Call us at (860) 238-3620 to learn more about active adult communities in Winchester Area
Winchester Area, CT 55+ active adult communities & homes for sale - Page 4
93 communities near Winchester Area
204 homes near Winchester Area
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3.6 rating (7 reviews)
![Heritage Village]()
$200ks
- $500ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
$100ks
- $300ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
$200ks
- $400ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
3 rating (2 reviews)
![Heritage Hills]()
$500ks
- $900ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1974 - 2006
|
2,600 homes
4 rating (1 reviews)
![Jefferson Village]()
$100ks
- $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
Want to learn more about 55+ communities in Winchester Area?
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Questions? Call us:
(860) 238-3620
$400ks
- $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
$400ks
- $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
125 homes
4 rating (8 reviews)
![Glenwood Village]()
$100ks
- $200ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
$300ks
- $400ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
Download the Ultimate 55+ Homebuying Guide
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$200ks
- $400ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 homes
5 rating (1 reviews)
![The Villages at Mount Sin...]()
$600ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
185 homes
$300ks
- $900ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
5 rating (1 reviews)
![Newtown Woods]()
$300ks
- $500ks
Newtown Woods, Newtown, CT
New and Resale
|
55+ age-restricted
|
Built 2011 - present
|
178 homes
$100ks
- $200ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
$300ks
- $400ks
Regency at Fishkill, Fishkill, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2020
|
164 homes
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(860) 238-3620
$300ks
- $400ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
$300ks
- $400ks
North Woods of Colchester, Colchester, CT
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
140 homes
$500ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only
|
55+ age-restricted
|
Built 2014 - 2020
|
225 homes
$300ks
- $800ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
|
312 homes
Download the Ultimate 55+ Homebuying Guide
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$500ks
- $700ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2014
|
90 homes
5 rating (1 reviews)
![Sunken Pond Estates]()
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
194 homes
$500ks
- $700ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 homes
$300ks
- $400ks
South Pond Village, Bloomfield, CT
Resale Only
|
55+ age-restricted
|
Built 1999 - 2005
|
151 homes
$200ks
- $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 1974 - 1985
|
226 homes
$500ks
- $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
70 homes
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Questions? Call us:
(860) 238-3620
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
92 homes
$200ks
- $300ks
Oak Meadow Estates, Torrington, CT
New and Resale
|
55+ age-restricted
|
Built 2013 - present
|
31 homes
$500ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2005
|
85 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.
$400ks
- $500ks
Evergreen, Cromwell, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
52 homes
$500ks
- $600ks
Setauket Meadows, Setauket, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
150 homes
$800ks
- $1Ms
Village Vistas, Port Jefferson, NY
Resale Only
|
55+ age-restricted
|
Built 2013 - 2017
|
43 homes
5 rating (1 reviews)
![Paris Square]()
$400ks
- $700ks
Paris Square, Northvale, NJ
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
88 homes
$300ks
- $400ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
$200ks
- $300ks
Villas at Seminary Hill, Carmel, NY
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
50 homes
3.5 rating (2 reviews)
![Foxwood Village]()
$200ks
- $400ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
$400ks
The Village at Whispering...Rotterdam, NY
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
85 homes
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
$300ks
- $400ks
Liberty at Newtown, Newtown, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2007
|
96 homes
$300ks
- $400ks
Bartlett Hill, Portland, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2011
|
82 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.
The Village at Oxford Greens
![1093 ST ANDREWS DR 7, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|2,454 sq ft
|Condo
1093 ST ANDREWS DR 7, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24155597 • EG Group Realty LLC, Shabnam Sadat
Fairview at Oxford Greens
![1091 ST ANDREWS DR 6, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|2,536 sq ft
|Condo
1091 ST ANDREWS DR 6, OXFORD, CT, 06478
Community: Fairview at Oxford Greens
MLS 24155594 • EG Group Realty LLC, Shabnam Sadat
The Village at Oxford Greens
![1091 ST ANDREWS DR 6, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|2,536 sq ft
|Condo
1091 ST ANDREWS DR 6, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24155594 • EG Group Realty LLC, Shabnam Sadat
Heritage Village
![103 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
103 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24156393 • Keller Williams Realty, Lou Capell...
Oronoque Village
![546 N TRL B, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,434 sq ft
|Condo
546 N TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24155906 • Coldwell Banker Realty, Mark Pires
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Heritage Hills
![228 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|3 baths
|1,700 sq ft
|Condo
228 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 955232 • Compass Greater NY, LLC, Colleen Cox...
Oronoque Village
![383 SEQUOIA LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,360 sq ft
|Condo
383 SEQUOIA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24154892 • Coldwell Banker Realty, Mary Kelle...
Regency at Wappinger
![27 DUTCH CT, WAPPINGER, NY, 12590, Wappinger, NY 12590]()
2 beds
|4 baths
|3,362 sq ft
|Condo
27 DUTCH CT, WAPPINGER, NY, 12590
Community: Regency at Wappinger
MLS 945353 • Century 21 Alliance Rlty Group, Caro...
Heritage Village
![191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24156103 • Century 21 Bette Real Estate, Just...
Spring Lake Village
![41 COACH DR 41, SOUTHINGTON, CT, 06489, Southington, CT 06489]()
2 beds
|2 baths
|1,232 sq ft
|Condo
41 COACH DR 41, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
MLS 24154460 • Calcagni Real Estate, Donna Pelleg...
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
![865 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
865 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24155103 • Showcase Realty, Inc., Gregory Bal...
Overlook
![2066 SUMMIT LOOP 68, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 963411 • Toll Brothers Real Estate Inc., Thom...
Heritage Village
![1041 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
2 beds
|2 baths
|1,000 sq ft
|Condo
1041 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24154431 • Carey & Guarrera Real Estate, Alet...
Jefferson Village
![41 JEFFERSON OVAL G, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
41 JEFFERSON OVAL G, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 961695 • Houlihan Lawrence Inc., Steve Fratta...
Jefferson Village
![113 VILLAGE RD B, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|2 baths
|1,200 sq ft
|Condo
113 VILLAGE RD B, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 962245 • Briante Realty Group, LLC, Lillian M...
Spring Lake Village
![6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489, Southington, CT 06489]()
3 beds
|3 baths
|1,471 sq ft
|Condo
6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
MLS 24154583 • eXp Realty, Eric Christmas
Want to learn more about 55+ communities in Winchester Area?
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Questions? Call us:
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Oronoque Village
![488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|2,199 sq ft
|Condo
488 COMMANCHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24154316 • Serhant Connecticut, LLC, Carmen D...
Heritage Village
![170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
170 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24152831 • Ascend Realty LLC, Michael Monteir...
Glassbury Court at Cold Spring
![15 REVOLUTION RD, PHILIPSTOWN, NY, 10516, Philipstown, NY 10516]()
2 beds
|3 baths
|1,785 sq ft
|Condo
15 REVOLUTION RD, PHILIPSTOWN, NY, 10516
Community: Glassbury Court at Cold Spring
MLS 959610 • House Finch Realty, LLC, Charlotte F...
Regency at Fishkill
![734 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524]()
2 beds
|2 baths
|1,499 sq ft
|Condo
734 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 959190 • Century 21 Alliance Rlty Group, Anth...
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.
Leisure Glen
![530 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,434 sq ft
|Condo
530 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
MLS 957040 • Signature Premier Properties, Mildre...
Heritage Hills
![40 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,139 sq ft
|Condo
40 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 954097 • Houlihan Lawrence Inc., Janet Ferran...
Heritage Village
![575 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
575 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24152837 • Drakeley Real Estate, Inc., Shelle...
South Pond Village
![81 SILO WAY 81, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002]()
2 beds
|2 baths
|1,204 sq ft
|Condo
81 SILO WAY 81, BLOOMFIELD, CT, 06002
Community: South Pond Village
MLS 24151413 • Berkshire Hathaway NE Prop., Sandy...
Heritage Hills
![680 HERITAGE HILLS DR C, SOMERS, NY, 105..., Somers, NY 10589]()
1 beds
|2 baths
|1,296 sq ft
|Condo
680 HERITAGE HILLS DR C, SOMERS, NY, 105...
Community: Heritage Hills
MLS 959581 • Houlihan Lawrence Inc., Donna O'Conn...
Villas at Seminary Hill
![7102 PANKIN DR, CARMEL, NY, 10512, Carmel, NY 10512]()
2 beds
|2 baths
|1,144 sq ft
|Condo
7102 PANKIN DR, CARMEL, NY, 10512
Community: Villas at Seminary Hill
MLS 959423 • River Realty Services, Inc., Ernest ...
Heritage Hills
![243 HERITAGE HILLS DR B, SOMERS, NY, 105..., Somers, NY 10589]()
3 beds
|2 baths
|1,689 sq ft
|Condo
243 HERITAGE HILLS DR B, SOMERS, NY, 105...
Community: Heritage Hills
MLS 956550 • Houlihan Lawrence Inc., Donna O'Conn...
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Oronoque Village
![133 BANNOCK LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|2,038 sq ft
|Condo
133 BANNOCK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24153059 • William Raveis Real Estate, Joseph...
Heritage Village
![914 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,144 sq ft
|Condo
914 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24152900 • Coldwell Banker Realty, Douglas Co...
Chatfield Farms
![8 WOODLAND PATH 8, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403]()
3 beds
|4 baths
|2,610 sq ft
|Condo
8 WOODLAND PATH 8, BEACON FALLS, CT, 064...
Community: Chatfield Farms
MLS 24153080 • KW Legacy Partners, Mela Veltri Ca...
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
![419 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
419 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24152323 • Berkshire Hathaway NE Prop., Jesse...
Overlook
![3014 EASTVIEW LN 110, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 959114 • Toll Brothers Real Estate Inc., Thom...
Heritage Village
![745 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
745 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24146008 • West View Properties, LLC, Kara Re...
Jefferson Village
![50 JEFFERSON OVAL A, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|2 baths
|910 sq ft
|Condo
50 JEFFERSON OVAL A, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 955863 • Coldwell Banker Realty, Jo Ann Cooga...
Village Vistas
![11 THERESA LN, BROOKHAVEN, NY, 11777, Brookhaven, NY 11777]()
2 beds
|4 baths
|3,000 sq ft
|Condo
11 THERESA LN, BROOKHAVEN, NY, 11777
Community: Village Vistas
MLS 956001 • Realty Connect USA L I Inc, Paul A. ...
Heritage Village
![968 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,071 sq ft
|Condo
968 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24151781 • Century 21 Bette Real Estate, Debo...
Leisure Knoll
![475 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
3 beds
|2 baths
|1,592 sq ft
|House
475 STRATFORD LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 953068 • Signature Premier Properties, Keith ...
Jefferson Village
![53 JEFFERSON OVAL B, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
53 JEFFERSON OVAL B, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 956533 • Jefferson Valley Realty, Kristine M....
Want to learn more about 55+ communities in Winchester Area?
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The Retreat at Carmel
![18 WHEELER CT, CARMEL, NY, 10512, Carmel, NY 10512]()
2 beds
|3 baths
|2,035 sq ft
|Condo
18 WHEELER CT, CARMEL, NY, 10512
Community: The Retreat at Carmel
MLS 953121 • Keller Williams Realty Partner, Rand...
Newtown Woods
![23 WOODS LN 23, NEWTOWN, CT, 06470, Newtown, CT 06470]()
MLS 24150894 • William Raveis Real Estate, Sandy ...
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.
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 788 days. The average price of homes for sale in these communities is approximately $389,900, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Oak Meadow Estates average around $389,900.
Want to learn more about 55+ communities in the Winchester Area?
- Insights and market stats
- Instant new home alerts
- Answers from local 55+ experts
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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: Apr 17, 2026.
This application does not include information on all of the properties available for sale at this time.
