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 6
95 communities near Winchester Area
226 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
4 rating (1 reviews)
![Jefferson Village]()
$100ks
- $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
5 rating (2 reviews)
![Oronoque Village]()
$200ks
- $400ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
3 rating (2 reviews)
![Heritage Hills]()
$400ks
- $800ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1974 - 2006
|
2,600 homes
$300ks
- $400ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
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4 rating (8 reviews)
![Glenwood Village]()
$100ks
- $200ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
$400ks
- $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
$100ks
- $300ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
$300ks
- $900ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
$200ks
- $400ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 homes
Download the Ultimate 55+ Homebuying Guide
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5 rating (1 reviews)
![Newtown Woods]()
$300ks
- $500ks
Newtown Woods, Newtown, CT
New and Resale
|
55+ age-restricted
|
Built 2011 - present
|
178 homes
$300ks
- $400ks
Regency at Fishkill, Fishkill, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2020
|
164 homes
$400ks
- $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
125 homes
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2016
|
176 homes
$500ks
- $700ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2014
|
90 homes
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Questions? Call us:
(860) 238-3620
3.5 rating (2 reviews)
![Foxwood Village]()
$200ks
- $400ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
$200ks
- $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 1974 - 1985
|
226 homes
$400ks
- $500ks
Saddle Lakes, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2000 - 2002
|
196 homes
1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$400ks
- $500ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
285 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
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
$300ks
- $400ks
Liberty at Newtown, Newtown, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2007
|
96 homes
$400ks
The Village at Whispering...Rotterdam, NY
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
85 homes
$300ks
- $500ks
Park Glen, New Milford, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2015
|
17 homes
$300ks
- $400ks
South Pond Village, Bloomfield, CT
Resale Only
|
55+ age-restricted
|
Built 1999 - 2005
|
151 homes
$800ks
- $1Ms
The Vineyards at Mount Si..., Mount Sinai, NY
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
91 homes
$400ks
- $600ks
Billingsgate, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2006
|
37 homes
Want to learn more about 55+ communities in Winchester Area?
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Questions? Call us:
(860) 238-3620
5 rating (1 reviews)
![Sunken Pond Estates]()
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
194 homes
$500ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only
|
55+ age-restricted
|
Built 2014 - 2020
|
225 homes
5 rating (3 reviews)
![Founders Ridge]()
$300ks
- $400ks
Founders Ridge, Middletown, CT
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
75 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.
$200ks
- $300ks
Hopmeadow Place, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2005
|
66 homes
$500ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2005
|
85 homes
$400ks
- $500ks
Founders Village, Southold, NY
Resale Only
|
55+ age-restricted
|
Built 1981 - 1985
|
92 homes
5 rating (1 reviews)
![Paris Square]()
$500ks
- $700ks
Paris Square, Northvale, NJ
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
88 homes
$500ks
Regency Meadows, Trumbull, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
51 homes
$500ks
- $700ks
Glassbury Court at Hunter..., Cortlandt, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2014
|
64 homes
$300ks
- $400ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
$500ks
- $700ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 homes
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
$200ks
- $300ks
Woodcrest at Jacobs Hill, Cortlandt, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2006
|
58 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
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.
Foxwood Village
![1407 MIDDLE RD 83, BROOKHAVEN, NY, 11933, Brookhaven, NY 11933]()
2 beds
|2 baths
|1,444 sq ft
|Manufactured Home
1407 MIDDLE RD 83, BROOKHAVEN, NY, 11933
Community: Foxwood Village
MLS 995626 • Coldwell Banker M&D Good Life, Donna... • Coldwell Banker M&D Good Life
Plymouth Estates at Mount Sinai
![26 ROSE LN, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766]()
2 beds
|2 baths
|1,563 sq ft
|Condo
26 ROSE LN, BROOKHAVEN, NY, 11766
Community: Plymouth Estates at Mount Sinai
MLS 999845 • American Way Real Estate Inc, David ... • American Way Real Estate Inc
Heritage Village
![2 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,572 sq ft
|Condo
2 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24175446 • William Raveis Real Estate, Ruth Z... • William Raveis Real Estate
Stoneleigh Woods at Riverhead
![47 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|3 baths
|1,942 sq ft
|Condo
47 STONELEIGH DR, RIVERHEAD, NY, 11901
Community: Stoneleigh Woods at Riverhead
MLS 998166 • Vesta Realty Group Inc, Bessie C. Co... • Vesta Realty Group Inc
Heritage Village
![916 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
916 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24172651 • Berkshire Hathaway NE Prop., Bonni... • Berkshire Hathaway NE Prop.
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55places can help!
Questions? Call us:
(860) 238-3620
Heritage Village
![14 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,000 sq ft
|Condo
14 HERITAGE CIR B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24173132 • Howard Hanna Rand Realty, Kimberly... • Howard Hanna Rand Realty
Heritage Village
![149 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
149 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24170635 • Coldwell Banker Realty, Maryanne B... • Coldwell Banker Realty
Heritage Village
![59 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,308 sq ft
|Condo
59 HERITAGE VLG F, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24170135 • Coldwell Banker Realty, Filomena R... • Coldwell Banker Realty
Oronoque Village
![619 ERIE LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,583 sq ft
|Condo
619 ERIE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24168547 • Coldwell Banker Realty, Christine ... • Coldwell Banker Realty
Stoneleigh Woods at Riverhead
![156 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|3 baths
|1,942 sq ft
|Condo
156 STONELEIGH DR, RIVERHEAD, NY, 11901
Community: Stoneleigh Woods at Riverhead
MLS 989122 • Northshore Properties Realty, Dylan ... • Northshore Properties Realty
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.
Oronoque Village
![638A ONONDAGA LN, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,175 sq ft
|Condo
638A ONONDAGA LN, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24168699 • William Raveis Real Estate, Sailoz... • William Raveis Real Estate
Oronoque Village
![377 PIUTE LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|2,025 sq ft
|Condo
377 PIUTE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24167595 • House Real Estate, Maureen Greenbe... • House Real Estate
Glenwood Village
![1661 OLD COUNTRY RD 417, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,344 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 417, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 984696 • Signature Premier Properties, Noreen... • Signature Premier Properties
Jefferson Village
![51 JEFFERSON OVAL F, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
51 JEFFERSON OVAL F, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 982984 • Howard Hanna Rand Realty, Soleil Jac... • Howard Hanna Rand Realty
Heritage Village
![930 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
930 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24166135 • Coldwell Banker Realty, Dawn Ciapp... • Coldwell Banker Realty
The Summit at Bethel
![20 GREAT HILL DR 20, BETHEL, CT, 06801, Bethel, CT 06801]()
3 beds
|3 baths
|2,159 sq ft
|Condo
20 GREAT HILL DR 20, BETHEL, CT, 06801
Community: The Summit at Bethel
MLS 24160876 • RE/MAX Right Choice, Jay Streaman • RE/MAX Right Choice
Want to learn more about 55+ communities in Winchester Area?
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Jefferson Village
![59 KIRBY CLOSE D, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|2 baths
|910 sq ft
|Condo
59 KIRBY CLOSE D, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 974096 • Coldwell Banker Realty, Jo Ann Cooga... • Coldwell Banker Realty
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... • Houlihan Lawrence Inc.
Heritage Village
![405 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
405 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24149715 • Mapleridge Realty, Tommy Dorso • Mapleridge Realty
Oronoque Village
![446 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614]()
3 beds
|3 baths
|1,426 sq ft
|Condo
446 HAMMERSTONE LN B, STRATFORD, CT, 066...
Community: Oronoque Village
MLS 24147937 • Realty ONE Group Connect, Monica O... • Realty ONE Group Connect
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 Village
![274 BERWICK CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|1 baths
|836 sq ft
|Condo
274 BERWICK CT A, BROOKHAVEN, NY, 11961
Community: Leisure Village
MLS 948785 • RE/MAX Signature Real Estate, Natali... • RE/MAX Signature Real Estate
Overlook
![2042 SUMMIT LOOP 58, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 939680 • Toll Brothers Real Estate Inc., Thom... • Toll Brothers Real Estate Inc.
Overlook
![2069 SUMMIT LOOP 98, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 934376 • Toll Brothers Real Estate Inc., Thom... • Toll Brothers Real Estate Inc.
Heritage Village
![73 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
73 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24136386 • Alpine Realty, Gary Gilroy • Alpine Realty
The Vineyards at Miller Place
![48 AVERY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764]()
2 beds
|3 baths
|1,486 sq ft
|Condo
48 AVERY LN, BROOKHAVEN, NY, 11764
Community: The Vineyards at Miller Place
MLS 925827 • Aliano Real Estate, Nicholas R. Alia... • Aliano Real Estate
Glenwood Village
![1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|1 baths
|840 sq ft
|Mobile Home
1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 922155 • Realty Connect USA L I Inc, Fengxia ... • Realty Connect USA L I Inc
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 281 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?
- Insights and market stats
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- Answers from local 55+ experts
Want to learn more about 55+ communities in 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: Sep 17, 2026.
This application does not include information on all of the properties available for sale at this time.
