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
93 communities near Winchester Area
171 homes near Winchester Area
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3.6 rating (7 reviews)
![Heritage Village]()
$100Ks
- $500Ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
3 rating (2 reviews)
![Heritage Hills]()
$300Ks
- $900Ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1974 - 2006
|
2,600 homes
$200Ks
- $400Ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
$200Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
$600Ks
- $700Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
Want to learn more about 55+ communities in Winchester Area?
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Questions? Call us:
(860) 238-3620
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4 rating (1 reviews)
![Jefferson Village]()
$200Ks
- $500Ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
4 rating (8 reviews)
![Glenwood Village]()
$100Ks
- $200Ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
$600Ks
- $700Ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
125 homes
$400Ks
- $800Ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 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.
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.
$400Ks
- $700Ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
|
312 homes
$400Ks
- $500Ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 homes
$600Ks
- $700Ks
Regency at Woodbridge, Woodbridge, CT
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
70 homes
$400Ks
- $500Ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
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(860) 238-3620
$200Ks
- $400Ks
South Pond Village, Bloomfield, CT
Resale Only
|
55+ age-restricted
|
Built 1999 - 2005
|
151 homes
$600Ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2005
|
85 homes
4.9 rating (14 reviews)
![Chatfield Farms]()
$500Ks
- $700Ks
Chatfield Farms, Beacon Falls, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
231 homes
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(860) 238-3620
$200Ks
- $300Ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 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.
5 rating (1 reviews)
![Newtown Woods]()
$400Ks
- $500Ks
Newtown Woods, Newtown, CT
New and Resale
|
55+ age-restricted
|
Built 2011 - present
|
178 homes
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.
$400Ks
The Village at Whispering...Rotterdam, NY
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
85 homes
1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$500Ks
- $600Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
285 homes
$600Ks
- $700Ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only
|
55+ age-restricted
|
Built 2014 - 2020
|
225 homes
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(860) 238-3620
$400Ks
Villas at Seminary Hill, Carmel, NY
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
50 homes
$500Ks
- $600Ks
The Residences at Butterf..., Cold Spring, NY
Resale Only
|
55+ age-restricted
|
Built 2018 - 2023
|
49 homes
$500Ks
- $700Ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2014
|
90 homes
$600Ks
- $700Ks
Granite Woods, Middlebury, CT
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
24 homes
5 rating (1 reviews)
![The Villages at Mount Sin...]()
$500Ks
- $700Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
185 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.
$500Ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
Want to learn more about 55+ rental communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
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.
3.5 rating (2 reviews)
![Foxwood Village]()
$400Ks
- $500Ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
5 rating (1 reviews)
![Paris Square]()
$400Ks
- $700Ks
Paris Square, Northvale, NJ
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
88 homes
Want to learn more about 55+ communities in Winchester Area?
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Questions? Call us:
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$500Ks
Evergreen, Cromwell, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
52 homes
$500Ks
- $700Ks
Glassbury Court at Hunter..., Cortlandt, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2014
|
64 homes
$300Ks
- $400Ks
Long Hill Village, Trumbull, CT
Resale Only
|
55+ age-restricted
|
Built 1997 - 1999
|
71 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.
$300Ks
- $400Ks
Liberty at Newtown, Newtown, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2007
|
96 homes
$500Ks
- $600Ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2016
|
176 homes
$500Ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
108 homes
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.
$400Ks
- $500Ks
Regency at Fishkill, Fishkill, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2020
|
164 homes
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Want to learn more about 55+ rental communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
$600Ks
- $700Ks
Setauket Meadows, Setauket, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
150 homes
New
Heritage Hills
![680 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589]()
1 beds
|2 baths
|1,296 sq ft
|Condo
680 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
MLS 959581 • Houlihan Lawrence Inc., Donna O'Conn...
New
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 ...
New
Leisure Knoll
![304 KINGSTON CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 959588 • Howard Hanna Coach, Kalliopi C. Suar...
New
Heritage Hills
![243 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|1,689 sq ft
|Condo
243 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 956550 • Houlihan Lawrence Inc., Donna O'Conn...
New
Oronoque Village
![133 BANNOCK LN, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|2,038 sq ft
|Condo
133 BANNOCK LN, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24153059 • William Raveis Real Estate, Joseph...
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55places can help!
Questions? Call us:
(860) 238-3620
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55places can help!
Questions? Call us:
(860) 238-3620
New
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...
New
Chatfield Farms
![8 WOODLAND PATH # 8, BEACON FALLS, CT, 0..., Beacon Falls, CT 06403]()
3 beds
|4 baths
|2,610 sq ft
8 WOODLAND PATH # 8, BEACON FALLS, CT, 0...
Community: Chatfield Farms
MLS 24153023 • KW Legacy Partners, Mela Veltri Ca...
New
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...
New
Leisure Village
![230 BLACKPOOL CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|836 sq ft
|Condo
230 BLACKPOOL CT A, RIDGE, NY, 11961
Community: Leisure Village
MLS 958476 • Aliano Real Estate, Nicholas R. Alia...
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.
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
Meadow Brook Estates
![215 MEADOW BROOK RD # 215, OXFORD, CT, 0..., Oxford, CT 06478]()
3 beds
|3 baths
|2,207 sq ft
|Condo
215 MEADOW BROOK RD # 215, OXFORD, CT, 0...
Community: Meadow Brook Estates
MLS 24152665 • William Pitt Sotheby's Int'l, Erik...
The Residences at Butterfield
![19 BUTTERFIELD RD UNIT 102B 102B, COLD S..., Cold Spring, NY 10516]()
2 beds
|2 baths
|1,322 sq ft
|Condo
19 BUTTERFIELD RD UNIT 102B 102B, COLD S...
Community: The Residences at Butterfield
MLS 953470 • Houlihan Lawrence Inc., Linda K. Hof...
Leisure Village
![406 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961]()
1 beds
|1 baths
|704 sq ft
|Condo
406 WOODBRIDGE DR B, RIDGE, NY, 11961
Community: Leisure Village
MLS 957458 • Signature Premier Properties, Bryn G...
Long Hill Village
![71 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611]()
1 beds
|3 baths
|1,370 sq ft
|Condo
71 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill Village
MLS 24152135 • Higgins Group Real Estate, Fredda ...
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(860) 238-3620
Leisure Knoll
![190 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|1 baths
|913 sq ft
|House
190 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 958383 • Frontline Realty Group LLC, Nicholas...
Heritage Village
![915 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
915 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24148897 • LPT Realty, Jessica Boswell
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...
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Oronoque Village
![445 NORTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,620 sq ft
|Condo
445 NORTH TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24152048 • Berkshire Hathaway NE Prop., Jacqu...
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.
Jefferson Village
![50 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|910 sq ft
|Condo
50 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
MLS 955863 • Coldwell Banker Realty, Jo Ann Cooga...
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.
Rivington
![1 WILDERSWOOD WAY # 1, DANBURY, CT, 0681..., Danbury, CT 06810]()
3 beds
|4 baths
|2,596 sq ft
|Condo
1 WILDERSWOOD WAY # 1, DANBURY, CT, 0681...
Community: Rivington
MLS 24152012 • William Pitt Sotheby's Int'l, Cole...
The Village at Oxford Greens
![909 TILLINGHAST DR # 909, OXFORD, CT, 06..., Oxford, CT 06478]()
2 beds
|3 baths
|2,239 sq ft
|Condo
909 TILLINGHAST DR # 909, OXFORD, CT, 06...
Community: The Village at Oxford Greens
MLS 24151108 • Coldwell Banker Realty, Michele Is...
Fairview at Oxford Greens
![909 TILLINGHAST DR # 909, OXFORD, CT, 06..., Oxford, CT 06478]()
2 beds
|3 baths
|2,239 sq ft
|Condo
909 TILLINGHAST DR # 909, OXFORD, CT, 06...
Community: Fairview at Oxford Greens
MLS 24151108 • Coldwell Banker Realty, Michele Is...
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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, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 953068 • Signature Premier Properties, Keith ...
Glenwood Village
![1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,156 sq ft
|Manufactured Home
1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190...
Community: Glenwood Village
MLS 957014 • Joanne Kane Gigantiello, Joanne Giga...
Chatfield Farms
![9 LAKEVIEW RISE # 9, BEACON FALLS, CT, 0..., Beacon Falls, CT 06403]()
2 beds
|3 baths
|1,700 sq ft
|Condo
9 LAKEVIEW RISE # 9, BEACON FALLS, CT, 0...
Community: Chatfield Farms
MLS 24150590 • Calcagni Real Estate, Irma Nesson
Jefferson Village
![53 JEFFERSON OVAL B, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
53 JEFFERSON OVAL B, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
MLS 956533 • Jefferson Valley Realty, Kristine M....
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.
Sonoma Woods
![60 SONOMA LN # 60, MIDDLETOWN, CT, 06457, Middletown, CT 06457]()
2 beds
|3 baths
|2,054 sq ft
|Condo
60 SONOMA LN # 60, MIDDLETOWN, CT, 06457
Community: Sonoma Woods
MLS 24151609 • Berkshire Hathaway NE Prop., Mark ...
Want to learn more about 55+ rental communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
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.
Heritage Hills
![339 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|3 baths
|1,550 sq ft
|Condo
339 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 954783 • Keller Williams Realty Partner, Anne...
South Pond Village
![162 THISTLE POND DR # 162, BLOOMFIELD, C..., Bloomfield, CT 06002]()
2 beds
|2 baths
|1,341 sq ft
|Condo
162 THISTLE POND DR # 162, BLOOMFIELD, C...
Community: South Pond Village
MLS 24151340 • Hill Top Real Estate, LLC, Craig I...
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Heritage Hills
![882 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|3 baths
|1,666 sq ft
|Condo
882 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
MLS 934009 • Houlihan Lawrence Inc., Gary Parker
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...
The Village at Oxford Greens
![117 COUNTRY CLUB DR 117, OXFORD, CT, 064..., Oxford, CT 06478]()
3 beds
|3 baths
|2,666 sq ft
117 COUNTRY CLUB DR 117, OXFORD, CT, 064...
Community: The Village at Oxford Greens
MLS 24151623 • Real Estate Two, Karen Berwick
Heritage Hills
![578 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589]()
1 beds
|2 baths
|967 sq ft
|Condo
578 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
MLS 950188 • Houlihan Lawrence Inc., Harding Maso...
Leisure Glen
![77 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
MLS 952676 • Signature Premier Properties, Lisa M...
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
![301 FAIRWAY DR 301, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|2 baths
|2,080 sq ft
|Condo
301 FAIRWAY DR 301, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24151318 • Coldwell Banker Realty, Carl Deman...
Granite Woods
![35 NUTMEG RD D1, MIDDLEBURY, CT, 06762, Middlebury, CT 06762]()
1 beds
|1 baths
|889 sq ft
|Condo
35 NUTMEG RD D1, MIDDLEBURY, CT, 06762
Community: Granite Woods
MLS 24150979 • Showcase Realty, Inc., Karen Stanc...
Regency at Wappinger
![61 FARMINGTON RD, WAPPINGERS FALLS, NY, ..., Wappingers Falls, NY 12590]()
2 beds
|2 baths
|1,738 sq ft
|House
61 FARMINGTON RD, WAPPINGERS FALLS, NY, ...
Community: Regency at Wappinger
MLS 955483 • Houlihan Lawrence Inc., Nicole Boisv...
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.
Oronoque Village
![635 NORTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,454 sq ft
|Condo
635 NORTH TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24148329 • Coldwell Banker Realty, Wendy Barr...
Want to learn more about 55+ communities in Winchester Area?
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Questions? Call us:
(860) 238-3620
Want to learn more about 55+ rental communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Heritage Hills
![656 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,296 sq ft
|Condo
656 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
MLS 950592 • Houlihan Lawrence Inc., Donna O'Conn...
Heritage Village
![73 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
73 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24150969 • RE/MAX Right Choice, Kimberly Came...
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?
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- 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: Feb 10, 2026.
This application does not include information on all of the properties available for sale at this time.
