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

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 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

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

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

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

Questions? Call us: (860) 238-3620

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

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

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

$500ks - $700ks

Paris Square, Northvale, NJ

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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

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

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

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

Whitney Glen

$500ks - $600ks

Whitney Glen, Westport, CT

Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

5 rating (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

New Construction | 55+ age-restricted | Built 2017 - present | 75 homes

Hopmeadow Place

$200ks - $300ks

Hopmeadow Place, Simsbury, CT

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

Newbury Village

$400ks - $500ks

Newbury Village, Brookfield, CT

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

Beckley Farms

$300ks - $400ks

Beckley Farms, Berlin, CT

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Stoneleigh Woods at Carme...

$400ks

Stoneleigh Woods at Carme..., Carmel, NY

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

1 2...3

New Regency at Prospect

196 SYCAMORE DR 196, PROSPECT, CT, 06712, Prospect, CT 06712

$307,127

3 beds

2 baths

1,500 sq ft

Condo

196 SYCAMORE DR 196, PROSPECT, CT, 06712

Community: Regency at Prospect

New Founders Ridge

11 WEBSTER LN 6, MIDDLETOWN, CT, 06457, Middletown, CT 06457

$599,900

3 beds

3 baths

1,579 sq ft

11 WEBSTER LN 6, MIDDLETOWN, CT, 06457

Community: Founders Ridge

New Heritage Village

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

$390,000

2 beds

2 baths

1,432 sq ft

Condo

916 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Oronoque Village

96 SEMINOLE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$469,000

2 beds

3 baths

1,438 sq ft

Condo

96 SEMINOLE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Leisure Knoll

1 AVON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$489,999

2 beds

2 baths

1,070 sq ft

Condo

1 AVON CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

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

Questions? Call us: (860) 238-3620

New Leisure Village

54 AYLESBURY CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$349,000

2 beds

1 baths

1,085 sq ft

Condo

54 AYLESBURY CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Setauket Meadows

100 COVE LN 100, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733

$769,000

2 beds

3 baths

1,820 sq ft

Condo

100 COVE LN 100, BROOKHAVEN, NY, 11733

Community: Setauket Meadows

New Oronoque Village

315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$549,000

2 beds

3 baths

1,434 sq ft

Condo

315 NAVAJO LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Leisure Village

395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ..., Brookhaven, NY 11961

$299,000

2 beds

1 baths

875 sq ft

Condo

395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ...

Community: Leisure Village

New Heritage Village

14 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$269,000

2 beds

2 baths

1,000 sq ft

Condo

14 HERITAGE CIR B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Leisure Knoll

541 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$529,000

3 beds

2 baths

1,412 sq ft

Condo

541 STRATFORD LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Heritage Village

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

$309,000

3 beds

2 baths

1,716 sq ft

Condo

847 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Oronoque Village

132 BISON LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$470,000

1 beds

3 baths

1,426 sq ft

Condo

132 BISON LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New Heritage Hills

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

$490,000

1 beds

2 baths

967 sq ft

Condo

969 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Heritage Village

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

$405,000

2 beds

2 baths

1,432 sq ft

Condo

648 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New The Gardens of Wilbraham

56 CHERRY DR 56, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$419,000

2 beds

2 baths

1,213 sq ft

Condo

56 CHERRY DR 56, 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

Foxwood Village

1407 MIDDLE RD 253, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$449,000

3 beds

2 baths

1,753 sq ft

House

1407 MIDDLE RD 253, RIVERHEAD, NY, 11933

Community: Foxwood Village

Leisure Village

265 NEWCASTLE CT B, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$335,000

2 beds

1 baths

875 sq ft

Condo

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

Community: Leisure Village

Rivington

79 WINDING RIDGE WAY 79, DANBURY, CT, 06..., Danbury, CT 06810

$1,039,000

3 beds

4 baths

2,596 sq ft

Condo

79 WINDING RIDGE WAY 79, DANBURY, CT, 06...

Community: Rivington

Heritage Hills

$589,000

1 beds

2 baths

1,098 sq ft

Condo

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

Community: Heritage Hills

Whitney Glen

32 WHITNEY GLN 32, WESTPORT, CT, 06880, Westport, CT 06880

$459,000

1 beds

2 baths

949 sq ft

Condo

32 WHITNEY GLN 32, WESTPORT, CT, 06880

Community: Whitney Glen

South Pond Village

20 REED CT 20, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$245,000

2 beds

2 baths

1,202 sq ft

Condo

20 REED CT 20, BLOOMFIELD, CT, 06002

Community: South Pond Village

Heritage Hills

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

$499,000

2 beds

2 baths

1,427 sq ft

Condo

234 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Pond Spring Village

35 OCTOBER LN 35, BEACON FALLS, CT, 0646..., Beacon Falls, CT 06468

$420,000

2 beds

3 baths

1,328 sq ft

Condo

35 OCTOBER LN 35, BEACON FALLS, CT, 0646...

Community: Pond Spring Village

Leisure Knoll

520 CRANSTON LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$499,999

2 beds

2 baths

1,574 sq ft

Condo

520 CRANSTON LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Heritage Village

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

$245,000

1 beds

1 baths

928 sq ft

Condo

551 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

298 BATON LN 298 A, STRATFORD, CT, 06614, Stratford, CT 06614

$435,000

1 beds

2 baths

1,175 sq ft

Condo

298 BATON LN 298 A, STRATFORD, CT, 06614

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

Community: Leisure Village

Leisure Village

110 EXMORE CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$389,900

2 beds

1 baths

1,085 sq ft

Condo

110 EXMORE CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

Regency at Prospect

156 SYCAMORE DR 156, PROSPECT, CT, 06712, Prospect, CT 06712

$559,000

2 beds

3 baths

2,067 sq ft

Condo

156 SYCAMORE DR 156, PROSPECT, CT, 06712

Community: Regency at Prospect

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

Questions? Call us: (860) 238-3620

Jefferson Village

37 SUSSEX DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$379,000

2 beds

1 baths

935 sq ft

Condo

37 SUSSEX DR B, YORKTOWN, NY, 10598

Community: Jefferson Village

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

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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: May 11, 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

204 homes near Winchester Area

3 beds

2 baths

1,500 sq ft

Condo

3 beds

3 baths

1,579 sq ft

2 beds

2 baths

1,432 sq ft

Condo

2 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,070 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds

3 baths

1,820 sq ft

Condo

2 beds

3 baths

1,434 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

3 beds

2 baths

1,412 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

1 beds

2 baths

967 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,213 sq ft

Condo

3 beds

2 baths

1,753 sq ft

House

2 beds

1 baths

875 sq ft

Condo

3 beds

4 baths

2,596 sq ft

Condo

1 beds

2 baths