CARMEL, NY, 10512
Community: Villas at Seminary Hill
MLS 857438 • Briante Realty Group, LLC, Kathleen ...
Leisure Village
![69 ENFIELD CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 858583 • Signature Premier Properties, Mauree...
Leisure Knoll
![190 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 863784 • Coldwell Banker American Homes, Bonn...
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
|Condo
4 OAKHURST CT, MOUNT SINAI, NY, 11766
Community: The Villages at Mount Sinai Park
MLS 856049 • Douglas Elliman Real Estate, Lisa A....
Founders Village
![2555 YOUNGS AVE 11D, SOUTHOLD, NY, 11971, Southold, NY 11971]()
2 beds
|2 baths
|1,100 sq ft
|Condo
2555 YOUNGS AVE 11D, SOUTHOLD, NY, 11971
Community: Founders Village
MLS 828475 • Signature Premier Properties, Patric...
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Jefferson Village
![32 CAMBRIDGE CT A, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598]()
2 beds
|1 baths
|951 sq ft
|Condo
32 CAMBRIDGE CT A, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
MLS 850166 • Real Broker NY LLC, Dani Dorman
Heritage Hills
![41 HERITAGE HILLS DR A, SOMERS, NY, 1058..., Somers, NY 10589]()
3 beds
|3 baths
|1,700 sq ft
|Condo
41 HERITAGE HILLS DR A, SOMERS, NY, 1058...
Community: Heritage Hills
MLS 859829 • Houlihan Lawrence Inc., Donna O'Conn...
Jefferson Village
![82 MOLLY PITCHER LN B, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
82 MOLLY PITCHER LN B, YORKTOWN HEIGHTS,...
Community: Jefferson Village
MLS 857536 • Julia B Fee Sothebys Int. Rlty, Jo A...
Jefferson Village
![40 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,350 sq ft
|Condo
40 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
MLS 850226 • Coldwell Banker Realty, Mary Anne M....
Heritage Hills
![234 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,427 sq ft
|Condo
234 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 828326 • Keller Williams Rlty Landmark, Maria...
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.
Woodridge Strathmore Terrace
![16 HEARTHSIDE DR, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
1 beds
|1 baths
|924 sq ft
|Condo
16 HEARTHSIDE DR, MOUNT SINAI, NY, 11766
Community: Woodridge Strathmore Terrace
MLS 850667 • Mazzella Realty Services, Michael A....
Heritage Hills
![196A HERITAGE HLS # 196A, SOMERS, NY, 10..., Somers, NY 10589]()
2 beds
|2 baths
|1,427 sq ft
|Condo
196A HERITAGE HLS # 196A, SOMERS, NY, 10...
Community: Heritage Hills
MLS 840157 • Julia B Fee Sothebys Int. Rlty, Zebe...
Leisure Village
![419 WEYMOUTH CT F, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 812541 • Howard Hanna Coach, Linda Stowell
Jefferson Village
![92 MOLLY PITCHER LN B, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598]()
1 beds
|1 baths
|800 sq ft
|Condo
92 MOLLY PITCHER LN B, YORKTOWN HEIGHTS,...
Community: Jefferson Village
MLS 855989 • Compass Greater NY, LLC, Daniel McKe...
Leisure Village
![332 WOODBRIDGE DR UNIT C WOODBRIDGE DR, ..., Ridge, NY 11961]()
2 beds
|1 baths
|1,000 sq ft
|Condo
332 WOODBRIDGE DR UNIT C WOODBRIDGE DR, ...
Community: Leisure Village
MLS 861217 • Howard Hanna Coach, Linda Stowell
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Leisure Village
![277 BERWICK CT UNIT D, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|875 sq ft
|Condo
277 BERWICK CT UNIT D, RIDGE, NY, 11961
Community: Leisure Village
MLS 858082 • Island Advantage Realty LLC, Jennife...
Leisure Village
![258 NEWCASTLE CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|875 sq ft
|Condo
258 NEWCASTLE CT A, RIDGE, NY, 11961
Community: Leisure Village
MLS 856345 • Coldwell Banker American Homes, Nord...
Foxwood Village
![1407-54 MIDDLE RD 54, RIVERHEAD, NY, 119..., Riverhead, NY 11933]()
2 beds
|2 baths
|1,280 sq ft
|House
1407-54 MIDDLE RD 54, RIVERHEAD, NY, 119...
Community: Foxwood Village
MLS 855435 • Signature Premier Properties, Jason ...
Leisure Village
![156 FALMOUTH CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,085 sq ft
|Condo
156 FALMOUTH CT A, RIDGE, NY, 11961
Community: Leisure Village
MLS 848587 • Baez Real Estate, Inc., Alex V. Baez
Heritage Hills
![239 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|1,689 sq ft
|Condo
239 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 815679 • Coldwell Banker Realty, Debra DeMeli...
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
![425 BRIDGEWATER DR UNIT A A, RIDGE, NY, ..., Ridge, NY 11961]()
2 beds
|2 baths
|966 sq ft
|Condo
425 BRIDGEWATER DR UNIT A A, RIDGE, NY, ...
Community: Leisure Village
MLS 840625 • Leisure Living Realty Inc, Laura Ruh...
Glenwood Village
![1661-563 OLD COUNTRY RD 563, RIVERHEAD, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,500 sq ft
|Manufactured Home
1661-563 OLD COUNTRY RD 563, RIVERHEAD, ...
Community: Glenwood Village
MLS 839070 • Keystone Realty USA Corp, Cynthia Mc...
Leisure Village
![135 EASTBOURNE CT UNIT C, RIDGE, NY, 119..., Ridge, NY 11961]()
2 beds
|1 baths
|1,118 sq ft
|Condo
135 EASTBOURNE CT UNIT C, RIDGE, NY, 119...
Community: Leisure Village
MLS 854336 • Coldwell Banker American Homes, Joy ...
Leisure Knoll
![460 SUMMERWOOD CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 841946 • Realty Connect USA L I Inc, Michele ...
Leisure Village
![269 BERWICK CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,048 sq ft
|Condo
269 BERWICK CT B, RIDGE, NY, 11961
Community: Leisure Village
MLS 856130 • Oversouth LLC, Deniz Ozgur
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
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...
Leisure Knoll
![176 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 840567 • Coldwell Banker American Homes, Donn...
Glenwood Village
![1661-308 OLD COUNTRY RD 308, RIVERHEAD, ..., Riverhead, NY 11901]()
2 beds
|1 baths
|840 sq ft
|Mobile Home
1661-308 OLD COUNTRY RD 308, RIVERHEAD, ...
Community: Glenwood Village
MLS L3583691 • Realty Connect USA L I Inc, Fengxi...
Leisure Glen
![460 LEISURE DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 830412 • RE/MAX Integrity Leaders, Karen L. R...
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 845085 • Center 24 Realty Corp, Heidi S. Will...
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 663 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.
207
homes
near Winchester Area
Remove Boundaries ×
Map
Satellite
Want to learn more about 55+ communities in Winchester Area?
