Winchester Area, CT 55+ active adult communities & homes for sale - Page 5

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

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

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

$400ks - $800ks

Heritage Hills, Somers, NY

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

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

Questions? Call us: (860) 238-3620

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

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

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.

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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

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 Summit at Bethel

$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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

The Village at Whispering...

$400ks

The Village at Whispering...Rotterdam, NY

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

5 rating (1 reviews)

Paris Square

$500ks - $700ks

Paris Square, Northvale, NJ

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

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

Questions? Call us: (860) 238-3620

The Vineyards at Miller P...

$500ks

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

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

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

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

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

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

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

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

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

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

Sunken Pond Estates

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

$475,000

2 beds

2 baths

1,587 sq ft

Condo

3006 AMEN COR, RIVERHEAD, NY, 11901

22 HERITAGE CIR A, SOUTHBURY, CT, 06488

1125 ST ANDREWS DR 47, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$708,775

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

Heritage Village

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

$589,900

3 beds

2 baths

1,716 sq ft

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

1041 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$259,900

2 beds

2 baths

1,000 sq ft

Condo

1041 HERITAGE VLG A, SOUTHBURY, CT, 0648...

Community: Heritage Village

Jefferson Village

41 JEFFERSON OVAL G, YORKTOWN, NY, 10598, Yorktown, NY 10598

$469,000

2 beds

2 baths

1,100 sq ft

Condo

41 JEFFERSON OVAL G, YORKTOWN, NY, 10598

Community: Jefferson Village

Spring Lake Village

6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489, Southington, CT 06489

$300,000

3 beds

3 baths

1,471 sq ft

Condo

6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

Heritage Hills

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

$615,000

2 beds

2 baths

1,139 sq ft

Condo

40 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

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

$275,000

2 beds

2 baths

1,144 sq ft

Condo

914 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$500,000

3 beds

2 baths

1,716 sq ft

Condo

419 HERITAGE VLG E, SOUTHBURY, CT, 06488

Community: Heritage Village

Village Vistas

11 THERESA LN, BROOKHAVEN, NY, 11777, Brookhaven, NY 11777

$1,299,000

2 beds

4 baths

3,000 sq ft

Condo

11 THERESA LN, BROOKHAVEN, NY, 11777

Community: Village Vistas

Glenwood Village

1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190..., Riverhead, NY 11901

$245,000

2 beds

2 baths

1,156 sq ft

Manufactured Home

1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190...

Community: Glenwood Village

Newtown Woods

23 WOODS LN 23, NEWTOWN, CT, 06470, Newtown, CT 06470

$610,000

2 beds

3 baths

2,073 sq ft

Condo

23 WOODS LN 23, NEWTOWN, CT, 06470

Community: Newtown Woods

Oronoque Village

13 ALGONQUIN LN C, STRATFORD, CT, 06614, Stratford, CT 06614

$389,000

1 beds

2 baths

1,330 sq ft

Condo

13 ALGONQUIN LN C, STRATFORD, CT, 06614

Condo

2080 SUMMIT LOOP 75, CARMEL, NY, 10512

Community: Overlook

The Village at Whispering Pines

125 WHISPERING PINES WAY, ROTTERDAM, NY,..., Rotterdam, NY 12306

$499,895

2 beds

2 baths

2,000 sq ft

House

125 WHISPERING PINES WAY, ROTTERDAM, NY,...

Community: The Village at Whispering Pines

The Gardens of Wilbraham

32 LODGE LN 32, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$565,000

2 beds

2 baths

1,610 sq ft

Condo

32 LODGE LN 32, WILBRAHAM, MA, 01095

Community: The Gardens of Wilbraham

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

Questions? Call us: (860) 238-3620

Heritage Village

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

$199,900

2 beds

2 baths

1,044 sq ft

Condo

73 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Overlook

2086 SUMMIT LOOP 78, CARMEL, NY, 10512, Carmel, NY 10512

$799,000

2 beds

3 baths

2,126 sq ft

Condo

2086 SUMMIT LOOP 78, CARMEL, NY, 10512

Community: Overlook

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 267 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

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: Jun 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 - Page 5

94 communities near Winchester Area

204 homes near Winchester Area

2 beds

2 baths

1,587 sq ft

Condo

1 beds

1 baths

928 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

1,398 sq ft

Condo

2 beds

2 baths

1,308 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

1,479 sq ft

Condo

2 beds

3 baths

2,040 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,504 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

3 beds

3 baths