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
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![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
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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
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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?
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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 Gardens of Wilbraham
![39 IVY CIR # 39, WILBRAHAM, MA, 01095, Wilbraham, MA 01095]()
1 beds
|2 baths
|1,218 sq ft
|Condo
39 IVY CIR # 39, WILBRAHAM, MA, 01095
Community: The Gardens of Wilbraham
MLS 73276030 • Witalisz & Associates, Inc., JoAnn...
The Gardens of Wilbraham
![45 IVY CIR # 45, WILBRAHAM, MA, 01095, Wilbraham, MA 01095]()
2 beds
|3 baths
|1,752 sq ft
|Condo
45 IVY CIR # 45, WILBRAHAM, MA, 01095
Community: The Gardens of Wilbraham
MLS 73328184 • Coldwell Banker Realty - Western M...
Paris Square
![152 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647]()
MLS 25018429 • Coldwell Banker, Alpine/Closter, A...
Paris Square
![2301 RIO VISTA LN # 2301, NORTHVALE, NJ,..., Northvale, NJ 07647]()
MLS 25004643 • Keller Williams Valley Realty, Reg...
Leisure Knoll
![209 KINGSTON DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 861828 • Coldwell Banker American Homes, Kath...
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Leisure Village
![374 WOODBRIDGE DR UNIT A A, RIDGE, NY, 1..., Ridge, NY 11961]()
2 beds
|1 baths
|1,187 sq ft
|Condo
374 WOODBRIDGE DR UNIT A A, RIDGE, NY, 1...
Community: Leisure Village
MLS 872874 • Coldwell Banker American Homes, Joy ...
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...
New
Leisure Village
![68A ENFIELD CT # 68A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,048 sq ft
|Condo
68A ENFIELD CT # 68A, RIDGE, NY, 11961
Community: Leisure Village
MLS 874348 • Signature Premier Properties, Rosann...
New
Saddle Lakes
![107 SCENIC LAKE DR # 107, RIVERHEAD, NY,..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,631 sq ft
|Condo
107 SCENIC LAKE DR # 107, RIVERHEAD, NY,...
Community: Saddle Lakes
MLS 874647 • Coldwell Banker American Homes, Davi...
Heritage Hills
![348 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,428 sq ft
|Condo
348 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 866206 • William Raveis-New York, LLC, Cynthi...
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.
Sunken Pond Estates
![1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901]()
2 beds
|3 baths
|1,350 sq ft
|Condo
1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
MLS 856851 • Signature Premier Properties, Ryan F...
Glenwood Village
![1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,152 sq ft
|Manufactured Home
1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190...
Community: Glenwood Village
MLS 857323 • Joanne Kane Gigantiello, Joanne Giga...
Glenwood Village
![1661 OLD COUNTRY RD UNIT 521, RIVERHEAD,..., Riverhead, NY 11901]()
MLS L3593702 • Moriches Bay Realty, Geraldine S. ...
Glenwood Village
![1661 OLD COUNTRY RD 435, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,270 sq ft
|Mobile Home
1661 OLD COUNTRY RD 435, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 827152 • Douglas Elliman Real Estate, Allison...
Jefferson Village
![60 KIRBY CLOSE F, YORKTOWN HEIGHTS, NY, ..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|910 sq ft
|Condo
60 KIRBY CLOSE F, YORKTOWN HEIGHTS, NY, ...
Community: Jefferson Village
MLS 866227 • HomeSmart Homes & Estates, Christoph...
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
New
Leisure Village
![231 BLACKPOOL CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 874532 • Daniel Gale Sothebys Intl Rlty, Nico...
New
Leisure Knoll
![145 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 874449 • Century 21 Cor Ace Realty Inc, Glori...
New
Leisure Village
![232 BLACKPOOL CT F, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|833 sq ft
|Condo
232 BLACKPOOL CT F, RIDGE, NY, 11961
Community: Leisure Village
MLS 873804 • Realty Connect USA LI, Margaret Tsou...
Heritage Hills
![480 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,468 sq ft
|Condo
480 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 837074 • William Raveis-New York, LLC, Gerald...
Founders Village
![2555 YOUNGS AVE 7D, SOUTHOLD, NY, 11971, Southold, NY 11971]()
2 beds
|2 baths
|1,100 sq ft
|Condo
2555 YOUNGS AVE 7D, SOUTHOLD, NY, 11971
Community: Founders Village
MLS 808158 • Signature Premier Properties, Timoth...
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
![8 LAKEVIEW CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
3 beds
|3 baths
|2,000 sq ft
|Condo
8 LAKEVIEW CT, RIVERHEAD, NY, 11901
Community: Stoneleigh Woods at Riverhead
MLS 872254 • Beninati Associates, Marie D. Benina...
New
Leisure Village
![305 TORQUAY CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|836 sq ft
|House
305 TORQUAY CT UNIT C, RIDGE, NY, 11961
Community: Leisure Village
MLS 872845 • Cornerstone Properties of LI, Jan H....
Leisure Knoll
![365 SHEFFIELD CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 872940 • Coldwell Banker American Homes, Anto...
Leisure Village
![28 TRENT CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 869368 • Signature Premier Properties, Jose A...
Jefferson Village
![143 FLINTLOCK WAY D, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,200 sq ft
|Condo
143 FLINTLOCK WAY D, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
MLS 867675 • RE/MAX Town & Country, James D'Amato
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Leisure Village
![119 EXMORE CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 872112 • Leisure Living Realty Inc, Paulina R...
Heritage Hills
![304 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|3 baths
|1,700 sq ft
|Condo
304 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
MLS 866789 • Coldwell Banker Realty, Kelly Castig...
Foxwood Village
![1407 MIDDLE RD 203, CALVERTON, NY, 11933, Calverton, NY 11933]()
3 beds
|2 baths
|1,568 sq ft
|Manufactured Home
1407 MIDDLE RD 203, CALVERTON, NY, 11933
Community: Foxwood Village
MLS 866087 • Joanne Kane Gigantiello, Joanne Giga...
Heritage Hills
![116 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,144 sq ft
|Condo
116 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 863774 • Houlihan Lawrence Inc., David J. Hov...
Leisure Knoll
![140A LAURANCE LN, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 857230 • Coldwell Banker American Homes, Mary...
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 Knoll
![407 BELFAST LN, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 864364 • Coldwell Banker American Homes, Nanc...
Leisure Glen
![11 CUTCHOGUE CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 867290 • Signature Premier Properties, Elaine...
Leisure Knoll
![561 STRATFORD LN # 561, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|2 baths
|1,150 sq ft
|Condo
561 STRATFORD LN # 561, RIDGE, NY, 11961
Community: Leisure Knoll
MLS 863767 • Leisure Living Realty Inc, Paulina R...
Plymouth Estates at Mount Sinai
![211 POND CIR, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
2 beds
|2 baths
|1,662 sq ft
|Condo
211 POND CIR, MOUNT SINAI, NY, 11766
Community: Plymouth Estates at Mount Sinai
MLS 862739 • Yes Homes Realty Ltd, Philip W. Alba
Leisure Village
![312C WOODBRIDGE DR 312C, BROOKHAVEN, NY,..., Brookhaven, NY 11961]()
1 beds
|1 baths
|679 sq ft
|Condo
312C WOODBRIDGE DR 312C, BROOKHAVEN, NY,...
Community: Leisure Village
MLS 842478 • Leisure Living Realty Inc, Laura Ruh...
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Leisure Village
![423 WOODBRIDGE D, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
1 beds
|1 baths
|782 sq ft
|Condo
423 WOODBRIDGE D, BROOKHAVEN, NY, 11961
Community: Leisure Village
MLS 802268 • Douglas Elliman Real Estate, Thomas ...
Leisure Village
![286 BERWICK CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,085 sq ft
|Condo
286 BERWICK CT A, RIDGE, NY, 11961
Community: Leisure Village
MLS 865765 • Peconic Realty Group LLC, Ryan Verba...
Leisure Knoll
![221 BELFAST LN, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 837048 • Coldwell Banker American Homes, Kath...
Leisure Glen
![437 LEISURE DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 860948 • RE/MAX Signature Real Estate, Julie ...
Leisure Glen
![12 SAYVILLE CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 828574 • BERKSHIRE HATHAWAY, Carole A. Dantuo...
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.
89
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near Winchester Area
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