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

1 communities near Winchester Area

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Sylvan Woods Westchester

$2,700s - $4000s / mo

Base rent from $2,860

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

Heritage Hills

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

$699,000

3 beds

2 baths

1,689 sq ft

Condo

59 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Leisure Village

423 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961

$250,000

1 beds

1 baths

782 sq ft

Condo

423 WOODBRIDGE DR B, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

432A FALMOUTH CT # 432A, RIDGE, NY, 1196..., Ridge, NY 11961

$389,000

2 beds

1 baths

1,074 sq ft

Condo

432A FALMOUTH CT # 432A, RIDGE, NY, 1196...

Community: Leisure Village

Glassbury Court at Hunterbrook

2279 DALTON DR, CORTLANDT MANOR, NY, 105..., Cortlandt Manor, NY 10567

$925,000

2 beds

4 baths

3,500 sq ft

Condo

2279 DALTON DR, CORTLANDT MANOR, NY, 105...

Community: Glassbury Court at Hunterbrook

Overlook

4073 FAIRWAYS DR # 137, CARMEL, NY, 1051..., Carmel, NY 10512

$665,000

3 beds

3 baths

1,914 sq ft

Condo

4073 FAIRWAYS DR # 137, CARMEL, NY, 1051...

Community: Overlook

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

Overlook

4071 FAIRWAYS DR 136, CARMEL, NY, 10512, Carmel, NY 10512

$649,000

2 beds

3 baths

1,914 sq ft

Condo

4071 FAIRWAYS DR 136, CARMEL, NY, 10512

Community: Overlook

Glassbury Court at Cold Spring

43 YESTERDAY DR, COLD SPRING, NY, 10516, Cold Spring, NY 10516

$727,000

2 beds

3 baths

2,620 sq ft

Condo

43 YESTERDAY DR, COLD SPRING, NY, 10516

Community: Glassbury Court at Cold Spring

Jefferson Village

15 ESSEX PL 15K, YORKTOWN, NY, 10598, Yorktown, NY 10598

$375,000

2 beds

1 baths

1,000 sq ft

Condo

15 ESSEX PL 15K, YORKTOWN, NY, 10598

Community: Jefferson Village

Leisure Village

169 VENTRY CT A, RIDGE, NY, 11961, Ridge, NY 11961

$289,000

2 beds

1 baths

875 sq ft

Condo

169 VENTRY CT A, RIDGE, NY, 11961

Community: Leisure Village

New The Retreat at Carmel

2 BLAIR HTS UNIT 3317, CARMEL, NY, 10512, Carmel, NY 10512

$475,000

2 beds

2 baths

1,323 sq ft

Condo

2 BLAIR HTS UNIT 3317, CARMEL, NY, 10512

Community: The Retreat at Carmel

New Leisure Village

373 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961

$415,000

2 beds

1 baths

1,171 sq ft

Condo

373 WOODBRIDGE DR B, RIDGE, NY, 11961

Community: Leisure Village

New Heritage Hills

537 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589

$600,000

2 beds

2 baths

1,470 sq ft

Condo

537 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Hills

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

$625,000

2 beds

2 baths

1,559 sq ft

Condo

443 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

New The Villages at Mount Sinai Park

4 OAKHURST CT, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$775,000

3 beds

3 baths

2,850 sq ft

House

4 OAKHURST CT, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

Saddle Lakes

98 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$749,990

3 beds

3 baths

1,837 sq ft

Condo

98 SCENIC LAKE DR, RIVERHEAD, NY, 11901

Community: Saddle Lakes

Leisure Knoll

190 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961

$434,999

2 beds

1 baths

787 sq ft

Condo

190 CANTERBURY DR, RIDGE, NY, 11961

Community: Leisure Knoll

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

Questions? Call us: (860) 238-3620

New Leisure Village

274 BERWICK CT A, RIDGE, NY, 11961, Ridge, NY 11961

$349,999

2 beds

1 baths

836 sq ft

Condo

274 BERWICK CT A, RIDGE, NY, 11961

Community: Leisure Village

Jefferson Village

96 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598

$479,000

2 beds

2 baths

1,050 sq ft

Condo

96 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,...

Community: Jefferson Village

Heritage Hills

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

$699,000

2 beds

2 baths

1,559 sq ft

Condo

390 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Leisure Glen

289 GLEN DR, RIDGE, NY, 11961, Ridge, NY 11961

$500,000

2 beds

2 baths

1,635 sq ft

Condo

289 GLEN DR, RIDGE, NY, 11961

Community: Leisure Glen

New Leisure Village

164 FALMOUTH CT E, RIDGE, NY, 11961, Ridge, NY 11961

$279,000

2 beds

1 baths

819 sq ft

Condo

164 FALMOUTH CT E, RIDGE, NY, 11961

Community: Leisure Village

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

Questions? Call us: (860) 238-3620

Leisure Knoll

195 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961

$479,990

2 beds

1 baths

1,020 sq ft

Condo

195 CANTERBURY DR, RIDGE, NY, 11961

Community: Leisure Knoll

Jefferson Village

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598

$560,000

2 beds

2 baths

1,300 sq ft

Condo

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,...

Community: Jefferson Village

Jefferson Village

98 MOLLY PITCHER LN A, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598

$525,000

2 beds

2 baths

1,100 sq ft

Condo

98 MOLLY PITCHER LN A, YORKTOWN HEIGHTS,...

Community: Jefferson Village

Leisure Village

360 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961

$459,000

2 beds

2 baths

1,250 sq ft

Condo

360 WOODBRIDGE DR A, RIDGE, NY, 11961

Community: Leisure Village

Heritage Hills

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

$779,000

2 beds

2 baths

1,526 sq ft

Condo

749 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Leisure Village

475 DARWEN DR B, RIDGE, NY, 11961, Ridge, NY 11961

$437,500

2 beds

2 baths

1,423 sq ft

Condo

475 DARWEN DR B, RIDGE, NY, 11961

Community: Leisure Village

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

Questions? Call us: (860) 238-3620

The Villages at Mount Sinai Park

78 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$799,000

2 beds

2 baths

2,135 sq ft

Condo

78 LOUDEN LOOP, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

Jefferson Village

17 HASTINGS B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$235,000

1 baths

600 sq ft

Condo

17 HASTINGS B, 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

Plymouth Estates at Mount Sinai

230 IRA RD # 230, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$589,999

2 beds

2 baths

1,317 sq ft

Condo

230 IRA RD # 230, MOUNT SINAI, NY, 11766

Community: Plymouth Estates at Mount Sinai

The Vineyards at Miller Place

45 HALLEY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764

$650,000

2 beds

3 baths

1,853 sq ft

Condo

45 HALLEY LN, MILLER PLACE, NY, 11764

Community: The Vineyards at Miller Place

Heritage Hills

798 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589

$609,000

2 beds

2 baths

1,296 sq ft

Condo

798 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Hills

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

$675,000

2 beds

2 baths

1,500 sq ft

Condo

55 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

The Retreat at Carmel

14 LANGDON GROVE, CARMEL, NY, 10512, Carmel, NY 10512

$699,900

2 beds

3 baths

1,957 sq ft

Condo

14 LANGDON GROVE, CARMEL, NY, 10512

Community: The Retreat at Carmel

Leisure Village

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119..., Ridge, NY 11961

$342,000

2 beds

1 baths

1,278 sq ft

Condo

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119...

Community: Leisure Village

Sunken Pond Estates

4006 SAINT ANDREWS AVE, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$519,888

2 beds

2 baths

1,587 sq ft

Condo

4006 SAINT ANDREWS AVE, RIVERHEAD, NY, 1...

Community: Sunken Pond Estates

Leisure Village

380 WOODBRIDGE DR D, RIDGE, NY, 11961, Ridge, NY 11961

$439,000

2 beds

2 baths

1,147 sq ft

Condo

380 WOODBRIDGE DR D, RIDGE, NY, 11961

Community: Leisure Village

Heritage Hills

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

$596,000

2 beds

2 baths

1,428 sq ft

Condo

348 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

Stoneleigh Woods at Riverhead

67 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$619,000

2 beds

3 baths

1,972 sq ft

Condo

67 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

Leisure Village

289 CARDIFF CT B, RIDGE, NY, 11961, Ridge, NY 11961

$420,000

2 beds

2 baths

1,308 sq ft

Condo

289 CARDIFF CT B, RIDGE, NY, 11961

Community: Leisure 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: Jan 11, 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

153 homes near Winchester Area

3 beds

2 baths

1,689 sq ft

Condo

1 beds

1 baths

782 sq ft

Condo

2 beds

1 baths

1,074 sq ft

Condo

2 beds

4 baths

3,500 sq ft

Condo

3 beds

3 baths

1,914 sq ft

Condo

2 beds

3 baths

1,914 sq ft

Condo

2 beds

3 baths

2,620 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

1,323 sq ft

Condo

2 beds

1 baths

1,171 sq ft

Condo

2 beds

2 baths

1,470 sq ft

Condo

2 beds

2 baths

1,559 sq ft

Condo

3 beds

3 baths

2,850 sq ft

House

3 beds

3 baths

1,837 sq ft

Condo

2 beds

1 baths

787 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

2 beds

2 baths

1,050 sq ft

Condo

2 beds

2 baths

1,559 sq ft

Condo

2 beds