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

95 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

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

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

New and Resale | 55+ age-restricted | Built 1959 - present | 588 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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Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

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

Questions? Call us: (860) 238-3620

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

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

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

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

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

5 rating (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

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

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

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

Woodcrest at Jacobs Hill

$200ks - $300ks

Woodcrest at Jacobs Hill, Cortlandt, NY

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

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

Questions? Call us: (860) 238-3620

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

New Construction | 55+ age-restricted | Built 2020 - present | 24 homes

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

Park Glen

$300ks - $500ks

Park Glen, New Milford, CT

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

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes

Hopmeadow Place

$200ks - $300ks

Hopmeadow Place, Simsbury, CT

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

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

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

Billingsgate

$400ks - $600ks

Billingsgate, Simsbury, CT

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

Newbury Village

$400ks - $500ks

Newbury Village, Brookfield, CT

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

1 2...3

Glenwood Village

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901

$410,000

2 beds

2 baths

1,624 sq ft

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...

Community: Glenwood Village

New Sonoma Woods

35 SONOMA LN 35, MIDDLETOWN, CT, 06457, Middletown, CT 06457

$589,000

2 beds

3 baths

1,798 sq ft

Condo

35 SONOMA LN 35, MIDDLETOWN, CT, 06457

Community: Sonoma Woods

New Heritage Village

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

$269,900

2 beds

2 baths

1,398 sq ft

Condo

955 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New The Village at Oxford Greens

155 COUNTRY CLUB DR 155, OXFORD, CT, 064..., Oxford, CT 06478

$659,000

3 beds

3 baths

2,008 sq ft

Condo

155 COUNTRY CLUB DR 155, OXFORD, CT, 064...

Community: The Village at Oxford Greens

New Spring Lake Village

28 COACH DR 28, SOUTHINGTON, CT, 06489, Southington, CT 06489

$230,000

2 beds

1 baths

985 sq ft

Condo

28 COACH DR 28, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

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

Questions? Call us: (860) 238-3620

New Heritage Village

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

$375,000

2 beds

2 baths

1,398 sq ft

Condo

616 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Spring Lake Village

401 LAKEVIEW DR 401, SOUTHINGTON, CT, 06..., Southington, CT 06489

$329,900

2 beds

2 baths

1,199 sq ft

Condo

401 LAKEVIEW DR 401, SOUTHINGTON, CT, 06...

Community: Spring Lake Village

New Spring Lake Village

102 TIMBER RDG 102, SOUTHINGTON, CT, 064..., Southington, CT 06489

$210,000

1 beds

1 baths

920 sq ft

Condo

102 TIMBER RDG 102, SOUTHINGTON, CT, 064...

Community: Spring Lake Village

New Woodridge Strathmore Terrace

19 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$459,000

2 beds

2 baths

1,105 sq ft

Condo

19 HEARTHSIDE DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

New Heritage Village

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

$414,900

2 beds

2 baths

1,398 sq ft

Condo

886 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Heritage Hills

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

$629,900

2 beds

2 baths

1,484 sq ft

Condo

351 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Regency Meadows

17 REGENCY CIR 17, TRUMBULL, CT, 06611, Trumbull, CT 06611

$765,000

4 beds

4 baths

2,597 sq ft

Condo

17 REGENCY CIR 17, TRUMBULL, CT, 06611

Community: Regency Meadows

Heritage Hills

606 HERITAGE HLS F, SOMERS, NY, 10589, Somers, NY 10589

$874,900

2 beds

2 baths

1,860 sq ft

Condo

606 HERITAGE HLS F, SOMERS, NY, 10589

Community: Heritage Hills

Oronoque Village

71 DAKOTA LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$600,000

1 beds

2 baths

1,375 sq ft

Condo

71 DAKOTA LN A, STRATFORD, CT, 06614

Community: Oronoque Village

The Summit at Bethel

15 BRIAR RIDGE DR 15, BETHEL, CT, 06801, Bethel, CT 06801

$689,000

2 beds

3 baths

2,104 sq ft

Condo

15 BRIAR RIDGE DR 15, BETHEL, CT, 06801

Community: The Summit at Bethel

Leisure Village

167 VENTRY CT D, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$259,000

1 beds

1 baths

684 sq ft

Condo

167 VENTRY CT D, 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

Windcrest East

90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193..., Riverhead, NY 11933

$799,000

3 beds

3 baths

2,620 sq ft

House

90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...

Community: Windcrest East

Founders Village

2555 YOUNGS AVE 11A, SOUTHOLD, NY, 11971, Southold, NY 11971

$605,000

2 beds

2 baths

1,200 sq ft

Condo

2555 YOUNGS AVE 11A, SOUTHOLD, NY, 11971

Community: Founders Village

Jefferson Village

52 JEFFERSON OVAL A, YORKTOWN, NY, 10598, Yorktown, NY 10598

$450,000

2 beds

2 baths

1,100 sq ft

Condo

52 JEFFERSON OVAL A, YORKTOWN, NY, 10598

Community: Jefferson Village

Jefferson Village

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

$399,000

2 beds

1 baths

925 sq ft

Condo

27 WALDEN CT F, YORKTOWN, NY, 10598

Community: Jefferson Village

Oronoque Village

476 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$565,000

1 beds

3 baths

1,426 sq ft

Condo

476 COMMANCHE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Leisure Village

250A NEWCASTLE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$359,000

2 beds

1 baths

1,085 sq ft

Condo

250A NEWCASTLE CT, BROOKHAVEN, NY, 11961

Community: Leisure Village

Leisure Knoll

330 BROWNFIELD DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$429,000

2 beds

1 baths

1,020 sq ft

Condo

330 BROWNFIELD DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Leisure Village

190 VENTRY CT F, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$269,000

1 beds

1 baths

684 sq ft

Condo

190 VENTRY CT F, BROOKHAVEN, NY, 11961

Community: Leisure Village

Heritage Village

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

$215,000

2 beds

2 baths

1,000 sq ft

Condo

751 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Regency at Fishkill

621 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$499,000

1 beds

2 baths

1,499 sq ft

Condo

621 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

Newtown Woods

1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064..., Newtown, CT 06470

$495,000

2 beds

2 baths

1,483 sq ft

Condo

1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064...

Community: Newtown Woods

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

Questions? Call us: (860) 238-3620

Leisure Glen

7 SAGAPONACK CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$599,000

2 beds

2 baths

1,867 sq ft

Condo

7 SAGAPONACK CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Regency at Prospect

112 CHERRY CIR 112, PROSPECT, CT, 06712, Prospect, CT 06712

$338,903

3 beds

2 baths

1,500 sq ft

Condo

112 CHERRY CIR 112, PROSPECT, CT, 06712

Community: Regency at Prospect

Meadow Brook Estates

107 MEADOW BROOK RD 107, OXFORD, CT, 064..., Oxford, CT 06478

$625,000

3 beds

3 baths

1,922 sq ft

Condo

107 MEADOW BROOK RD 107, OXFORD, CT, 064...

Community: Meadow Brook Estates

Heritage Hills

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

$444,900

2 beds

2 baths

1,205 sq ft

Condo

175 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

40 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488

$270,000

2 beds

2 baths

1,308 sq ft

Condo

40 HERITAGE VLG F, SOUTHBURY, CT, 06488

Community: Heritage Village

The Summit at Bethel

14 GREAT HILL DR 14, BETHEL, CT, 06801, Bethel, CT 06801

$699,000

3 beds

3 baths

2,744 sq ft

Condo

14 GREAT HILL DR 14, BETHEL, CT, 06801

Community: The Summit at Bethel

Oronoque Village

615 CHEROKEE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$574,900

2 beds

3 baths

1,426 sq ft

Condo

615 CHEROKEE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Jefferson Village

153 FLINTLOCK WAY A, YORKTOWN, NY, 10598, Yorktown, NY 10598

$335,000

1 beds

1 baths

845 sq ft

Condo

153 FLINTLOCK WAY A, YORKTOWN, NY, 10598

Community: Jefferson Village

The Village at Whispering Pines

48 WHISPERING PINES WAY, ROTTERDAM, NY, ..., Rotterdam, NY 12306

$459,900

3 beds

2 baths

2,020 sq ft

House

48 WHISPERING PINES WAY, ROTTERDAM, NY, ...

Community: The Village at Whispering Pines

Jefferson Village

109 VILLAGE RD D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$365,000

1 beds

1 baths

850 sq ft

Condo

109 VILLAGE RD D, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Hills

$600,000

2 beds

2 baths

1,483 sq ft

Condo

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

Community: Heritage Hills

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

Questions? Call us: (860) 238-3620

Founders Ridge

UNIT 2-41 WEBSTER LN 145, MIDDLETOWN, CT..., Middletown, CT 06457

$689,000

2 beds

2 baths

1,555 sq ft

UNIT 2-41 WEBSTER LN 145, MIDDLETOWN, CT...

Community: Founders Ridge

Leisure Glen

20 WAINSCOTT CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$599,999

2 beds

2 baths

1,666 sq ft

Condo

20 WAINSCOTT CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

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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

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

Call us: (860) 238-3620

95 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: Sep 23, 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

95 communities near Winchester Area

220 homes near Winchester Area

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

3 baths

1,798 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

3 beds

3 baths

2,008 sq ft

Condo

2 beds

1 baths

985 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,199 sq ft

Condo

1 beds

1 baths

920 sq ft

Condo

2 beds

2 baths

1,105 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,484 sq ft

Condo

4 beds

4 baths

2,597 sq ft

Condo

2 beds

2 baths

1,860 sq ft

Condo

1 beds

2 baths

1,375 sq ft

Condo

2 beds

3 baths

2,104 sq ft

Condo

1 beds

1 baths

684 sq ft

Condo

3 beds

3 baths

2,620 sq ft

House

2 beds

2 baths

1,200 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

2 beds