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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 699 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$350,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

699 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 399 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,900

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

399 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Newbury Village 7 STILL WATER CIR # 7, BROOKFIELD, CT, 0..., Brookfield, CT 06804
$670,000

2 beds

|

4 baths

|

2,420 sq ft

|

Condo

7 STILL WATER CIR # 7, BROOKFIELD, CT, 0...
Community: Newbury Village
Long Hill Village 84 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611
$475,000

2 beds

|

2 baths

|

1,370 sq ft

|

Condo

84 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill Village
Heritage Village 16 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

16 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 607 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$279,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

607 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 843 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$235,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

843 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 345 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$409,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

345 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 894 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$359,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

894 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 737 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

737 HERITAGE VLG A, 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.
Bartlett Hollow 39 BARTLETT HOLW # 39, MIDDLETOWN, CT, 0..., Middletown, CT 06457
$574,000

3 beds

|

3 baths

|

3,147 sq ft

39 BARTLETT HOLW # 39, MIDDLETOWN, CT, 0...
Community: Bartlett Hollow
Heritage Village 79 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$199,900

1 beds

|

1 baths

|

928 sq ft

|

Condo

79 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 419 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$274,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

419 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 51 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$225,000

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

51 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 198 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,900

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

198 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
O'Meara Farm 8 MULBERRY LN # 8, FARMINGTON, CT, 06032, Farmington, CT 06032
$479,999

3 beds

|

3 baths

|

1,896 sq ft

8 MULBERRY LN # 8, FARMINGTON, CT, 06032
Community: O'Meara Farm
Newbury Village 21 GREAT HERON LN # 21, BROOKFIELD, CT, ..., Brookfield, CT 06804
$755,000

3 beds

|

4 baths

|

2,644 sq ft

|

Condo

21 GREAT HERON LN # 21, BROOKFIELD, CT, ...
Community: Newbury Village
Heritage Village 78 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$319,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

78 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 621 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$205,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

621 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 575 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$430,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

575 HERITAGE VLG A, 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.
South Pond Village 139 THISTLE POND DR # 139, BLOOMFIELD, C..., Bloomfield, CT 06002
$399,900

2 beds

|

2 baths

|

1,601 sq ft

|

Condo

139 THISTLE POND DR # 139, BLOOMFIELD, C...
Community: South Pond Village
Long Hill Village 13 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611
$445,000

2 beds

|

2 baths

|

1,370 sq ft

|

Condo

13 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill Village
Regency at Prospect 189 SYCAMORE DR # 189, PROSPECT, CT, 067..., Prospect, CT 06712
$525,000

2 beds

|

3 baths

|

1,850 sq ft

|

Condo

189 SYCAMORE DR # 189, PROSPECT, CT, 067...
Community: Regency at Prospect
Gloria Commons 21 MICKEL LN # 21, MILFORD, CT, 06461, Milford, CT 06461
$489,900

3 beds

|

3 baths

|

1,955 sq ft

|

Condo

21 MICKEL LN # 21, MILFORD, CT, 06461
Community: Gloria Commons
Heritage Village 786 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$305,000

2 beds

|

2 baths

|

1,063 sq ft

|

Condo

786 HERITAGE VLG D, 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 311 STILL WATER CIR # 311, BROOKFIELD, C..., Brookfield, CT 06804
$570,000

2 beds

|

2 baths

|

1,741 sq ft

|

Condo

311 STILL WATER CIR # 311, BROOKFIELD, C...
Community: Newbury Village
Heritage Village 53 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$312,500

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

53 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 93 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$247,000

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

93 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
Park Glen 10 HARMONY TRL # 10, NEW MILFORD, CT, 06..., New Milford, CT 06776
$645,000

2 beds

|

3 baths

|

4,023 sq ft

|

Condo

10 HARMONY TRL # 10, NEW MILFORD, CT, 06...
Community: Park Glen
Heritage Village 948 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,900

2 beds

|

2 baths

|

1,071 sq ft

|

Condo

948 HERITAGE VLG A, 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.
Park Glen 15 HARMONY TRL # 15, NEW MILFORD, CT, 06..., New Milford, CT 06776
$699,900

2 beds

|

4 baths

|

2,720 sq ft

|

Condo

15 HARMONY TRL # 15, NEW MILFORD, CT, 06...
Community: Park Glen
Heritage Village 761 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$245,000

2 beds

|

2 baths

|

1,063 sq ft

|

Condo

761 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Regency at Prospect 9 LILAC LN # 9, PROSPECT, CT, 06712, Prospect, CT 06712
$454,900

2 beds

|

2 baths

|

1,503 sq ft

|

Condo

9 LILAC LN # 9, PROSPECT, CT, 06712
Community: Regency at Prospect
Meadow Brook Estates 199 MEADOW BROOK RD # 199, OXFORD, CT, 0..., Oxford, CT 06478
$595,000

2 beds

|

3 baths

|

1,876 sq ft

199 MEADOW BROOK RD # 199, OXFORD, CT, 0...
Heritage Village 999 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$324,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

999 HERITAGE VLG 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
Heritage Village 139 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$429,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

139 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Buckingham 23 KENINGTON RD # 23, AVON, CT, 06001, Avon, CT 06001
$590,000

3 beds

|

3 baths

|

2,430 sq ft

|

Condo

23 KENINGTON RD # 23, AVON, CT, 06001
Spring Lake Village 4 HICKORY HL, SOUTHINGTON, CT, 06489, Southington, CT 06489
$239,900

2 beds

|

2 baths

|

1,285 sq ft

|

Condo

4 HICKORY HL, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Oronoque Village 186 APACHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$449,000

3 beds

|

3 baths

|

1,438 sq ft

|

Condo

186 APACHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 1005 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$274,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

1005 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village



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234 homes near Winchester Area
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