Winchester Area, CT 55+ active adult communities & homes for sale - Page 2

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

Sunken Pond Estates

403 WINGED FOOT WAY, RIVERHEAD, NY, 1190..., Riverhead, NY 11901

$520,000

2 beds

2 baths

1,350 sq ft

Condo

403 WINGED FOOT WAY, RIVERHEAD, NY, 1190...

Community: Sunken Pond Estates

Saddle Lakes

157 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$595,000

2 beds

2 baths

1,386 sq ft

Condo

157 SCENIC LAKE DR, RIVERHEAD, NY, 11901

Community: Saddle Lakes

Regency at Prospect

133 SYCAMORE DR, PROSPECT, CT, 06712, Prospect, CT 06712

$550,000

2 beds

3 baths

1,850 sq ft

Condo

133 SYCAMORE DR, PROSPECT, CT, 06712

Community: Regency at Prospect

Leisure Glen

279 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$569,999

2 beds

2 baths

1,542 sq ft

Condo

279 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Newtown Woods

623 BROOKSIDE CT 623, NEWTOWN, CT, 06470, Newtown, CT 06470

$498,900

2 beds

2 baths

1,504 sq ft

Condo

623 BROOKSIDE CT 623, 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

Heritage Hills

675 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589

$825,000

2 beds

2 baths

1,663 sq ft

Condo

675 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

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

$225,000

1 beds

1 baths

928 sq ft

Condo

875 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Retreat at Carmel

88 BLAIR HEIGHTS, CARMEL, NY, 10512, Carmel, NY 10512

$699,000

3 beds

3 baths

2,695 sq ft

Condo

88 BLAIR HEIGHTS, CARMEL, NY, 10512

Community: The Retreat at Carmel

Heritage Hills

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

$679,000

2 beds

2 baths

1,470 sq ft

Condo

370 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

The Village at Buckingham

13 KENINGTON RD 13, AVON, CT, 06001, Avon, CT 06001

$639,900

3 beds

3 baths

2,024 sq ft

Condo

13 KENINGTON RD 13, AVON, CT, 06001

Community: The Village at Buckingham

Heritage Village

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

$269,900

2 beds

2 baths

1,032 sq ft

Condo

23 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$465,000

2 beds

2 baths

1,398 sq ft

Condo

4 HERITAGE CIR A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$315,000

2 beds

2 baths

1,032 sq ft

Condo

569 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Meadow Brook Estates

188 EASTWOOD DR 188, SEYMOUR, CT, 06483, Seymour, CT 06483

$624,500

2 beds

3 baths

2,358 sq ft

Condo

188 EASTWOOD DR 188, SEYMOUR, CT, 06483

Community: Meadow Brook Estates

Heritage Hills

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

$799,000

2 beds

2 baths

1,353 sq ft

Condo

481 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Oronoque Village

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

$475,000

2 beds

3 baths

1,434 sq ft

Condo

315 NAVAJO LN A, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (860) 238-3620

Overlook

2050 SUMMIT LOOP 61, CARMEL, NY, 10512, Carmel, NY 10512

$929,000

2 beds

2 baths

2,102 sq ft

Condo

2050 SUMMIT LOOP 61, CARMEL, NY, 10512

Community: Overlook

Oronoque Village

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

$480,000

2 beds

3 baths

1,438 sq ft

Condo

138 BISON LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$325,000

2 beds

2 baths

1,432 sq ft

Condo

774 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Woodridge Strathmore Terrace

8 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$549,000

2 beds

2 baths

1,240 sq ft

Condo

8 CHIPPENDALE DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

Heritage Village

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

$232,000

1 beds

1 baths

928 sq ft

Condo

28 HERITAGE CIR B, SOUTHBURY, CT, 06488

Community: Heritage Village

Jefferson Village

148 FLINTLOCK WAY G, YORKTOWN, NY, 10598, Yorktown, NY 10598

$579,900

2 beds

2 baths

1,302 sq ft

Condo

148 FLINTLOCK WAY G, YORKTOWN, NY, 10598

Community: Jefferson Village

Oronoque Village

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

$499,000

1 beds

3 baths

1,175 sq ft

Condo

443 N TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$200,000

2 beds

2 baths

1,076 sq ft

Condo

214 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

238 BLACKPOOL CT A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$369,000

2 beds

1 baths

1,085 sq ft

Condo

238 BLACKPOOL CT A, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Leisure Glen

15 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$569,900

2 beds

2 baths

1,476 sq ft

Condo

15 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Leisure Knoll

232 BELFAST LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$499,999

2 beds

2 baths

1,172 sq ft

Condo

232 BELFAST LN, 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

South Pond Village

37 REED CT 37, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$299,000

2 beds

3 baths

1,258 sq ft

Condo

37 REED CT 37, BLOOMFIELD, CT, 06002

Community: South Pond Village

Oronoque Village

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

$649,000

2 beds

2 baths

1,426 sq ft

Condo

237 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

Glassbury Court at Hunterbrook

2314 DEPEYSTER DR, YORKTOWN, NY, 10567, Yorktown, NY 10567

$952,900

2 beds

3 baths

2,265 sq ft

Condo

2314 DEPEYSTER DR, YORKTOWN, NY, 10567

Community: Glassbury Court at Hunterbrook

Heritage Village

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

$235,000

2 beds

2 baths

1,000 sq ft

Condo

732 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Park Glen

4 RAINBOW CT 4, NEW MILFORD, CT, 06776, New Milford, CT 06776

$649,000

2 beds

4 baths

2,600 sq ft

Condo

4 RAINBOW CT 4, NEW MILFORD, CT, 06776

Community: Park Glen

Heritage Village

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

$395,000

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

$329,900

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

$224,900

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

$430,000

2 beds

2 baths

1,151 sq ft

Condo

6 COBBLESTONE WAY, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

Foxwood Village

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$469,999

3 beds

2 baths

1,792 sq ft

Manufactured Home

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933

Community: Foxwood Village

Leisure Village

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

$389,990

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

South Pond Village

78 SILO WAY 78, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$289,500

3 beds

3 baths

1,639 sq ft

Condo

78 SILO WAY 78, BLOOMFIELD, CT, 06002

Community: South Pond 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?

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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Answers from local 55+ experts

Thanks! A local 55+ expert will be in touch shortly.

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 2

95 communities near Winchester Area

226 homes near Winchester Area

2 beds

2 baths

1,350 sq ft

Condo

2 beds

2 baths

1,386 sq ft

Condo

2 beds

3 baths

1,850 sq ft

Condo

2 beds

2 baths

1,542 sq ft

Condo

2 beds

2 baths

1,504 sq ft

Condo

2 beds

2 baths

1,663 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

3 beds

3 baths

2,695 sq ft

Condo

2 beds

2 baths

1,470 sq ft

Condo

3 beds

3 baths

2,024 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

2 beds

3 baths

2,358 sq ft

Condo

2 beds

2 baths

1,353 sq ft

Condo

2 beds

3 baths

1,434 sq ft

Condo

2 beds

2 baths

2,102 sq ft

Condo

2 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds