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Winchester Area, CT 55+ active adult communities & homes for sale

246 homes near Winchester Area

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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
$300Ks - $900Ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
3.6 rating (7 reviews) Heritage Village
$100Ks - $500Ks
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 - $500Ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
4 rating (1 reviews) Jefferson Village
$200Ks - $600Ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes
No reviews yet Oronoque Village
$300Ks - $600Ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
No reviews yet The Village at Oxford Gre...
$500Ks - $700Ks
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 - $400Ks
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
$300Ks - $500Ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
No reviews yet The Retreat at Carmel
$400Ks - $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
No reviews yet Overlook
$600Ks - $900Ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
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
$600Ks - $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 | 231 homes
No reviews yet Woodridge Strathmore Terr...
$400Ks - $400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
No reviews yet Regency at Wappinger
$600Ks - $700Ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 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 - $500Ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
5 rating (1 reviews) The Villages at Mount Sin...
$600Ks - $700Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes
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 - $400Ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
No reviews yet Stoneleigh Woods at River...
$600Ks - $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
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 Regency at Fishkill
$400Ks - $500Ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
No reviews yet South Pond Village
$100Ks - $200Ks
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
$500Ks - $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? 55places can help!
Questions? Call us: (860) 238-3620
No reviews yet Windcrest East
$600Ks - $600Ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes
No reviews yet Fairview at Oxford Greens
$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
No reviews yet Newbury Village
$600Ks - $700Ks
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
Jefferson Village 15 ESSEX PL 15K, YORKTOWN, NY, 10598, Yorktown, NY 10598
$375,000

2 beds

|

1 baths

|

1,000 sq ft

|

Condo

15 ESSEX PL 15K, YORKTOWN, NY, 10598
Community: Jefferson Village
Heritage Hills 593 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$1,100,000

3 beds

|

2 baths

|

1,905 sq ft

|

Condo

593 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Leisure Glen 244 GLEN DR, RIDGE, NY, 11961, Ridge, NY 11961
$499,000

2 beds

|

2 baths

|

1,456 sq ft

|

Condo

244 GLEN DR, RIDGE, NY, 11961
Community: Leisure Glen
Heritage Hills 972 C HERITAGE HLS Y., SOMERS, NY, 10589, Somers, NY 10589
$575,000

2 beds

|

2 baths

|

1,468 sq ft

|

Condo

972 C HERITAGE HLS Y., SOMERS, NY, 10589
Community: Heritage Hills
Leisure Village 310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119..., Ridge, NY 11961
$344,000

2 beds

|

1 baths

|

1,278 sq ft

|

Condo

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119...
Community: Leisure Village
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Sunken Pond Estates 4006 SAINT ANDREWS AVE, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$519,888

2 beds

|

2 baths

|

1,587 sq ft

|

Condo

4006 SAINT ANDREWS AVE, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
Regency at Fishkill 334 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$539,900

2 beds

|

2 baths

|

1,499 sq ft

|

Condo

334 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Leisure Knoll 407 BELFAST LN, RIDGE, NY, 11961, Ridge, NY 11961
$514,990

2 beds

|

2 baths

|

100 sq ft

|

Condo

407 BELFAST LN, RIDGE, NY, 11961
Community: Leisure Knoll
Glenwood Village 1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ..., Riverhead, NY 11901
$149,000

2 beds

|

1 baths

|

840 sq ft

|

Mobile Home

1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ...
Community: Glenwood Village
Leisure Village 488A FAIRWAY CT # 488A, RIDGE, NY, 11961, Ridge, NY 11961
$449,000

2 beds

|

2 baths

|

1,180 sq ft

|

Condo

488A FAIRWAY CT # 488A, RIDGE, NY, 11961
Community: Leisure Village
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 46 TRENT CT C, RIDGE, NY, 11961, Ridge, NY 11961
$365,000

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

46 TRENT CT C, RIDGE, NY, 11961
Community: Leisure Village
Leisure Village 231 BLACKPOOL CT F, RIDGE, NY, 11961, Ridge, NY 11961
$305,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

231 BLACKPOOL CT F, RIDGE, NY, 11961
Community: Leisure Village
Jefferson Village 141 FLINTLOCK WAY B, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598
$699,000

2 beds

|

2 baths

|

1,555 sq ft

|

Condo

141 FLINTLOCK WAY B, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
Jefferson Village 34 WARWICK PL D, YORKTOWN HEIGHTS, NY, 1..., Yorktown Heights, NY 10598
$389,900

2 beds

|

2 baths

|

970 sq ft

|

House

34 WARWICK PL D, YORKTOWN HEIGHTS, NY, 1...
Community: Jefferson Village
The Vineyards at Miller Place 43 HALLEY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764
$659,000

2 beds

|

3 baths

|

1,350 sq ft

|

Condo

43 HALLEY LN, MILLER PLACE, NY, 11764
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Leisure Village 405 WOODBRIDGE DR D, RIDGE, NY, 11961, Ridge, NY 11961
$290,000

2 beds

|

1 baths

|

874 sq ft

|

Condo

405 WOODBRIDGE DR D, RIDGE, NY, 11961
Community: Leisure Village
Stoneleigh Woods at Riverhead 67 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$660,000

2 beds

|

3 baths

|

1,972 sq ft

|

Condo

67 STONELEIGH DR, RIVERHEAD, NY, 11901
Leisure Village 167 VENTRY CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961
$215,500

1 beds

|

1 baths

|

684 sq ft

|

Condo

167 VENTRY CT UNIT C, RIDGE, NY, 11961
Community: Leisure Village
Regency at Fishkill 145 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$569,800

2 beds

|

2 baths

|

1,803 sq ft

|

Condo

145 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Leisure Village 120 EXMORE CT D, RIDGE, NY, 11961, Ridge, NY 11961
$239,990

1 beds

|

1 baths

|

684 sq ft

|

Condo

120 EXMORE CT D, RIDGE, NY, 11961
Community: Leisure Village
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 Glen 19 VILLANOVA CT, RIDGE, NY, 11961, Ridge, NY 11961
$495,000

2 beds

|

2 baths

|

1,451 sq ft

|

Condo

19 VILLANOVA CT, RIDGE, NY, 11961
Community: Leisure Glen
Leisure Village 96 ENFIELD CT B, RIDGE, NY, 11961, Ridge, NY 11961
$424,000

2 beds

|

2 baths

|

1,486 sq ft

|

Condo

96 ENFIELD CT B, RIDGE, NY, 11961
Community: Leisure Village
Jefferson Village 156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598
$339,000

1 beds

|

1 baths

|

850 sq ft

|

Condo

156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
Leisure Village 269 BERWICK CT B, RIDGE, NY, 11961, Ridge, NY 11961
$364,900

2 beds

|

1 baths

|

1,048 sq ft

|

Condo

269 BERWICK CT B, RIDGE, NY, 11961
Community: Leisure Village
Leisure Village 350B WOODBRIDGE DR 350B, BROOKHAVEN, NY,..., Brookhaven, NY 11961
$335,000

2 beds

|

1 baths

|

1,100 sq ft

|

Condo

350B WOODBRIDGE DR 350B, BROOKHAVEN, NY,...
Community: Leisure Village
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Leisure Village 276 BERWICK CT A, RIDGE, NY, 11961, Ridge, NY 11961
$315,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

276 BERWICK CT A, RIDGE, NY, 11961
Community: Leisure Village
Glenwood Village 1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ..., Riverhead, NY 11901
$164,999

2 beds

|

1 baths

|

816 sq ft

|

Mobile Home

1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ...
Community: Glenwood Village
Leisure Village 195 E NEWCASTLE CT, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$229,000

1 beds

|

1 baths

|

684 sq ft

|

Condo

195 E NEWCASTLE CT, BROOKHAVEN, NY, 1196...
Community: Leisure Village
Glenwood Village 1661 OLD COUNTRY RD UNIT 508, RIVERHEAD,..., Riverhead, NY 11901
$399,000

2 beds

|

2 baths

|

1,500 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD UNIT 508, RIVERHEAD,...
Community: Glenwood Village
Leisure Village 419 WEYMOUTH CT UNIT F F, RIDGE, NY, 119..., Ridge, NY 11961
$260,000

1 beds

|

1 baths

|

782 sq ft

|

Condo

419 WEYMOUTH CT UNIT F F, RIDGE, NY, 119...
Community: Leisure Village
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 166 VENTRY CT B, RIDGE, NY, 11961, Ridge, NY 11961
$259,000

1 beds

|

1 baths

|

680 sq ft

|

House

166 VENTRY CT B, RIDGE, NY, 11961
Community: Leisure Village
Plymouth Estates at Mount Sinai 166 IRA RD, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766
$579,999

2 beds

|

2 baths

|

1,820 sq ft

|

Townhouse

166 IRA RD, MOUNT SINAI, NY, 11766
Plymouth Estates at Mount Sinai 164 IRA RD, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766
$579,999

2 beds

|

2 baths

|

1,820 sq ft

|

Condo

164 IRA RD, MOUNT SINAI, NY, 11766
Heritage Village 862 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$499,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

862 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 7 HERITAGE CRST B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$449,900

2 beds

|

2 baths

|

1,447 sq ft

|

Condo

7 HERITAGE CRST B, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Newbury Village 21 GREAT HERON LN # 21, BROOKFIELD, CT, ..., Brookfield, CT 06804
$720,000

3 beds

|

4 baths

|

2,644 sq ft

|

Condo

21 GREAT HERON LN # 21, BROOKFIELD, CT, ...
Community: Newbury Village
New Regency at Woodbridge 21 HERITAGE LN # 60, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$729,000

3 beds

|

3 baths

|

Condo

21 HERITAGE LN # 60, WOODBRIDGE, CT, 065...
New Regency at Woodbridge 6 WHISPER RIDGE WAY # 42, WOODBRIDGE, CT..., Woodbridge, CT 06525
$619,000

3 beds

|

3 baths

|

Condo

6 WHISPER RIDGE WAY # 42, WOODBRIDGE, CT...
New Regency at Woodbridge 12 WHISPER RIDGE WAY # 45, WOODBRIDGE, C..., Woodbridge, CT 06525
$679,000

3 beds

|

3 baths

|

Condo

12 WHISPER RIDGE WAY # 45, WOODBRIDGE, C...
New Heritage Village 1008 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$399,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

1008 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village



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246 homes near Winchester Area
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REIN updates its listings on a daily basis. Data last updated: Oct 29, 2025.
This application does not include information on all of the properties available for sale at this time.

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