Winchester Area, CT 55+ active adult communities & homes for sale - Page 4

226 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

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

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

5 rating (2 reviews)

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

3 rating (2 reviews)

Heritage Hills

$400ks - $800ks

Heritage Hills, Somers, NY

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

$100ks - $300ks

Leisure Village, Ridge, NY

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

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5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

The Village at Whispering...

$400ks

The Village at Whispering...Rotterdam, NY

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

Park Glen

$300ks - $500ks

Park Glen, New Milford, CT

Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Billingsgate

$400ks - $600ks

Billingsgate, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes

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

Questions? Call us: (860) 238-3620

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

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

The Vineyards at Miller P...

$500ks

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

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

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes

5 rating (1 reviews)

Paris Square

$500ks - $700ks

Paris Square, Northvale, NJ

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

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

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

Glassbury Court at Hunter...

$500ks - $700ks

Glassbury Court at Hunter..., Cortlandt, NY

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

Woodcrest at Jacobs Hill

$200ks - $300ks

Woodcrest at Jacobs Hill, Cortlandt, NY

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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

1 2...3

The Vineyards at Mount Sinai

72 FARM ACRE CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$999,999

2 beds

4 baths

3,736 sq ft

Condo

72 FARM ACRE CIR, BROOKHAVEN, NY, 11766

Community: The Vineyards at Mount Sinai

Jefferson Village

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

$369,000

2 beds

2 baths

1,000 sq ft

Condo

39 SUSSEX DR B, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Village

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

$374,500

2 beds

2 baths

1,398 sq ft

Condo

643 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Jefferson Village

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

$330,000

1 beds

1 baths

800 sq ft

Condo

20 HASTINGS CT A, YORKTOWN, NY, 10598

Community: Jefferson Village

Glenwood Village

1661 OLD COUNTRY RD 254, RIVERHEAD, NY, ..., Riverhead, NY 11901

$185,000

2 beds

2 baths

1,036 sq ft

Manufactured Home

1661 OLD COUNTRY RD 254, RIVERHEAD, NY, ...

Community: Glenwood Village

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

Questions? Call us: (860) 238-3620

Rivington

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

$485,000

2 beds

2 baths

1,258 sq ft

Condo

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

Community: Rivington

Leisure Knoll

7 AVON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$469,999

2 beds

2 baths

1,070 sq ft

Condo

7 AVON CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Regency at Woodbridge

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

$599,900

3 beds

3 baths

Condo

27 HERITAGE LN, WOODBRIDGE, CT, 06525

Community: Regency at Woodbridge

Heritage Hills

813 HERITAGE HLS, SOMERS, NY, 10589, Somers, NY 10589

$850,000

2 beds

2 baths

1,663 sq ft

Condo

813 HERITAGE HLS, SOMERS, NY, 10589

Community: Heritage Hills

Regency at Fishkill

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

$490,000

1 beds

2 baths

1,499 sq ft

Condo

732 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

Glenwood Village

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

$375,000

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

$386,000

3 beds

2 baths

1,716 sq ft

Condo

345 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

232 BLACKPOOL CT F, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$339,000

2 beds

1 baths

875 sq ft

Condo

232 BLACKPOOL CT F, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Leisure Glen

29 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$549,900

2 beds

2 baths

1,314 sq ft

Condo

29 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

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

Glenwood Village

1661 OLD COUNTRY RD 189, RIVERHEAD, NY, ..., Riverhead, NY 11901

$205,000

2 beds

2 baths

1,036 sq ft

Manufactured Home

1661 OLD COUNTRY RD 189, RIVERHEAD, NY, ...

Community: Glenwood Village

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

Questions? Call us: (860) 238-3620

Heritage Hills

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

$640,000

2 beds

2 baths

1,470 sq ft

Condo

456 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Liberty at Newtown

16 FRANKLIN CT 16, NEWTOWN, CT, 06470, Newtown, CT 06470

$599,000

2 beds

3 baths

1,940 sq ft

Condo

16 FRANKLIN CT 16, NEWTOWN, CT, 06470

Community: Liberty at Newtown

Fairview 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: Fairview at Oxford Greens

The Village at Oxford Greens

$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

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

$778,585

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

$778,585

2 beds

3 baths

2,454 sq ft

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478

Community: The Village at Oxford Greens

The Village at Oxford Greens

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

$754,150

2 beds

3 baths

1,955 sq ft

Condo

1138 ST ANDREWS DR 90, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$754,150

2 beds

3 baths

1,955 sq ft

Condo

1138 ST ANDREWS DR 90, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

Oronoque Village

372 PIUTE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$384,900

1 beds

2 baths

1,375 sq ft

Condo

372 PIUTE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Jefferson Village

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

$339,900

1 beds

1 baths

800 sq ft

Condo

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

Community: Jefferson Village

Jefferson Village

149 FLINTLOCK WAY E, YORKTOWN, NY, 10598, Yorktown, NY 10598

$375,000

1 beds

1 baths

853 sq ft

Condo

149 FLINTLOCK WAY E, YORKTOWN, NY, 10598

Community: Jefferson Village

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

Questions? Call us: (860) 238-3620

Newtown Woods

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

$575,000

2 beds

3 baths

2,073 sq ft

Condo

23 WOODS LN 23, NEWTOWN, CT, 06470

Community: Newtown Woods

Heritage Village

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

$342,500

2 beds

2 baths

1,398 sq ft

Condo

581 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Jefferson Village

56 KIRBY CLOSE B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$474,500

2 beds

2 baths

970 sq ft

Condo

56 KIRBY CLOSE B, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Village

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

$349,900

2 beds

2 baths

1,398 sq ft

Condo

895 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Stoneleigh Woods at Riverhead

159 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$674,999

2 beds

3 baths

2,172 sq ft

Condo

159 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

Heritage Village

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

$389,900

2 beds

2 baths

1,432 sq ft

Condo

16 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

626 OVERLOOK PATH 626, SOUTHINGTON, CT, ..., Southington, CT 06489

$350,000

2 beds

2 baths

1,230 sq ft

Condo

626 OVERLOOK PATH 626, SOUTHINGTON, CT, ...

Community: Spring Lake Village

Heritage Village

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

$299,900

2 beds

2 baths

1,032 sq ft

Condo

38 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

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

$439,000

1 beds

2 baths

1,360 sq ft

Condo

407 MONTAUK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Baldwin Station

15 JASMINE CIR 15, MILFORD, CT, 06461, Milford, CT 06461

$599,000

2 beds

3 baths

2,331 sq ft

Condo

15 JASMINE CIR 15, MILFORD, CT, 06461

Community: Baldwin Station

Fairview at Oxford Greens

941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478

$674,900

2 beds

2 baths

1,682 sq ft

941 MACKENZIE LN 941, 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

$674,900

2 beds

2 baths

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Rivington

64 WARRINGTON ROUND 64, DANBURY, CT, 068..., Danbury, CT 06810

$615,000

3 beds

3 baths

1,600 sq ft

Condo

64 WARRINGTON ROUND 64, DANBURY, CT, 068...

Community: Rivington

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 281 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
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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

226 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: Sep 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 4

95 communities near Winchester Area

226 homes near Winchester Area

2 beds

4 baths

3,736 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

1 beds

1 baths

800 sq ft

Condo

2 beds

2 baths

1,036 sq ft

Manufactured Home

2 beds

2 baths

1,258 sq ft

Condo

2 beds

2 baths

1,070 sq ft

Condo

3 beds

3 baths

Condo

2 beds

2 baths

1,663 sq ft

Condo

1 beds

2 baths

1,499 sq ft

Condo

3 beds

2 baths

1,317 sq ft

Manufactured Home

3 beds

2 baths

1,716 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

1,314 sq ft

Condo

2 beds

2 baths

1,974 sq ft

Condo

2 beds

2 baths

1,036 sq ft

Manufactured Home

2 beds

2 baths

1,470 sq ft

Condo

2 beds

3 baths

1,940 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths