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 2
95 communities near Winchester Area
228 homes near Winchester Area
Sort by:
Relevance
3.6 rating (7 reviews)
$200ks
- $500ks
Heritage Village, Southbury, CT
Resale Only |
55+ age-restricted |
Built 1967 - 2005 |
2,580 homes
3 rating (2 reviews)
$400ks
- $900ks
Heritage Hills, Somers, NY
Resale Only |
Age-targeted |
Built 1974 - 2006 |
2,600 homes
4 rating (1 review)
$100ks
- $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only |
55+ age-restricted |
Built 1967 - 1982 |
1,000 homes
$400ks
- $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale |
55+ age-restricted |
Built 2004 - present |
835 homes
$300ks
- $400ks
Leisure Glen, Ridge, NY
Resale Only |
55+ age-restricted |
Built 1985 - 2010 |
646 homes
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
$100ks
- $300ks
Leisure Village, Ridge, NY
Resale Only |
55+ age-restricted |
Built 1969 - 1986 |
1,500 homes
5 rating (2 reviews)
$200ks
- $400ks
Oronoque Village, Stratford, CT
Resale Only |
55+ age-restricted |
Built 1971 - 1977 |
929 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
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
- $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale |
55+ age-restricted |
Built 2019 - present |
125 homes
$300ks
- $400ks
Regency at Fishkill, Fishkill, NY
Resale Only |
55+ age-restricted |
Built 2008 - 2020 |
164 homes
$300ks
- $400ks
Meadow Brook Estates, Oxford, CT
Resale Only |
55+ age-restricted |
Built 2003 - 2020 |
246 homes
5 rating (1 review)
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only |
55+ age-restricted |
Built 2003 - 2005 |
194 homes
5 rating (1 review)
$300ks
- $500ks
Newtown Woods, Newtown, CT
New and Resale |
55+ age-restricted |
Built 2011 - present |
178 homes
4 rating (8 reviews)
$100ks
- $200ks
Glenwood Village, Riverhead, NY
New and Resale |
55+ age-restricted |
Built 1959 - present |
588 homes
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
3.5 rating (2 reviews)
$200ks
- $400ks
Foxwood Village, Calverton, NY
Resale Only |
55+ age-restricted |
Built 1986 - 2007 |
294 homes
$400ks
- $500ks
Saddle Lakes, Riverhead, NY
Resale Only |
55+ age-restricted |
Built 2000 - 2002 |
196 homes
$500ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only |
55+ age-restricted |
Built 2004 - 2005 |
85 homes
$300ks
Sonoma Woods, Middletown, CT
Resale Only |
55+ age-restricted |
Built 2005 - 2015 |
68 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
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only |
55+ age-restricted |
Built 1974 - 1985 |
226 homes
1 rating (1 review)
$400ks
- $500ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only |
55+ age-restricted |
Built 2006 - 2013 |
285 homes
$400ks
- $500ks
Windcrest East, Calverton, NY
Resale Only |
55+ age-restricted |
Built 2004 - 2005 |
126 homes
$600ks
- $700ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only |
55+ age-restricted |
Built 2009 - 2014 |
90 homes
$300ks
- $400ks
Liberty at Newtown, Newtown, CT
Resale Only |
55+ age-restricted |
Built 2003 - 2007 |
96 homes
$100ks
- $200ks
Spring Lake Village, Southington, CT
Resale Only |
55+ age-restricted |
Built 1970 - 2004 |
640 homes
$500ks
- $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction |
55+ age-restricted |
Built 2023 - present |
70 homes
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only |
55+ age-restricted |
Built 2007 - 2016 |
176 homes
$300ks
- $400ks
The Village at Buckingham, Avon, CT
Resale Only |
55+ age-restricted |
Built 2002 - 2006 |
56 homes
$500ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only |
55+ age-restricted |
Built 2014 - 2020 |
225 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
- $700ks
Glassbury Court at Hunter..., Cortlandt, NY
Resale Only |
55+ age-restricted |
Built 2007 - 2014 |
64 homes
5 rating (2 reviews)
$400ks
- $600ks
Benson Woods, Middlebury, CT
New and Resale |
55+ age-restricted |
Built 2004 - present |
79 homes
$300ks
- $400ks
Regency at Prospect, Prospect, CT
Resale Only |
55+ age-restricted |
Built 2006 - 2020 |
379 homes
5 rating (3 reviews)
$300ks
- $400ks
Founders Ridge, Middletown, CT
New Construction |
55+ age-restricted |
Built 2017 - present |
75 homes
$200ks
- $300ks
Woodcrest at Jacobs Hill, Cortlandt, NY
Resale Only |
55+ age-restricted |
Built 2005 - 2006 |
58 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
$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
5 rating (1 review)
$600ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only |
55+ age-restricted |
Built 2005 - 2007 |
185 homes
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale |
55+ age-restricted |
Built 2005 - present |
92 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.
Heritage Village
3 beds
|2 baths
|1,716 sq ft
|Condo
847 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24214838 • Coldwell Banker Realty, Joe Rohins... • Coldwell Banker Realty
Heritage Village
1 beds
|1 baths
|928 sq ft
|Condo
369 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24214819 • William Raveis Real Estate, Nancy ... • William Raveis Real Estate
Heritage Village
2 beds
|2 baths
|1,432 sq ft
|Condo
26 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24214534 • Century 21 Bette Real Estate, Just... • Century 21 Bette Real Estate
Heritage Village
2 beds
|2 baths
|1,217 sq ft
|Condo
24 HERITAGE CRST B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24214726 • Coldwell Banker Realty, Charles Kn... • Coldwell Banker Realty
Rivington
3 beds
|4 baths
|2,709 sq ft
|Condo
42 COUNTRY VIEW RD 42, DANBURY, CT, 0681...
Community: Rivington
MLS 24214323 • Keller Williams Realty, Dee Braate... • Keller Williams Realty
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
The Village at Buckingham
MLS 24214390 • Berkshire Hathaway NE Prop., Fern ... • Berkshire Hathaway NE Prop.
Sunken Pond Estates
2 beds
|2 baths
|1,258 sq ft
|House
1504 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
MLS 1061656 • Compass Greater NY LLC, Diane M. Mo... • Compass Greater NY LLC
Jefferson Village
2 beds
|2 baths
|1,555 sq ft
|Condo
163 CARRIAGE CT A, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 1061959 • Coldwell Banker Realty, Donna Bruno • Coldwell Banker Realty
Bidwell Village
3 beds
|3 baths
|1,905 sq ft
|Condo
94 STONEHOUSE RD 6, COVENTRY, CT, 06238
Community: Bidwell Village
MLS 24213347 • Berkshire Hathaway NE Prop., Joyce... • Berkshire Hathaway NE Prop.
Heritage Village
3 beds
|2 baths
|1,716 sq ft
|Condo
191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24213898 • Century 21 Bette Real Estate, Just... • Century 21 Bette 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.
Liberty at Newtown
2 beds
|3 baths
|2,341 sq ft
|Condo
22 FRANKLIN CT 22, NEWTOWN, CT, 06470
Community: Liberty at Newtown
MLS 24213811 • Jorge A. Zea, Jorge Zea • Jorge A. Zea
Oronoque Village
2 beds
|3 baths
|2,226 sq ft
|Condo
532 NARRAGANSET LN A, STRATFORD, CT, 066...
Community: Oronoque Village
MLS 24212080 • Higgins Group Real Estate, Larry V... • Higgins Group Real Estate
Leisure Village
2 beds
|1 baths
|1,085 sq ft
|Condo
222 BLACKPOOL CT A, BROOKHAVEN, NY, 1196...
Community: Leisure Village
MLS 1061479 • Douglas Elliman Real Estate, Noelle... • Douglas Elliman Real Estate
Sonoma Woods
MLS 24213623 • Berkshire Hathaway NE Prop., Laura... • Berkshire Hathaway NE Prop.
Regency at Fishkill
2 beds
|2 baths
|1,100 sq ft
|Condo
811 REGENCY DR 802, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 1061451 • Toll Brothers Real Estate Inc., Tho... • Toll Brothers Real Estate Inc.
Jefferson Village
2 beds
|2 baths
|910 sq ft
|Condo
59 KIRBY CLOSE D, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 1061035 • eXp Realty, Dvora E. Price • eXp Realty
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Heritage Village
2 beds
|2 baths
|1,398 sq ft
|Condo
701 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24213703 • Exceptional Real Estate LLC, Teren... • Exceptional Real Estate LLC
Heritage Village
2 beds
|2 baths
|1,432 sq ft
|Condo
170 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24213530 • Ascend Realty LLC, Michael Monteir... • Ascend Realty LLC
Heritage Village
2 beds
|2 baths
|1,432 sq ft
|Condo
778 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24213485 • Berkshire Hathaway NE Prop., Miche... • Berkshire Hathaway NE Prop.
Heritage Village
2 beds
|2 baths
|1,044 sq ft
|Condo
176 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24213308 • Keller Williams Realty, Jeff Jones • Keller Williams 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.
Glassbury Court at Hunterbrook
2 beds
|4 baths
|3,500 sq ft
|Condo
2329 DEPEYSTER DR, YORKTOWN, NY, 10567
Community: Glassbury Court at Hunterbrook
MLS 1059584 • Coldwell Banker Realty, Audra Macca... • Coldwell Banker Realty
Heritage Hills
MLS 1052880 • KW MidHudson, Philip E. Risi • KW MidHudson
Heritage Hills
MLS 1060798 • Mark Seiden Real Estate Team, Mark ... • Mark Seiden Real Estate Team
Leisure Village
2 beds
|2 baths
|1,767 sq ft
|Condo
387 WOODBRIDGE DR A, BROOKHAVEN, NY, 119...
Community: Leisure Village
MLS 1059451 • Douglas Elliman Real Estate, Joyce ... • Douglas Elliman Real Estate
Glenwood Village
2 beds
|2 baths
|1,624 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 1059912 • BH&G R E Realty Connect, Paul M. Pe... • BH&G R E Realty Connect
Meadow Brook Estates
2 beds
|3 baths
|2,258 sq ft
|Condo
802 SAGE HILL DR 802, OXFORD, CT, 06478
Community: Meadow Brook Estates
MLS 24212165 • William Raveis Real Estate, Pat Bl... • William Raveis Real Estate
Leisure Knoll
2 beds
|1 baths
|1,050 sq ft
|Condo
346 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 1060052 • Leisure Living Realty Inc, Laura Ru... • Leisure Living Realty Inc
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Sunken Pond Estates
2 beds
|2 baths
|1,587 sq ft
|Condo
3102 AMEN COR, RIVERHEAD, NY, 11901
Community: Sunken Pond Estates
MLS 1058899 • American Real Estate Assoc Inc, Gin... • American Real Estate Assoc Inc
Rivington
3 beds
|3 baths
|1,704 sq ft
|Condo
71 WARRINGTON ROUND 71, DANBURY, CT, 068...
Community: Rivington
MLS 24212105 • Houlihan Lawrence, Barbara Sawin • Houlihan Lawrence
Rivington
MLS 24212267 • Houlihan Lawrence, Barbara Sawin • Houlihan Lawrence
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
3 beds
|2 baths
|1,793 sq ft
|Condo
350 HERITAGE HILLS DR C, SOMERS, NY, 105...
Community: Heritage Hills
MLS 1058470 • Houlihan Lawrence Inc., Donna O'Con... • Houlihan Lawrence Inc.
Leisure Knoll
2 beds
|1 baths
|1,116 sq ft
|Condo
177 CANTERBURY DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 1058085 • Signature Premier Properties, Jolen... • Signature Premier Properties
Jefferson Village
MLS 1057688 • Coldwell Banker Realty, Elizabeth K... • Coldwell Banker Realty
Foxwood Village
3 beds
|2 baths
|1,792 sq ft
|Manufactured Home
1407 MIDDLE RD 271, RIVERHEAD, NY, 11933
Community: Foxwood Village
MLS 1060050 • Coldwell Banker American Homes, Kel... • Coldwell Banker American Homes
Regency at Fishkill
1 beds
|2 baths
|1,499 sq ft
|Condo
231 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 1059790 • Houlihan Lawrence Inc., Jennifer St... • Houlihan Lawrence Inc.
Windcrest East
3 beds
|3 baths
|2,620 sq ft
|Condo
90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...
Community: Windcrest East
MLS 1059777 • Howard Hanna Coach, Julie P. Lapaso... • Howard Hanna Coach
Windcrest East
3 beds
|3 baths
|2,531 sq ft
|Condo
29 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...
Community: Windcrest East
MLS 1059787 • Howard Hanna Coach, Julie P. Lapaso... • Howard Hanna Coach
Meadow Brook Estates
2 beds
|3 baths
|1,920 sq ft
|Condo
130 MEADOW BROOK RD 130, OXFORD, CT, 064...
Community: Meadow Brook Estates
MLS 24208378 • Drakeley Real Estate, Inc., Jeffre... • Drakeley Real Estate, Inc.
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Jefferson Village
1 beds
|1 baths
|953 sq ft
|Condo
160 CARRIAGE CT D, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 1058502 • Houlihan Lawrence Inc., Patricia D'... • Houlihan Lawrence Inc.
Setauket Meadows
MLS 1057931 • Coldwell Banker American Homes, Kev... • Coldwell Banker American 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.
Frequently Asked Questions
Of the 2 55+ communities in the Winchester Area, 2 are for sale and none are rentals. By size, 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 397 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
- Instant new home alerts
- Answers from local 55+ experts
Want to learn more about 55+ communities in Winchester Area?
228
homes
Remove Boundaries ×
Map
Satellite
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: Nov 02, 2026.
This application does not include information on all of the properties available for sale at this time.
