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

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

Glenwood Village

1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,..., Riverhead, NY 11901

$469,000

2 beds

2 baths

1,500 sq ft

Manufactured Home

1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,...

Community: Glenwood Village

Heritage Village

1008 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$518,000

3 beds

2 baths

1,716 sq ft

Condo

1008 HERITAGE VLG A, SOUTHBURY, CT, 0648...

Community: Heritage Village

Heritage Village

773 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$235,000

2 beds

2 baths

1,071 sq ft

Condo

773 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Hills

358 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$620,000

2 beds

3 baths

1,550 sq ft

Condo

358 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Newtown Woods

232 BROOKSIDE CT 232, NEWTOWN, CT, 06470, Newtown, CT 06470

$595,000

2 beds

2 baths

1,747 sq ft

Condo

232 BROOKSIDE CT 232, NEWTOWN, CT, 06470

Community: Newtown Woods

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

Questions? Call us: (860) 238-3620

Glassbury Court at Cold Spring

10 MAGGIE MAY WAY, PHILIPSTOWN, NY, 1051..., Philipstown, NY 10516

$698,000

2 beds

2 baths

1,974 sq ft

Condo

10 MAGGIE MAY WAY, PHILIPSTOWN, NY, 1051...

Community: Glassbury Court at Cold Spring

Glenwood Village

1661 OLD COUNTRY RD 233, RIVERHEAD, NY, ..., Riverhead, NY 11901

$239,999

2 beds

2 baths

980 sq ft

Manufactured Home

1661 OLD COUNTRY RD 233, RIVERHEAD, NY, ...

Community: Glenwood Village

Heritage Hills

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

$575,000

2 beds

2 baths

1,265 sq ft

Condo

600 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

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

$360,000

2 beds

2 baths

1,432 sq ft

Condo

972 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

176 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$279,900

2 beds

2 baths

1,044 sq ft

Condo

176 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

46 BUCKSKIN LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$559,900

1 beds

2 baths

1,375 sq ft

Condo

46 BUCKSKIN LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Hills

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

$625,000

3 beds

2 baths

1,689 sq ft

Condo

156 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

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

$389,900

2 beds

2 baths

1,398 sq ft

Condo

701 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$579,900

3 beds

2 baths

1,716 sq ft

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Cottages at Wire Mill

16 WIRE MILL RD A, STAMFORD, CT, 06903, Stamford, CT 06903

$1,495,000

3 beds

4 baths

3,244 sq ft

16 WIRE MILL RD A, STAMFORD, CT, 06903

Community: The Cottages at Wire Mill

Heritage Village

24-B HERITAGE CRST B, SOUTHBURY, CT, 064..., Southbury, CT 06488

$398,500

2 beds

2 baths

1,217 sq ft

Condo

24-B HERITAGE CRST B, SOUTHBURY, CT, 064...

Community: Heritage Village

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

Questions? Call us: (860) 238-3620

Jefferson Village

5 DEVON CT B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$366,750

2 beds

1 baths

989 sq ft

Condo

5 DEVON CT B, YORKTOWN, NY, 10598

Community: Jefferson Village

Jefferson Village

27 WALDEN CT J, YORKTOWN, NY, 10598, Yorktown, NY 10598

$349,900

1 beds

1 baths

800 sq ft

Condo

27 WALDEN CT J, YORKTOWN, NY, 10598

Community: Jefferson Village

Billingsgate

$750,000

2 beds

3 baths

2,729 sq ft

Condo

14 BILLINGSGATE DR 14, SIMSBURY, CT, 060...

Community: Billingsgate

Heritage Village

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

$199,900

1 beds

1 baths

928 sq ft

Condo

184 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$315,000

2 beds

2 baths

1,432 sq ft

Condo

333 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Hills

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

$780,000

3 beds

2 baths

1,780 sq ft

Condo

103 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Saddle Lakes

174 ADELE CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$619,000

2 beds

2 baths

1,631 sq ft

Condo

174 ADELE CT, RIVERHEAD, NY, 11901

Community: Saddle Lakes

The Powder Forest Homes

15 BANTRY RD 15, SIMSBURY, CT, 06070, Simsbury, CT 06070

$899,000

4 beds

3 baths

1,878 sq ft

15 BANTRY RD 15, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

Oronoque Village

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

$625,000

2 beds

3 baths

1,415 sq ft

Condo

283 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

10 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$353,900

3 beds

2 baths

1,716 sq ft

Condo

10 HERITAGE CIR A, SOUTHBURY, CT, 06488

Community: Heritage Village

Liberty at Newtown

49 JO AL CT 49, NEWTOWN, CT, 06470, Newtown, CT 06470

$619,000

2 beds

3 baths

2,341 sq ft

Condo

49 JO AL CT 49, NEWTOWN, CT, 06470

Community: Liberty at Newtown

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

Questions? Call us: (860) 238-3620

Heritage Village

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

$225,000

2 beds

2 baths

1,044 sq ft

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$245,000

2 beds

2 baths

1,076 sq ft

Condo

59 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

93 SEMINOLE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$539,000

2 beds

3 baths

2,542 sq ft

Condo

93 SEMINOLE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Liberty at Newtown

25 FRANKLIN CT 25, NEWTOWN, CT, 06470, Newtown, CT 06470

$499,000

2 beds

2 baths

1,413 sq ft

Condo

25 FRANKLIN CT 25, NEWTOWN, CT, 06470

Community: Liberty at Newtown

Leisure Knoll

183 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$415,000

2 beds

1 baths

960 sq ft

Condo

183 KINGSTON DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

The Village at Oxford Greens

527 PUTTING GREEN LN 527, OXFORD, CT, 06..., Oxford, CT 06478

$650,000

3 beds

3 baths

2,008 sq ft

Condo

527 PUTTING GREEN LN 527, OXFORD, CT, 06...

Community: The Village at Oxford Greens

Regency at Fishkill

811 REGENCY DR 802, FISHKILL, NY, 12524, Fishkill, NY 12524

$161,450

2 beds

2 baths

1,100 sq ft

Condo

811 REGENCY DR 802, FISHKILL, NY, 12524

Community: Regency at Fishkill

Jefferson Village

51 JEFFERSON OVAL E, YORKTOWN, NY, 10598, Yorktown, NY 10598

$439,000

2 beds

2 baths

1,100 sq ft

Condo

51 JEFFERSON OVAL E, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Hills

$649,000

2 beds

2 baths

1,500 sq ft

Condo

101 HERITAGE HILLS DR A, SOMERS, NY, 105...

Community: Heritage Hills

Oronoque Village

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

$396,000

1 beds

2 baths

1,480 sq ft

Condo

13 ALGONQUIN LN B, STRATFORD, CT, 06614

Community: Oronoque Village

The Summit at Bethel

6 LOCKWOOD CIR 6, BETHEL, CT, 06801, Bethel, CT 06801

$599,000

3 beds

3 baths

1,771 sq ft

Condo

6 LOCKWOOD CIR 6, BETHEL, CT, 06801

Community: The Summit at Bethel

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

Questions? Call us: (860) 238-3620

Regency Meadows

108 IMPERIAL CT 108, TRUMBULL, CT, 06611, Trumbull, CT 06611

$719,000

2 beds

3 baths

2,891 sq ft

Condo

108 IMPERIAL CT 108, TRUMBULL, CT, 06611

Community: Regency Meadows

Heritage Village

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

$409,000

2 beds

2 baths

1,432 sq ft

Condo

139 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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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?

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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 5

95 communities near Winchester Area

226 homes near Winchester Area

2 beds

2 baths

1,500 sq ft

Manufactured Home

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,071 sq ft

Condo

2 beds

3 baths

1,550 sq ft

Condo

2 beds

2 baths

1,747 sq ft

Condo

2 beds

2 baths

1,974 sq ft

Condo

2 beds

2 baths

980 sq ft

Manufactured Home

2 beds

2 baths

1,265 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

1 beds

2 baths

1,375 sq ft

Condo

3 beds

2 baths

1,689 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

3 beds

4 baths

3,244 sq ft

2 beds

2 baths

1,217 sq ft

Condo

2 beds

1 baths

989 sq ft

Condo

1 beds

1 baths

800 sq ft

Condo

2 beds

3 baths

2,729 sq ft

Condo

1 beds

1 baths