Winchester Area, CT 55+ active adult communities & homes for sale - Page 3

204 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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

3 rating (2 reviews)

Heritage Hills

$500ks - $900ks

Heritage Hills, Somers, NY

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 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+ communities in Winchester Area? 55places can help!

Questions? Call us: (860) 238-3620

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

North Woods of Colchester

$300ks - $400ks

North Woods of Colchester, Colchester, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

Regency at Woodbridge

$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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

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

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

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

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

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

5 rating (1 reviews)

Paris Square

$400ks - $700ks

Paris Square, Northvale, NJ

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

Villas at Seminary Hill

$200ks - $300ks

Villas at Seminary Hill, Carmel, NY

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

The Village at Whispering...

$400ks

The Village at Whispering...Rotterdam, NY

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

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

Questions? Call us: (860) 238-3620

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

1 2...3

Sunken Pond Estates

3006 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$499,000

2 beds

2 baths

1,587 sq ft

Condo

3006 AMEN COR, RIVERHEAD, NY, 11901

71 DAKOTA LN A, 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

Heritage Village

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

$520,000

3 beds

2 baths

1,716 sq ft

Condo

977 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

731 CHAMPIONSHIP DR 731, OXFORD, CT, 064..., Oxford, CT 06478

$629,900

2 beds

2 baths

1,539 sq ft

Condo

731 CHAMPIONSHIP DR 731, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Jefferson Village

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

$395,000

2 beds

1 baths

1,000 sq ft

Condo

18L HASTINGS CT, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Village

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

$199,999

2 beds

2 baths

1,032 sq ft

Condo

151 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$229,000

1 beds

1 baths

928 sq ft

Condo

79 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

207 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$499,000

2 beds

2 baths

1,308 sq ft

Condo

207 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...

Community: Leisure Village

Leisure Village

427 AYLESBURY CT A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$380,000

2 beds

2 baths

972 sq ft

Condo

427 AYLESBURY CT A, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Heritage Village

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

$509,000

3 beds

2 baths

1,716 sq ft

Condo

644 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

86 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$535,000

2 beds

3 baths

2,734 sq ft

Condo

86 S TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

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

$639,000

2 beds

3 baths

2,494 sq ft

Condo

252 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$280,000

2 beds

2 baths

1,032 sq ft

Condo

78 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

Rivington

424 CENTER MEADOW LN 424, DANBURY, CT, 0..., Danbury, CT 06810

$495,000

2 beds

2 baths

1,258 sq ft

Condo

424 CENTER MEADOW LN 424, DANBURY, CT, 0...

Community: Rivington

Bartlett Hill

9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480, Portland, CT 06480

1 baths

550 sq ft

Condo

26 DORSET CT A, YORKTOWN, NY, 10598

Community: Jefferson Village

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

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

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

Paris Square

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

$735,000

2 beds

2 baths

Condo

5201 RIO VISTA LN, NORTHVALE, NJ, 07647

Community: Paris Square

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

Questions? Call us: (860) 238-3620

Overlook

3004 EASTVIEW DR 105, CARMEL, NY, 10512, Carmel, NY 10512

$722,000

2 beds

3 baths

2,040 sq ft

Condo

3004 EASTVIEW DR 105, CARMEL, NY, 10512

Community: Overlook

Regency at Fishkill

323 REGENCY DR 323, FISHKILL, NY, 12524, Fishkill, NY 12524

$485,000

1 beds

2 baths

1,450 sq ft

House

323 REGENCY DR 323, FISHKILL, NY, 12524

Community: Regency at Fishkill

Leisure Village

421 WEYMOUTH CT D, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$349,000

2 beds

1 baths

875 sq ft

Condo

421 WEYMOUTH CT D, BROOKHAVEN, NY, 11961

Community: Leisure Village

Meadow Brook Estates

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

$509,900

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

Heritage Village

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

$509,000

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

Fairview 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: Fairview at Oxford Greens

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

Questions? Call us: (860) 238-3620

The Village at Oxford Greens

$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

Fairview 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: Fairview at Oxford Greens

1 2 3 4 5…6

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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

204 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: Apr 17, 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 3

93 communities near Winchester Area

204 homes near Winchester Area

2 beds

2 baths

1,587 sq ft

Condo

2 beds

2 baths

2,008 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

1 beds

3 baths

1,118 sq ft

Condo

1 beds

2 baths

1,375 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,539 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

2 baths

1,308 sq ft

Condo

2 beds

2 baths

972 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

3 baths

2,734 sq ft

Condo

2 beds

3 baths

2,494 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

2 beds

3 baths

1,404 sq ft

2 beds

3 baths

1,438 sq ft

Condo

3 beds

3 baths