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

1 communities near Winchester Area

Sort by:

Relevance

Sylvan Woods Westchester

$3,138.78 - $4,685.78 / mo

Base rent from $3,003

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

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 Glenwood Village

1661 OLD COUNTRY RD 417, RIVERHEAD, NY, ..., Riverhead, NY 11901

$339,000

2 beds

2 baths

1,344 sq ft

Manufactured Home

1661 OLD COUNTRY RD 417, RIVERHEAD, NY, ...

Community: Glenwood Village

New Setauket Meadows

86 BRIANNA DR, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733

$775,000

2 beds

3 baths

1,991 sq ft

Condo

86 BRIANNA DR, BROOKHAVEN, NY, 11733

Community: Setauket Meadows

New The Powder Forest Homes

37 BANTRY RD 37, SIMSBURY, CT, 06070, Simsbury, CT 06070

$899,000

3 beds

5 baths

2,724 sq ft

37 BANTRY RD 37, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

New Jefferson Village

51 JEFFERSON OVAL F, YORKTOWN, NY, 10598, Yorktown, NY 10598

$448,500

2 beds

2 baths

1,100 sq ft

Condo

51 JEFFERSON OVAL F, YORKTOWN, NY, 10598

Community: Jefferson Village

New Regency at Wappinger

50 STRATFORD LN, WAPPINGER, NY, 12590, Wappinger, NY 12590

$689,000

2 beds

3 baths

1,823 sq ft

Condo

50 STRATFORD LN, WAPPINGER, NY, 12590

Community: Regency at Wappinger

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 Leisure Village

368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$419,990

2 beds

1 baths

Condo

368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119...

Community: Leisure Village

New The Village at Oxford Greens

114 COUNTRY CLUB DR 114, OXFORD, CT, 064..., Oxford, CT 06478

$575,000

2 beds

2 baths

1,590 sq ft

114 COUNTRY CLUB DR 114, OXFORD, CT, 064...

Community: The Village at Oxford Greens

New Leisure Knoll

204 BELFAST LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$460,000

2 beds

2 baths

849 sq ft

House

204 BELFAST LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Newtown Woods

1211 BROOKSIDE CT 1211, NEWTOWN, CT, 064..., Newtown, CT 06470

$485,000

2 beds

2 baths

1,483 sq ft

Condo

1211 BROOKSIDE CT 1211, NEWTOWN, CT, 064...

Community: Newtown Woods

New Heritage Village

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

$489,900

2 beds

2 baths

1,398 sq ft

Condo

930 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Leisure Village

124 EXMORE CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$354,900

2 beds

1 baths

1,085 sq ft

Condo

124 EXMORE CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Liberty at Newtown

66 SUZIE DR 66, NEWTOWN, CT, 06470, Newtown, CT 06470

$636,000

2 beds

3 baths

2,407 sq ft

Condo

66 SUZIE DR 66, NEWTOWN, CT, 06470

Community: Liberty at Newtown

New Glassbury Court at Cold Spring

19 REVOLUTION RD, PHILIPSTOWN, NY, 10516, Philipstown, NY 10516

$567,358

2 beds

3 baths

1,806 sq ft

Condo

19 REVOLUTION RD, PHILIPSTOWN, NY, 10516

Community: Glassbury Court at Cold Spring

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

Questions? Call us: (860) 238-3620

New Jefferson Village

173 LONG HILL DR I, YORKTOWN, NY, 10598, Yorktown, NY 10598

$330,000

1 beds

1 baths

850 sq ft

Condo

173 LONG HILL DR I, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Hills

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

$649,000

2 beds

2 baths

1,483 sq ft

Condo

612 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Meadow Brook Estates

194 EASTWOOD DR 194, SEYMOUR, CT, 06483, Seymour, CT 06483

$599,000

2 beds

3 baths

2,295 sq ft

Condo

194 EASTWOOD DR 194, SEYMOUR, CT, 06483

Community: Meadow Brook Estates

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

Questions? Call us: (860) 238-3620

The Powder Forest Homes

47 ASHTON CIR 47, SIMSBURY, CT, 06070, Simsbury, CT 06070

$695,000

2 beds

3 baths

1,843 sq ft

47 ASHTON CIR 47, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

Heritage Village

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

$229,900

2 beds

2 baths

1,044 sq ft

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

214 WATERS EDGE DR 214, SOUTHINGTON, CT,..., Southington, CT 06489

$317,000

2 beds

3 baths

1,564 sq ft

Condo

214 WATERS EDGE DR 214, SOUTHINGTON, CT,...

Community: Spring Lake Village

Heritage Village

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

$358,000

2 beds

2 baths

1,398 sq ft

Condo

889 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

64 ENFIELD CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$369,000

2 beds

1 baths

1,085 sq ft

Condo

64 ENFIELD CT A, 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

Woodridge Strathmore Terrace

7 COBBLESTONE WAY, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$449,000

2 beds

2 baths

840 sq ft

Condo

7 COBBLESTONE WAY, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

North Woods of Colchester

24 CENTER CT 24, COLCHESTER, CT, 06415, Colchester, CT 06415

$515,000

2 beds

2 baths

1,357 sq ft

Condo

24 CENTER CT 24, COLCHESTER, CT, 06415

Community: North Woods of Colchester

Oronoque Village

402 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$515,000

2 beds

3 baths

1,118 sq ft

Condo

402 MONTAUK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Leisure Village

248 NEWCASTLE CT A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$415,000

2 beds

1 baths

1,085 sq ft

Condo

248 NEWCASTLE CT A, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Leisure Village

375 WOODBRIDGE DR C, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$389,000

2 beds

1 baths

1,171 sq ft

Condo

375 WOODBRIDGE DR C, BROOKHAVEN, NY, 119...

Community: Leisure Village

Heritage Village

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

$525,000

3 beds

2 baths

1,716 sq ft

Condo

36 HERITAGE CIR B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (860) 238-3620

South Pond Village

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

$289,900

3 beds

3 baths

1,639 sq ft

Condo

78 SILO WAY 78, BLOOMFIELD, CT, 06002

Community: South Pond Village

The Powder Forest Homes

3 RONAN WAY 3, SIMSBURY, CT, 06070, Simsbury, CT 06070

$629,900

2 beds

3 baths

1,284 sq ft

Condo

3 RONAN WAY 3, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

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

Questions? Call us: (860) 238-3620

Heritage Hills

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

$569,900

2 beds

2 baths

1,500 sq ft

Condo

272 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

The Village at Oxford Greens

575 INVERNESS CT 575, OXFORD, CT, 06478, Oxford, CT 06478

$699,900

3 beds

3 baths

2,008 sq ft

575 INVERNESS CT 575, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Oak Meadow Estates

65 OAK MEADOW LN 65, TORRINGTON, CT, 067..., Torrington, CT 06790

$485,000

2 beds

4 baths

2,164 sq ft

Condo

65 OAK MEADOW LN 65, TORRINGTON, CT, 067...

Community: Oak Meadow Estates

Jefferson Village

119 VILLAGE RD H, YORKTOWN, NY, 10598, Yorktown, NY 10598

$439,000

2 beds

2 baths

1,100 sq ft

Condo

119 VILLAGE RD H, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Hills

725 HERITAGE HLS, SOMERS, NY, 10589, Somers, NY 10589

$774,900

2 beds

2 baths

1,526 sq ft

Condo

725 HERITAGE HLS, SOMERS, NY, 10589

Community: Heritage Hills

Leisure Village

273 BERWICK CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$289,000

2 beds

1 baths

836 sq ft

Condo

273 BERWICK CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

Heritage Village

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

$249,000

1 beds

1 baths

928 sq ft

Condo

4 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Jefferson Village

129 COLUMBIA CT D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$469,999

2 beds

2 baths

1,100 sq ft

Condo

129 COLUMBIA CT D, YORKTOWN, NY, 10598

Community: Jefferson Village

Fairview at Oxford Greens

1077 AUGUSTA DR 1077, OXFORD, CT, 06478, Oxford, CT 06478

$684,900

3 beds

3 baths

2,256 sq ft

Condo

1077 AUGUSTA DR 1077, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

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

The Village at Oxford Greens

$684,900

3 beds

3 baths

2,256 sq ft

Condo

1077 AUGUSTA DR 1077, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Overlook

2079 SUMMIT LOOP 103, CARMEL, NY, 10512, Carmel, NY 10512

$899,000

2 beds

2 baths

1,948 sq ft

Condo

2079 SUMMIT LOOP 103, CARMEL, NY, 10512

Community: Overlook

Home
Connecticut
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

Remove Boundaries ×

Map Satellite

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: Apr 15, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

1 communities near Winchester Area

200 homes near Winchester Area

2 beds

2 baths

1,344 sq ft

Manufactured Home

2 beds

3 baths

1,991 sq ft

Condo

3 beds

5 baths

2,724 sq ft

2 beds

2 baths

1,100 sq ft

Condo

2 beds

3 baths

1,823 sq ft

Condo

2 beds

1 baths

Condo

2 beds

2 baths

1,590 sq ft

2 beds

2 baths

849 sq ft

House

2 beds

2 baths

1,483 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds

3 baths

2,407 sq ft

Condo

2 beds

3 baths

1,806 sq ft

Condo

1 beds

1 baths

850 sq ft

Condo

2 beds

2 baths

1,483 sq ft

Condo

2 beds

3 baths

2,295 sq ft

Condo

2 beds

3 baths

1,843 sq ft

2 beds

2 baths

1,044 sq ft

Condo

2 beds

3 baths

1,564 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds