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

93 communities near Winchester Area

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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

The Woods at Dunham Pond

$200ks - $400ks

The Woods at Dunham Pond, New Fairfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

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

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

Questions? Call us: (860) 238-3620

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Questions? Call us: (860) 238-3620

Bidwell Village

$300ks - $400ks

Bidwell Village, Coventry, CT

New Construction | 55+ age-restricted | Built 2020 - present | 37 homes

Cobblestone Court

$400ks - $500ks

Cobblestone Court, Essex, CT

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

Forest Mews

$300ks - $400ks

Forest Mews, Avon, CT

Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 homes

The Village at Hunt Glen

$300ks

The Village at Hunt Glen, Granby, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 homes

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O'Meara Farm

$400ks

O'Meara Farm, Farmington, CT

Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 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

Shaker Heights

$400ks - $500ks

Shaker Heights, Enfield, CT

New Construction | 55+ age-restricted | Built 2018 - present | 77 homes

Bramble Ridge

$300ks

Bramble Ridge, Suffield, CT

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

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

Questions? Call us: (860) 238-3620

Autumn Fields

$200ks - $300ks

Autumn Fields, Enfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 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

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

Questions? Call us: (860) 238-3620

Whitney Glen

$500ks - $600ks

Whitney Glen, Westport, CT

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Stoneleigh Woods at Carme...

$400ks

Stoneleigh Woods at Carme..., Carmel, NY

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

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

Woodcrest at Jacobs Hill

$200ks - $300ks

Woodcrest at Jacobs Hill, Cortlandt, NY

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

Glassbury Court at Hunter...

$500ks - $700ks

Glassbury Court at Hunter..., Cortlandt, NY

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

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

Questions? Call us: (860) 238-3620

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

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

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

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

Harvest Pointe

$800ks - $3Ms

Harvest Pointe, Cutchogue, NY

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

The Residences at Butterf...

$500ks - $600ks

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

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

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

Newbury Village

$400ks - $500ks

Newbury Village, Brookfield, CT

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

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

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

Questions? Call us: (860) 238-3620

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

Questions? Call us: (860) 238-3620

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

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

Fieldstone Village

$500ks - $800ks

Fieldstone Village, Orange, CT

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

1 2...3

New Oronoque Village

546 N TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$679,000

2 beds

3 baths

1,434 sq ft

Condo

546 N TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

New Oronoque Village

87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$419,900

1 beds

2 baths

1,454 sq ft

Condo

87 CREEK LN A, STRATFORD, CT, 06614

919 HERITAGE VLG 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

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

Questions? Call us: (860) 238-3620

New Newington Ridge Preserve

2 DEMING FARM DR 2, NEWINGTON, CT, 06111, Newington, CT 06111

$519,900

2 beds

2 baths

1,812 sq ft

2 DEMING FARM DR 2, NEWINGTON, CT, 06111

Community: Newington Ridge Preserve

New Regency at Wappinger

27 DUTCH CT, WAPPINGER, NY, 12590, Wappinger, NY 12590

$815,000

2 beds

4 baths

3,362 sq ft

Condo

27 DUTCH CT, WAPPINGER, NY, 12590

Community: Regency at Wappinger

New Heritage Village

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

$599,900

3 beds

2 baths

1,716 sq ft

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Autumn Fields

11 PARTRIDGE RUN 11, ENFIELD, CT, 06082, Enfield, CT 06082

$399,900

2 beds

2 baths

1,296 sq ft

Condo

11 PARTRIDGE RUN 11, ENFIELD, CT, 06082

Community: Autumn Fields

New Leisure Knoll

2 BEDFORD CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$459,000

2 beds

2 baths

1,096 sq ft

House

2 BEDFORD CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Heritage Hills

499B HERITAGE HLS 499B, SOMERS, NY, 1058..., Somers, NY 10589

$569,000

2 beds

2 baths

1,470 sq ft

Condo

499B HERITAGE HLS 499B, SOMERS, NY, 1058...

Community: Heritage Hills

New Oronoque Village

483 COMMANCHE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$400,000

1 beds

2 baths

1,454 sq ft

Condo

483 COMMANCHE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Jefferson Village

98 MOLLY PITCHER LN I, YORKTOWN, NY, 105..., Yorktown, NY 10598

$349,000

1 beds

1 baths

800 sq ft

Condo

98 MOLLY PITCHER LN I, YORKTOWN, NY, 105...

Condo

1025 COUNTRY VIEW RD 1025, DANBURY, CT, ...

Condo

1041 HERITAGE VLG A, SOUTHBURY, CT, 0648...

Community: Heritage Village

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

Questions? Call us: (860) 238-3620

Jefferson Village

41 JEFFERSON OVAL G, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598

$480,000

2 beds

2 baths

1,100 sq ft

Condo

41 JEFFERSON OVAL G, YORKTOWN HEIGHTS, N...

Community: Jefferson Village

Heritage Hills

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

$790,000

2 beds

2 baths

1,663 sq ft

Condo

772 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Rivington

13 MERCY ST 13, DANBURY, CT, 06810, Danbury, CT 06810

$645,000

3 beds

3 baths

1,572 sq ft

Condo

13 MERCY ST 13, DANBURY, CT, 06810

Community: Rivington

Jefferson Village

120H COLUMBIA CT, YORKTOWN, NY, 10598, Yorktown, NY 10598

$350,000

1 beds

1 baths

793 sq ft

Condo

120H COLUMBIA CT, YORKTOWN, NY, 10598

Community: Jefferson Village

Leisure Village

306 TORQUAY CT E, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$239,000

1 beds

1 baths

684 sq ft

Condo

306 TORQUAY CT E, BROOKHAVEN, NY, 11961

Community: Leisure Village

Jefferson Village

113 VILLAGE RD B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$469,999

2 beds

2 baths

1,200 sq ft

Condo

113 VILLAGE RD B, YORKTOWN, NY, 10598

Community: Jefferson Village

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

Questions? Call us: (860) 238-3620

Heritage Village

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

$285,000

2 beds

2 baths

1,432 sq ft

Condo

972 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489, Southington, CT 06489

$320,000

3 beds

3 baths

1,471 sq ft

Condo

6 LAKEVIEW DR 6, 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

Woodridge Strathmore Terrace

35 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$449,999

2 beds

2 baths

1,240 sq ft

Condo

35 CHIPPENDALE DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

Glenwood Village

181 GLYNWOOD 181, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$265,000

2 beds

1 baths

1,100 sq ft

Manufactured On Land

181 GLYNWOOD 181, RIVERHEAD, NY, 11901

Community: Glenwood Village

Rivington

503 CENTER MEADOW LN 503, DANBURY, CT, 0..., Danbury, CT 06810

$514,950

2 beds

2 baths

1,258 sq ft

Condo

503 CENTER MEADOW LN 503, DANBURY, CT, 0...

Community: Rivington

Oronoque Village

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

$599,000

1 beds

3 baths

2,199 sq ft

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$359,900

2 beds

2 baths

1,432 sq ft

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Glassbury Court at Cold Spring

15 REVOLUTION RD, COLD SPRING, NY, 10516, Cold Spring, NY 10516

$556,904

2 beds

3 baths

1,785 sq ft

Condo

15 REVOLUTION RD, COLD SPRING, NY, 10516

Community: Glassbury Court at Cold Spring

Park Glen

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

$629,000

2 beds

3 baths

2,573 sq ft

Condo

4 BLOSSOM CT, NEW MILFORD, CT, 06776

Community: Park Glen

Leisure Knoll

206 BELFAST LN, RIDGE, NY, 11961, Ridge, NY 11961

$345,000

2 beds

1 baths

658 sq ft

Condo

206 BELFAST LN, RIDGE, NY, 11961

Community: Leisure Knoll

Regency at Fishkill

734 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$569,900

2 beds

2 baths

1,450 sq ft

Condo

734 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

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

Questions? Call us: (860) 238-3620

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Questions? Call us: (860) 238-3620

Glenwood Village

1661 OLD COUNTRY RD 275, RIVERHEAD, NY, ..., Riverhead, NY 11901

$249,850

2 beds

2 baths

1,050 sq ft

Mobile Home

1661 OLD COUNTRY RD 275, RIVERHEAD, NY, ...

Community: Glenwood Village

Leisure Glen

530 LEISURE DR, RIDGE, NY, 11961, Ridge, NY 11961

$595,000

2 beds

2 baths

1,434 sq ft

Condo

530 LEISURE DR, RIDGE, NY, 11961

Community: Leisure Glen

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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 788 days. The average price of homes for sale in these communities is approximately $389,900, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Oak Meadow Estates average around $389,900.

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

Insights and market stats
Instant new home alerts
Answers from local 55+ experts

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

Call us: (860) 238-3620

93 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: Feb 28, 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

93 communities near Winchester Area

169 homes near Winchester Area

2 beds

3 baths

1,434 sq ft

Condo

1 beds

2 baths

1,454 sq ft

Condo

3 beds

3 baths

1,700 sq ft

Condo

1 beds

2 baths

1,360 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,812 sq ft

2 beds

4 baths

3,362 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,296 sq ft

Condo

2 beds

2 baths

1,096 sq ft

House

2 beds

2 baths

1,470 sq ft

Condo

1 beds

2 baths

1,454 sq ft

Condo

1 beds

1 baths

800 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,232 sq ft

Condo

2 beds

2 baths

1,292 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,503 sq ft

Condo

2 beds

2 baths

1,412 sq ft

Condo

2 beds

3 baths