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Winsted, CT 55+ rental communities & homes for rent

1 communities near Winsted

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Sylvan Woods Westchester
Sylvan Woods Westchester
$2,885.12 - $4,810.12 / mo
Base rent from $2,750
Sylvan Woods Westchester, Buchanan, NY
New Construction | 55+ age-restricted | Built 2025 - present | 148 rental homes
148 rental homes Apartments
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
New Regency at Wappinger 5 PALMERTON DR, WAPPINGER, NY, 12590, Wappinger, NY 12590
$829,900

2 beds

|

3 baths

|

3,156 sq ft

|

Condo

5 PALMERTON DR, WAPPINGER, NY, 12590
Community: Regency at Wappinger
MLS 1036134 • Howard Hanna Rand Realty, Mary Ann ... • Howard Hanna Rand Realty
New The Village at Oxford Greens 84 LINKS WAY 84, OXFORD, CT, 06478, Oxford, CT 06478
$710,000

3 beds

|

3 baths

|

2,008 sq ft

|

Condo

84 LINKS WAY 84, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24205048 • Berkshire Hathaway NE Prop., Patty... • Berkshire Hathaway NE Prop.
New Autumn Fields 24 QUAIL HOLW 24, ENFIELD, CT, 06082, Enfield, CT 06082
$339,000

1 beds

|

2 baths

|

1,235 sq ft

|

Condo

24 QUAIL HOLW 24, ENFIELD, CT, 06082
Community: Autumn Fields
MLS 24204618 • Coldwell Banker Realty, Emilie Cou... • Coldwell Banker Realty
Heritage Village 722 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$310,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

722 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24193881 • Coldwell Banker Realty, Beth Canto... • Coldwell Banker Realty
Heritage Village 970 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$309,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

970 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24204589 • William Pitt Sotheby's Int'l, Liz ... • William Pitt Sotheby's Int'l
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Questions? Call us: (860) 909-8066
Rivington 44 WARRINGTON ROUND ST 44, DANBURY, CT, ..., Danbury, CT 06810
$628,000

3 beds

|

3 baths

|

1,600 sq ft

|

Condo

44 WARRINGTON ROUND ST 44, DANBURY, CT, ...
Community: Rivington
MLS 24203305 • ERA Insite Realty Services, Donna ... • ERA Insite Realty Services
Heritage Village 411 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$427,500

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

411 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24203559 • William Raveis Real Estate, Giusep... • William Raveis Real Estate
Heritage Village 620 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$319,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

620 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24204374 • Golden Heights LLC, Li Zhang • Golden Heights LLC
The Village at Oxford Greens 733 CHAMPIONSHIP DR 733, OXFORD, CT, 064..., Oxford, CT 06478
$624,900

2 beds

|

3 baths

|

1,673 sq ft

|

Condo

733 CHAMPIONSHIP DR 733, OXFORD, CT, 064...
Community: The Village at Oxford Greens
MLS 24203270 • West View Properties, LLC, Matthew... • West View Properties, LLC
Regency at Prospect 133 SYCAMORE DR, PROSPECT, CT, 06712, Prospect, CT 06712
$550,000

2 beds

|

3 baths

|

1,850 sq ft

|

Condo

133 SYCAMORE DR, PROSPECT, CT, 06712
Community: Regency at Prospect
MLS 24204172 • William Raveis Real Estate, Luis C... • William Raveis Real Estate
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.
Newtown Woods 623 BROOKSIDE CT 623, NEWTOWN, CT, 06470, Newtown, CT 06470
$498,900

2 beds

|

2 baths

|

1,504 sq ft

|

Condo

623 BROOKSIDE CT 623, NEWTOWN, CT, 06470
Community: Newtown Woods
MLS 24203843 • Berkshire Hathaway NE Prop., Jill ... • Berkshire Hathaway NE Prop.
Heritage Hills 675 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$825,000

2 beds

|

2 baths

|

1,663 sq ft

|

Condo

675 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1045730 • William Raveis-New York LLC, Lindsa... • William Raveis-New York LLC
Heritage Village 875 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$225,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

875 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24203544 • Greg DeFazio, Greg DeFazio • Greg DeFazio
The Retreat at Carmel 88 BLAIR HEIGHTS, CARMEL, NY, 10512, Carmel, NY 10512
$699,000

3 beds

|

3 baths

|

2,695 sq ft

|

Condo

88 BLAIR HEIGHTS, CARMEL, NY, 10512
Community: The Retreat at Carmel
MLS 1045319 • Coldwell Banker Realty, Sherri Malo... • Coldwell Banker Realty
Heritage Hills 370 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$679,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

370 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1044903 • Houlihan Lawrence Inc., Lynn Conway • Houlihan Lawrence Inc.
The Village at Buckingham 13 KENINGTON RD 13, AVON, CT, 06001, Avon, CT 06001
$639,900

3 beds

|

3 baths

|

2,024 sq ft

|

Condo

13 KENINGTON RD 13, AVON, CT, 06001
Community: The Village at Buckingham
MLS 24203661 • Coldwell Banker Realty, Victoria S... • Coldwell Banker Realty
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Heritage Village 23 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$269,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

23 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24203566 • BHGRE Gaetano Marra Homes, Stephan... • BHGRE Gaetano Marra Homes
Heritage Village 4 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$465,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

4 HERITAGE CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24201102 • William Raveis Real Estate, Elizab... • William Raveis Real Estate
Heritage Village 569 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$315,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

569 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24203817 • Home Sweet Home Realty & Devel, Je... • Home Sweet Home Realty & Devel
Meadow Brook Estates 188 EASTWOOD DR 188, SEYMOUR, CT, 06483, Seymour, CT 06483
$624,500

2 beds

|

3 baths

|

2,358 sq ft

|

Condo

188 EASTWOOD DR 188, SEYMOUR, CT, 06483
Community: Meadow Brook Estates
MLS 24202554 • William Raveis Real Estate, Connie... • William Raveis Real Estate
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 Hills 481A HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$799,000

2 beds

|

2 baths

|

1,353 sq ft

|

Condo

481A HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1012375 • Prime GO Realty, Inc., Richard Giac... • Prime GO Realty, Inc.
Oronoque Village 315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$475,000

2 beds

|

3 baths

|

1,434 sq ft

|

Condo

315 NAVAJO LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24203114 • eXp Realty, Tracey Jefferson • eXp Realty
Overlook 2050 SUMMIT LOOP 61, CARMEL, NY, 10512, Carmel, NY 10512
$929,000

2 beds

|

2 baths

|

2,102 sq ft

|

Condo

2050 SUMMIT LOOP 61, CARMEL, NY, 10512
Community: Overlook
MLS 1045206 • Toll Brothers Real Estate Inc., Tho... • Toll Brothers Real Estate Inc.
Oronoque Village 138 BISON LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$480,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

138 BISON LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24203180 • Coldwell Banker Realty, Christine ... • Coldwell Banker Realty
Heritage Village 774 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$325,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

774 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24202986 • Berkshire Hathaway NE Prop., Scott... • Berkshire Hathaway NE Prop.
Spring Lake Village 20 VILLAGE RD 20, SOUTHINGTON, CT, 06489, Southington, CT 06489
$219,000

2 beds

|

2 baths

|

1,224 sq ft

|

Condo

20 VILLAGE RD 20, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
MLS 24202679 • Better Living Realty, LLC, Angela ... • Better Living Realty, LLC
Heritage Village 28 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$232,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

28 HERITAGE CIR B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24202157 • Berkshire Hathaway NE Prop., Scott... • Berkshire Hathaway NE Prop.
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Jefferson Village 148 FLINTLOCK WAY G, YORKTOWN, NY, 10598, Yorktown, NY 10598
$599,900

2 beds

|

2 baths

|

1,302 sq ft

|

Condo

148 FLINTLOCK WAY G, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 1038322 • Houlihan Lawrence Inc., Jo-Ella Del... • Houlihan Lawrence Inc.
Oronoque Village 443 N TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$499,000

1 beds

|

3 baths

|

1,175 sq ft

|

Condo

443 N TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24202352 • William Raveis Real Estate, Jeff R... • William Raveis Real Estate
South Pond Village 8 S POND RD 8, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002
$499,900

3 beds

|

3 baths

|

1,912 sq ft

|

Condo

8 S POND RD 8, BLOOMFIELD, CT, 06002
Community: South Pond Village
MLS 24202421 • Berkshire Hathaway NE Prop., Lisa ... • Berkshire Hathaway NE Prop.
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 214 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$200,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

214 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24202470 • William Raveis Real Estate, Ruth Z... • William Raveis Real Estate
South Pond Village 37 REED CT 37, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002
$299,000

2 beds

|

3 baths

|

1,258 sq ft

|

Condo

37 REED CT 37, BLOOMFIELD, CT, 06002
Community: South Pond Village
MLS 24201749 • William Raveis Real Estate, Evan B... • William Raveis Real Estate
Oronoque Village 237 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614
$649,000

2 beds

|

2 baths

|

1,426 sq ft

|

Condo

237 AGAWAM DR A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24200218 • Colonial Properties Inc, Tony Vitt... • Colonial Properties Inc
Glassbury Court at Hunterbrook 2314 DEPEYSTER DR, YORKTOWN, NY, 10567, Yorktown, NY 10567
$952,900

2 beds

|

3 baths

|

2,265 sq ft

|

Condo

2314 DEPEYSTER DR, YORKTOWN, NY, 10567
Community: Glassbury Court at Hunterbrook
MLS 1038201 • Houlihan Lawrence Inc., Lisa Bucolo • Houlihan Lawrence Inc.
Heritage Village 732 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$235,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

732 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24201968 • William Raveis Real Estate, Ruth Z... • William Raveis Real Estate
Park Glen 4 RAINBOW CT 4, NEW MILFORD, CT, 06776, New Milford, CT 06776
$649,000

2 beds

|

4 baths

|

2,600 sq ft

|

Condo

4 RAINBOW CT 4, NEW MILFORD, CT, 06776
Community: Park Glen
MLS 24202235 • Coldwell Banker Realty, Antonio Za... • Coldwell Banker Realty
Heritage Village 783 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$395,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

783 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24202257 • Century 21 Bette Real Estate, Barb... • Century 21 Bette Real Estate
Heritage Village 738 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$329,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

738 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24202019 • Lamacchia Realty, Stephanie Plaza • Lamacchia Realty
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Granite Woods 35 NUTMEG RD B2, MIDDLEBURY, CT, 06762, Middlebury, CT 06762
$224,900

1 beds

|

1 baths

|

889 sq ft

|

Condo

35 NUTMEG RD B2, MIDDLEBURY, CT, 06762
Community: Granite Woods
MLS 24202228 • RE/MAX RISE, Maria Pinheiro • RE/MAX RISE
Oronoque Village 393 OTTAWA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$350,000

1 beds

|

3 baths

|

1,118 sq ft

|

Condo

393 OTTAWA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24202099 • Joy Real Estate, Richard Persico • Joy Real Estate
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.

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