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Winchester Area, CT 55+ active adult communities & homes for sale - Page 2
94 communities near Winchester Area
204 homes near Winchester Area
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$400ks
- $500ks
Shaker Heights, Enfield, CT
New Construction
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55+ age-restricted
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Built 2018 - present
|
77 homes
$200ks
- $300ks
Autumn Fields, Enfield, CT
Resale Only
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55+ age-restricted
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Built 2004 - 2006
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56 homes
$300ks
- $800ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
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312 homes
$400ks
Stoneleigh Woods at Carme..., Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2012 - 2017
|
68 homes
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$400ks
- $500ks
Saddle Lakes, Riverhead, NY
Resale Only
|
55+ age-restricted
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Built 2000 - 2002
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196 homes
$500ks
- $700ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only
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55+ age-restricted
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Built 2009 - 2014
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90 homes
$200ks
- $300ks
Woodcrest at Jacobs Hill, Cortlandt, NY
Resale Only
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55+ age-restricted
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Built 2005 - 2006
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58 homes
$500ks
- $700ks
Glassbury Court at Hunter..., Cortlandt, NY
Resale Only
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55+ age-restricted
|
Built 2007 - 2014
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64 homes
$400ks
- $500ks
Founders Village, Southold, NY
Resale Only
|
55+ age-restricted
|
Built 1981 - 1985
|
92 homes
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3.5 rating (2 reviews)
![Harvest Pointe]()
$800ks
- $3Ms
Harvest Pointe, Cutchogue, NY
New Construction
|
55+ age-restricted
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Built 2017 - present
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124 homes
$500ks
- $600ks
The Residences at Butterf..., Cold Spring, NY
Resale Only
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55+ age-restricted
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Built 2018 - 2023
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49 homes
$200ks
- $300ks
Villas at Seminary Hill, Carmel, NY
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
50 homes
$500ks
- $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction
|
55+ age-restricted
|
Built 2023 - present
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70 homes
$600ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction
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55+ age-restricted
|
Built 2025 - present
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99 homes
$500ks
Rivington Landing, Danbury, CT
New Construction
|
Age-targeted
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Built 2025 - 2026
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25 homes
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$600ks
- $700ks
Granite Woods, Middlebury, CT
New Construction
|
55+ age-restricted
|
Built 2020 - present
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24 homes
5 rating (2 reviews)
![Benson Woods]()
$400ks
- $600ks
Benson Woods, Middlebury, CT
New and Resale
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55+ age-restricted
|
Built 2004 - present
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79 homes
$400ks
- $500ks
Newbury Village, Brookfield, CT
New and Resale
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55+ age-restricted
|
Built 2005 - present
|
120 homes
$100ks
Clockmaker's Hill, Winsted, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2014
|
38 homes
Download the Ultimate 55+ Homebuying Guide
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$300ks
- $400ks
The Village at Buckingham, Avon, CT
Resale Only
|
55+ age-restricted
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Built 2002 - 2006
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56 homes
$300ks
- $400ks
Bartlett Hill, Portland, CT
Resale Only
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55+ age-restricted
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Built 2005 - 2011
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82 homes
$500ks
- $800ks
Fieldstone Village, Orange, CT
Resale Only
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55+ age-restricted
|
Built 2010 - 2018
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142 homes
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale
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55+ age-restricted
|
Built 2005 - present
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92 homes
$300ks
- $400ks
Beckley Farms, Berlin, CT
New and Resale
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55+ age-restricted
|
Built 2010 - present
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170 homes
$500ks
- $600ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only
|
55+ age-restricted
|
Built 2007 - 2022
|
88 homes
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4.9 rating (14 reviews)
![Chatfield Farms]()
$400ks
- $700ks
Chatfield Farms, Beacon Falls, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
231 homes
$300ks
- $400ks
North Woods of Colchester, Colchester, CT
New and Resale
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55+ age-restricted
|
Built 2007 - present
|
140 homes
$500ks
- $700ks
Chimney Hill, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
44 homes
Download the Ultimate 55+ Homebuying Guide
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$500ks
- $600ks
RiverWalk, Branford, CT
New and Resale
|
55+ age-restricted
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Built 2007 - present
|
60 homes
$300ks
- $400ks
Newington Ridge Preserve, Newington, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
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16 homes
5 rating (3 reviews)
![Founders Ridge]()
$300ks
- $400ks
Founders Ridge, Middletown, CT
New Construction
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55+ age-restricted
|
Built 2017 - present
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75 homes
$400ks
- $700ks
77 Sunset Lane, Ridgefield, CT
Resale Only
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55+ age-restricted
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Built 2016 - 2018
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54 homes
$200ks
- $400ks
Bartlett Hollow, Middletown, CT
New Construction
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55+ age-restricted
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Built 2015 - present
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25 homes
$500ks
- $600ks
Autumn Estates, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 2011 - 2017
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30 homes
<$100k
The Atrium of Portland, Portland, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2004
|
56 homes
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$400ks
- $600ks
Billingsgate, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2006
|
37 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.
New
Glenwood Village
![1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,624 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 1011541 • Gateway to The Hamptons R E, Vivian...
Heritage Hills
![567 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
1 beds
|2 baths
|967 sq ft
|Condo
567 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 987091 • Coldwell Banker Realty, Sherri Malon...
New
Heritage Hills
![300 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,500 sq ft
|Condo
300 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1012311 • Mancini Realty Inc., Stephen Mancin...
New
Oronoque Village
![253 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,426 sq ft
|Condo
253 AGAWAM DR A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24181187 • Coldwell Banker Realty, Mary Kelle...
New
Leisure Knoll
![183 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|1 baths
|960 sq ft
|Condo
183 KINGSTON DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 1011932 • Leesa Byrnes Realty Inc, Jeanine L....
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New
Regency at Prospect
![6 LILAC LN 6, PROSPECT, CT, 06712, Prospect, CT 06712]()
2 beds
|3 baths
|1,552 sq ft
|Condo
6 LILAC LN 6, PROSPECT, CT, 06712
Community: Regency at Prospect
MLS 24181880 • Pavlik Real Estate LLC, Deborah Ri...
New
Stoneleigh Woods at Carmel
![705 EGRETS LNDG, CARMEL, NY, 10512, Carmel, NY 10512]()
2 beds
|2 baths
|1,382 sq ft
|Condo
705 EGRETS LNDG, CARMEL, NY, 10512
Community: Stoneleigh Woods at Carmel
MLS 1006207 • Briante Realty Group, LLC, Vanessa ...
New
Leisure Village
![200 NEWCASTLE CT E, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961]()
1 beds
|1 baths
|684 sq ft
|Condo
200 NEWCASTLE CT E, BROOKHAVEN, NY, 1196...
Community: Leisure Village
MLS 1010736 • JoAnn Cilla Real Estate, JoAnn Cill...
New
Rivington
![11 ORWICH CT 11, DANBURY, CT, 06810, Danbury, CT 06810]()
MLS 24182863 • William Raveis Real Estate, Svetla...
New
Windcrest East
![116 GOLDEN SPRUCE DR, RIVERHEAD, NY, 119..., Riverhead, NY 11933]()
3 beds
|3 baths
|2,200 sq ft
|House
116 GOLDEN SPRUCE DR, RIVERHEAD, NY, 119...
Community: Windcrest East
MLS 1009716 • Howard Hanna Coach, Julie P. Lapaso...
Download the Ultimate 55+ Homebuying Guide
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New
Jefferson Village
![17 HASTINGS CT A, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
MLS 1009641 • Keller Williams Realty Partner, Zar...
New
Woodridge Strathmore Terrace
![32 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766]()
2 beds
|2 baths
|Condo
32 HEARTHSIDE DR, BROOKHAVEN, NY, 11766
Community: Woodridge Strathmore Terrace
MLS 1010672 • Signature Premier Properties, Janic...
New
Heritage Village
![912 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
912 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24178295 • Keller Williams Realty, Donna Doyl...
New
Leisure Glen
![576 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,652 sq ft
|Condo
576 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
MLS 1005385 • RE/MAX Integrity Leaders, Karen L. ...
New
The Village at Oxford Greens
![527 PUTTING GREEN LN 527, OXFORD, CT, 06..., Oxford, CT 06478]()
3 beds
|3 baths
|2,008 sq ft
|Condo
527 PUTTING GREEN LN 527, OXFORD, CT, 06...
Community: The Village at Oxford Greens
MLS 24182673 • All Connecticut Realty, Mark Grass...
New
Heritage Hills
![758 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|2,030 sq ft
|Condo
758 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1006822 • William Raveis-New York LLC, Wendy ...
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New
The Gardens of Wilbraham
![77 CHERRY DR 77, WILBRAHAM, MA, 01095, Wilbraham, MA 01095]()
2 beds
|2 baths
|1,586 sq ft
|Condo
77 CHERRY DR 77, WILBRAHAM, MA, 01095
Community: The Gardens of Wilbraham
MLS 73532545 • Kempf-Vanderburgh Realty Consultan...
New
Regency at Prospect
![10 ASH LN 10, PROSPECT, CT, 06712, Prospect, CT 06712]()
2 beds
|3 baths
|1,928 sq ft
|Condo
10 ASH LN 10, PROSPECT, CT, 06712
Community: Regency at Prospect
MLS 24181908 • West View Properties, LLC, Marybet...
New
Oronoque Village
![493 PAWNEE LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,175 sq ft
|Condo
493 PAWNEE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24181818 • Keller Williams Realty Prtnrs., Ry...
New
Regency at Fishkill
![811 REGENCY DR 802, FISHKILL, NY, 12524, Fishkill, NY 12524]()
2 beds
|2 baths
|1,100 sq ft
|Condo
811 REGENCY DR 802, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 1010789 • Toll Brothers Real Estate Inc., Tho...
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.
New
Newtown Woods
![1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064..., Newtown, CT 06470]()
2 beds
|2 baths
|1,483 sq ft
|Condo
1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064...
Community: Newtown Woods
MLS 24180598 • Keller Williams Realty, Mary Pat S...
Glassbury Court at Cold Spring
![28 YESTERDAY DR, PHILIPSTOWN, NY, 10516, Philipstown, NY 10516]()
2 beds
|2 baths
|2,071 sq ft
|House
28 YESTERDAY DR, PHILIPSTOWN, NY, 10516
Community: Glassbury Court at Cold Spring
MLS 1010018 • William Raveis-New York LLC, Lance ...
Heritage Village
![18 HERITAGE CRST D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,735 sq ft
|Condo
18 HERITAGE CRST D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24181734 • William Raveis Real Estate, Betty ...
The Village at Oxford Greens
![1131 ST ANDREWS DR 50, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|2,536 sq ft
|Condo
1131 ST ANDREWS DR 50, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24181733 • EG Group Realty LLC, Jason Helton
Fairview at Oxford Greens
![1131 ST ANDREWS DR 50, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|2,536 sq ft
|Condo
1131 ST ANDREWS DR 50, OXFORD, CT, 06478
Community: Fairview at Oxford Greens
MLS 24181733 • EG Group Realty LLC, Jason Helton
Heritage Village
![28 HERITAGE CRST E, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,735 sq ft
|Condo
28 HERITAGE CRST E, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24180783 • Berkshire Hathaway NE Prop., Maria...
Sunken Pond Estates
![2201 PEBBLE BEACH PATH 2201, RIVERHEAD, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,258 sq ft
|Condo
2201 PEBBLE BEACH PATH 2201, RIVERHEAD, ...
Community: Sunken Pond Estates
MLS 1004037 • Douglas Elliman Real Estate, Patric...
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Jefferson Village
![51 JEFFERSON OVAL E, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
51 JEFFERSON OVAL E, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 1008809 • DeMarsh Properties Inc., Carla DeMa...
Oronoque Village
![44 BUCKSKIN LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|2 baths
|1,400 sq ft
|Condo
44 BUCKSKIN LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24180732 • Coldwell Banker Realty, Alicia Hal...
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The Vineyards at Mount Sinai
![51 FARM ACRE CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766]()
2 beds
|3 baths
|3,214 sq ft
|Condo
51 FARM ACRE CIR, BROOKHAVEN, NY, 11766
Community: The Vineyards at Mount Sinai
MLS 1008377 • Pinpoint Realty LI, Maryann Kelly
Heritage Village
![29 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,076 sq ft
|Condo
29 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24180713 • Berkshire Hathaway NE Prop., Jacqu...
Oronoque Village
![513 OPA LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,620 sq ft
|Condo
513 OPA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24178763 • Coldwell Banker Realty, Michael Si...
Heritage Hills
![900 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|3 baths
|1,552 sq ft
|Condo
900 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1007130 • Houlihan Lawrence Inc., Barbara Har...
The Summit at Bethel
![50 GREAT HILL DR, BETHEL, CT, 06801, Bethel, CT 06801]()
2 beds
|3 baths
|1,623 sq ft
|Condo
50 GREAT HILL DR, BETHEL, CT, 06801
Community: The Summit at Bethel
MLS 24178005 • Coldwell Banker Realty, Kim Giffor...
Regency at Prospect
![59 CHERRY CIR 59, PROSPECT, CT, 06712, Prospect, CT 06712]()
2 beds
|3 baths
|2,067 sq ft
|Condo
59 CHERRY CIR 59, PROSPECT, CT, 06712
Community: Regency at Prospect
MLS 24176447 • Pavlik Real Estate LLC, Deborah Ri...
Regency at Fishkill
![835 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524]()
2 beds
|2 baths
|1,803 sq ft
|Condo
835 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 1007847 • Houlihan Lawrence Inc., Jennifer St...
South Pond Village
![174 THISTLE POND DR 174, BLOOMFIELD, CT,..., Bloomfield, CT 06002]()
2 beds
|2 baths
|1,535 sq ft
|Condo
174 THISTLE POND DR 174, BLOOMFIELD, CT,...
Community: South Pond Village
MLS 24180284 • Berkshire Hathaway NE Prop., Lisa ...
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Oronoque Village
![778 QUINNIPIAC LN A, STRATFORD, CT, 0661..., Stratford, CT 06614]()
1 beds
|3 baths
|1,175 sq ft
|Condo
778 QUINNIPIAC LN A, STRATFORD, CT, 0661...
Community: Oronoque Village
MLS 24176136 • Coldwell Banker Realty, Mary Kelle...
Heritage Hills
![91 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|3 baths
|1,545 sq ft
|Condo
91 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1005564 • Keller Williams Realty Partner, Mar...
Download the Ultimate 55+ Homebuying Guide
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Frequently Asked Questions
In the Winchester Area, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.
The smallest 55+ communities in the Winchester Area has 31 homes, the largest has 38 homes, and the average communities consists of 34 homes.
Yes, there is new 55+ home available in the Winchester Area. The most recent communities started in the Winchester Area include Oak Meadow Estates, Clockmaker's Hill. There is also 1 communities in the Winchester Area that offers new construction homes, including Oak Meadow Estates.
No, there are no gated 55+ communities in the Winchester Area.
On average, listings in 55+ communities in the Winchester Area stay on the market for around 267 days. The average price of homes for sale in these communities is approximately $485,000, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Oak Meadow Estates average around $485,000.
Want to learn more about 55+ communities in the Winchester Area?
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The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Jun 12, 2026.
This application does not include information on all of the properties available for sale at this time.
