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

1 communities near Winchester Area

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Sylvan Woods Westchester

$2,885.12 - $4,810.12 / mo

Base rent from $2,750

Sylvan Woods Westchester, Buchanan, NY

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

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

Questions? Call us: (860) 238-3620

Jefferson Village

39 SUSSEX DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$369,000

2 beds

2 baths

1,000 sq ft

Condo

39 SUSSEX DR B, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Village

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

$386,000

3 beds

2 baths

1,716 sq ft

Condo

345 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Glenwood Village

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

$419,000

2 beds

2 baths

1,624 sq ft

Manufactured Home

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

Community: Glenwood Village

New Spring Lake Village

20 VILLAGE RD 20, SOUTHINGTON, CT, 06489, Southington, CT 06489

$219,000

2 beds

2 baths

1,224 sq ft

Condo

20 VILLAGE RD 20, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

New Heritage Village

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

$232,000

1 beds

1 baths

928 sq ft

Condo

28 HERITAGE CIR 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

New Jefferson Village

148 FLINTLOCK WAY G, YORKTOWN, NY, 10598, Yorktown, NY 10598

$599,900

2 beds

2 baths

1,302 sq ft

Condo

148 FLINTLOCK WAY G, YORKTOWN, NY, 10598

Community: Jefferson Village

New Oronoque Village

443 N TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$499,000

1 beds

3 baths

1,175 sq ft

Condo

443 N TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

New South Pond Village

8 S POND RD 8, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$499,900

3 beds

3 baths

1,912 sq ft

Condo

8 S POND RD 8, BLOOMFIELD, CT, 06002

Community: South Pond Village

New Heritage Village

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

$210,000

2 beds

2 baths

1,076 sq ft

Condo

214 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Leisure Village

238 BLACKPOOL CT A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$369,000

2 beds

1 baths

1,085 sq ft

2,265 sq ft

Condo

2314 DEPEYSTER DR, YORKTOWN, NY, 10567

Community: Glassbury Court at Hunterbrook

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

Questions? Call us: (860) 238-3620

New Heritage Village

732 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$235,000

2 beds

2 baths

1,000 sq ft

Condo

732 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

New Park Glen

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

$649,000

2 beds

4 baths

2,600 sq ft

Condo

4 RAINBOW CT 4, NEW MILFORD, CT, 06776

Community: Park Glen

New Heritage Village

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

$395,000

2 beds

2 baths

1,432 sq ft

Condo

783 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Hopmeadow Place

1 W ST 315, SIMSBURY, CT, 06070, Simsbury, CT 06070

$385,000

2 beds

2 baths

1,477 sq ft

Condo

1 W ST 315, SIMSBURY, CT, 06070

Community: Hopmeadow Place

New Heritage Village

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

$329,900

2 beds

2 baths

1,398 sq ft

Condo

738 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Granite Woods

35 NUTMEG RD B2, MIDDLEBURY, CT, 06762, Middlebury, CT 06762

$239,900

1 beds

1 baths

889 sq ft

Condo

35 NUTMEG RD B2, MIDDLEBURY, CT, 06762

Community: Granite Woods

New Woodridge Strathmore Terrace

6 COBBLESTONE WAY, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$430,000

2 beds

2 baths

1,151 sq ft

Condo

6 COBBLESTONE WAY, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

New Oronoque Village

393 OTTAWA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$350,000

1 beds

3 baths

1,118 sq ft

Condo

393 OTTAWA LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New Foxwood Village

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$469,999

3 beds

2 baths

1,792 sq ft

Manufactured Home

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933

Community: Foxwood Village

New Leisure Village

463 B OLDHAM CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$389,990

2 beds

1 baths

1,074 sq ft

Condo

463 B OLDHAM CT, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Leisure Village

472 DARWEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$408,000

2 beds

2 baths

1,200 sq ft

Condo

472 DARWEN DR, 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

New South Pond Village

78 SILO WAY 78, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$289,500

3 beds

3 baths

1,639 sq ft

Condo

78 SILO WAY 78, BLOOMFIELD, CT, 06002

Community: South Pond Village

New Plymouth Estates at Mount Sinai

7 POND CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$665,000

2 beds

2 baths

1,274 sq ft

Condo

7 POND CIR, BROOKHAVEN, NY, 11766

Community: Plymouth Estates at Mount Sinai

New Heritage Hills

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

$599,000

2 beds

3 baths

1,550 sq ft

Condo

332 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Leisure Knoll

152A LAURANCE LN A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$399,999

2 beds

1 baths

724 sq ft

Condo

152A LAURANCE LN A, BROOKHAVEN, NY, 1196...

Community: Leisure Knoll

New Newbury Village

23 STILL WATER CIR 23, BROOKFIELD, CT, 0..., Brookfield, CT 06804

$735,000

3 beds

4 baths

2,684 sq ft

Condo

23 STILL WATER CIR 23, BROOKFIELD, CT, 0...

Community: Newbury Village

New Leisure Glen

6 OAKDALE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$559,000

2 beds

2 baths

1,666 sq ft

Condo

6 OAKDALE CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Leisure Glen

428 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$649,000

2 beds

2 baths

1,652 sq ft

Condo

428 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Oronoque Village

138 BISON LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$480,000

2 beds

3 baths

1,438 sq ft

857 HERITAGE VLG A, 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

Heritage Village

9 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$275,000

2 beds

2 baths

1,071 sq ft

Condo

9 HERITAGE CIR A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$329,900

2 beds

2 baths

1,432 sq ft

Condo

353 HERITAGE VLG B, 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 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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Want to learn more about 55+ communities in Winchester Area?

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1 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.
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REIN updates its listings on a daily basis. Data last updated: Aug 29, 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+ rental communities & homes for rent

1 communities near Winchester Area

234 homes near Winchester Area

2 beds

2 baths

1,000 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

1,224 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

2 baths

1,302 sq ft

Condo

1 beds

3 baths

1,175 sq ft

Condo

3 beds

3 baths

1,912 sq ft

Condo

2 beds

2 baths

1,076 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds

2 baths

1,476 sq ft

Condo

2 beds

2 baths

1,172 sq ft

Condo

2 beds

2 baths

912 sq ft

Condo

2 beds

3 baths

1,258 sq ft

Condo

2 beds

2 baths

1,426 sq ft

Condo

2 beds

3 baths

2,265 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

4 baths

2,600 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds