Winchester Area, CT 55+ active adult communities & homes for sale - Page 3

93 communities near Winchester Area

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Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

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

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

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

RiverWalk

$500ks - $600ks

RiverWalk, Branford, CT

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

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes

5 rating (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

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

77 Sunset Lane

$400ks - $700ks

77 Sunset Lane, Ridgefield, CT

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

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

Bartlett Hollow

$200ks - $400ks

Bartlett Hollow, Middletown, CT

New Construction | 55+ age-restricted | Built 2015 - present | 25 homes

Autumn Estates

$500ks - $600ks

Autumn Estates, Farmington, CT

Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

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

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Questions? Call us: (860) 238-3620

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

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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

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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 3

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