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

1 communities near Winchester Area

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Sylvan Woods Westchester

$3,095.12 - $4,810.12 / mo

Base rent from $2,960

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

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 Setauket Meadows

66 BRIANNA DR, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733

$739,999

2 beds

3 baths

1,878 sq ft

Condo

66 BRIANNA DR, BROOKHAVEN, NY, 11733

Community: Setauket Meadows

New Heritage Village

773 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$255,000

2 beds

2 baths

1,071 sq ft

Condo

773 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

New Heritage Hills

358 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$620,000

2 beds

3 baths

1,550 sq ft

Condo

358 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

New Newtown Woods

232 BROOKSIDE CT 232, NEWTOWN, CT, 06470, Newtown, CT 06470

$595,000

2 beds

2 baths

1,747 sq ft

Condo

232 BROOKSIDE CT 232, NEWTOWN, CT, 06470

Community: Newtown Woods

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Questions? Call us: (860) 238-3620

New Heritage Village

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

$200,000

2 beds

2 baths

1,000 sq ft

Condo

883 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

New Glassbury Court at Cold Spring

10 MAGGIE MAY WAY, PHILIPSTOWN, NY, 1051..., Philipstown, NY 10516

$698,000

2 beds

2 baths

1,974 sq ft

Condo

10 MAGGIE MAY WAY, PHILIPSTOWN, NY, 1051...

Community: Glassbury Court at Cold Spring

New Heritage Village

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

$449,000

2 beds

2 baths

1,432 sq ft

Condo

818 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Leisure Village

176 VENTRY CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$399,000

2 beds

1 baths

1,085 sq ft

Condo

176 VENTRY CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Glenwood Village

1661 OLD COUNTRY RD 233, RIVERHEAD, NY, ..., Riverhead, NY 11901

$239,999

2 beds

2 baths

980 sq ft

Manufactured Home

1661 OLD COUNTRY RD 233, RIVERHEAD, NY, ...

Community: Glenwood Village

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New Pond Spring Village

111 PONDVIEW CIR, BEACON FALLS, CT, 0640..., Beacon Falls, CT 06403

$438,000

2 beds

2 baths

1,328 sq ft

Condo

111 PONDVIEW CIR, BEACON FALLS, CT, 0640...

Community: Pond Spring Village

Heritage Village

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

$310,000

2 beds

2 baths

1,398 sq ft

Condo

233 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Hills

571 HERITAGE HLS F, SOMERS, NY, 10589, Somers, NY 10589

$525,000

1 beds

2 baths

967 sq ft

Condo

571 HERITAGE HLS F, SOMERS, NY, 10589

Community: Heritage Hills

The Village at Oxford Greens

349 NIBLICK LN 349, OXFORD, CT, 06478, Oxford, CT 06478

$689,000

3 beds

2 baths

2,008 sq ft

Condo

349 NIBLICK LN 349, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Heritage Hills

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

$599,000

2 beds

2 baths

1,265 sq ft

Condo

600 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

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

$385,000

2 beds

2 baths

1,432 sq ft

Condo

972 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

The Village at Oxford Greens

349 NIBLICK LN, OXFORD, CT, 06478, Oxford, CT 06478

$689,000

3 beds

2 baths

2,152 sq ft

349 NIBLICK LN, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Heritage Village

176 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$289,900

2 beds

2 baths

1,044 sq ft

Condo

176 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

21 HICKORY HL 21, SOUTHINGTON, CT, 06489, Southington, CT 06489

$248,000

2 beds

2 baths

1,285 sq ft

Condo

21 HICKORY HL 21, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

Heritage Hills

34 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$625,000

2 beds

3 baths

1,545 sq ft

Condo

34 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Oronoque Village

46 BUCKSKIN LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$559,900

1 beds

2 baths

1,375 sq ft

Condo

46 BUCKSKIN LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Leisure Glen

187 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$525,000

2 beds

2 baths

1,451 sq ft

Condo

187 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

The Retreat at Carmel

4 REESE CT, CARMEL, NY, 10512, Carmel, NY 10512

$699,000

2 beds

2 baths

1,979 sq ft

House

4 REESE CT, CARMEL, NY, 10512

Community: The Retreat at Carmel

Heritage Hills

$450,000

1 beds

1 baths

955 sq ft

Condo

128 HERITAGE HILLS DR B, SOMERS, NY, 105...

Community: Heritage Hills

Heritage Hills

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

$649,000

3 beds

2 baths

1,689 sq ft

Condo

156 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

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

$275,000

2 beds

2 baths

1,432 sq ft

Condo

874 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Gardens of Wilbraham

137 CHERRY DR 137, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$400,000

2 beds

2 baths

1,241 sq ft

Condo

137 CHERRY DR 137, WILBRAHAM, MA, 01095

Community: The Gardens of Wilbraham

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

Questions? Call us: (860) 238-3620

Rivington

11 MERCY ST 11, DANBURY, CT, 06810, Danbury, CT 06810

$630,000

2 beds

4 baths

1,572 sq ft

11 MERCY ST 11, DANBURY, CT, 06810

Community: Rivington

Heritage Village

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

$399,900

2 beds

2 baths

1,398 sq ft

Condo

701 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$589,900

3 beds

2 baths

1,716 sq ft

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

157 COUNTRY CLUB DR 157, OXFORD, CT, 064..., Oxford, CT 06478

$649,900

3 beds

3 baths

2,008 sq ft

Condo

157 COUNTRY CLUB DR 157, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Overlook

2059 SUMMIT LOOP 97, CARMEL, NY, 10512, Carmel, NY 10512

$920,000

2 beds

3 baths

2,873 sq ft

Condo

2059 SUMMIT LOOP 97, CARMEL, NY, 10512

Community: Overlook

Overlook

2057 SUMMIT LOOP 96, CARMEL, NY, 10512, Carmel, NY 10512

$885,000

2 beds

2 baths

1,948 sq ft

Condo

2057 SUMMIT LOOP 96, CARMEL, NY, 10512

Community: Overlook

Overlook

4091 FAIRWAYS DR 146, CARMEL, NY, 10512, Carmel, NY 10512

$772,000

3 beds

4 baths

2,131 sq ft

Condo

4091 FAIRWAYS DR 146, CARMEL, NY, 10512

Community: Overlook

Overlook

2003 SUMMIT LOOP 82, CARMEL, NY, 10512, Carmel, NY 10512

$799,000

2 beds

2 baths

1,948 sq ft

Condo

2003 SUMMIT LOOP 82, CARMEL, NY, 10512

Community: Overlook

Overlook

4085 FAIRWAYS DR 143, CARMEL, NY, 10512, Carmel, NY 10512

$689,000

3 beds

3 baths

1,931 sq ft

Condo

4085 FAIRWAYS DR 143, CARMEL, NY, 10512

Community: Overlook

Overlook

4087 FAIRWAYS DR 144, CARMEL, NY, 10512, Carmel, NY 10512

$669,000

3 beds

4 baths

2,141 sq ft

Condo

4087 FAIRWAYS DR 144, CARMEL, NY, 10512

Community: Overlook

Heritage Village

24-B HERITAGE CRST B, SOUTHBURY, CT, 064..., Southbury, CT 06488

$419,900

2 beds

2 baths

1,217 sq ft

Condo

24-B HERITAGE CRST B, SOUTHBURY, CT, 064...

Community: Heritage Village

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

Questions? Call us: (860) 238-3620

Heritage Village

593 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$205,000

2 beds

2 baths

1,044 sq ft

Condo

593 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Stoneleigh Woods at Carmel

205 EGRETS LNDG 205, CARMEL, NY, 10512, Carmel, NY 10512

$475,000

2 beds

2 baths

1,344 sq ft

Condo

205 EGRETS LNDG 205, CARMEL, NY, 10512

Community: Stoneleigh Woods at Carmel

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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
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: Jul 15, 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

196 homes near Winchester Area

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

3 baths

1,878 sq ft

Condo

2 beds

2 baths

1,071 sq ft

Condo

2 beds

3 baths

1,550 sq ft

Condo

2 beds

2 baths

1,747 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,974 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds

2 baths

980 sq ft

Manufactured Home

2 beds

2 baths

1,328 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

1 beds

2 baths

967 sq ft

Condo

3 beds

2 baths

2,008 sq ft

Condo

2 beds

2 baths

1,265 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

2 baths

2,152 sq ft

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,285 sq ft

Condo

2 beds

3 baths