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

95 communities near Winchester Area

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The Cottages at Wire Mill

$1Ms

The Cottages at Wire Mill, Stamford, CT

New Construction | 55+ age-restricted | Built 2026 - present | 9 homes

Glassbury Court at Hunter...

$500ks - $700ks

Glassbury Court at Hunter..., Cortlandt, NY

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

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

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

Park Glen

$300ks - $500ks

Park Glen, New Milford, CT

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

Hopmeadow Place

$200ks - $300ks

Hopmeadow Place, Simsbury, CT

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

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

Questions? Call us: (860) 238-3620

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes

Rivington Landing

$500ks

Rivington Landing, Danbury, CT

New Construction | Age-targeted | Built 2025 - 2026 | 25 homes

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

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

The Bridges at Oxford Gre...

$600ks

The Bridges at Oxford Gre..., Oxford, CT

New Construction | 55+ age-restricted | Built 2025 - present | 99 homes

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 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.

Bramble Ridge

$300ks

Bramble Ridge, Suffield, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 homes

Stoneleigh Woods at Carme...

$400ks

Stoneleigh Woods at Carme..., Carmel, NY

Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes

5 rating (1 reviews)

The Villages at Mount Sin...

$600ks

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

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

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes

3.5 rating (2 reviews)

Harvest Pointe

$800ks - $3Ms

Harvest Pointe, Cutchogue, NY

New Construction | 55+ age-restricted | Built 2017 - present | 124 homes

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

Questions? Call us: (860) 238-3620

The Residences at Butterf...

$500ks - $600ks

The Residences at Butterf..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2018 - 2023 | 49 homes

Villas at Seminary Hill

$200ks - $300ks

Villas at Seminary Hill, Carmel, NY

New Construction | 55+ age-restricted | Built 2018 - present | 50 homes

Fieldstone Village

$500ks - $800ks

Fieldstone Village, Orange, CT

Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes

4.9 rating (14 reviews)

Chatfield Farms

$400ks - $700ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

RiverWalk

$500ks - $600ks

RiverWalk, Branford, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

77 Sunset Lane

$400ks - $700ks

77 Sunset Lane, Ridgefield, CT

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes

Gloria Commons

$200ks - $300ks

Gloria Commons, Milford, CT

Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes

RiverBend Estates

$400ks

RiverBend Estates, Oxford, CT

New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes

Summer Wind Estates

$300ks - $400ks

Summer Wind Estates, North Haven, CT

New Construction | 55+ age-restricted | Built 2015 - present | 18 homes

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

Questions? Call us: (860) 238-3620

Cobblestone Court

$400ks - $500ks

Cobblestone Court, Essex, CT

New and Resale | 55+ age-restricted | Built 2017 - present | 8 homes

The Coach Homes at Ridgef...

$300ks - $400ks

The Coach Homes at Ridgef..., Ridgefield, CT

New Construction | 55+ age-restricted | Built 2019 - present | 30 homes

Whitney Glen

$500ks - $600ks

Whitney Glen, Westport, CT

Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

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

Clockmaker's Hill

$100ks

Clockmaker's Hill, Winsted, CT

Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes

The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

1 rating (1 reviews)

Beckley Farms

$300ks - $400ks

Beckley Farms, Berlin, CT

New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes

Castle Heights of Cheshir...

$500ks - $600ks

Castle Heights of Cheshir..., Cheshire, CT

Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes

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

Questions? Call us: (860) 238-3620

North Woods of Colchester

$300ks - $400ks

North Woods of Colchester, Colchester, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes

Chimney Hill

$500ks - $700ks

Chimney Hill, Farmington, CT

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 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 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

New 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

New 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

New 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

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

Questions? Call us: (860) 238-3620

New 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

New 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

New Leisure Village

299 CARDIFF CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$489,000

2 beds

2 baths

1,308 sq ft

Condo

299 CARDIFF CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

New 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

New 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

New 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

New 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

Heritage Village

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

$429,900

2 beds

2 baths

1,420 sq ft

Condo

28 HERITAGE CRST B, 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

The Summit at Bethel

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

$719,000

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

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

$459,900

3 beds

2 baths

2,020 sq ft

House

47 WHISPERING PINES WAY, ROTTERDAM, NY, ...

Community: The Village at Whispering Pines

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

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

Leisure Glen

9 OAKDALE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$619,000

2 beds

2 baths

1,882 sq ft

House

9 OAKDALE CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Regency at Wappinger

5 PALMERTON DR, WAPPINGER, NY, 12590, Wappinger, NY 12590

$829,900

2 beds

3 baths

3,156 sq ft

Condo

5 PALMERTON DR, WAPPINGER, NY, 12590

Community: Regency at Wappinger

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

Questions? Call us: (860) 238-3620

The Village at Oxford Greens

84 LINKS WAY 84, OXFORD, CT, 06478, Oxford, CT 06478

$710,000

3 beds

3 baths

2,008 sq ft

Condo

84 LINKS WAY 84, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Heritage Village

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

$310,000

2 beds

2 baths

1,432 sq ft

Condo

722 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$309,000

2 beds

2 baths

1,432 sq ft

Condo

970 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Rivington

44 WARRINGTON ROUND, DANBURY, CT, 06810, Danbury, CT 06810

$628,000

3 beds

3 baths

1,600 sq ft

Condo

44 WARRINGTON ROUND, DANBURY, CT, 06810

Community: Rivington

Leisure Glen

477 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$589,000

2 beds

2 baths

1,434 sq ft

Condo

477 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Heritage Village

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

$427,500

2 beds

2 baths

1,398 sq ft

Condo

411 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$319,000

2 beds

2 baths

1,432 sq ft

Condo

620 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

733 CHAMPIONSHIP DR 733, OXFORD, CT, 064..., Oxford, CT 06478

$624,900

2 beds

3 baths

1,673 sq ft

Condo

733 CHAMPIONSHIP DR 733, OXFORD, CT, 064...

Community: The Village at Oxford Greens

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

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

Questions? Call us: (860) 238-3620

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

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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

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

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 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

1,624 sq ft

Manufactured Home

2 beds

1 baths

925 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds

1 baths

1,020 sq ft

Condo

1 beds

1 baths

684 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,308 sq ft

Condo

1 beds

2 baths

1,499 sq ft

Condo

2 beds

2 baths

1,483 sq ft

Condo

2 beds

2 baths

1,867 sq ft

Condo

3 beds

2 baths

1,500 sq ft

Condo

3 beds

3 baths

1,922 sq ft

Condo

2 beds

2 baths

1,205 sq ft

Condo

2 beds

2 baths

1,308 sq ft

Condo

2 beds

2 baths

1,420 sq ft

Condo

3 beds

3 baths

2,744 sq ft

Condo

2 beds

3 baths

1,426 sq ft

Condo

1 beds

1 baths

845 sq ft

Condo

3 beds