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

234 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 - $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 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
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
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
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
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
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
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.
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...
The Village at Oxford Greens 1049 AUGUSTA DR # 1049, OXFORD, CT, 0647..., Oxford, CT 06478
$599,900

2 beds

|

3 baths

|

1,968 sq ft

|

Condo

1049 AUGUSTA DR # 1049, OXFORD, CT, 0647...
Regency at Woodbridge 11 HERITAGE LN # 65, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$659,000

3 beds

|

3 baths

|

2,028 sq ft

|

Condo

11 HERITAGE LN # 65, WOODBRIDGE, CT, 065...
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...
Regency at Woodbridge 13 HERITAGE LN # 64, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$669,000

3 beds

|

3 baths

|

2,239 sq ft

|

Condo

13 HERITAGE LN # 64, WOODBRIDGE, CT, 065...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Fairview at Oxford Greens 1049 AUGUSTA DR # 1049, OXFORD, CT, 0647..., Oxford, CT 06478
$599,900

2 beds

|

3 baths

|

1,968 sq ft

|

Condo

1049 AUGUSTA DR # 1049, OXFORD, CT, 0647...
Heritage Village 740 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$424,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

740 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Regency at Woodbridge 29 HERITAGE LN # 56, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$719,000

3 beds

|

3 baths

|

2,239 sq ft

|

Condo

29 HERITAGE LN # 56, WOODBRIDGE, CT, 065...
Heritage Village 133 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$349,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

133 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 701 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$380,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

701 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.
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...
Heritage Village 793 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,900

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

793 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
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
Heritage Village 9 HERITAGE CIR D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$255,000

2 beds

|

2 baths

|

1,071 sq ft

|

Condo

9 HERITAGE CIR D, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 98 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$347,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

98 HERITAGE VLG A, 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
Heritage Village 953 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$279,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

953 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 669 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$278,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

669 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Long Hill Village 65 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611
$489,000

2 beds

|

2 baths

|

1,370 sq ft

|

Condo

65 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill Village
Oronoque Village 475 COMMANCHE LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$389,000

1 beds

|

3 baths

|

2,171 sq ft

|

Condo

475 COMMANCHE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$390,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

170 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 920 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$379,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

920 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 128 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$390,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

128 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Newtown Woods 605 BROOKSIDE CT # 605, NEWTOWN, CT, 064..., Newtown, CT 06470
$594,500

2 beds

|

2 baths

|

1,877 sq ft

|

Condo

605 BROOKSIDE CT # 605, NEWTOWN, CT, 064...
Community: Newtown Woods
Heritage Village 884 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$315,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

884 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Bidwell Village 94 STONEHOUSE RD UNIT 36, COVENTRY, CT, ..., Coventry, CT 06238
$472,900

2 beds

|

2 baths

|

1,641 sq ft

|

Condo

94 STONEHOUSE RD UNIT 36, COVENTRY, CT, ...
Community: Bidwell Village
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (860) 238-3620
Heritage Village 648 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$425,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

648 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 855 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$215,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

855 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 900 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$278,500

1 beds

|

1 baths

|

928 sq ft

|

Condo

900 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 45 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$289,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

45 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Benson Woods 112 PERIWINKLE DR # 112, MIDDLEBURY, CT,..., Middlebury, CT 06762
$534,900

2 beds

|

3 baths

|

2,593 sq ft

|

Condo

112 PERIWINKLE DR # 112, MIDDLEBURY, CT,...
Community: Benson Woods



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234 homes near Winchester Area
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