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

93 communities 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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

3 rating (2 reviews)

Heritage Hills

- $900ks

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

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

Questions? Call us: (860) 238-3620

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 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.

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Rivington

$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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

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

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

Questions? Call us: (860) 238-3620

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

5 rating (1 reviews)

Paris Square

$500ks - $700ks

Paris Square, Northvale, NJ

New and Resale | 55+ age-restricted | Built 2000 - present | 88 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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes

Hopmeadow Place

$200ks - $300ks

Hopmeadow Place, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

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

Questions? Call us: (860) 238-3620

The Woods at Dunham Pond

$200ks - $400ks

The Woods at Dunham Pond, New Fairfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes

Beckley Farms

$300ks - $400ks

Beckley Farms, Berlin, CT

New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes

Newbury Village

$400ks - $500ks

Newbury Village, Brookfield, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

New Construction | 55+ age-restricted | Built 2023 - present | 70 homes

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes

The Village at Whispering...

$400ks

The Village at Whispering...Rotterdam, NY

New Construction | 55+ age-restricted | Built 2025 - present | 85 homes

Glassbury Court at Hunter...

$500ks - $700ks

Glassbury Court at Hunter..., Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes

Stoneleigh Woods at Carme...

$400ks

Stoneleigh Woods at Carme..., Carmel, NY

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

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

Questions? Call us: (860) 238-3620

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 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

New Heritage Village

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

$229,000

1 beds

1 baths

928 sq ft

Condo

149 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Heritage Hills

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

$750,000

2 beds

3 baths

1,666 sq ft

Condo

414 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Heritage Hills

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

$530,000

1 beds

2 baths

967 sq ft

Condo

582 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Heritage Village

59 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488

$219,900

2 beds

2 baths

1,308 sq ft

Condo

59 HERITAGE VLG F, SOUTHBURY, CT, 06488

Community: Heritage Village

New Oronoque Village

619 ERIE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$639,000

1 beds

3 baths

1,583 sq ft

Condo

619 ERIE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (860) 238-3620

New Fairview at Oxford Greens

1126 ST ANDREWS DR 96, OXFORD, CT, 06478, Oxford, CT 06478

$749,900

2 beds

3 baths

1,955 sq ft

Condo

1126 ST ANDREWS DR 96, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

New The Village at Oxford Greens

$749,900

2 beds

3 baths

1,955 sq ft

Condo

1126 ST ANDREWS DR 96, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Oronoque Village

765 NYACK LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$649,900

2 beds

3 baths

1,642 sq ft

Condo

765 NYACK LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Jefferson Village

157 CARRIAGE CT E, YORKTOWN, NY, 10598, Yorktown, NY 10598

$324,000

1 beds

1 baths

845 sq ft

Condo

157 CARRIAGE CT E, YORKTOWN, NY, 10598

Community: Jefferson Village

New Leisure Glen

289 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$585,000

2 beds

2 baths

1,666 sq ft

Condo

289 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Leisure Village

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

$475,000

2 beds

2 baths

1,278 sq ft

Condo

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

Community: Leisure Village

New Heritage Village

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

$265,000

1 beds

1 baths

928 sq ft

Condo

953 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New The Retreat at Carmel

2 BLAIR HEIGHTS 3331, CARMEL, NY, 10512, Carmel, NY 10512

$500,000

2 beds

2 baths

1,733 sq ft

Condo

2 BLAIR HEIGHTS 3331, CARMEL, NY, 10512

Community: The Retreat at Carmel

New Heritage Hills

177A HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$395,000

1 beds

1 baths

900 sq ft

Condo

177A HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Regency at Fishkill

734 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$559,000

2 beds

2 baths

1,499 sq ft

Condo

734 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

New The Woods at Dunham Pond

30 HERON VIEW RD, NEW FAIRFIELD, CT, 068..., New Fairfield, CT 06812

$559,900

1 beds

3 baths

3,230 sq ft

Condo

30 HERON VIEW RD, NEW FAIRFIELD, CT, 068...

Community: The Woods at Dunham Pond

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

Questions? Call us: (860) 238-3620

Heritage Hills

955 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$485,000

1 beds

2 baths

967 sq ft

Condo

955 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Stoneleigh Woods at Riverhead

156 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$659,000

2 beds

3 baths

1,942 sq ft

Condo

156 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

Jefferson Village

78 INDEPENDENCE CT I, YORKTOWN, NY, 1059..., Yorktown, NY 10598

$360,000

1 beds

1 baths

800 sq ft

Condo

78 INDEPENDENCE CT I, YORKTOWN, NY, 1059...

Community: Jefferson Village

Jefferson Village

67 INDEPENDENCE CT B, YORKTOWN, NY, 1059..., Yorktown, NY 10598

$539,900

2 beds

2 baths

1,000 sq ft

Condo

67 INDEPENDENCE CT B, YORKTOWN, NY, 1059...

Community: Jefferson Village

Leisure Glen

155 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$495,000

2 beds

2 baths

1,456 sq ft

Condo

155 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Overlook

2075 SUMMIT LOOP 101, CARMEL, NY, 10512, Carmel, NY 10512

$960,000

2 beds

2 baths

1,948 sq ft

Condo

2075 SUMMIT LOOP 101, CARMEL, NY, 10512

Community: Overlook

Overlook

2052 SUMMIT LOOP 62, CARMEL, NY, 10512, Carmel, NY 10512

$954,000

2 beds

2 baths

2,102 sq ft

Condo

2052 SUMMIT LOOP 62, CARMEL, NY, 10512

Community: Overlook

Oronoque Village

564 PEQUOT LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$599,900

2 beds

2 baths

1,438 sq ft

Condo

564 PEQUOT LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Hopmeadow Place

1 W ST 223, SIMSBURY, CT, 06070, Simsbury, CT 06070

$385,000

2 beds

2 baths

1,477 sq ft

Condo

1 W ST 223, SIMSBURY, CT, 06070

Community: Hopmeadow Place

Oronoque Village

638A ONONDAGA LN, STRATFORD, CT, 06614, Stratford, CT 06614

$539,000

1 beds

3 baths

1,175 sq ft

Condo

638A ONONDAGA LN, STRATFORD, CT, 06614

Community: Oronoque Village

Stoneleigh Woods at Carmel

807 EGRETS LNDG, CARMEL, NY, 10512, Carmel, NY 10512

$575,000

3 beds

3 baths

2,788 sq ft

Condo

807 EGRETS LNDG, CARMEL, NY, 10512

Community: Stoneleigh Woods at Carmel

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

Questions? Call us: (860) 238-3620

Heritage Village

44 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488

$205,000

2 beds

2 baths

1,308 sq ft

Condo

44 HERITAGE VLG F, SOUTHBURY, CT, 06488

Community: Heritage Village

Rivington

80 WINDING RIDGE WAY 80, DANBURY, CT, 06..., Danbury, CT 06810

$775,000

3 beds

3 baths

2,204 sq ft

Condo

80 WINDING RIDGE WAY 80, DANBURY, CT, 06...

Community: Rivington

Heritage Village

69 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488

$289,000

2 beds

2 baths

1,432 sq ft

Condo

69 HERITAGE VLG E, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Hills

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

$650,000

2 beds

2 baths

1,470 sq ft

Condo

371 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

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

$399,999

3 beds

2 baths

1,716 sq ft

Condo

110 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Glassbury Court at Hunterbrook

2272 DALTON DR, CORTLANDT, NY, 10567, Cortlandt, NY 10567

$944,500

2 beds

3 baths

2,265 sq ft

Condo

2272 DALTON DR, CORTLANDT, NY, 10567

Community: Glassbury Court at Hunterbrook

Setauket Meadows

113 BRIANNA DR, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733

$779,000

2 beds

3 baths

1,842 sq ft

Condo

113 BRIANNA DR, BROOKHAVEN, NY, 11733

Community: Setauket Meadows

Regency at Prospect

28 TAMARACK CT 28, PROSPECT, CT, 06712, Prospect, CT 06712

$635,000

2 beds

3 baths

2,005 sq ft

Condo

28 TAMARACK CT 28, PROSPECT, CT, 06712

Community: Regency at Prospect

Setauket Meadows

58 BLAIR RD 58, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733

$849,999

2 beds

4 baths

1,773 sq ft

House

58 BLAIR RD 58, BROOKHAVEN, NY, 11733

Community: Setauket Meadows

Newbury Village

46 GREAT HERON LN 46, BROOKFIELD, CT, 06..., Brookfield, CT 06804

$725,000

2 beds

4 baths

2,560 sq ft

Condo

46 GREAT HERON LN 46, BROOKFIELD, CT, 06...

Community: Newbury Village

Leisure Village

150 EASTBOURNE CT B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$419,000

2 beds

2 baths

1,515 sq ft

Condo

150 EASTBOURNE CT B, BROOKHAVEN, NY, 119...

Community: Leisure Village

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

Questions? Call us: (860) 238-3620

Heritage Village

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

$289,900

2 beds

2 baths

1,032 sq ft

Condo

32 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$239,900

1 beds

1 baths

928 sq ft

Condo

12 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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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 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

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

Call us: (860) 238-3620

93 communities

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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 29, 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

93 communities near Winchester Area

208 homes near Winchester Area

1 beds

1 baths

928 sq ft

Condo

2 beds

3 baths

1,666 sq ft

Condo

1 beds

2 baths

967 sq ft

Condo

2 beds

2 baths

1,308 sq ft

Condo

1 beds

3 baths

1,583 sq ft

Condo

2 beds

3 baths

1,955 sq ft

Condo

2 beds

3 baths

1,955 sq ft

Condo

2 beds

3 baths

1,642 sq ft

Condo

1 beds

1 baths

845 sq ft

Condo

2 beds

2 baths

1,666 sq ft

Condo

2 beds

2 baths

1,278 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

2 baths

1,733 sq ft

Condo

1 beds

1 baths

900 sq ft

Condo

2 beds

2 baths

1,499 sq ft

Condo

1 beds

3 baths

3,230 sq ft

Condo

1 beds

2 baths

967 sq ft

Condo

2 beds

3 baths

1,942 sq ft

Condo

1 beds

1 baths

800 sq ft

Condo

2 beds