Winchester Area, CT 55+ rental communities & homes for rent

1 communities near Winchester Area

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Sylvan Woods Westchester

$3,095.78 - - $4,685.78 / mo

Base rent from $2,960

Sylvan Woods Westchester, Buchanan, NY

New Construction | 55+ age-restricted | Built 2025 - present | 148 rental homes

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Questions? Call us: (860) 238-3620

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.

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.

Want to learn more about 55+ 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

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 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...

Community: Jefferson Village

Heritage Village

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

$225,000

2 beds

2 baths

1,398 sq ft

Condo

411 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

41 COACH DR # 41, SOUTHINGTON, CT, 06489, Southington, CT 06489

$249,900

2 beds

2 baths

1,232 sq ft

Condo

41 COACH DR # 41, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

The Village at Hunt Glen

59 HUNT GLEN DR 59, GRANBY, CT, 06035, Granby, CT 06035

$545,000

2 beds

4 baths

1,848 sq ft

59 HUNT GLEN DR 59, GRANBY, CT, 06035

Community: The Village at Hunt Glen

Rivington

1025 COUNTRY VIEW RD 1025, DANBURY, CT, ..., Danbury, CT 06810

$499,000

2 beds

2 baths

1,292 sq ft

Condo

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

Community: Rivington

Heritage Village

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

$349,900

2 beds

2 baths

1,398 sq ft

Condo

865 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

Regency at Prospect

50 LILAC LN 50, PROSPECT, CT, 06712, Prospect, CT 06712

$489,000

2 beds

2 baths

1,503 sq ft

Condo

50 LILAC LN 50, PROSPECT, CT, 06712

Community: Regency at Prospect

Leisure Knoll

498 CRANSTON LN, RIDGE, NY, 11961, Ridge, NY 11961

$479,000

2 beds

2 baths

1,412 sq ft

Condo

498 CRANSTON LN, RIDGE, NY, 11961

Community: Leisure Knoll

Overlook

2066 SUMMIT LOOP # 68, CARMEL, NY, 10512, Carmel, NY 10512

$879,000

2 beds

3 baths

2,126 sq ft

Condo

2066 SUMMIT LOOP # 68, CARMEL, NY, 10512

Community: Overlook

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Questions? Call us: (860) 238-3620

Heritage Village

1041 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$299,900

2 beds

2 baths

1,000 sq ft

Condo

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

Community: Heritage Village

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

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

Questions? Call us: (860) 238-3620

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

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

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

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

Questions? Call us: (860) 238-3620

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

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

Questions? Call us: (860) 238-3620

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

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

Spring Lake Village

40 HICKORY HL # 40, SOUTHINGTON, CT, 064..., Southington, CT 06489

$233,527

2 beds

2 baths

1,211 sq ft

Condo

40 HICKORY HL # 40, SOUTHINGTON, CT, 064...

Community: Spring Lake Village

Heritage Hills

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

$633,000

2 beds

2 baths

1,139 sq ft

Condo

40 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

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

Heritage Village

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

$399,000

3 beds

2 baths

1,716 sq ft

Condo

575 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$260,000

2 beds

2 baths

1,398 sq ft

Condo

701 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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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

1 communities

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REIN updates its listings on a daily basis. Data last updated: Feb 28, 2026.
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Winchester Area, CT 55+ rental communities & homes for rent

1 communities near Winchester Area

165 homes near Winchester Area

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

4 baths

1,848 sq ft

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

2,126 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

2 beds

2 baths

1,663 sq ft

Condo

3 beds

3 baths

1,572 sq ft