Winchester Area, CT 55+ active adult communities & homes for sale - Page 2

199 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

3 rating (2 reviews)

Heritage Hills

$400ks - $800ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 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

The Village at Oxford Gre...

$400ks - $500ks

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? 55places can help!

Questions? Call us: (860) 238-3620

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes

Spring Lake Village

$100ks - $200ks

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.

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes

Rivington

$300ks - $900ks

Rivington, Danbury, CT

New and Resale | Age-targeted | Built 2006 - present | 1,050 homes

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes

Leisure Glen

$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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes

Glassbury Court at Cold S...

$500ks - $700ks

Glassbury Court at Cold S..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes

Woodcrest at Jacobs Hill

$200ks - $300ks

Woodcrest at Jacobs Hill, Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 homes

Billingsgate

$400ks - $600ks

Billingsgate, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes

The Vineyards at Mount Si...

$800ks - $1Ms

The Vineyards at Mount Si..., Mount Sinai, NY

New Construction | 55+ age-restricted | Built 2020 - present | 91 homes

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes

Stoneleigh Woods at Carme...

$400ks

Stoneleigh Woods at Carme..., Carmel, NY

Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes

Want to learn more about 55+ communities in Winchester Area? 55places can help!

Questions? Call us: (860) 238-3620

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes

4.9 rating (14 reviews)

Chatfield Farms

$400ks - $700ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

Want to learn more about 55+ communities in Winchester Area? 55places can help!

Questions? Call us: (860) 238-3620

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

The Vineyards at Miller P...

$500ks

The Vineyards at Miller P..., Miller Place, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes

1 2...3

Heritage Hills

181 HERITAGE HLS F, SOMERS, NY, 10589, Somers, NY 10589

$499,999

2 beds

2 baths

1,205 sq ft

Condo

181 HERITAGE HLS F, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

16 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$389,900

2 beds

2 baths

1,432 sq ft

Condo

16 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

274 BERWICK CT C, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$359,000

2 beds

1 baths

836 sq ft

Condo

274 BERWICK CT C, BROOKHAVEN, NY, 11961

Community: Leisure Village

Spring Lake Village

626 OVERLOOK PATH 626, SOUTHINGTON, CT, ..., Southington, CT 06489

$350,000

2 beds

2 baths

1,230 sq ft

Condo

626 OVERLOOK PATH 626, SOUTHINGTON, CT, ...

Community: Spring Lake Village

Bartlett Hill

19 PLUMROSE CT 19, PORTLAND, CT, 06480, Portland, CT 06480

$500,000

2 beds

3 baths

1,503 sq ft

19 PLUMROSE CT 19, PORTLAND, CT, 06480

Community: Bartlett Hill

Want to learn more about 55+ communities in Winchester Area? 55places can help!

Questions? Call us: (860) 238-3620

Heritage Village

38 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$299,900

2 beds

2 baths

1,032 sq ft

Condo

38 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

407 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$450,000

1 beds

2 baths

1,360 sq ft

Condo

407 MONTAUK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Leisure Village

368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$394,990

2 beds

1 baths

Condo

368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119...

Community: Leisure Village

Baldwin Station

15 JASMINE CIR 15, MILFORD, CT, 06461, Milford, CT 06461

$599,000

2 beds

3 baths

2,331 sq ft

Condo

15 JASMINE CIR 15, MILFORD, CT, 06461

Community: Baldwin Station

The Village at Oxford Greens

941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478

$699,900

2 beds

2 baths

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$699,900

2 beds

2 baths

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

Leisure Glen

581 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$625,000

2 beds

2 baths

1,685 sq ft

Condo

581 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Rivington

64 WARRINGTON ROUND 64, DANBURY, CT, 068..., Danbury, CT 06810

$649,900

3 beds

3 baths

1,600 sq ft

Condo

64 WARRINGTON ROUND 64, DANBURY, CT, 068...

Community: Rivington

The Gardens of Wilbraham

79 CHERRY DR 79, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$435,000

2 beds

2 baths

1,376 sq ft

Condo

79 CHERRY DR 79, WILBRAHAM, MA, 01095

Community: The Gardens of Wilbraham

Leisure Knoll

190 CANTERBURY DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$519,900

2 beds

1 baths

1,220 sq ft

Condo

190 CANTERBURY DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Glenwood Village

1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,..., Riverhead, NY 11901

$469,000

2 beds

2 baths

1,500 sq ft

Manufactured Home

1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,...

Community: Glenwood Village

Want to learn more about 55+ communities in Winchester Area? 55places can help!

Questions? Call us: (860) 238-3620

Foxwood Village

1407 MIDDLE RD 277, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$515,000

2 beds

2 baths

1,568 sq ft

Manufactured Home

1407 MIDDLE RD 277, RIVERHEAD, NY, 11933

Community: Foxwood Village

Regency at Wappinger

36 FARMINGTON RD, WAPPINGER, NY, 12590, Wappinger, NY 12590

$750,000

2 beds

3 baths

2,600 sq ft

House

36 FARMINGTON RD, WAPPINGER, NY, 12590

Community: Regency at Wappinger

Heritage Village

1008 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$518,000

3 beds

2 baths

1,716 sq ft

Condo

1008 HERITAGE VLG A, SOUTHBURY, CT, 0648...

Community: Heritage Village

Jefferson Village

18 HASTINGS CT B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$349,000

1 beds

1 baths

850 sq ft

Condo

18 HASTINGS CT B, YORKTOWN, NY, 10598

Community: Jefferson Village

Leisure Village

66 ENFIELD CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$359,900

2 beds

1 baths

1,085 sq ft

Condo

66 ENFIELD CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

Heritage Village

76 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$249,000

2 beds

2 baths

1,308 sq ft

Condo

76 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Setauket Meadows

66 BRIANNA DR, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733

$739,999

2 beds

3 baths

1,878 sq ft

Condo

66 BRIANNA DR, BROOKHAVEN, NY, 11733

Community: Setauket Meadows

Heritage Village

773 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$255,000

2 beds

2 baths

1,071 sq ft

Condo

773 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Hills

358 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$620,000

2 beds

3 baths

1,550 sq ft

Condo

358 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Newtown Woods

232 BROOKSIDE CT 232, NEWTOWN, CT, 06470, Newtown, CT 06470

$595,000

2 beds

2 baths

1,747 sq ft

Condo

232 BROOKSIDE CT 232, NEWTOWN, CT, 06470

Community: Newtown Woods

Glassbury Court at Cold Spring

10 MAGGIE MAY WAY, PHILIPSTOWN, NY, 1051..., Philipstown, NY 10516

$698,000

2 beds

2 baths

1,974 sq ft

Condo

10 MAGGIE MAY WAY, PHILIPSTOWN, NY, 1051...

Community: Glassbury Court at Cold Spring

Want to learn more about 55+ communities in Winchester Area? 55places can help!

Questions? Call us: (860) 238-3620

Heritage Village

818 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$449,000

2 beds

2 baths

1,432 sq ft

Condo

818 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

176 VENTRY CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$399,000

2 beds

1 baths

1,085 sq ft

Condo

176 VENTRY CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

Glenwood Village

1661 OLD COUNTRY RD 233, RIVERHEAD, NY, ..., Riverhead, NY 11901

$239,999

2 beds

2 baths

980 sq ft

Manufactured Home

1661 OLD COUNTRY RD 233, RIVERHEAD, NY, ...

Community: Glenwood Village

Pond Spring Village

111 PONDVIEW CIR, BEACON FALLS, CT, 0640..., Beacon Falls, CT 06403

$438,000

2 beds

2 baths

1,328 sq ft

Condo

111 PONDVIEW CIR, BEACON FALLS, CT, 0640...

Community: Pond Spring Village

Heritage Village

233 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$310,000

2 beds

2 baths

1,398 sq ft

Condo

233 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

349 NIBLICK LN 349, OXFORD, CT, 06478, Oxford, CT 06478

$689,000

3 beds

2 baths

2,008 sq ft

Condo

349 NIBLICK LN 349, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Heritage Hills

600 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$599,000

2 beds

2 baths

1,265 sq ft

Condo

600 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

972 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$375,000

2 beds

2 baths

1,432 sq ft

Condo

972 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

349 NIBLICK LN, OXFORD, CT, 06478, Oxford, CT 06478

$689,000

3 beds

2 baths

2,152 sq ft

349 NIBLICK LN, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Heritage Village

176 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$284,900

2 beds

2 baths

1,044 sq ft

Condo

176 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

21 HICKORY HL 21, SOUTHINGTON, CT, 06489, Southington, CT 06489

$248,000

2 beds

2 baths

1,285 sq ft

Condo

21 HICKORY HL 21, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

Want to learn more about 55+ communities in Winchester Area? 55places can help!

Questions? Call us: (860) 238-3620

Oronoque Village

46 BUCKSKIN LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$559,900

1 beds

2 baths

1,375 sq ft

Condo

46 BUCKSKIN LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Hills

$450,000

1 beds

1 baths

955 sq ft

Condo

128 HERITAGE HILLS DR B, SOMERS, NY, 105...

Community: Heritage Hills

1 2 3 4…5

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Connecticut
Winchester Area

Frequently Asked Questions

What size 55+ communities are there in the Winchester Area?

In the Winchester Area, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in the Winchester Area?

The smallest 55+ communities in the Winchester Area has 31 homes, the largest has 38 homes, and the average communities consists of 34 homes.

Are there new 55+ homes available in the Winchester Area?

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.

Are there gated 55+ communities in the Winchester Area?

No, there are no gated 55+ communities in the Winchester Area.

How long do listings in 55+ communities in the Winchester Area typically stay on the market, and what is the average price of homes for sale?

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
Instant new home alerts
Answers from local 55+ experts

Want to learn more about 55+ communities in Winchester Area?

Call us: (860) 238-3620

199 homes

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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: Aug 02, 2026.
This application does not include information on all of the properties available for sale at this time.

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Winchester Area, CT 55+ active adult communities & homes for sale - Page 2

94 communities near Winchester Area

199 homes near Winchester Area

2 beds

2 baths

1,205 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Condo

2 beds

3 baths

1,503 sq ft

2 beds

2 baths

1,032 sq ft

Condo

1 beds

2 baths

1,360 sq ft

Condo

2 beds

1 baths

Condo

2 beds

3 baths

2,331 sq ft

Condo

2 beds

2 baths

1,682 sq ft

2 beds

2 baths

1,682 sq ft

2 beds

2 baths

1,685 sq ft

Condo

3 beds

3 baths

1,600 sq ft

Condo

2 beds

2 baths

1,376 sq ft

Condo

2 beds

1 baths

1,220 sq ft

Condo

2 beds

2 baths

1,500 sq ft

Manufactured Home

2 beds

2 baths

1,568 sq ft

Manufactured Home

2 beds

3 baths

2,600 sq ft

House

3 beds

2 baths

1,716 sq ft

Condo

1 beds

1 baths

850 sq ft

Condo

2 beds