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

3 rating (2 reviews)

Heritage Hills

$400ks - $1Ms

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

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

Questions? Call us: (860) 238-3620

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4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

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Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

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

Questions? Call us: (860) 238-3620

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

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

Questions? Call us: (860) 238-3620

The Village at Whispering...

$400ks

The Village at Whispering...Rotterdam, NY

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

New Construction | 55+ age-restricted | Built 2020 - present | 24 homes

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

Questions? Call us: (860) 238-3620

Villas at Seminary Hill

$200ks - $300ks

Villas at Seminary Hill, Carmel, NY

New Construction | 55+ age-restricted | Built 2018 - present | 50 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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

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

Questions? Call us: (860) 238-3620

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

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

Questions? Call us: (860) 238-3620

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes

5 rating (1 reviews)

Paris Square

$400ks - $700ks

Paris Square, Northvale, NJ

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

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

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

Questions? Call us: (860) 238-3620

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes

Autumn Estates

$500ks - $600ks

Autumn Estates, Farmington, CT

Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes

1 2...3

New Sunken Pond Estates

1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$489,000

2 beds

3 baths

1,350 sq ft

Condo

1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...

Community: Sunken Pond Estates

New Jefferson Village

68A INDEPENDENCE CT A, YORKTOWN, NY, 105..., Yorktown, NY 10598

$459,500

2 beds

2 baths

1,050 sq ft

Condo

68A INDEPENDENCE CT A, YORKTOWN, NY, 105...

Community: Jefferson Village

New Jefferson Village

26 DORSET CT A, YORKTOWN, NY, 10598, Yorktown, NY 10598

$230,000

1 baths

550 sq ft

Condo

26 DORSET CT A, YORKTOWN, NY, 10598

Community: Jefferson Village

New Leisure Knoll

506 LANCASTER CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$549,000

2 beds

2 baths

1,394 sq ft

House

506 LANCASTER CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Heritage Hills

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

$979,000

3 beds

2 baths

1,793 sq ft

Condo

392 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

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

New Heritage Village

41 E MEADOW RD, SOUTHBURY, CT, 06488, Southbury, CT 06488

$399,900

2 beds

3 baths

1,479 sq ft

Condo

41 E MEADOW RD, SOUTHBURY, CT, 06488

Community: Heritage Village

New Paris Square

5201 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647

1 beds

1 baths

684 sq ft

Condo

260 NEWCASTLE CT B, BROOKHAVEN, NY, 1196...

Community: Leisure Village

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

Questions? Call us: (860) 238-3620

Meadow Brook Estates

312 SPRUCE HILL DR 312, OXFORD, CT, 0647..., Oxford, CT 06478

$529,900

2 beds

3 baths

1,564 sq ft

Condo

312 SPRUCE HILL DR 312, OXFORD, CT, 0647...

Community: Meadow Brook Estates

Leisure Knoll

151 LAURANCE LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$489,000

2 beds

1 baths

1,000 sq ft

Condo

151 LAURANCE LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Heritage Hills

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

$690,000

1 beds

2 baths

1,296 sq ft

Condo

769 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

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

Questions? Call us: (860) 238-3620

Heritage Village

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

$524,900

3 beds

2 baths

1,716 sq ft

Condo

665 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Newtown Woods

433 BROOKSIDE CT 433, NEWTOWN, CT, 06470, Newtown, CT 06470

$499,900

2 beds

2 baths

1,504 sq ft

Condo

433 BROOKSIDE CT 433, NEWTOWN, CT, 06470

Community: Newtown Woods

Glenwood Village

1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$249,999

2 beds

2 baths

924 sq ft

Manufactured Home

1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1...

Community: Glenwood Village

Oronoque Village

261 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614

$600,000

2 beds

3 baths

1,620 sq ft

Condo

261 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

The Village at Oxford Greens

1125 ST ANDREWS DR 47, OXFORD, CT, 06478, Oxford, CT 06478

$689,900

2 beds

3 baths

2,454 sq ft

Condo

1125 ST ANDREWS DR 47, OXFORD, CT, 06478

Community: The Village at Oxford Greens

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

Questions? Call us: (860) 238-3620

Fairview at Oxford Greens

$689,900

2 beds

3 baths

2,454 sq ft

Condo

1125 ST ANDREWS DR 47, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

1093 ST ANDREWS DR 7, OXFORD, CT, 06478, Oxford, CT 06478

$689,900

2 beds

3 baths

2,454 sq ft

Condo

1093 ST ANDREWS DR 7, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$689,900

2 beds

3 baths

2,454 sq ft

Condo

1093 ST ANDREWS DR 7, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

Fairview at Oxford Greens

1091 ST ANDREWS DR 6, OXFORD, CT, 06478, Oxford, CT 06478

$739,900

2 beds

3 baths

2,536 sq ft

Condo

1091 ST ANDREWS DR 6, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$739,900

2 beds

3 baths

2,536 sq ft

Condo

1091 ST ANDREWS DR 6, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Leisure Glen

2 KISMET CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$472,000

2 beds

2 baths

1,312 sq ft

Condo

2 KISMET CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

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

Questions? Call us: (860) 238-3620

Overlook

2027 SUMMIT LOOP 87, CARMEL, NY, 10512, Carmel, NY 10512

$819,000

2 beds

2 baths

1,948 sq ft

Condo

2027 SUMMIT LOOP 87, CARMEL, NY, 10512

Community: Overlook

Overlook

3008 EASTVIEW LN 107, CARMEL, NY, 10512, Carmel, NY 10512

$912,000

2 beds

4 baths

3,302 sq ft

Condo

3008 EASTVIEW LN 107, CARMEL, NY, 10512

Community: Overlook

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

Questions? Call us: (860) 238-3620

Saddle Lakes

104 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$449,000

2 beds

2 baths

1,247 sq ft

Condo

104 SCENIC LAKE DR, RIVERHEAD, NY, 11901

Community: Saddle Lakes

Heritage Village

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

$289,900

2 beds

2 baths

1,044 sq ft

Condo

103 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Hills

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

$465,000

2 beds

2 baths

1,205 sq ft

Condo

179 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Hills

831 HERITAGE HLS, SOMERS, NY, 10589, Somers, NY 10589

$900,000

2 beds

2 baths

1,663 sq ft

Condo

831 HERITAGE HLS, SOMERS, NY, 10589

Community: Heritage Hills

Oronoque Village

546 N TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$679,000

2 beds

3 baths

1,434 sq ft

Condo

546 N TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$419,900

1 beds

2 baths

1,454 sq ft

Condo

87 CREEK LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Hills

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

$699,900

3 beds

3 baths

1,700 sq ft

Condo

228 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Oronoque Village

383 SEQUOIA LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$635,000

1 beds

2 baths

1,360 sq ft

Condo

383 SEQUOIA LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$424,900

2 beds

2 baths

1,432 sq ft

Condo

919 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Regency at Wappinger

27 DUTCH CT, WAPPINGER, NY, 12590, Wappinger, NY 12590

$815,000

2 beds

4 baths

3,362 sq ft

Condo

27 DUTCH CT, WAPPINGER, NY, 12590

Community: Regency at Wappinger

Heritage Village

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

$599,900

3 beds

2 baths

1,716 sq ft

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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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: Mar 12, 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

181 homes near Winchester Area

2 beds

3 baths

1,350 sq ft

Condo

2 beds

2 baths

1,050 sq ft

Condo

1 baths

550 sq ft

Condo

2 beds

2 baths

1,394 sq ft

House

3 beds

2 baths

1,793 sq ft

Condo

2 beds

3 baths

1,479 sq ft

Condo

2 beds

2 baths

Condo

2 beds

3 baths

2,040 sq ft

Condo

2 beds

2 baths

1,948 sq ft

Condo

2 beds

4 baths

1,982 sq ft

Condo

1 beds

2 baths

1,450 sq ft

House

2 beds

1 baths

875 sq ft

Condo

1 beds

1 baths

684 sq ft

Condo

2 beds

3 baths

1,564 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

1 beds

2 baths

1,296 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,504 sq ft

Condo

2 beds

2 baths

924 sq ft

Manufactured Home

2 beds

3 baths

1,620 sq ft