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

228 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

3 rating (2 reviews)

Heritage Hills

$400ks - $900ks

Heritage Hills, Somers, NY

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

4 rating (1 review)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

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

Questions? Call us: (860) 238-3620

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

5 rating (2 reviews)

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

New and Resale | Age-targeted | Built 2006 - present | 1,050 homes

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

5 rating (1 review)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

5 rating (1 review)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

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

Questions? Call us: (860) 238-3620

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

1 rating (1 review)

Plymouth Estates at Mount...

$400ks - $500ks

Plymouth Estates at Mount..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

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

Glassbury Court at Cold S...

$600ks - $700ks

Glassbury Court at Cold S..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 homes

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

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

Glassbury Court at Hunter...

$500ks - $700ks

Glassbury Court at Hunter..., Cortlandt, NY

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

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

5 rating (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

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

Woodcrest at Jacobs Hill

$200ks - $300ks

Woodcrest at Jacobs Hill, Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 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

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

5 rating (1 review)

The Villages at Mount Sin...

$600ks

The Villages at Mount Sin..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

1 2...3

Heritage Village

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

$335,000

2 beds

2 baths

1,432 sq ft

Condo

783 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$299,900

2 beds

2 baths

1,398 sq ft

Condo

738 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Granite Woods

35 NUTMEG RD B2, MIDDLEBURY, CT, 06762, Middlebury, CT 06762

$219,900

1 beds

1 baths

889 sq ft

Condo

35 NUTMEG RD B2, MIDDLEBURY, CT, 06762

Community: Granite Woods

Woodridge Strathmore Terrace

6 COBBLESTONE WAY, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$408,500

2 beds

2 baths

1,151 sq ft

Condo

6 COBBLESTONE WAY, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

Leisure Village

463 B OLDHAM CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$359,990

2 beds

1 baths

1,074 sq ft

Condo

463 B OLDHAM CT, BROOKHAVEN, NY, 11961

Community: Leisure Village

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

Questions? Call us: (860) 238-3620

Leisure Village

472A DARWEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$408,000

2 beds

2 baths

1,200 sq ft

Condo

472A DARWEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Village

Leisure Knoll

152A LAURANCE LN A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$349,000

2 beds

1 baths

755 sq ft

Condo

152A LAURANCE LN A, BROOKHAVEN, NY, 1196...

Community: Leisure Knoll

Leisure Glen

6 OAKDALE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$539,000

2 beds

2 baths

1,666 sq ft

Condo

6 OAKDALE CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Leisure Glen

428 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$649,000

2 beds

2 baths

1,652 sq ft

Condo

428 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Leisure Village

134 EASTBOURNE CT A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$335,000

2 beds

1 baths

836 sq ft

Condo

134 EASTBOURNE CT A, BROOKHAVEN, NY, 119...

Community: Leisure Village

Heritage Village

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

$299,900

2 beds

2 baths

1,432 sq ft

Condo

559 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Hills

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

$769,000

3 beds

2 baths

1,793 sq ft

Condo

590 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Rivington

714 CENTER MEADOW LN 714, DANBURY, CT, 0..., Danbury, CT 06810

$474,900

2 beds

2 baths

1,258 sq ft

Condo

714 CENTER MEADOW LN 714, DANBURY, CT, 0...

Community: Rivington

The Village at Oxford Greens

521 PUTTING GREEN LN 521, OXFORD, CT, 06..., Oxford, CT 06478

$675,000

3 beds

3 baths

2,735 sq ft

Condo

521 PUTTING GREEN LN 521, OXFORD, CT, 06...

Community: The Village at Oxford Greens

Oronoque Village

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

$445,000

2 beds

3 baths

1,434 sq ft

Condo

546 N TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

Woodcrest at Jacobs Hill

1104 JACOBS HILL RD, CORTLANDT, NY, 1056..., Cortlandt, NY 10567

$389,000

2 beds

2 baths

1,145 sq ft

House

1104 JACOBS HILL RD, CORTLANDT, NY, 1056...

Community: Woodcrest at Jacobs Hill

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

Questions? Call us: (860) 238-3620

Heritage Village

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

$219,900

1 beds

1 baths

928 sq ft

Condo

65 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

261B HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488

$254,000

2 beds

2 baths

1,032 sq ft

Condo

261B HERITAGE VLG, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

504 CARRIAGE DR 504, SOUTHINGTON, CT, 06..., Southington, CT 06489

$320,000

2 beds

2 baths

1,313 sq ft

Condo

504 CARRIAGE DR 504, SOUTHINGTON, CT, 06...

Community: Spring Lake Village

The Village at Oxford Greens

171 COUNTRY CLUB DR 171, OXFORD, CT, 064..., Oxford, CT 06478

$705,000

3 beds

3 baths

2,750 sq ft

Condo

171 COUNTRY CLUB DR 171, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Heritage Hills

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

$670,000

2 beds

3 baths

1,585 sq ft

Condo

88 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Hopmeadow Place

1 W ST 215, SIMSBURY, CT, 06070, Simsbury, CT 06070

$385,000

2 beds

2 baths

1,477 sq ft

Condo

1 W ST 215, SIMSBURY, CT, 06070

Community: Hopmeadow Place

Jefferson Village

34 WARWICK PL B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$359,000

2 beds

2 baths

1,000 sq ft

Condo

34 WARWICK PL B, YORKTOWN, NY, 10598

Community: Jefferson Village

Jefferson Village

20 HASTINGS CT A, YORKTOWN, NY, 10598, Yorktown, NY 10598

$324,000

1 beds

1 baths

800 sq ft

Condo

20 HASTINGS CT A, YORKTOWN, NY, 10598

Community: Jefferson Village

Rivington

215 CENTER MEADOW LN 215, DANBURY, CT, 0..., Danbury, CT 06810

$475,000

2 beds

2 baths

1,258 sq ft

Condo

215 CENTER MEADOW LN 215, DANBURY, CT, 0...

Community: Rivington

Regency at Woodbridge

27 HERITAGE LN, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525

$599,900

3 beds

3 baths

2,006 sq ft

Condo

27 HERITAGE LN, WOODBRIDGE, CT, 06525

Community: Regency at Woodbridge

Regency at Fishkill

732 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$475,000

1 beds

2 baths

1,499 sq ft

Condo

732 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

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

Questions? Call us: (860) 238-3620

Glenwood Village

1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ..., Riverhead, NY 11901

$369,000

3 beds

2 baths

1,317 sq ft

Manufactured Home

1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ...

Community: Glenwood Village

Heritage Village

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

$350,000

3 beds

2 baths

1,716 sq ft

Condo

345 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Glassbury Court at Cold Spring

5 MAGGIE MAY WAY, PHILIPSTOWN, NY, 10516, Philipstown, NY 10516

$712,000

2 beds

2 baths

1,974 sq ft

Condo

5 MAGGIE MAY WAY, PHILIPSTOWN, NY, 10516

Community: Glassbury Court at Cold Spring

The Village at Oxford Greens

1129 ST ANDREWS DR 49, OXFORD, CT, 06478, Oxford, CT 06478

$709,555

2 beds

3 baths

2,454 sq ft

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$709,555

2 beds

3 baths

2,454 sq ft

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

Fairview at Oxford Greens

1111 ST ANDREWS DR 16, OXFORD, CT, 06478, Oxford, CT 06478

$749,900

2 beds

3 baths

2,454 sq ft

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$749,900

2 beds

3 baths

2,454 sq ft

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

1138 ST ANDREWS DR 90, OXFORD, CT, 06478, Oxford, CT 06478

$799,655

2 beds

3 baths

1,955 sq ft

Condo

1138 ST ANDREWS DR 90, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$799,655

2 beds

3 baths

1,955 sq ft

Condo

1138 ST ANDREWS DR 90, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Jefferson Village

90 MOLLY PITCHER LN F, YORKTOWN, NY, 105..., Yorktown, NY 10598

$309,999

1 beds

1 baths

800 sq ft

Condo

90 MOLLY PITCHER LN F, YORKTOWN, NY, 105...

Community: Jefferson Village

Heritage Village

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

$329,900

2 beds

2 baths

1,398 sq ft

Condo

895 HERITAGE VLG A, 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

Heritage Village

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

$349,900

2 beds

2 baths

1,432 sq ft

Condo

16 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

407 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$429,000

1 beds

2 baths

1,360 sq ft

Condo

407 MONTAUK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

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?

Of the 2 55+ communities in the Winchester Area, 2 are for sale and none are rentals. By size, 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 397 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?

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Answers from local 55+ experts

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

Call us: (860) 238-3620

228 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: Nov 02, 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

95 communities near Winchester Area

228 homes near Winchester Area

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

1 beds

1 baths

889 sq ft

Condo

2 beds

2 baths

1,151 sq ft

Condo

2 beds

1 baths

1,074 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Condo

2 beds

1 baths

755 sq ft

Condo

2 beds

2 baths

1,666 sq ft

Condo

2 beds

2 baths

1,652 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

2 baths

1,793 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

3 beds

3 baths

2,735 sq ft

Condo

2 beds

3 baths

1,434 sq ft

Condo

2 beds

2 baths

1,145 sq ft

House

1 beds

1 baths

928 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

2 beds

2 baths

1,313 sq ft

Condo

3 beds