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

89 communities 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 - $400Ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes
No reviews yet Leisure Village
$200Ks - $500Ks
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
$500Ks - $900Ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
4 rating (1 reviews) Jefferson Village
$200Ks - $500Ks
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
$200Ks - $400Ks
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 - $300Ks
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
$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
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
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...
$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
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 - $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
No reviews yet O'Meara Farm
$400Ks - $500Ks
O'Meara Farm, Farmington, CT
Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes
Heritage Village 1 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$359,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
The Summit at Bethel 63 GREAT HILL DR # 63, BETHEL, CT, 06801, Bethel, CT 06801
$695,000

3 beds

|

3 baths

|

2,743 sq ft

|

Condo

63 GREAT HILL DR # 63, BETHEL, CT, 06801
New Oronoque Village 248 SOUTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614
$475,000

2 beds

|

3 baths

|

1,175 sq ft

|

Condo

248 SOUTH TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
New Oronoque Village 535 NARRAGANSET LN B, STRATFORD, CT, 066..., Stratford, CT 06614
$409,900

2 beds

|

2 baths

|

1,434 sq ft

|

Condo

535 NARRAGANSET LN B, STRATFORD, CT, 066...
Community: Oronoque Village
Oronoque Village 87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$449,900

1 beds

|

2 baths

|

1,454 sq ft

|

Condo

87 CREEK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Oronoque Village 288 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614
$389,000

1 beds

|

2 baths

|

1,175 sq ft

|

Condo

288 AGAWAM DR B, STRATFORD, CT, 06614
Community: Oronoque Village
New The Summit at Bethel 81 GREAT HILL DR # 81, BETHEL, CT, 06801, Bethel, CT 06801
$699,000

3 beds

|

3 baths

|

2,447 sq ft

|

Condo

81 GREAT HILL DR # 81, BETHEL, CT, 06801
Founders Ridge 22 WEBSTER LN # 22, MIDDLETOWN, CT, 0645..., Middletown, CT 06457
$575,000

2 beds

|

2 baths

|

1,412 sq ft

|

Condo

22 WEBSTER LN # 22, MIDDLETOWN, CT, 0645...
Community: Founders Ridge
New Baldwin Station 26 JASMINE CIR # 26, MILFORD, CT, 06461, Milford, CT 06461
$649,900

2 beds

|

3 baths

|

2,331 sq ft

|

Condo

26 JASMINE CIR # 26, MILFORD, CT, 06461
Community: Baldwin Station
Oronoque Village 383 SEQUOIA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$490,000

1 beds

|

2 baths

|

1,360 sq ft

|

Condo

383 SEQUOIA LN A, STRATFORD, CT, 06614
Community: Oronoque 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.
Heritage Village 143 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$369,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

143 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 32 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$214,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

32 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 194 BAYFIELD LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$660,000

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

194 BAYFIELD LN A, STRATFORD, CT, 06614
Community: Oronoque Village
New Spring Lake Village 434 LAKEVIEW DR # 434, SOUTHINGTON, CT, ..., Southington, CT 06489
$319,900

2 beds

|

2 baths

|

1,199 sq ft

|

Condo

434 LAKEVIEW DR # 434, SOUTHINGTON, CT, ...
Community: Spring Lake Village
Rivington 5 BRINSCALL CT # 5, DANBURY, CT, 06810, Danbury, CT 06810
$540,000

2 beds

|

3 baths

|

1,467 sq ft

|

Condo

5 BRINSCALL CT # 5, DANBURY, CT, 06810
Community: Rivington
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
New Gloria Commons 10 LUCIUS CT # 10, MILFORD, CT, 06461, Milford, CT 06461
$489,900

2 beds

|

3 baths

|

2,061 sq ft

|

Condo

10 LUCIUS CT # 10, MILFORD, CT, 06461
Community: Gloria Commons
The Village at Oxford Greens 217 CHIP SHOT LN # 217, OXFORD, CT, 0647..., Oxford, CT 06478
$729,900

2 beds

|

2 baths

|

2,080 sq ft

|

Condo

217 CHIP SHOT LN # 217, OXFORD, CT, 0647...
Heritage Village 231 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

231 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Spring Lake Village 9 VILLAGE RD # 9, SOUTHINGTON, CT, 06489, Southington, CT 06489
$254,900

2 beds

|

2 baths

|

1,264 sq ft

|

Condo

9 VILLAGE RD # 9, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Heritage Village 264 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$300,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

264 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage 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.
Heritage Village 280 HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488
$199,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

280 HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 740 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$345,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

740 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 185 COUNTRY CLUB DR # 185, OXFORD, CT, 0..., Oxford, CT 06478
$690,000

3 beds

|

3 baths

|

2,595 sq ft

|

Condo

185 COUNTRY CLUB DR # 185, OXFORD, CT, 0...
Heritage Village 132 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$424,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

132 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 445 NORTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$534,900

1 beds

|

3 baths

|

1,620 sq ft

|

Condo

445 NORTH TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Heritage Village 1013 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$350,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

1013 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
The Woods at Dunham Pond 45 HERON VIEW RD # 45, NEW FAIRFIELD, CT..., New Fairfield, CT 06812
$425,000

1 beds

|

2 baths

|

1,550 sq ft

|

Condo

45 HERON VIEW RD # 45, NEW FAIRFIELD, CT...
Regency Meadows 7 REGENCY CIR # 7, TRUMBULL, CT, 06611, Trumbull, CT 06611
$749,900

3 beds

|

4 baths

|

2,338 sq ft

|

Condo

7 REGENCY CIR # 7, TRUMBULL, CT, 06611
Community: Regency Meadows
The Summit at Bethel 18 BRIAR RIDGE DR # 18, BETHEL, CT, 0680..., Bethel, CT 06801
$699,000

3 beds

|

3 baths

|

2,226 sq ft

|

Condo

18 BRIAR RIDGE DR # 18, BETHEL, CT, 0680...
Heritage Village 859 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,999

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

859 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage 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.
Heritage Village 987 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$279,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

987 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 21 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

21 HERITAGE CIR B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 741 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$239,900

1 beds

|

1 baths

|

928 sq ft

|

Condo

741 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 633 CHAMPIONSHIP DR # 633, OXFORD, CT, 0..., Oxford, CT 06478
$599,900

2 beds

|

3 baths

|

1,983 sq ft

|

Condo

633 CHAMPIONSHIP DR # 633, OXFORD, CT, 0...
Oronoque Village 518 IROQUOIS LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$514,900

2 beds

|

3 baths

|

1,426 sq ft

|

Condo

518 IROQUOIS LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Rivington 45 WINDING RIDGE WAY # 45, DANBURY, CT, ..., Danbury, CT 06810
$925,000

3 beds

|

5 baths

|

2,592 sq ft

|

Condo

45 WINDING RIDGE WAY # 45, DANBURY, CT, ...
Community: Rivington
Regency at Woodbridge 5 HERITAGE LN # 68, WOODBRIDGE, CT, 0652..., Woodbridge, CT 06525
$589,000

3 beds

|

3 baths

|

2,006 sq ft

|

Condo

5 HERITAGE LN # 68, WOODBRIDGE, CT, 0652...
Heritage Village 12 HERITAGE CRST E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$485,000

2 beds

|

2 baths

|

1,447 sq ft

|

Condo

12 HERITAGE CRST E, SOUTHBURY, CT, 06488
Community: Heritage Village
Regency at Woodbridge 3 HERITAGE LN # 69, WOODBRIDGE, CT, 0652..., Woodbridge, CT 06525
$619,000

3 beds

|

3 baths

|

Condo

3 HERITAGE LN # 69, WOODBRIDGE, CT, 0652...
Regency at Woodbridge 4 WHISPER RIDGE WAY # 41, WOODBRIDGE, CT..., Woodbridge, CT 06525
$569,000

3 beds

|

3 baths

|

Condo

4 WHISPER RIDGE WAY # 41, WOODBRIDGE, CT...



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